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WO2024180161A1 - Solvants eutectiques profonds à composants multiples, leur préparation et leur utilisation - Google Patents

Solvants eutectiques profonds à composants multiples, leur préparation et leur utilisation Download PDF

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Publication number
WO2024180161A1
WO2024180161A1 PCT/EP2024/055165 EP2024055165W WO2024180161A1 WO 2024180161 A1 WO2024180161 A1 WO 2024180161A1 EP 2024055165 W EP2024055165 W EP 2024055165W WO 2024180161 A1 WO2024180161 A1 WO 2024180161A1
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yes
glycerol
tmao
urea
dess
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Thanos Andreou
Marina CVJETKO BUBALO
Dimitrios KALIAS
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Vio Invent Private Co
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • 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
    • A61K9/08—Solutions

Definitions

  • the present invention belongs to the fields of chemistry and biotechnology, more precisely to the field of deep eutectic solvents for various uses.
  • the invention relates to multicomponent deep eutectic solvents (DESs), methods for their preparation and use of said multicomponent DESs.
  • Neoteric systems that effectively mimic the natural environment of various biological systems and of the biomolecules they consist of, i.e., any organic molecule that includes carbohydrates, protein, lipids, and/or nucleic acids, the so-called Deep Eutectic Solvents (DESs), have been in the past years intensively studied as nontoxic and highly tunable solvents in food, agrochemicals, cosmetics, and pharmaceuticals production (Vanda et al; 2019: Natural deep eutectic solvents: From their discovery to their applications. in Deep Eutectic Solvents: Synthesis, Properties, and Applications 61–81).
  • DESs Deep Eutectic Solvents
  • a DES is a mixture of two or more, usually solid compounds combined in a suitable molar ratio to form a liquid at ambient temperature (Hansen et al., 2021: Chem. Rev.121, 1232–1285).
  • Natural DESs NADESs
  • DESs only consist of compounds that occur in nature (Dai et al., 2013: Anal. Chim. Acta 766, 61–68).
  • DESs usually have negligible volatility, are non-flammable, water-tolerant, and are easy to prepare with high purity at low price.
  • DESs are usually considered green solvents due to their typical biodegradability and biocompatibility.
  • DESs are highly tunable through varying the components or relative ratio of components and thus have a wide variety of potential applications.
  • novel DESs systems with novel and/or even more diverse properties are required.
  • the present invention aims to address this need.
  • Most notably, currently known DESs are mostly used for extraction, but are thereafter discarded or need to be recycled.
  • Choline chloride (ChCl) is often used due to its low price. ChCl is manufactured from ethylene oxide, which comes from ethylene, made from fossil fuels (petroleum or natural gas). For reasons of sustainability, elimination of ChCl is preferred.
  • patent EP3870227 relates to a deep eutectic solvent (DES) composition, comprising a combination of a glycol with a polymer solubilizer component, which polymer solubilizer component is selected from the group consisting of esters and lactones of organic acids; dicarboxylic acids; esters of dicarboxylic acids; esters, ethers and carbonates of diols and triols; and mixtures thereof, in a molar ratio of a glycol to the polymer solubilizer component in the range of between 12 to 1 and 1 to 10, preferably in a range of between 8 to 1 and 1 to 2, and more preferably in a range of between 4 to 1 and 1 to 1; the composition further comprising at least one DES constituent.
  • DES deep eutectic solvent
  • Patent application EP3971230 discloses a DES comprising: ⁇ at least one carboxylic acid which comprises at least two carboxylic acid functional groups and has a number of carbon atoms in the range of from 4 to 10; ⁇ at least one alcohol which comprises at least two alcohol functional groups, and which is selected from the group consisting of: o alcohols having several carbon atoms in the range of from 2 to 12 carbon atoms, o polyethylene glycol and o polypropylene glycol; and ⁇ water in an amount of from 10 to 50 wt.% of the total weight of the DES.
  • Patent application EP3485874 describes a method of preparing or optimizing a system comprising a NADESs and one or more active ingredients, comprising the following steps: a) analysing an active ingredient or target compound; b) matching the active ingredient to at least one potential NADES starting composition; c) synthesizing a stable, liquid NADESs-active ingredient system; and d) optimizing the system prepared in step (c).
  • Patent application WO2017134190 discloses a DES consisting of (2-hydroxyethyl) trimethyl ammonium chloride and dithiothreitol in a molar ratio of from 1:2 to 1:3 and from 0% to 10% co-solvent, and methods of enzymatic production of polypeptides using the DES.
  • Esquieri et al. (2013; Phys. Chem. Chem. Phys., 15, 11248 – 11256) studied the stability of hen's egg white lysozyme in different choline chloride-based pseudo-concentrated and neat DESs has been studied by means of intrinsic fluorescence and CD spectroscopy.
  • Thermal unfolding experiments carried out in non-diluted urea:choline chloride and glycerol:choline chloride eutectic solvents (UChCl-DES and GChCl-DES, respectively) showed the accumulation at certain temperatures of discrete, partially folded intermediates that displayed a high content of secondary structure and a disrupted tertiary structure.
  • betaine:urea, choline chloride: urea, glycerol:betaine, , glycerol:choline chloride, malic acid:choloride, lactic acid:betaine, levulinic acid:betaine, pyruvic acid:betaine, urea:betaine HCl, betaine:sorbitol, proline:levulinic acid, betaine:proline, proline:glucose, betaine:glucose, lysine:levulinic acid, sorbitol:levulinic acid, xylitol:levulinic acid, glucose:levulinic acid, glucose:levulinic acid, glycerol:sorbitol, glycerol:lactic acid, sorbitol: lactic acid, and glycerol:levulinic acid are disclosed.
  • the multicomponent DESs according to the first aspect of the invention comprises at least 2 components, wherein at least one of the components is selected in the group consisting of ectoine, trimethylamine N-oxide (TMAO), sarcosine, glycerophosphocholine (GPC), dimethylsulfonopropionate (DMSP), guanidine, arginine, and taurine.
  • TMAO trimethylamine N-oxide
  • GPC glycerophosphocholine
  • DMSP dimethylsulfonopropionate
  • guanidine arginine
  • taurine guanidine
  • the multicomponent DESs has 3, more preferably 4 components.
  • the DESs also comprises water. It has been observed that these multicomponent DESs improve biomolecule stability, as well as stability and viability of cells stored at lower temperatures, while maintaining the biomolecule function or even improving it. Consequently, a possible embodiment of the invention is also a medium for stabilization of biomolecules or cryoprotection of cells/tissues comprising the DESs comprising at least two components, wherein at least one of the components is selected in the group consisting of ectoine, TMAO, sarcosine, GPC, DMSP, guanidine, arginine and taurine.
  • a method for stabilization of biomolecules or for of biological systems, such as organisms, organs, organelles, cells or tissues comprises at least a step in which the biomolecule or biological systems, cells or tissues or artifical engineered constructs are exposed to the above-mentioned medium.
  • the medium may be supplemented with any other components and storage of the mixture of medium and biomolecules, biological systems, cells or tissues is performed in any suitable manner.
  • preservation relates to any kind of processes for storing biological systems or biomolecules that aims to maintain usual biological, chemical and/or physical properties of the biological system or biomolecules, respectively.
  • preservation may relate to storage at any given temperature, including cryopreservation at low temperatures, typically in the range from -80 °C to -196 °C, or preservation at temperatures above -80 °C.
  • a second aspect of the present invention showing the same technical effect as the DESs described above is a multicomponent DESs comprising at least 4 components.
  • at least one of the components of the DESs are selected in the group comprising naturally occurring osmolytes. Therefore, another possible embodiment of the invention is also a medium for stabilization of biomolecules or preservation, for example cryoprotection, of biological systems, cells or tissues comprising the DESs comprising at least four components.
  • a method for stabilization of biomolecules or for preservation/cryoprotection of biological systems, cells or tissues comprises at least a step in which the biomolecule or cells/tissue are exposed to the above-mentioned medium.
  • the medium may be supplemented with any other components and storage of the mixture of medium and biomolecules, biological systems, cells or tissues is performed in any suitable manner.
  • the naturally occurring osmolytes are preferably selected in the group comprising: (i) polyols and sugar polyols, for example glycerol, sorbitol, xylitol; (ii) sugars and their derivatives, for example glucose, sucrose, trehalose; (iii) amino acids and their derivatives, for example glycine, proline, ectoine, taurine; (iv) methylamines, for example trimethylamine N-oxide (TMAO), sarcosine, betaine, glycerophosphocholine (GPC); (v) methylsulfonium compounds, for example dimethylsulfoniopropionate (DMSP); (vi) Y-conjugated compounds, for example urea, guanidine and arginine.
  • polyols and sugar polyols for example glycerol, sorbitol, xylitol
  • sugars and their derivatives for example glucose, suc
  • the naturally occurring osmolytes are selected in the group consisting of ectoine, TMAO, sarcosine, GPC, DMSP, guanidine, arginine, and taurine.
  • the DESs may optionally comprise water.
  • the other remaining components of the multicomponent DESs can be selected among common DES/IL compounds, such as methylamines, methylsulfonium compounds, organic acids, sugars, polyols, amino acids and Y-conjugated compounds.
  • the DES may be formulated with or without water, such as solution comprising a DES essentially free of water.
  • Methylamines may be selected from trimethylamine N-oxide (TMAO), betaine, glycerophosphocholine (GPC), carnitine, homarine, and derivatives thereof, for example, their halide forms, such as betaine halides (betaine HCl).
  • Methyl sulfonium compounds may be selected from dimethylsulfonopropionate (DMSP) and other compounds containing a methylsulfonium moiety.
  • Organic acids may be selected from levulinic acid, lactic acid, malic acid, maleic acid, pyruvic acid, fumaric acid, succinic acid, citric acid, citraconic acid, glutaric acid, glycolic acid, acetic acid, aconitic acid, tartaric acid, ascorbic acid, malonic acid, oxalic acid, glucuronic add, neuraminic acid, sialic acid, shikimic acid, phytic acid, galacturonic acid, iduronic acid, hyaluronic acid, hydroxycitric acid, lactone derivatives and derivatives thereof.
  • Sugars may be selected from trehalose, glucose, sucrose, lactose, ribose, galactose, fructose, etc. and derivatives thereof.
  • Polyols may be selected from glycerol, erythritol, mannitol, sorbitol, xylitol, ethylene glycol, propylene glycol, ribitol, aldonitol, propanediol, inositol, pentylene glycol, and derivatives thereof (such as o-methyl-inositol).
  • Amino acids may be selected from glycine, proline, taurine, lysine, etc. and derivatives thereof (e.g.
  • Y-conjugated compounds may be selected from urea, guanidine, arginine and compounds that incorporate the guanidino moiety (such as creatine, glycocyamine, agmatine, 4- guanidinobutanoic acid etc.) and derivatives thereof, such as guanidinium halides (for example guanidine HCl).
  • the molar ratio of each DES component with respect to the total moles of the DES may range from 0.001 to 0.9.
  • Molar ratio is defined as unit of the amount of a component (expressed in moles), n i , divided by the total amount of all components in a mixture (also expressed in moles), n tot .
  • the molar ratio of each DES component with respect to the total moles of the DES may be between 0.003 and 0.7.
  • the molar ratio of each DES component with respect to the total moles of the DES may be between 0.005 and 0.6.
  • the preferred ratios may also depend on the combination of components in the DES as well as on the targetted use of the DES.
  • the DES may be formulated with or without water (such as solution comprising a DES wherein said solution is essentially free of water).
  • the water used in the DESs may be from 0% to 90%, as from about 0.00001, 0.0001, 0.001, 0.01, 0.1, 0.5, 1, 5, 10, 15, 20, 30 or about 40% to about 90, 80, 70, 60 or about 50%. In a preferred embodiment, the water used in from about 5% to about 30%, such as about 10%, 20% 25% or about 30%.
  • the DESs as prepared may also be further diluted. In the most preferred embodiments of the invention the multicomponent DESs comprise the components in combinations as given in the Tables 2 and 3 below. Table 2.
  • Preferred embodiments of the multi-component deep eutectic solvents comprising naturally occurring osmolytes Components
  • ⁇ stabilization of biomolecules ⁇ preservation of biological systems, including cryoprotection, ⁇ pharmaceutical preparations, such as pharmaceutical excipients and similar components, ⁇ cosmetics, ⁇ food, and ⁇ preparation of extracts, wherein the DESs is optionally a component of the final extract.
  • DES systems are possible for the extraction, stabilization, analysis, formulation, preservation and/or any form of culture, monitoring, handling, treatment and use of organisms, organs, tissues, organelles, biological systems, cells, biomolecules and bioactive compounds, including but not limited to plants, animals, algae, bacteria, fungi and other microorganisms, whole cells, membranes and other cell components, proteins, enzymes, antibodies, peptides and other molecules consisting of aminoacids or aminoacid derivatives, polysaccharides and biopolymers of any composition, lipids and supramolecular structures containing lipids, nucleotides, nucleosides and their precursors and derivatives, polynucleotides of any length, sense and molecular weight and composition, including but not limited to all types of DNA and RNA, all types of gels, emulsions, dispersions, liquid and/or solid compositions comprising the DESs according to the present invention and/or biomolecules and/or other payloads, including
  • the invention or preparations comprising the DESs according to the invention may be used as pharmaceutical excipients, cosmetic compositions, nutritional compositions, feed compositions, biomass extracts, nutritional products, etc.
  • An aspect of the invention is thus a stabilizing composition comprising any of the DESs described above for use in stabilization of biomolecules, particularly proteins, most preferably enzymes.
  • Another aspect of the invention is a composition or medium for preservation, for example cryoprotection of biological systems, cells, tissues and molecules comprising any of the DESs described above.
  • the medium may be supplemented with any other components and storage of the mixture of medium and biomolecules, biological systems, cells or tissues is performed in any suitable manner.
  • An additional aspect of the invention is also the method for stabilization of biomolecules or for preservation/cryoprotection of biological systems, cells or tissues, said method comprising at least a step in which the biomolecule, biological systems, cells or tissue are exposed to the above-mentioned medium.
  • the multicomponent DESs comprise the components in combinations and ratios as given in the Table 4 below. Table 4.
  • Exemplary embodiments of the multi-component deep eutectic solvents comprising naturally occurring osmolytes Water Components Components content molar ratio (wt.
  • Table 6 Multiple-component DESs Water Components DES Components content molar ratio (wt. %) 20 ChCl:Gly ChCl:Glycerol 1:2 40 Bet:U Betaine:Urea 1:1 20 TMAO:Gly TMAO:Glycerol 1:2 40 20 Sar:Gly Sarcosine:Glycerol 1:2 40 20 DMPS:Gly DMSP:Glycerol 1:2 40 20 Ect:Gly Ectoine:Glycerol 1:2 40 Bet:Sor:Tau:GPC:U Betaine:Sorbitol:Taurine:GPC:Urea 1:3.1:0.1:2.8:7.1 20 TMAO:Bet:Tau:U TMAO:Betaine:Taurine:Urea 1:0.1:0.1:1.5 20 Bet:Gly:Sor Betaine:Glycerol:Sorbitol 1:1:2 20 Bet:Gly:Sor:Ect Betaine:Glycerol:Sorbitol:Ectoine 1:4:2:1 20
  • Example 2 Lysozyme stabilization at 25 °C by selected DESs prepared in example 1 Lysozyme activity was determined according to the method of Shugar et al. (1952, Biochim Biophys Acta 8: 302–9), which is based on the decrease in turbidity of the substrate, Micrococcus lysodeikticus, in a suspension. Lysozyme solutions at a concentration of 0.1 mg ml -1 were prepared in different DESs and in 10 mM sodium phosphate buffer solution (pH 7). The solutions were incubated at different temperatures (25, 45, 70°C) for 1, 3, 5 and 7 days (Examples 2 and 3) or 15, 60 and 120 min (Example 4).
  • Table 7 Incubation of lysozyme in different DES and 10 mM sodium phosphate buffer solution (pH 7) at 25°C for 1, 3, 5 and 7 days. Results are presented as residual activity - relative to the enzyme activity prior incubation (%).
  • Example 3 Lysozyme stabilization at 45 °C by selected DESs prepared in example 1 The experiment was performed in the same manner as described for Example 2, except that the incubation temperature was 45 °C.
  • Table 8 Incubation of lysozyme in different DES and 10 mM sodium phosphate buffer solution (pH 7) at 45°C for 1, 3, 5 and 7 days. Results are presented as residual activity - relative to the enzyme activity prior incubation (%).
  • Example 4 Lysozyme stabilization at 70 °C by selected DESs prepared in example 1 The experiment was performed in the same manner as described for Example 2, except that the incubation temperature was 70 °C and incubation times were 15, 60 and 120 minutes, respectively.
  • Table 9 Incubation of lysozyme in different DES and 10 mM sodium phosphate buffer solution (pH 7) at 70°C (heat shock) for 15-, 60- or 120-min. Results are presented as residual activity - relative to the enzyme activity prior incubation (%).
  • YADH solutions at a concentration of 0.4 mg ml -1 were prepared in different DESs and in glycine-pyrophosphate buffer (pH 9). The solutions were incubated at different temperatures (25 and 45°C) for 2, 5, 8, 24 and 48 h (at 25°C) or 1, 2, 4, 8 and 24 h (at 45°C). Briefly, to 975 ⁇ l of glycine-pyrophosphate buffer (pH 9) in a plastic disposable cuvette 5 ⁇ l of NAD + in PBS buffer (50 mg ml -1 ), 10 ⁇ l of ethanol (96%) and 10 ⁇ l of the YADH solution were added.
  • Results are presented as residual activity - relative to the enzyme activity prior incubation (%).
  • R esidual activity (%) after incubation at 45°C for DESs Water 1 h 2 h 4 h 8 h 24 h content
  • Control 1 (phosphate buffer) 0 0 0 0 0 0
  • Control 2 (ChCl:Gly 1:2) 20 2.1 0 0 0 0 40 1.7 Sar:Gly 20 136.9 138.6 66.9 34.4 11.3
  • Bet:Sor:Tau:GPC:U 20 25.0 2.6 0 0 0
  • the results shown in tables 10 and 11 show that some DESs according to the invention can stabilize YADH to a higher degree than conventionally used buffers or stabilizing media.

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Abstract

La présente invention appartient aux domaines de la chimie et de la biotechnologie, plus précisément au domaine des solvants eutectiques profonds pour diverses utilisations. L'invention concerne des solvants eutectiques profonds (DES) à composants multiples, leurs procédés de préparation et d'utilisation. Les DES à composants multiples selon le premier aspect de l'invention comprennent au moins 2 composants, au moins l'un des composants étant choisi dans le groupe constitué par l'ectoïne, la triméthylamine N-oxide (TMAO), la sarcosine, la glycérophosphocholine (GPC), le diméthylsulfonopropionate (DMSP), la guanidine, l'arginine et la taurine. Un second aspect de la présente invention est un DES à composants multiples comprenant au moins 4 composants. Dans un mode de réalisation préféré, au moins un des composants des DES est sélectionné dans le groupe comprenant des osmolytes naturels.
PCT/EP2024/055165 2023-03-01 2024-02-28 Solvants eutectiques profonds à composants multiples, leur préparation et leur utilisation Pending WO2024180161A1 (fr)

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CN119367269A (zh) * 2024-10-16 2025-01-28 四川大学 一种具有细胞渗透性与多重抗炎作用的自组装共析凝胶及其制备方法和应用
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