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WO2015099624A1 - Nanostructures recouvertes d'espèces présentant des lieurs clivables photothermiquement pour l'administration contrôlée d'une charge - Google Patents

Nanostructures recouvertes d'espèces présentant des lieurs clivables photothermiquement pour l'administration contrôlée d'une charge Download PDF

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Publication number
WO2015099624A1
WO2015099624A1 PCT/TR2014/000440 TR2014000440W WO2015099624A1 WO 2015099624 A1 WO2015099624 A1 WO 2015099624A1 TR 2014000440 W TR2014000440 W TR 2014000440W WO 2015099624 A1 WO2015099624 A1 WO 2015099624A1
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WO
WIPO (PCT)
Prior art keywords
cargo
thermolabile
photothermally
azo
species
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/TR2014/000440
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English (en)
Inventor
Mustafa Selman YAVUZ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO2015099624A1 publication Critical patent/WO2015099624A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0009—Galenical forms characterised by the drug release technique; Application systems commanded by energy involving or responsive to electricity, magnetism or acoustic waves; Galenical aspects of sonophoresis, iontophoresis, electroporation or electroosmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/0052—Thermotherapy; Hyperthermia; Magnetic induction; Induction heating therapy
    • 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

Definitions

  • thermolabile molecules having photothermally cleavable linkers (azo, peroxide, anhydride, carbamate, carbonate, etc.).
  • thermolabile species on the nanocapsules can be cleaved or degradated by using external stimuli (laser light, heat, magnetic field, radio frequencies, etc.) which is resulted a controlled release of species (dye, drugs, genes, proteins, peptides, enzymes, DNA, RNA, etc.).
  • the nanocapsules used in drug delivery are fabricated by encapsulation of the cargo.
  • the cargo is released from these nanocapsules in a specific area by using various techniques.
  • encapsulation of small cargo or molecules especially cancer drugs
  • the encapsulated small molecules are often unwillingly diffuse from the nanocapsules to the solution media. For this reason, it is nearly impossible to keep the encapsulated cargo (small species) inside the nanocapsules.
  • thermolabile molecules which is composed of cargo (dye, drugs, genes, proteins, peptides, enzymes, DNA, RNA. retc), photocleavable linkers (azo, peroxide, anhydride, carbamate, carbonate, etc.) and different functional groups (for conjugation to the metal nanostructures).
  • cargo drug, genes, proteins, peptides, enzymes, DNA, RNA. retc
  • photocleavable linkers azo, peroxide, anhydride, carbamate, carbonate, etc.
  • different functional groups for conjugation to the metal nanostructures.
  • FIG. 1 A schematic representation of the release system
  • the invention is about the release of at least one cargo (1) from at least one thermolabile group (2) conjugated at least one nanostructure (3) by using at least one external stimulus (4).
  • Cargo (1) is the released species such as dye, drugs, genes, biomolecules, proteins, peptides, enzymes, DNA, RNA, etc.
  • Thermolabile molecules (2) contain photothermally cleavable linkers such as. azo, peroxide, anhydride, carbamate, carbonate, etc, and any functional groups for the conjugation to the nanostructures.
  • the nanostructures (carrier) (3) are different shapes and sizes of metallic nanostructures such as gold, silver, iron, platinum, copper, bismuth, quantum dots, etc.
  • External stimuli (4) are all different wavelengths of laser light, heat, magnetic field, radio frequencies, etc.
  • the invention is about the conjugation of photothermally cleavable thermolabile groups (2) (azo, peroxide, anhydride, carbamate, carbonate, etc.) on different shape and size of metal nanostructures (gold, silver, iron, platinum, copper, bismuth, quantum dots, etc.) and the release of cargo (1) (dye, drugs, genes, biomolecules, proteins, peptides, enzymes, DNA, RNA, etc.) from these nanostructures by using external stimuli (4) (all different wavelengths of laser light, heat, magnetic field, radio frequencies, etc.).
  • photothermally cleavable thermolabile groups (2) azo, peroxide, anhydride, carbamate, carbonate, etc.
  • metal nanostructures gold, silver, iron, platinum, copper, bismuth, quantum dots, etc.
  • cargo (1) die, drugs, genes, biomolecules, proteins, peptides, enzymes, DNA, RNA, etc.
  • Thermolabile groups (2) are consists of three parts. These are;
  • the functional groups which strongly binds to the metal surface disulfides, thiols, amines, amides, esters, alcohols, alkyls, etc.
  • Photothermally cleavable linkers azo, peroxide, anhydride, carbamate, carbonate, retro diels-alder, etc.
  • Cargo (1) dyes, drugs, genes, biomolecules, amino acids, proteins, peptides, enzymes, DNA, RNA, etc
  • the metal nanostructures (carriers) (3) are different shape and size of metal nanostructures (gold, silver, iron, platinum, copper, bismuth, quantum dots, etc.).
  • the external stimuli (4) are all different wavelengths of laser light, heat, magnetic field, radio frequencies, etc. in order to release the cargo (1) after photothermally cleavage of the linker on the thermolabile groups (2).
  • the invention solves the recent crucial hurdle which is the undesired release of the small species from the drug delivery systems.
  • chemically modification of the cargo (1) which results strongly conjugation to the nanostructures, the undesired release of the cargo (1) is prevented.
  • the cargo (1) can only be released temporarily and spatially by using external stimuli. Especially temporarily and spatially release of the cancer drugs from the metal nanostructures in the cancer area by cleavage of the linkers on the thermolabile groups (2) will have a great impact in medicine and biomedical fields.
  • thermolabile groups Some examples of the synthesis of thermolabile groups:
  • U-01 will be synthesized by esterification reaction of K-01 with Azo-01 in the presence of coupling reagents.
  • U-01 can be synthesized by reaction of K-01 acid chloride with Azo-01 in the presence of a base.
  • U-02 will be synthesized by esterification reaction of K-02 with Azo-02 in the presence of coupling reagents.
  • U-02 can be synthesized by reaction of Azo-02 acid chloride with K-02 in the presence of a base.
  • U-03 will be synthesized by esterification reaction of K-03 with Azo-02 in the presence of coupling reagents.
  • U-03 can be synthesized by reaction of Azo-02 acid chloride with K-03 in the presence of a base.
  • U-04 will be synthesized by esterification reaction of K-04 with Azo-02 in the presence of coupling reagents.
  • U-04 can be synthesized by reaction of Azo-02 acid chloride with K-04 in the presence of a base.
  • U-05 will be synthesized by esterification reaction of K-01 with Azo-03 in the presence of coupling reagents.
  • U-05 can be synthesized by reaction of K-01 acid chloride with Azo-03 in the presence of a base.
  • U-06 can be synthesized by reaction of K-02 with Azo-04 in the presence of a base.
  • U-07 can be synthesized by reaction of K-03 with Azo-04 in the presence of a base.
  • U-08 can be synthesized by reaction of K-04 with Azo-04 in the presence of a base.
  • U-09 can be synthesized by Curtius rearrangement reaction of K- 02 with Azo-05 in the presence of a base.
  • U-10 can be synthesized by Curtius rearrangement reaction of K- 03 with Azo-05 in the presence of a base.
  • U-11 can be synthesized by Curtius rearrangement reaction of K- 04 with Azo-05 in the presence of a base.
  • U-15 will be synthesized by substitution reaction of K-02 with P-02 in the presence of a base.
  • U-16 will be synthesized by the reaction of K-01 with A-01 in the presence of a base.
  • U-18 can be synthesized by Curtius rearrangement reaction of K- 02 with 1-01 in the presence of a base.
  • U-19 can be synthesized by Curtius rearrangement reaction of A- 02 with K-03 in the presence of a base.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physics & Mathematics (AREA)
  • Biomedical Technology (AREA)
  • Nanotechnology (AREA)
  • Optics & Photonics (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne des nanocapsules qui sont composées de nanostructures métalliques (or, argent, fer, cuivre, bismuth, etc.) recouvertes de molécules thermolabiles présentant des lieurs clivables photothermiquement (azo, peroxyde, anhydride, carbamate, carbonate, etc.). En outre, ces espèces thermolabiles sur les nanocapsules peuvent être clivées ou dégradées par l'utilisation de stimuli externes (lumière laser, chaleur, champ magnétique, radiofréquences, etc.), ce qui entraîne une libération contrôlée des espèces (colorant, médicaments, gènes, protéines, peptides, enzymes, ADN, ARN, etc.).
PCT/TR2014/000440 2013-12-26 2014-11-19 Nanostructures recouvertes d'espèces présentant des lieurs clivables photothermiquement pour l'administration contrôlée d'une charge Ceased WO2015099624A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2013/15287 2013-12-26
TR201315287 2013-12-26

Publications (1)

Publication Number Publication Date
WO2015099624A1 true WO2015099624A1 (fr) 2015-07-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/TR2014/000440 Ceased WO2015099624A1 (fr) 2013-12-26 2014-11-19 Nanostructures recouvertes d'espèces présentant des lieurs clivables photothermiquement pour l'administration contrôlée d'une charge

Country Status (1)

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WO (1) WO2015099624A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013001451A1 (fr) * 2011-06-27 2013-01-03 Fondazione Istituto Italiano Di Tecnologia Vecteur pour la libération d'un composant actif qui est photoclivable par irradiation dans le visible

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013001451A1 (fr) * 2011-06-27 2013-01-03 Fondazione Istituto Italiano Di Tecnologia Vecteur pour la libération d'un composant actif qui est photoclivable par irradiation dans le visible

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