CA2289078A1 - Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes - Google Patents

Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes Download PDF

Info

Publication number
CA2289078A1
CA2289078A1 CA002289078A CA2289078A CA2289078A1 CA 2289078 A1 CA2289078 A1 CA 2289078A1 CA 002289078 A CA002289078 A CA 002289078A CA 2289078 A CA2289078 A CA 2289078A CA 2289078 A1 CA2289078 A1 CA 2289078A1
Authority
CA
Canada
Prior art keywords
compound
cells
aco
pharmaceutically acceptable
transfection
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.)
Abandoned
Application number
CA002289078A
Other languages
English (en)
Inventor
Alberto Haces
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 CA2289078A1 publication Critical patent/CA2289078A1/fr
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Dispersion Chemistry (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention concerne un lipide cationique destiné à la transfection d'acides nucléiques et composé d'un mélange d'un acide nucléique et d'un composé représenté par la formule (I) dans laquelle Y est Cl-, Br-, I- et AcO- ou tout anion pharmaceutiquement acceptable; X est O, S(O), CH¿2?; R¿1? et R¿1'? sont indépendamment hydrocarbure linéaire C¿1?-C¿18?; m et n sont égaux à 1, 2 ou 3; R¿2? et R¿2'? sont indépendamment H; alkyle linéaire C¿1?-C¿18?, cyanoéthyle, aminopropyle, aminobutyle, guanidinium ou amidinium d'alkyle C¿2?-C¿4?, N,N,N-indépendamment aminobutyle ou aminopropyle (C¿1?-C¿18?), spermine ou spermidine à substitution C ou N,N,N-alkyl(C¿4?-C¿18?)-4-aminobutyrylaminopropyle; p = 0 ou 1; i = 0 ou 1; R¿3? et R¿3'? sont indépendamment alkyle linéaire C¿1?-C¿6?, acétoxyéthyle, CH¿2?CO¿2?CH¿2?CH¿3?; X étant différent de CH¿2? lorsque R¿2?, R¿2'? sont alkyle linéaire C¿1?-C¿6? et lorsque p = 1 et m et n sont différents de 1.
CA002289078A 1996-05-13 1997-05-09 Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes Abandoned CA2289078A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US1729896P 1996-05-13 1996-05-13
US60/017,298 1996-05-13
PCT/US1997/009093 WO1997042819A1 (fr) 1996-05-13 1997-05-09 Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes

Publications (1)

Publication Number Publication Date
CA2289078A1 true CA2289078A1 (fr) 1997-11-20

Family

ID=21781830

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002289078A Abandoned CA2289078A1 (fr) 1996-05-13 1997-05-09 Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes

Country Status (2)

Country Link
CA (1) CA2289078A1 (fr)
WO (1) WO1997042819A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5674908A (en) 1993-12-20 1997-10-07 Life Technologies, Inc. Highly packed polycationic ammonium, sulfonium and phosphonium lipids
US6989434B1 (en) 1994-02-11 2006-01-24 Invitrogen Corporation Reagents for intracellular delivery of macromolecules
US7166745B1 (en) * 1998-11-12 2007-01-23 Invitrogen Corporation Transfection reagents
CA2299119C (fr) * 1999-02-23 2013-02-05 Qiagen Gmbh Une methode pour stabiliser et/ou isoler des acides nucleiques
GB9914085D0 (en) * 1999-06-16 1999-08-18 Smithkline Beecham Plc New use
WO2001013933A2 (fr) * 1999-08-25 2001-03-01 Gmp Companies, Inc. Renforcement de l'apport en oxygene chez des mammiferes, procedes et reactifs correspondants
US6610702B2 (en) 2000-08-01 2003-08-26 Gmp Oxycell, Inc. Ammonium salts of inositol hexaphosphate, and uses thereof
US20030096414A1 (en) 2001-03-27 2003-05-22 Invitrogen Corporation Culture medium for cell growth and transfection
US7923207B2 (en) 2004-11-22 2011-04-12 Dharmacon, Inc. Apparatus and system having dry gene silencing pools
EP2068936B1 (fr) * 2006-09-27 2016-06-22 Paolo Botti Moyens et procédés pour améliorer une administration à des systèmes biologiques
CN106572974B (zh) 2014-07-15 2021-04-23 生命技术公司 用于将分子有效递送到细胞的具有脂质聚集体的组合物和方法
US10501404B1 (en) 2019-07-30 2019-12-10 Factor Bioscience Inc. Cationic lipids and transfection methods

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5264618A (en) * 1990-04-19 1993-11-23 Vical, Inc. Cationic lipids for intracellular delivery of biologically active molecules

Also Published As

Publication number Publication date
WO1997042819A1 (fr) 1997-11-20

Similar Documents

Publication Publication Date Title
AU693507B2 (en) Highly packed polycationic ammonium, sulfonium and phosphonium lipids
JP4854853B2 (ja) トランスフェクション薬剤
Remy et al. Gene transfer with a series of lipophilic DNA-binding molecules
US5925623A (en) Formulations and methods for generating active cytofectin: polynucleotide transfection complexes
US5783565A (en) Cationic amphiphiles containing spermine or spermidine cationic group for intracellular delivery of therapeutic molecules
WO2000030444A1 (fr) Liposomes cationiques pour transfert genique
WO1996018372A2 (fr) Amphiphiles cationiques et plasmides destines a la liberation intracellulaire de molecules therapeutiques
US20090215067A1 (en) Novel lipids for transfection of nucleic acids
WO1999058152A1 (fr) Lipides cationiques a liaisons disulfure pour l'administration intracellulaire de substances therapeutiques
CA2289078A1 (fr) Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes
WO1997042819A9 (fr) Lipides cationiques destines a la transfection de molecules neutres ou chargees negativement a l'interieur de cellules vivantes
AU8113398A (en) Novel lipid complexes for transferring at least one therapeutically active substance, in particular a polynucleotide, into a target cell, and use in gene therapy
US6281371B1 (en) Lipopolyamines, and the preparation and use thereof
WO2000012454A9 (fr) Nouveaux lipides cationiques
CA2233064C (fr) Cytofectines cationiques polyfonctionnelles, formulations et procede de generation de complexes actifs de transfection cytofectine:polynucleotide
CZ303963B6 (cs) Lipopolyaminy sperminového typu pro konstrukci liposomálních transfekcních systému
AU736143B2 (en) Cationic amphiphile compositions for intracellular delivery of therapeutic molecules
AU734980B2 (en) Cationic amphiphiles and plasmids for intracellular delivery of therapeutic molecules
EP1300161A1 (fr) Lipides cationiques pour le transfert de gènes

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued