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WO2025068637A1 - Microparticules et/ou nanoparticules lipidiques, leur procédé de préparation, produits comprenant les microparticules lipidiques et/ou les nanoparticules et utilisation de la subérine - Google Patents

Microparticules et/ou nanoparticules lipidiques, leur procédé de préparation, produits comprenant les microparticules lipidiques et/ou les nanoparticules et utilisation de la subérine Download PDF

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Publication number
WO2025068637A1
WO2025068637A1 PCT/FI2024/050504 FI2024050504W WO2025068637A1 WO 2025068637 A1 WO2025068637 A1 WO 2025068637A1 FI 2024050504 W FI2024050504 W FI 2024050504W WO 2025068637 A1 WO2025068637 A1 WO 2025068637A1
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Prior art keywords
nanoparticles
suberin
lipid
weight
derivative
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Inventor
Mohammad KARZARJEDDI
Henrikki LIIMATAINEN
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Oulu University of
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Oulu University of
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/5123—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm

Definitions

  • Lipid microparticles and/or nanoparticles a method for preparing thereof, products comprising the lipid microparticles and/or nanoparticles and use of suberin
  • the present disclosure provides a method for preparing lipid microparticles and/or nanoparticles.
  • the present disclosure also provides products comprising the lipid microparticles and/or nanoparticles including pharmaceutical products and personal care and cosmetic products.
  • the present disclosure also provides use of suberin and/or derivative thereof for preparing the lipid microparticles and/or nanoparticles.
  • Lipid-based particles find extensive applications in industries such as pharmaceuticals and personal care and cosmetics (PCCP) for the transportation of active substances.
  • PCCP personal care and cosmetics
  • the utilization of these particles comes with a set of daunting challenges throughout their development and application. Ensuring their biocompatibility necessitates comprehensive scrutiny, as safety concerns and potential toxicity issues loom.
  • These particles are vulnerable to environmental factors, posing challenges related to stability and shelf-life. To facilitate wider adoption, the development of large-scale production methods and cost-effective manufacturing processes is imperative. Targeted delivery to specific cells or tissues remains a daunting obstacle due to immune responses and biological barriers.
  • stringent regulatory approval and adherence to rigorous testing protocols are pivotal in the context of medical applications. The limited payload capacity of these particles may constrain their utility, particularly in cosmetic applications. A thorough comprehension of biodistribution and clearance is indispensable for safe utilization, with a concurrent emphasis on minimizing concerns surrounding immunogenicity and the potential for adverse reactions.
  • lipid-containing particles also faces challenges in terms of environmental impact, resource utilization, waste management, and biodegradability. Lipid-containing particle production can contribute to environmental problems if not sourced sustainably. Proper waste management, regulatory approval, sustainable scale-up and social and ethical considerations are significant challenges.
  • lipid-containing particles in drug delivery and PCCPs have been tackled through a range of approaches.
  • researchers have tried to optimize existing formulations, selecting appropriate lipid components typically from glycerophospholipids, cationic lipids, sterol lipids, and PEGylated lipids to reduce toxicity, improve stability, and enhance drug encapsulation efficiency.
  • Advancements in manufacturing technologies have facilitated large- scale production while maintaining consistency in product quality. Surface modifications have been explored to enhance LNPs' targeting specificity, minimizing off-target effects.
  • the present disclosure introduces a new generation microparticles and nanoparticles from sustainable bioresources.
  • the disclosure relates to specific extracted biomaterials from natural resources and their versatile application.
  • the present disclosure relates to sustainable micro and nano size lipids that are produced from bioresources, especially suberin, using environmentally friendly and renewable materials, with a focus on minimizing their impact on the environment and human health.
  • the lipid microparticles and/or nanoparticles can be formed from suberin into stable forms that can overcome drawbacks of prior art.
  • the obtained lipid micro and/or nanoparticles can be used in a variety of fields, such as in pharmaceuticals, personal care, cosmetics, nutraceuticals, food and beverages, diagnostics, biotechnology, agrochemicals, veterinary medicine, and coating applications as a main or additive in formulations.
  • the present disclosure provides lipid microparticles and/or nanoparticles comprising suberin and/or derivative thereof, and one or more surfactants and/or other additives.
  • the present disclosure provides a pharmaceutical and/or a medical product comprising the lipid microparticles and/or nanoparticles.
  • the present disclosure provides a personal care and/or cosmetic product comprising the lipid microparticles and/or nanoparticles of any of preceding claims.
  • the present disclosure provides use of suberin and/or derivative thereof for preparing the lipid microparticles and/or nanoparticles, the pharmaceutical and/or a medical product, or the personal care and/or cosmetic product.
  • Suberin as the raw material can provide several effects in the present fields of applications.
  • Suberins as natural products provide a sustainable and safe material and a source of the material.
  • the present materials also provides a reduced environmental impact, which addresses concerns such as ones relating to plastic pollution and chemical waste. Also, biocompatibility of the materials minimizes the risk of adverse reactions, thus ensuring synthesizing safer car- rier systems, such as for drug delivery products.
  • the present particles are biodegradable and bioresorbable.
  • the present invention provides new market opportunities, attracting environmentally conscious consumers, investors, and industry partners, and is likely to receive favourable attention from regulatory bodies due to its sustainability and safety. Overall, the present invention marks a significant step forward in sustainable and effective formulations for different industries.
  • Figure 1 shows Field Emissions Scanning Electron Microscopy (FE-SEM) images and Transmission Electron Microscopy (TEM) images of synthesized solid-lipid nanoparticles (SLNs) and solid-lipid microparticles (a-d).
  • Figures 1 a (FE-SEM photo) and 1 b show the SLNs synthesized by applying suberin as the main sources using ultrasonication method.
  • Figure 1 c is a TEM photo.
  • Figure 1d shows FE-SEM image of the prepared NLCs.
  • Figure 2 shows particle size analysis of synthesized SLNs.
  • FIG. 3 shows a flowchart of the preparation method
  • Disclosed dimensions may be measured by image analysis of microscope images, such as images from a light microscope, a field emission scanning electron microscope (FE-SEM), a transmission electron microscope (TEM), such as a cryogenic transmission electron microscope (CRYO-TEM), or an atomic force microscope (AFM).
  • FE-SEM field emission scanning electron microscope
  • TEM transmission electron microscope
  • CYO-TEM cryogenic transmission electron microscope
  • AFM atomic force microscope
  • Surface morphology, nanoparticle aggregation and interaction surfaces of LNPs can be evaluated using suitable imaging techniques, especially FE-SEM and TEM.
  • lipid microparticles (20) and/or nanoparticles (20) comprising suberin (10) and/or derivative thereof (10) comprising isolated and/or purified suberin components, and one or more surfactants (12).
  • the present products provide bioresource-based lipids in the micro to nano size ranges.
  • the suberin can be engineered to produce different class of lipid nanoparticles (LNPs) as well as lipid microparticles (LMPs).
  • LNPs lipid nanoparticles
  • LMPs lipid microparticles
  • a lipid nanoparticle may comprise a lipid shell surrounding an internal core, which may comprise or be composed of reverse micelles, that can encapsulate and deliver active ingredients,
  • Suberin refers to a mixture of lipids, which may be present in suberin preparation. Suberin may be used as a derivative, which may include combinations of isolated and/or purified suberin components, and/or lipids synthesized or derivatized by using suberin lipids disclosed herein as starting material.
  • the suberin may be obtained from any suitable source of suberin.
  • the sources include trees, such as hardwood, for example birch.
  • Suberin may be obtained from bark of the trees or from roots.
  • Suberin is found in the phellem layer of the periderm (or cork), which is outermost layer of the bark.
  • suberin is deposited in the radial and transverse/tangential cell walls of the endodermal cells.
  • Suberin can also be found in various other plant structures. For example, they are present in the lenticels on the stems of many plants and the net structure in the rind of a netted melon is composed of suberised cells.
  • Suberin can be obtained from the raw material by any suitable isolation method.
  • methods used for isolating suberin include extraction, such as by using alkali and ethanol, organic solvents, ionic liquids, for example cholinium hexanoate; ultrafast supercritical hydrolysis, and the like methods used in the art.
  • Suberin comprises two domains, a polyaromatic and a polyaliphatic domain The polyaromatics are predominantly located within the primary cell wall, and the polyaliphatics are located between the primary cell wall and the cell membrane. The two domains may be cross-linked. The exact qualitative and quantitative composition of suberin monomers varies in different species.
  • Some common aliphatic monomers include a-hydroxyacids (mainly 18-hydroxyocta- dec-9-enoic acid) and a,oo-diacids (mainly octadec-9-ene-1 ,18-dioic acid).
  • the monomers of the polyaromatics are hydroxycinnamic acids and derivatives, such as feruloyltyramine.
  • suberin comprises one or more of
  • Suberin possesses valuable properties that make it highly useful in various industrial applications, including pharmaceuticals and cosmetics. Suberin can serve skin as a barrier, exceptional healing, and nurturing agent. Moreover, suberin can protect skin from dehydration by avoiding moisture evaporation. Therefore, developing products, such as LNPs, based on bioresources like suberin enable introducing novel lipids classes especially in skin-related applications. However the suberin-based particles can be used in other applications as well. Suberin can be used to replace stearic acid and the like fatty acids in products such as pharmaceuticals and other micro and/or nano particle-containing products.
  • the present disclosure provides lipid particles, such as lipid microparticles and/or nanoparticles, comprising suberin and/or derivative thereof.
  • the suberin may be present in an amount of 10% by weight or more, such 20% by weight or more of the total microparticles and/or nanoparticles.
  • the suberin content may be higher, such as 30% by weight or more, 50% by weight or more, or 70% by weight or more. It is possible to obtain a suberin content up to 90% by weight or more.
  • the suberin content may be up to 50.0% by weight, up to 60.0% by weight, up to 70.0% by weight, up to 80.0% by weight, up to 90.0% by weight or even up to 95.0% by weight.
  • the lipid microparticles and/or nanoparticles may comprise other lipids in addition to the suberin and/or derivative thereof, such as stearic acid, castor oil, soybean oil and/or the like.
  • suberin can enhance formulations by providing a barrier function that retains moisture and shields against pollutants. It offers antimicrobial protection, aids in wound healing, and improves the stability and longevity of products. Additionally, suberin can act as a preservative in low concentrations within the formulations.
  • suberin fatty acids at low concentrations significantly improved water vapor barrier properties of films.
  • the extraction of suberin monomers through depolymerization methods has revealed their potential in the polymer, food, and pharmaceutical applications, highlighting suberin’s role as a sustainable and valuable biopolymer.
  • the lipid microparticles and/or nanoparticles comprise 0.01 % by weight or more, 0.1 % by weight or more, 1 .0% by weight or more, such as 2.0% by weight or more, for example 5.0% by weight or more, suberin and/or derivative thereof.
  • suberin and/or suberin derivative content examples include 1.0-90.0% by weight, 2.0-90.0% by weight, 5.0-90.0% by weight, 10.0- 90.0% by weight, 20.0-90.0% by weight 1 .0-80.0% by weight, 2.0-80.0% by weight, 5.0-80.0% by weight, 10.0-80.0% by weight, 20.0-80.0% by weight, 1 .0-70.0% by weight, 2.0-70.0% by weight, 5.0-70.0% by weight, 10.0-70.0% by weight, 20.0-70.0% by weight, or any other combination of lower and upper limits disclosed herein. It was found out that to obtain lipid microparticles and lipid nanoparticles, it was advantageous to include one or more surfactants during the preparation. In the final lipid microparticles and lipid nanoparticles the surfactant is present in or as a shell layer, which significantly enhances stability of the lipid particles. It was possible to prepare such micro and/or nanoparticles with a variety of methods.
  • the surfactant may comprise one or more suitable surfactants, such as ionic surfactants, for example anionic or cationic surfactants, and/or nonionic surfactants.
  • suitable surfactants include Tween-80, sodium lignosulfonate, lecithin and the like surfactant.
  • the surfactant is provided in suitable amounts, such as in the range of 0.01-50% by weight, such as 0.1-50% by weight, 1- 50% by weight, 1.0-50% by weight, 0.1-10% by weight, 1-10% by weight, 1 .0-10% by weight, 5-50% by weight, 5.0-50% by weight, 1-5.0% by weight, 1 .0-5.0% by weight or 0.1-1 .0% by weight or 0.1-1 .0% by weight of the aqueous solution before, after and/or during adding the suberin and the other ingredients.
  • suitable amounts such as in the range of 0.01-50% by weight, such as 0.1-50% by weight, 1- 50% by weight, 1.0-50% by weight, 0.1-10% by weight, 1-10% by weight, 1 .0-10% by weight, 5-50% by weight, 5.0-50% by weight, 1-5.0% by weight, 1 .0-5.0% by weight or 0.1-1 .0% by weight or 0.1-1 .0% by weight of the aqueous solution before, after and/or
  • the lipid microparticles and/or nanoparticles may comprise one or more additives 14, such as surface modifiers and/or stabilizers, active ingredients and/or other additives disclosed herein.
  • the surface modifiers and/or stabilizers can be selected from different categories such as ligands, biopolymers, or lipids such as cationic lipids, cholesterol, or phospholipids, based on the specific formulation objectives and the type of loaded materials.
  • the additives such as surface modifiers and/or stabilizers, may be provided in suitable amounts, such as in the range of 0.01-50% by weight, such as 0.1-50% by weight, 0.1- 10% by weight, 0.1-5.0% by weight or 0.1-1 .0% by weight of the aqueous solution before, after and/or during adding the suberin and the other ingredients.
  • the surface modifiers and/or stabilizers may be added in a post-treatment, such as after particles have been formed.
  • the ingredients sum up to 100%.
  • a surface modifier refers to one or more agents capable of modifying the surface of the formed and/or obtained microparticles and/or nanoparticles.
  • the surface modifier is preferably not a surfactant, but a surface modifier may comprise or be an agent or mixture of agents capable of altering/modifying surface properties of capsules, such as surface charge, release profile, or biocompatibility.
  • a stabilizer refers to one or more agents capable of stabilizing the formed and/or obtained microparticles and/or nanoparticles.
  • the stabilizer may not be a surfactant, or the stabilizer may be a stabilizing surfactant.
  • Stabilizers such as lecithin, offer advantages like prolonging shelf life, improving texture, and controlling release of LNPs by preventing phase separation in emul- sions/suspensions.
  • the lipid micro and/or nanoparticles may further comprise one or more active ingredients incorporated in the micro and/or nanoparticles.
  • the active ingredient may be a cargo of the microparticle and/or nanoparticle.
  • the active ingredient may comprise a bioactive compound, such as a pharmaceutical compound, a cosmetic compound, or any other suitable compound exhibiting activity when introduced to a biological system, such as a living body, or in vitro system, which may include cells or tissue, and the like, or to another system or environment.
  • the active ingredient may be encapsulated, such as it may be in the shell, in the matrix, and/or in the core of a lipid particle.
  • the encapsulated active ingredients may be or comprise hydrophilic, hydrophobic, amphiphilic, and oleophilic/lipophilic materials.
  • the active ingredient is provided in amount effective for providing a desired effect, such as in the range of 0.01-50% by weight, 0.01-40% by weight, 0.01-30% by weight 0.01-20% by weight, such as 0.1-20% by weight, 0.1-10% by weight, or 0.1 -5.0% by weight or 0.1-1 .0% by weight of the aqueous solution or the lipid microparticle and/or nanoparticle.
  • the active ingredient may comprise one or more active pharmaceutical ingredients) (API), which may refer to any suitable drug or the like compound or a combination thereof.
  • An active pharmaceutical ingredient is a biologically active component of a drug product that produces the intended effect(s) .
  • the active ingredient may comprise an organic drug molecule, a nucleic acid, such as DNA or RNA, for example mRNA or siRNA, plasmid DNA or a protein.
  • a drug molecule i.e. a pharmacon, may be any suitable pharmaceutical compound, a therapeutic agent or a drug molecule, which terms may be used interchangeably, such as ones selected from antibiotics, pain relievers, such as lidocaine; nicotine; opioids, such as fentanyl or buprenorphine; hormones, such as estrogen, contraceptives or testosterone; nitroglycerin; scopolamine; clonidine; antidepressants, such as selegiline; ADHD medication, such as methylphenidate; vitamins, such as B12 or cyanocobalamin; 5-hydroxytrypto- phan; Alzheimer’s medication, such as rivastigmine; acne medication; an- tipsoriatics, glucocorticoids such as hydrocortisone; or any other medication for treating diseases or disorders of a skin.
  • the active ingredient may comprise a nutraceutical, an antioxidant and/or a vitamin or an organic cofactor, such as vitamins E, Bi , B2, Be, B12, niacin, folic acid, K, C; and non-vitamins, such as adenoside triphosphate, S-adenosyl methionine, coenzymes B, M and Q, cytidine triphosphate, glutathione, heme, lipoamide, methanofuran, molybdopterin, nucleotide sugars, 2’- phosphoadenosine-5’-phosphosulphate, pyrroloquinoline quinone, tetrahydrobiopterin, and tetrahydromethanopterin.
  • a nutraceutical such as vitamins E, Bi , B2, Be, B12, niacin, folic acid, K, C
  • non-vitamins such as adenoside triphosphate, S-adenosyl methion
  • the present disclosure provides a pharmaceutical and/or a medical product comprising the lipid microparticles and/or nanoparticles 20.
  • the pharmaceutical and/or the medical product may further comprise one or more of the active ingredients, such as one or more of active pharmaceutical ingredients, nutraceuticals, vitamins, organic cofactors and/or the like substances incorporated in the particles.
  • the pharmaceutical and/or a medical product may be provided in a suitable form or a formulation, such as for a specific administration, for example for topical, for oral, for inhalation, for intravenous or for intramuscular administration, for example as a vaccine. These products can be provided for use in therapeutic methods, such as for treating a subject in need of medical treatment with the one or more active ingredients.
  • Intravenously administered LNPs with net positive, neutral, and negative charges can be targeted to the lungs, liver, and spleen, respectively.
  • Intramuscular administration is commonly used for vaccines, as it facilitates lymph node targeting and activation of the immune response.
  • APCs antigen-presenting cells
  • macrophages and dendritic cells are recruited to the delivery site, where they can encounter vaccine antigens. They then migrate to lymph nodes where they stimulate T cell responses.
  • the active ingredient may comprise a personal care agent, a cosmetic agent and/or a sunscreen agent.
  • a personal care agent may exhibit bioactivity, or it may exhibit other activities, such as the sunscreens agents, which may provide pigments and/or agents commonly used in sunscreens, such as cosmetic agents, fragrance (perfume) agents, and the like.
  • the present disclosure provides personal care and/or cosmetic products comprising the present lipid micro and/or nanoparticles 20, and one or more other agents, such as cosmetic and/or personal care agents. It may not be straightforward to classify an agent as either cosmetic or as a personal care agent, as the agents included in such products may overlap and have more than one function.
  • Such products may comprise one or more active agents, which may be incorporated in the lipid micro and/or nanoparticles.
  • the lipid micro and/or nanoparticles may also be present without additional active agents, and provide their action by the effect of the lipids included in the particles.
  • a cosmetic product may comprise make-up products, such as eyeliners, mascaras, lipsticks, foundations, fragrances (perfumes), and the like.
  • Cosmetic products may be used for example for treating pimples, acneic skin, brown sports, wrinkles, oily skin, dry skin, aged skin, spider veins, after sun erythemas, black circles etc.
  • a personal care product may comprise cleaning compositions, such as facial cleansers, shower gels, shampoos, deodorants, antiperspirants, creams, ointments, skin conditioning products, hair conditioning products, sunscreen product and/or the like.
  • cleaning compositions such as facial cleansers, shower gels, shampoos, deodorants, antiperspirants, creams, ointments, skin conditioning products, hair conditioning products, sunscreen product and/or the like.
  • Examples of personal care and cosmetic agents include probiotics, prebiotics and postbiotics; forms of vitamins and precursors thereof, such as vitamin A; for example retinoids, such as retinaldehyde (retinal), retinoic acid, retinyl palmitate and retinyl retinoate, ascorbic acid, alpha-hydroxy acids such as glycolic acid and lactic acid; glycols; biotechnology products; keratolytics; amino acids; antimicrobials; moisturizers; pigments; antioxidants; plant extracts; cleansing agents or make-up removers; anti-cellulite agents such as caffeine, carnitine, ginkgo biloba and horse-chestnut; conditioners; fragrances such as aromatherapy agents and perfumes; humectants such as urea, hyaluronic acid, lactic acid and glycerine; emollients such as lanolin, triglycerides and fatty acid esters; FR scavengers, singlet
  • the active ingredient may comprise a pesticide and/or a fertilizer.
  • a pesticide may comprise herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampricide.
  • a fertilizer may comprise one or more of main macronutrients N, P and K, secondary macronutrients Ca, Mg and S, and micronutrients Cu, Fe, Mn, Mo, Zn, B, Si, Co and V in suitable form, for example as salts, such as inorganic and/or organic salts or other forms comprising thereof.
  • the lipid microparticles and/or nanoparticles may comprise a targeting molecule on the surface of the particle.
  • a targeting molecule is a molecule, that recognized and binds a target molecule in a cell, such as a cell in a subject.
  • a targeting molecule in the micro/nanoparticle it is possible to specifically deliver the lipid microparticles and/or nanoparticles to a desired target in the subject.
  • the subject may be a human or animal subject, or even a plant subject.
  • the subject may be in need of therapy, which may be provided with the present lipid micro and/or nanoparticles, which may contain one or more active pharmaceutical ingredients or other active agents.
  • the lipid microparticles and/or nanoparticles may be in a form of one or more selected from solid-lipid nanoparticles (SLN), nanostructured lipid carriers (NLC), drug loaded liposomes, targeted liposomes, stealth liposomes, mRNA- carrying LNPs, cubosomes, liposomes, micelles, emulsions, lipid-coated nanoparticles, lipid-drug conjugates, lipid nanotubes, and ceramide-based lipid nanoparticles.
  • SSN solid-lipid nanoparticles
  • NLC nanostructured lipid carriers
  • drug loaded liposomes targeted liposomes
  • stealth liposomes mRNA- carrying LNPs
  • mRNA- carrying LNPs cubosomes, liposomes, micelles, emulsions, lipid-coated nanoparticles, lipid-drug conjugates, lipid nanotubes, and ceramide-based lipid nanoparticles.
  • Liposomes comprise one or more lipid bilayers and an aqueous core. They can be further classified by lamellarity and size. Liposomes can be used for delivery of hydrophobic and/or hydrophilic small molecules.
  • Solid lipid nanoparticles comprise a surfactant shell surrounding a core matrix composed of solid lipids. They can be used for encapsulation of hydro- phobic and/or hydrophilic cargo.
  • Nanostructured lipid carriers comprise a surfactant shell surrounding a core matrix composed of solid and liquid lipids. They can be used for encapsulation of hydrophobic and/or hydrophilic cargo.
  • Micelles comprise self-assemblies of lipid monolayers in aqueous solutions. They have a hydrophobic core, where the phospholipid tails are oriented towards the interior, and can be used for encapsulation of small hydrophobic cargo.
  • Reverse micelles comprise an inverted structure compared with traditional micelles. They form a hydrophilic core, with the phospholipid tails oriented towards the exterior, and can be used for encapsulation of small hydrophilic cargo, like oligonucleotides in LNPs.
  • the lipid microparticles and/or nanoparticles may be spherical or substantially spherical, and may be specified as having a very high sphericity and roundness, preferably close to 1 each, such as 0.90 or more, for example 0.95 or more.
  • Sphericity is a measure of how closely the shape of an object resembles that of a perfect sphere.
  • Roundness is the measure of how closely the shape of an object approaches that of a mathematically perfect circle.
  • the present lipid microparticles may be considered as nanoparticles, beads, such as nanobeads or microbeads, spheres, microparticles, nanospheres, microspheres, nanocapsules, or microcapsules, which can be used in a variety of applications and targets, for example to replace microplastics and other forms of microparticles, which may have been used in applications such as PCCPs.
  • the present lipid nanoparticles can be used in a variety of applications and targets, for example to replace other forms of nanoparticles.
  • the lipid microparticles and/or nanoparticles may have an average diameter in the range of 10-500 000 nm determined microscopically.
  • the average diameter may be the smallest diameter, such as a smallest diameter of a substantially spherical particle or a diameter of a tube or other elongated particle.
  • the average diameter may be in the range of 10-100 000 nm, such as 10- 10 000 nm, 10-1000 nm, or 100-100 000 nm, such as 100-10 000 nm, 100- 1000 nm, 400-1500 nm, or 500-2000 nm.
  • particles having an average diameter below 1000 nm or below 500 nm may be considered as nanoparticles.
  • the lipid nanoparticles may have an average diameter in the range of 10-1000 nm, such as 10-500 nm, 100-500 nm, 100-1000 nm, 140-1000 nm, 100-800 nm, 100-600 nm, or 140-500 nm.
  • particles having an average diameter below 2000 nm, or even below 100 nm may be considered as nanoparticles. This may depend on the field of application, and the behaviour of the particles in the target environment, for example in medical and scientific applications particles of this size can be especially useful.
  • the lipid nanoparticles may have an average diameter in the range of 10-200 nm, such as 10-150 nm, 10-100 nm, 20-200 nm, 20-100 nm, 20-150 nm, 50-250 nm, 50-200 nm, or 100-200 nm.
  • the particles may have an average diameter in the range of 100-500 nm, such as 100-300 nm, for example 100- 200 nm.
  • the particle size alters the pharmacokinetics of the administered particle. Smaller particles typically have longer circulation half-lives, as they evade elimination by the MPS. Particles less than 100 nm can easily pass through fenestrated endothelium to penetrate target tissues.
  • the lipid microparticles and/or nanoparticles may comprise one or more of a surface modifier, a stabilizer, a formula modifier, a preservative, and one or more other additives.
  • the additive may be selected from biomaterials or biopolymers, such as cellulose fibers, microfibrillated cellulose (microfibrillar cellulose), nanocrystalline cellulose, nanofibrillated cellulose (nanofibrillar cellulose), lignin, chitosan, alginate, hemicellulose and polyvinyl alcohol.
  • the lipid microparticles and/or nanoparticles may further comprise one or more further lipids, such as one or more selected from bio based lipids, betulin, tall oil fatty acids, rosin acids, other tall oil derivatives, berry wax, and ceramides.
  • the further lipids may comprise any combination of lipids disclosed in previous, and/or a combination of one or more of said lipids with one or more lipids selected from lipid categories fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, prenol lipids, saccharolipids, sterol lipids, such as cholesterol, for example 7a-hydroxy cholesterol, or cholesteryl sulfate, and polykeitides.
  • the further lipids may comprise any one or a combination of two or more of the fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, prenol lipids, saccharolipids, sterol lipids, and polykeitides.
  • Glycerophospholipids are a class of phospholipid that contains a hydrophilic head group and two hydrophobic fatty acyl tails attached to a glycerol backbone.
  • the hydrophilic head determines the charge of the LBDD particle, which can be neutral, anionic (negative), or cationic (positive).
  • Examples of phospholipid head groups with an overall neutral charge include phosphatidylcholine (PC) and phosphatidylethanolamine (PE).
  • Phosphatidylglycerol (PG), phosphatidylinositol (PI), phosphatidylserine (PS), and phosphatidic acid (PA) are examples of phospholipids that contain anionic head groups.
  • the present lipid microparticles and/or nanoparticles can be prepared and formed with a variety of methods.
  • the method may comprise, or the forming of the lipid micro and/or nanoparticles may be carried out with, one or more methods and/or mechanisms selected from: high shear mixing, high shear homogenizing, using microflu id izer, using microfluidics, high pressure homogenizing (HPH), such as cold HPH or hot HPH, sonication such as ultrasonication methods, coacervation, self-assembly, phase inversion, reverse phase evaporation, microemulsion technique, emulsification-solvent evaporation, bulk nanoprecipitation (solvent displacement), supercritical fluid (SCF) technology, spray drying, fluid-bed coating, dripping method, double emulsion- solvent evaporation, solvent emulsification evaporation, solvent injection or nanoprecipitation, injection method, membrane contactors, co-extrusion, extrusion such as
  • the present lipid microparticles and/or nanoparticles may be obtained with any of the methods disclosed herein, such as presented in the flowchart of Figure 3.
  • the present disclosure provides a method for preparing lipid microparticles and/or nanoparticles 20 comprising suberin and/or derivative thereof 10, such as 0.01 % by weight or more suberin and/or derivative thereof, the method comprising
  • a mixture 16 such as a dispersion, comprising 0.01-50% by weight surfactant
  • lipid microparticles and/or nanoparticles 20 comprising suberin and/or derivative thereof, such as 0.01 % by weight or more suberin and/or derivative thereof, from the mixture 16.
  • the suberin and/or derivative thereof 10 may be provided in solid form, or it may be mixed, such as dissolved and/or dispersed, in a suitable solvent, or it may be provided as mixed, dissolved and/or dispersed in a suitable solvent.
  • the solvent may be water or other aqueous solvent or solution, or it may be or comprise organic solvent or solution. The selection of solvent may depend on the preparation method.
  • the method may comprise mixing one or more active ingredients with the suberin and/or the solvent to incorporate the one or more active ingredients to the lipid microparticles and/or nanoparticles.
  • the active ingredient may comprise one or more of the active ingredients disclosed herein, such as the bioactive agents.
  • the method may comprise mixing one or more further lipids with the suberin and/or the solvent to incorporate the one or more further lipids, such as one or more selected from bio based lipids, betulin, tall oil fatty acids, rosin acids, other tall oil derivatives, berry wax, fatty acyls, glycerolipids, glycerophospho- lipids, sphingolipids, prenol lipids, saccharolipids, sterol lipids, polykeitides and ceramides, to the lipid micro and/or nanoparticles.
  • bio based lipids such as one or more selected from bio based lipids, betulin, tall oil fatty acids, rosin acids, other tall oil derivatives, berry wax, fatty acyls, glycerolipids, glycerophospho- lipids, sphingolipids, prenol lipids, saccharolipids, sterol lipids, polykeitides and cer
  • the method may comprise mixing one or more further additives 14 with the suberin or derivative thereof 10, the solvent and/or the obtained particles to incorporate the one or more further additives to the lipid microparticles and/or nanoparticles 20.
  • the further additives 14 may be selected from one or more of a surface modifier, a formula modifier, a surfactant, and an additive selected from biomaterials or biopolymers, such as cellulose derivatives, cellulose fibers, micro fibrillated cellulose, nanocrystalline cellulose, nanofibrillated cellulose, lignin, chitosan, alginate, hemicellulose and polyvinyl alcohol, or other substances disclosed herein.
  • a mixture 16 is obtained after the ingredients are combined.
  • the mixture may be then subjected to further method steps, such as post-treatment of the particles, which contribute to the formation of the desired particles 20.
  • further ingredients also after the formation of the particles 20, such as ingredients which are intended to be located on the surfaces of the particles, for example a targeting molecule and/or surface modifiers.
  • the method may comprise milling the mixture 16.
  • Any suitable milling device may be used, such as one or more selected from cryogenic mills, ball mills, colloid mills, jet mills, or ultrasonic mills. Milling is less intensive treatment compared to homogenization. Milling can optimize the LNPs production process by reduction of particle size. By milling before LNP production, homogenized, small, and stable nanoparticles can be achieved. Moreover, particles might have higher loading capacity for various ingredients.
  • the method may comprise homogenizing the mixture 16 to obtain homogenized mixture, and forming lipid microparticles and/or nanoparticles comprising suberin and/or derivative thereof from the homogenized mixture.
  • the homogenization is carried out by using one or more homogenizers or other suitable devices.
  • the homogenization may include one or more passes or cycles, wherein the number of passes may have an impact to the size and/or size distribution of the obtained particles.
  • a homogenizer may be a rotor-stator homogenizer, such as a disperser, a piston-gap homogenizer or a fluidizer. When a disperser type of homogenizer is used, the mixture may be passed through the homogenizer for 5-15 cycles in the pressure of 500-2000 bar.
  • a fluidizer which may be a microflu id izer, may utilize one or more interaction chambers, and may include an inlet reservoir for the dispersion, a pump for pressurizing the dispersion, wherein the pressurizer dispersion is conveyed to the interaction chamber, wherein it is homogenized, and outputted from the chamber.
  • Lipid micro and/or nanoparticles may start forming after the homogenizing, and the formation may be further facilitated by further process steps.
  • the homogenizing may be high pressure homogenizing (HPH), which may be hot or cold high pressure homogenizing. Hot homogenization uses heat above the lipid melting point to obtain an aqueous phase.
  • High pressure homogenizers combine both pressure and mechanical forces to achieve a uniform and consistent product. Mechanical forces may include turbulence, shear, cavitation, impact, and process intensity. These forces can be controlled and adjusted, which allows optimizing product results. Because of the significant amount of pressure imparted on the product, alongside the actions of mechanical forces, high pressure homogenizers allow for synthesis of smaller particle sizes, which provides increased nanoparticle surface area and bioavailability. Such nanoparticles are especially suitable for drug delivery systems and other pharmaceutical purposes.
  • the method may also comprise ultrasonicating the homogenized mixture, wherein the lipid micro and/or nanoparticles are formed from the ultrasonicated mixture, more particularly from the homogenized and ultrasonicated mixture. This allows further controlling the formation of the particles and adjusting the properties thereof.
  • the method may also comprise applying the formed lipid microparticles and/or nanoparticles 20 from any of the previous steps, preferably in the form of a dispersion, to water at lowered temperature, such as at a temperature below 10°C, or below 5°C, for example at about 4°C.
  • the water which may be purified water, is provided in excess volume compared to the aqueous dispersion (mixture) comprising the lipid micro and/or nanoparticles, such as 10 or more times the volume of the dispersion/mixture.
  • the applying to the water solution may be carried out immediately.
  • the lipid microparticles and/or nanoparticles may be formed in a basic solution/dispersion, which may be then applied to an excess amount of acidic aqueous solution, such as a solution of HCI.
  • the solvent or the solution is water or aqueous solution.
  • the aqueous solution refers to any water-based solutions, which may include one or more mixed, dissolved and/or dispersed substances.
  • the solvent or the solution is organic solvent, or comprises organic solvent.
  • Organic solvents such as only organic solvent, i.e. in absence of water, however preferably water-miscible organic solvent, may be used in methods such as anti-solvent process.
  • the method may comprise melting the suberin and/or derivative thereof at elevated temperature, such as at about 90°C or more, before mixing, dispersing and/or dissolving into the aqueous solution.
  • the aqueous solution and/or the obtained dispersion or mixture may have an elevated temperature of, or the temperature of the solution or the mixture may be increased to, about 90°C or more.
  • the method may comprise cooling the dispersion or the mixture, and milling the cooled mixture.
  • the cooled and/or the milled mixture may be homogenized, dispersed and/or ultrasonicated.
  • the cooling may be carried out by using cooling means, such as liquid nitrogen, ice bath, cooled liquid or by providing a cooling element, for example of a cooling device.
  • the mixture may be added controllably, such as dropwise, for example by using suitable adding means, such as dropping system, to cooled liquid, such as liquid nitrogen.
  • the method may comprise
  • the method may comprise cooling the homogenized, dispersed and/or the ultrasonicated, mixture to form the microparticles and/or nanoparticles.
  • the final cooling may be carried out by allowing the mixture to cool, such as without active cooling, or the mixture may be cooled by using cooling means, such as by cooling the mixture and/or a container containing the mixture with external cooling means, such as liquid nitrogen, ice bath, cooled liquid or by providing a cooling element, for example of a cooling device.
  • the method may comprise adding acid to the aqueous solution and/or the obtained mixture to precipitate microparticles and/or nanoparticles.
  • the acid may be added dropwise, preferably until a desired effect is obtained, such as formation of the particles and/or change on colour of the mixture.
  • One example of the method comprises melting suberin at elevated temperature, such as 60°C or more, for example 70°C or more, 80°C or more or 90°C or more.
  • the temperature may be in the range of 60-95°C, which covers most melting points of different suberins, or in the range of 80-95°C.
  • One or more surfactants are provided in aqueous solution, such as 0.01-50% by weight, such as 0.1-50% by weight, 0.1-10% by weight or 0.1-1 .0% by weight of the solution, preferably at increased temperature, such as at substantially the same temperature as the melted suberin, and the suberin is mixed with the aqueous solution comprising the surfactant to obtain a mixture comprising suberin.
  • any other ingredients or additives desired in the final product may be added to the aqueous solution or to the mixture comprising suberin, preferably before homogenizing or before carrying out further steps, such as ultrasonicating.
  • the other ingredients may include other lipids, active ingredients, surface modifiers, stabilizers, formula modifiers, preservatives, and other additives such as biomaterials or biopolymers.
  • the mixture comprising suberin may be homogenized by using a homogenizer for 5-20 minutes, such as 5-15 minutes, for example about 10 minutes, to obtain dispersed suberin, which forms particles.
  • the dispersed solution may be sonicated with an ultrason icator, for example for 10-20 minutes, to obtain final lipid nanoparticles.
  • the nanoparticles are cooled or allowed to cool, preferably to room temperature.
  • One example of the method comprises dissolving suberin to a base solution, such as a solution of NaOH.
  • One or more surfactants are provided in the base solution, such as 0.01-50% by weight, such as 0.1-50% by weight, 0.1-10% by weight or 0.1-1 .0% by weight of the surfactant.
  • the obtained mixture may be mixed, for example with a stirrer, for a prolonged time, such as for 20 hours or more, for example about 24 hours.
  • Lipid micro and/or nanoparticles are then precipitated by adding acid solution dropwise, such as HCI solution, until the colour of the mixture turns to white, thus indicating the formation of the particles.
  • One example of the method comprises melting the suberin and optionally one or more active ingredients at elevated temperature, such as 60°C or more, for example 70°C or more, 80°C or more or 90°C or more.
  • the obtained mixture may be mixed and/or milled at the elevated temperature, such as for 10-20 seconds.
  • the mixed mixture is then milled in contact with liquid nitrogen to form micro/nanoparticles.
  • the obtained dispersion containing premixed micro/nanoparticles may be dispersed with a disperser, or a homogenizer, in excess volume of water, such as purified water, containing one or more surfactants.
  • the excess volume may be 10 or more times the volume of the dis- persion/mixture
  • the premixed particles may be passed through the disperser, or the homogenizer, for 5-15 cycles in the pressure of 500-2000 bar. With this method it was possible to obtain nanoparticles with a narrow particle size distribution.
  • the dispersed particles may be ultrasonicated, as disclosed herein.
  • One example of the method comprises melting the suberin and optionally one or more active ingredients at elevated temperature, such as 60°C or more, for example 70°C or more, 80°C or more or 90°C or more.
  • the obtained mixture may be mixed and/or milled at the elevated temperature, such as for 10-20 seconds.
  • the mixed mixture is subsequently added dropwise to liquid nitrogen, preferably by using a suitable dropping system, such as one or more needles with different inner diameter gauge sizes.
  • the obtained particles are mixed in an aqueous surfactant solution. Controlling synthesis parameters enables production of LNPs with particle sizes ranging from 1 to 500 pm. However, by applying combined techniques it is possible to make smaller or larger particles.
  • the lipid microparticles and/or nanoparticles can be prepared with methods involving solvent/anti-solvent process. Also with this method it was possible to obtain stable lipid nanoparticles.
  • the selected solvent is at least partly water- miscible solvent and capable of dissolving the suberin and optionally other ingredients.
  • a supersaturated solution of the compounds is obtained, wherein nuclei are formed.
  • Aqueous solution acts as the anti-solvent, and nanoparticles are formed in nucleation process from growing nuclei by the effect of the added anti-solvent.
  • the surfactants were present, the formed lipid microparticles and/or nanoparticles were more stable than without surfactant.
  • the solvent is organic solvent, or comprises water-miscible solvent or partly water-miscible solvent, the method comprising
  • the suberin and/or derivative as a solution comprising the suberin and/or derivative thereof dissolved in the organic solvent, such as a solvent comprising or consisting of acetone,
  • One example of the method comprises dissolving suberin to a solution of acetone and ethanol, such as about 1 :1 by volume mixture, and adding the obtained mixture dropwise to aqueous solution of acid, such as HCI, comprising one or more surfactants.
  • the lipid microparticles and/or nanoparticles, such as ones comprising 10% by weight or more suberin and/or derivative thereof, obtained with the method disclosed herein may be any of the lipid microparticles and/or nanoparticles disclosed herein.
  • the lipid microparticles and/or nanoparticles disclosed herein can be identified, characterized and analysed by using common methods and devices, such as electron microscopy, HPLC, particle size analyzer, surface charge analyzer, X-ray crystallography, or the like.
  • the particles may be solubilized into a solvent and the separated in- gredients can be identified and preferably quantified for example by using HPLC, ultraviolet-visible spectroscopy and/or other suitable methods.
  • the present disclosure provides use of suberin and/or derivative thereof for preparing the lipid microparticles and/or nanoparticles, the pharmaceutical and/or a medical product, or the personal care and/or cosmetic product disclosed herein, preferably with any of the methods disclosed herein.
  • FIG. 1 a-and 1 b show Field Emissions Scanning Electron Microscopy (FE-SEM) images and Transmission Electron Microscopy (TEM) images of the obtained nanoparticles, which may be also called as solid-lipid nanoparticles (SLNs). Modifying synthesis parameters enabled production of LNPs with particle sizes ranging from larger than 10 nanometres to a few micrometres.
  • 0.1 g of suberin was dissolved in 10 ml acetone and ethanol (1 :1 ) and added dropwise to 40 ml of aqueous 1 M HCI solution containing 0.1 g Tween 80. Stabile LNPs were formed.
  • Example 8 1 g of suberin was melted at 90°C for 10-20 seconds. Later the obtained lipid preparation was milled in contact with liquid nitrogen and the achieved particles were dispersed by an Ultra Turrax homogenizer for 10 min in 200 ml of deionized water and samples of Tween 80 solution (1-10% by weight). The premixed particles were passed through a homogenizer for 5-15 cycles in the pressure of 500-2000 bar.
  • the obtained solid-lipid nanoparticles were analyzed for particle size distribution. As shown in Figure 2, the particles had an average particle diameter of about 140 nm, and 90% or more of the particles had a particle diameter in the range of 100-190 nm.

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Abstract

La présente invention concerne des microparticules lipidiques et/ou des nanoparticules (20) comprenant de la subérine et/ou un dérivé de celles-ci (10), et un ou plusieurs tensioactifs (12). La présente invention concerne également un procédé de préparation de microparticules et/ou de nanoparticules lipidiques (20) comprenant de la subérine et/ou un dérivé de celle-ci (10). La présente invention concerne également des produits comprenant les microparticules et/ou nanoparticules lipidiques (20) comprenant des produits pharmaceutiques et/ou médicaux et des produits de soins personnels et cosmétiques. La présente invention concerne également l'utilisation de la subérine et/ou d'un dérivé de celle-ci (10) pour la préparation préalable des microparticules et/ou nanoparticules lipidiques (20) ou des produits.
PCT/FI2024/050504 2023-09-28 2024-09-27 Microparticules et/ou nanoparticules lipidiques, leur procédé de préparation, produits comprenant les microparticules lipidiques et/ou les nanoparticules et utilisation de la subérine Pending WO2025068637A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040151750A1 (en) * 2000-12-12 2004-08-05 Robert O' Leary Compositions and methods of crop protection
WO2022082218A1 (fr) * 2020-10-14 2022-04-21 Reza Babapour Compositions dermatologiques améliorées et leurs utilisations

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040151750A1 (en) * 2000-12-12 2004-08-05 Robert O' Leary Compositions and methods of crop protection
WO2022082218A1 (fr) * 2020-10-14 2022-04-21 Reza Babapour Compositions dermatologiques améliorées et leurs utilisations

Non-Patent Citations (3)

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Title
LIAKOS IOANNIS L ET AL: "Suberin/trans-Cinnamaldehyde Oil Nanoparticles with Antimicrobial Activity and Anticancer Properties When Loaded with Paclitaxel", ACS APPLIED BIO MATERIALS, AMERICAN CHEMICAL SOCIETY, US, vol. 2, no. 8, 19 August 2019 (2019-08-19), pages 3484 - 3497, XP009532651, ISSN: 2576-6422, DOI: 10.1021/ACSABM.9B00408 *
RUBEN MIGUEL LOPES RODRIGUES: "Suberin biotech potential: from bactericidal nanoparticles to optical sensors", PHD DISSERTATION, 1 November 2021 (2021-11-01), XP093229246, Retrieved from the Internet <URL:https://run.unl.pt/handle/10362/128745?locale=en> *
SAZALEE SYAIDATUL ATIQAH ET AL: "Investigation of self-assembly properties and the effect of tween series co-surfactants on the stability of nonionic branched-chain glycolipid hexosomes", COLLOIDS AND SURFACES A : PHYSIOCHEMICAL AND ENGINEERINGS ASPECTS, ELSEVIER, AMSTERDAM, NL, vol. 529, 3 June 2017 (2017-06-03), pages 210 - 221, XP085147959, ISSN: 0927-7757, DOI: 10.1016/J.COLSURFA.2017.05.085 *

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