WO2001011068A3 - Composes lipidiques cationiques et leur utilisation pour le transfert de substances d'interet therapeutique chargees negativement - Google Patents

Composes lipidiques cationiques et leur utilisation pour le transfert de substances d'interet therapeutique chargees negativement Download PDF

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Publication number
WO2001011068A3
WO2001011068A3 PCT/FR2000/002234 FR0002234W WO0111068A3 WO 2001011068 A3 WO2001011068 A3 WO 2001011068A3 FR 0002234 W FR0002234 W FR 0002234W WO 0111068 A3 WO0111068 A3 WO 0111068A3
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WO
WIPO (PCT)
Prior art keywords
radical
lipid compound
vivo
general formula
dicationic
Prior art date
Application number
PCT/FR2000/002234
Other languages
English (en)
Other versions
WO2001011068A2 (fr
Inventor
Eliane Taillandier
Xuan An Cao
Robert Coudert
Regine Naejus
Original Assignee
Univ Paris Nord
Eliane Taillandier
Xuan An Cao
Robert Coudert
Regine Naejus
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 Univ Paris Nord, Eliane Taillandier, Xuan An Cao, Robert Coudert, Regine Naejus filed Critical Univ Paris Nord
Priority to AU68495/00A priority Critical patent/AU6849500A/en
Priority to EP00956608A priority patent/EP1218033A2/fr
Priority to CA002381224A priority patent/CA2381224A1/fr
Publication of WO2001011068A2 publication Critical patent/WO2001011068A2/fr
Publication of WO2001011068A3 publication Critical patent/WO2001011068A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/87—Introduction of foreign genetic material using processes not otherwise provided for, e.g. co-transformation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K48/00—Medicinal preparations containing genetic material which is inserted into cells of the living body to treat genetic diseases; Gene 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Zoology (AREA)
  • Medicinal Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Plant Pathology (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • Physics & Mathematics (AREA)
  • Steroid Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne l'utilisation d'un composé lipidique monocationique répondant à la formule générale I(A): R1O-CO-NH-(CH2)n-N+(C2H5)3, I- dans laquelle R¿1? représente le radical cholestéryle, n représente un entier égal à 1, 2 ou 3 et notamment le 3-β[N-(N',N',N'-triéthylaminopropane iodure)-carbamoyle] cholestérol (TEAPC-Chol) et/ou d'un composé lipidique monocationique de formule générale I(B) R2-CO-NH-(CH2)n-N?+(R)¿3,X- dans laquelle R¿2? représente notamment le radical de l'acide abiétique, ou le radical d'un dérivé de l'acide cholanique (cholique, déoxycholique, déhydrocholique, lithocholique), R représente notamment un radical méthyle ou éthyle, n représente un nombre entier égal à 2 ou 3, X représente notamment un atome de chlore ou d'iode, et/ou d'un composé lipidique dicationique de formule générale II(A) R?1¿O-CO-N[CH¿2?-CH2-N?+(R)¿3,X-]2 et/ou d'un composé lipidique dicationique de formule générale II(B) R1O-CO-CH2-CH2-CO-N[CH2-CH2-N+(R)3,X-]2 et/ou d'un composé lipidique dicationique de formule générale (II)(C) R2-co-N[CH2-CH2-N+(R)3,X-]2; dans lesquelles R1 représente le radical cholestéryle, R2 représente notamment le radical de l'acide abiétique, ou le radical d'un dérivé de l'acide cholanique (cholique, déoxycholique, déhydrocholique, lithocholique, R représente notamment un atome d'hydrogène, un radical méthyle ou éthyle, X représente notamment un atome de chlore ou d'iode, pour la transfection d'organismes vivants in vivo, d'organes in vivo, de tumeurs in vivo, ou de cellules in vitro ou ex vivo.
PCT/FR2000/002234 1999-08-04 2000-08-03 Composes lipidiques cationiques et leur utilisation pour le transfert de substances d'interet therapeutique chargees negativement WO2001011068A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU68495/00A AU6849500A (en) 1999-08-04 2000-08-03 Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest
EP00956608A EP1218033A2 (fr) 1999-08-04 2000-08-03 Composes lipidiques cationiques et leur utilisation pour le transfert de substances d'interet therapeutique chargees negativement
CA002381224A CA2381224A1 (fr) 1999-08-04 2000-08-03 Composes lipidiques cationiques et leur utilisation pour le transfert de substances d'interet therapeutique chargees negativement

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9910141A FR2797188A1 (fr) 1999-08-04 1999-08-04 Composes lipidiques cationiques et leurs utilisation pour le transfert de substances d'interet therapeutique chargees negativement
FR99/10141 1999-08-04

Publications (2)

Publication Number Publication Date
WO2001011068A2 WO2001011068A2 (fr) 2001-02-15
WO2001011068A3 true WO2001011068A3 (fr) 2002-05-02

Family

ID=9548888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2000/002234 WO2001011068A2 (fr) 1999-08-04 2000-08-03 Composes lipidiques cationiques et leur utilisation pour le transfert de substances d'interet therapeutique chargees negativement

Country Status (5)

Country Link
EP (1) EP1218033A2 (fr)
AU (1) AU6849500A (fr)
CA (1) CA2381224A1 (fr)
FR (1) FR2797188A1 (fr)
WO (1) WO2001011068A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4423107A1 (fr) * 2021-10-29 2024-09-04 ModernaTX, Inc. Amines lipidiques

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005162A1 (fr) * 1991-08-28 1993-03-18 The University Of Tennessee Research Corporation Procede de transfert des acides nucleiques dans les cellules
WO1996014831A1 (fr) * 1994-11-14 1996-05-23 Pasteur Merieux Serums & Vaccins Adjuvant pour composition vaccinale
WO1997045442A1 (fr) * 1996-05-24 1997-12-04 Imperial College Of Science Technology And Medicine Derives polycationiques de sterol en tant qu'agents de transfection
WO1998000110A1 (fr) * 1996-07-03 1998-01-08 University Of Pittsburgh Formulations d'emulsions pour des agents actifs hydrophiles
WO1998005678A2 (fr) * 1996-08-02 1998-02-12 Max-Delbrück-Centrum für Molekulare Medizin Amphiphiles cationiques d'un type nouveau utilises pour le transfert liposomal de genes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005162A1 (fr) * 1991-08-28 1993-03-18 The University Of Tennessee Research Corporation Procede de transfert des acides nucleiques dans les cellules
WO1996014831A1 (fr) * 1994-11-14 1996-05-23 Pasteur Merieux Serums & Vaccins Adjuvant pour composition vaccinale
WO1997045442A1 (fr) * 1996-05-24 1997-12-04 Imperial College Of Science Technology And Medicine Derives polycationiques de sterol en tant qu'agents de transfection
WO1998000110A1 (fr) * 1996-07-03 1998-01-08 University Of Pittsburgh Formulations d'emulsions pour des agents actifs hydrophiles
WO1998005678A2 (fr) * 1996-08-02 1998-02-12 Max-Delbrück-Centrum für Molekulare Medizin Amphiphiles cationiques d'un type nouveau utilises pour le transfert liposomal de genes

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
HARA T ET AL: "In vivo gene delivery to the liver using reconstituted chylomicron remnants as a novel nonviral vector", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF USA., vol. 94, no. 26, 23 December 1997 (1997-12-23), pages 14547 - 14552, XP002160608 *
KAWAURA C ET AL: "Atomic force microscopy for studying gene transfection mediated by cationic liposomes with a cationic cholesterol derivative", FEBS LETTERS., vol. 421, 1998, pages 69 - 72, XP002141707 *
TAKEUCHI K ET AL: "Effect of zeta potential of cationic liposomes containing cationic cholesterol derivatives on gene transfection", FEBS LETT, vol. 397, no. 2-3, 18 November 1996 (1996-11-18), pages 207 - 209, XP002160609 *

Also Published As

Publication number Publication date
EP1218033A2 (fr) 2002-07-03
CA2381224A1 (fr) 2001-02-15
AU6849500A (en) 2001-03-05
WO2001011068A2 (fr) 2001-02-15
FR2797188A1 (fr) 2001-02-09

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