WO2001011068A3 - Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest - Google Patents

Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest 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
Authority
WO
WIPO (PCT)
Prior art keywords
radical
lipid compound
vivo
general formula
dicationic
Prior art date
Application number
PCT/FR2000/002234
Other languages
French (fr)
Other versions
WO2001011068A2 (en
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 CA002381224A priority Critical patent/CA2381224A1/en
Priority to AU68495/00A priority patent/AU6849500A/en
Priority to EP00956608A priority patent/EP1218033A2/en
Publication of WO2001011068A2 publication Critical patent/WO2001011068A2/en
Publication of WO2001011068A3 publication Critical patent/WO2001011068A3/en

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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

Abstract

The invention concerns the use of a monocationic lipid compound of general formula I(A): R1O-CO-NH-(CH2)n-N+(C2H5)3, I- wherein: R¿1? represents the cholesteryl radical; n represents an integer equal to 1, 2 or 3 and in particular 3-β[N-(N',N',N'-triethylaminopropane iodide)-carbamoyl] cholesterol (TEAPC-Chol) and/or a monocationic lipid compound of general formula I(B): R2-CO-NH-(CH2)n-N?+(R)¿3,X- wherein: R¿2? represents in particular the abietic acid radical, or the radical of a derivative of cholanic (cholic, deoxycholic, dehydrocholic, lithocholic) acid; R represents in particular a methyl or ethyl radical; n represents an integer equal to 2 or 3; X represents in particular a chlorine or iodine atom; and/or a dicationic lipid compound of general formula II(A): R1O-CO-N[CH2- CH2-N?+(R)¿3,X-]2; and/or a dicationic lipid compound of general formula II(B): R1O-CO-CH2-CH2-CO-N[CH2-CH2-N+(R)3, X-]2; and/or a dicationic lipid compound of formula II(C): R2-CO-N[CH2-CH2-N+(R)3,X-]2 wherein R1 represents the cholesteryl radical; R2 represents in particular the abietic acid radical or the radical of a derivative of a cholanic (cholic, deoxycholic, dehydrocholic, lithocholic) acid; R represents in particular a hydrogen atom, a methyl or ethyl radical; X represents in particular a chlorine or iodine atom. Said compounds are useful for transfecting living organisms in vivo, organs in vivo, tumours in vivo, or cells in vitro or ex vivo.
PCT/FR2000/002234 1999-08-04 2000-08-03 Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest WO2001011068A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA002381224A CA2381224A1 (en) 1999-08-04 2000-08-03 Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest
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 (en) 1999-08-04 2000-08-03 Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9910141A FR2797188A1 (en) 1999-08-04 1999-08-04 CATIONIC LIPID COMPOUNDS AND THEIR USE FOR THE TRANSFER OF NEGATIVELY CHARGED SUBSTANCES OF THERAPEUTIC INTEREST
FR99/10141 1999-08-04

Publications (2)

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

Family

ID=9548888

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2000/002234 WO2001011068A2 (en) 1999-08-04 2000-08-03 Cationic lipid compounds and use thereof for transferring negatively charged substances of therapeutic interest

Country Status (5)

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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW202332467A (en) * 2021-10-29 2023-08-16 美商現代公司 Lipid amines

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005162A1 (en) * 1991-08-28 1993-03-18 The University Of Tennessee Research Corporation Method for delivering nucleic acids into cells
WO1996014831A1 (en) * 1994-11-14 1996-05-23 Pasteur Merieux Serums & Vaccins Adjuvant for a vaccine composition
WO1997045442A1 (en) * 1996-05-24 1997-12-04 Imperial College Of Science Technology And Medicine Polycationic sterol derivatives as transfection agents
WO1998000110A1 (en) * 1996-07-03 1998-01-08 University Of Pittsburgh Emulsion formulations for hydrophilic active agents
WO1998005678A2 (en) * 1996-08-02 1998-02-12 Max-Delbrück-Centrum für Molekulare Medizin Novel cationic amphiphilic lipids for liposomal gene transfer

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005162A1 (en) * 1991-08-28 1993-03-18 The University Of Tennessee Research Corporation Method for delivering nucleic acids into cells
WO1996014831A1 (en) * 1994-11-14 1996-05-23 Pasteur Merieux Serums & Vaccins Adjuvant for a vaccine composition
WO1997045442A1 (en) * 1996-05-24 1997-12-04 Imperial College Of Science Technology And Medicine Polycationic sterol derivatives as transfection agents
WO1998000110A1 (en) * 1996-07-03 1998-01-08 University Of Pittsburgh Emulsion formulations for hydrophilic active agents
WO1998005678A2 (en) * 1996-08-02 1998-02-12 Max-Delbrück-Centrum für Molekulare Medizin Novel cationic amphiphilic lipids for liposomal gene transfer

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

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