FR2869616A1 - NOVEL AMPHIPHILIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS IN PARTICULAR FOR TRANSFECTION - Google Patents

NOVEL AMPHIPHILIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS IN PARTICULAR FOR TRANSFECTION

Info

Publication number
FR2869616A1
FR2869616A1 FR0404554A FR0404554A FR2869616A1 FR 2869616 A1 FR2869616 A1 FR 2869616A1 FR 0404554 A FR0404554 A FR 0404554A FR 0404554 A FR0404554 A FR 0404554A FR 2869616 A1 FR2869616 A1 FR 2869616A1
Authority
FR
France
Prior art keywords
alkyl
transfection
applications
preparation
amphiphilic compounds
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.)
Granted
Application number
FR0404554A
Other languages
French (fr)
Other versions
FR2869616B1 (en
Inventor
Philippe Barthelemy
Michel Camplo
Mark W Grinstaff
Louis Moreau
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.)
D AVIGNON ET DES PAYS DU, University of
Aix Marseille Universite
Centre National de la Recherche Scientifique CNRS
Universite de la Mediterranee
Universite dAvignon et des Pays de Vaucluse
Original Assignee
D AVIGNON ET DES PAYS DU, University of
Centre National de la Recherche Scientifique CNRS
Universite de la Mediterranee
Universite de la Mediterranee Aix Marseille II
Universite dAvignon et des Pays de Vaucluse
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 D AVIGNON ET DES PAYS DU, University of, Centre National de la Recherche Scientifique CNRS, Universite de la Mediterranee, Universite de la Mediterranee Aix Marseille II, Universite dAvignon et des Pays de Vaucluse filed Critical D AVIGNON ET DES PAYS DU, University of
Priority to FR0404554A priority Critical patent/FR2869616B1/en
Priority to PCT/FR2005/001042 priority patent/WO2005116043A1/en
Priority to EP05767494A priority patent/EP1745061A1/en
Publication of FR2869616A1 publication Critical patent/FR2869616A1/en
Application granted granted Critical
Publication of FR2869616B1 publication Critical patent/FR2869616B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • 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

Abstract

Composé cationique de formule (I)où X = O ou S, B = base purique ou pyrimidique, L1, L2, = groupement oxycarbonyl, thiocarbamate, carbonate et carbamate, ou O, R1, R2 = chaîne hydrophobe linéaire ou ramifiée, R3 = groupement hydroxy, amino, phosphate, phosphonate, O-alkyl phosphatidylcholine, thiophosphate, phosphonium, NH2-R4, reste cyclodextrine, NHR4R5 ou NR4R5R6 où R4, R5 et R6, = H ou radical alkyle ou hydroxyalkyle ou resteouoù V et W = liaison -O-,-S-, ou -NH-, Z = R3, R1 et R2, n = 1 à 500 et A1 et A2 = alkyle C1 C5 ou acyle C1 C5 et le contre-ion est anion choisi parmi tosylate, halogénure, nitrate, sulfate, sulfonate, et thiosulfate.Cationic compound of formula (I) where X = O or S, B = purine or pyrimidine base, L1, L2, = oxycarbonyl, thiocarbamate, carbonate and carbamate group, or O, R1, R2 = linear or branched hydrophobic chain, R3 = hydroxy, amino, phosphate, phosphonate, O-alkyl phosphatidylcholine, thiophosphate, phosphonium, NH2-R4, cyclodextrin residue, NHR4R5 or NR4R5R6 where R4, R5 and R6, = H or alkyl or hydroxyalkyl radical or residue or where V and W = bond - O -, - S-, or -NH-, Z = R3, R1 and R2, n = 1 to 500 and A1 and A2 = C1 C5 alkyl or C1 C5 acyl and the counterion is an anion chosen from tosylate, halide, nitrate, sulfate, sulfonate, and thiosulfate.

FR0404554A 2004-04-29 2004-04-29 NOVEL AMPHIPHILIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS IN PARTICULAR FOR TRANSFECTION Expired - Lifetime FR2869616B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR0404554A FR2869616B1 (en) 2004-04-29 2004-04-29 NOVEL AMPHIPHILIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS IN PARTICULAR FOR TRANSFECTION
PCT/FR2005/001042 WO2005116043A1 (en) 2004-04-29 2005-04-27 Novel amphiphilic compounds, preparation method thereof and applications of same
EP05767494A EP1745061A1 (en) 2004-04-29 2005-04-27 Novel amphiphilic compounds, preparation method thereof and applications of same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0404554A FR2869616B1 (en) 2004-04-29 2004-04-29 NOVEL AMPHIPHILIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS IN PARTICULAR FOR TRANSFECTION

Publications (2)

Publication Number Publication Date
FR2869616A1 true FR2869616A1 (en) 2005-11-04
FR2869616B1 FR2869616B1 (en) 2008-10-24

Family

ID=34946821

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0404554A Expired - Lifetime FR2869616B1 (en) 2004-04-29 2004-04-29 NOVEL AMPHIPHILIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATIONS IN PARTICULAR FOR TRANSFECTION

Country Status (3)

Country Link
EP (1) EP1745061A1 (en)
FR (1) FR2869616B1 (en)
WO (1) WO2005116043A1 (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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FR2924430B1 (en) * 2007-11-30 2010-03-19 Univ Bordeaux 2 PROCESS FOR THE PREPARATION OF NANOPARTICLES BASED ON FUNCTIONAL AMPHIPHILIC MOLECULES OR MACROMOLECULES AND THEIR USE
FR2945946B1 (en) * 2009-05-29 2011-08-26 Univ Victor Segalen Bordeaux 2 MULTI-COMPARTMENT FORMULATIONS BASED ON FUNCTIONAL AMPHIPHILIC MOLECULES OR MACROMOLECULES
CN103764169B (en) * 2011-03-31 2017-06-13 康斯坦策·沙费尔 For the perfluorochemical of non-viral transfer nucleic acid
FR2985916B1 (en) 2012-01-25 2015-12-04 Univ Bordeaux Segalen HYDROGEL DECONTAMINATION OF AQUEOUS SAMPLES CONTAINING NANOPARTICLES
EP3085360A1 (en) 2015-04-20 2016-10-26 Universite De Bordeaux Lipid based nanocarrier compositions loaded with metal nanoparticles and therapeutic agent
EP3095790A1 (en) * 2015-05-22 2016-11-23 Universite De Bordeaux Nucleoside-lipid compounds with ph-sensitive dialkylorthoester chains and their use for transportation or vectorization of at least one therapeutic agent
EP3502684A1 (en) 2017-12-22 2019-06-26 Universite De Bordeaux Method for metal ion detection in aqueous solutions using nucleolipid compounds
FR3078064A1 (en) 2018-02-22 2019-08-23 Universite de Bordeaux PROCESS FOR DECONTAMINATING AN AQUEOUS LIQUID MEDIUM CONTAINING MICROPOLLUTANTS
WO2022194926A1 (en) 2021-03-17 2022-09-22 Institut National De La Sante Et De La Recherche Medicale (Inserm) Nanoparticles comprising a core with a phenazine derivative and a shell with a nucleolipid and uses thereof
WO2023135299A1 (en) 2022-01-17 2023-07-20 INSERM (Institut National de la Santé et de la Recherche Médicale) Oligonucleotide solid nucleolipid nanoparticles for tackling antibiotic resistance

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Publication number Priority date Publication date Assignee Title
DE2626792A1 (en) * 1976-06-15 1977-12-29 Kowa Co Adenosine-5'-phosphoric acid derivs. and their salts - prepd. by acylating adenosine-5'-phosphate and opt. desalting or salt exchanging
AU2003296601A1 (en) * 2002-12-10 2004-06-30 F. Hoffmann-La Roche Ag Antiviral nucleoside derivatives
WO2005007810A2 (en) * 2003-06-16 2005-01-27 Grinstaff Mark W Functional synthetic molecules and macromolecules for gene delivery

Non-Patent Citations (7)

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Title
D.T, WARNER ET AL.: "Nucleic acids. 13. 3'-O- and 2'-O-esters of 1-beta-D-arabinofurabosylcytosine as antileukemic and immunosuppressive agents", J. MED. CHEM., vol. 15, 1972, pages 790 - 792, XP002317619 *
L. MOREAU ET AL.: "Supramolecular assemblies of nucleoside phosphocholine amphiphiles", J. AM. CHEM. SOC., vol. 126, 2004, pages 7533 - 7539, XP002317621 *
L.A. JONES ET AL.: "Di- and triester prodrugs of the Varicella-Zoster agent 6-methoxypurine arabinoside", J. MED. CHEM., vol. 35, 1992, pages 56 - 63, XP002317620 *
MACDONALD R C ET AL: "Physical and biological properties of cationic triesters of phosphatidylcholine", BIOPHYSICAL JOURNAL, NEW YORK, US, US, vol. 77, no. 5, November 1999 (1999-11-01), pages 2612 - 2629, XP002286481, ISSN: 0006-3495 *
MILLER A D: "CATIONIC LIPOSOMES FOR GENE THERAPY", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, VERLAG CHEMIE. WEINHEIM, DE, vol. 37, no. 13, 3 August 1998 (1998-08-03), pages 1768 - 1785, XP000772935, ISSN: 0570-0833 *
MOREAU L ET AL: "HYDROGELS OF PLASMID DNA AND NUCLEOSIDE-BASED PHOSPHOCHOLINE AMPHIPHILES", ABSTRACTS OF PAPERS. ACS NATIONAL MEETING, XX, XX, 28 March 2004 (2004-03-28), XP008042335 *
TAKAMURA T ET AL: "Synthesis and antitumor activities of N6,N6-dimethyladenosine carboxylate analogues", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO, JP, vol. 37, no. 10, 1989, pages 2828 - 2831, XP002181857, ISSN: 0009-2363 *

Also Published As

Publication number Publication date
FR2869616B1 (en) 2008-10-24
EP1745061A1 (en) 2007-01-24
WO2005116043A1 (en) 2005-12-08

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