Cationic lipophosphoramidates with two disulfide motifs: synthesis, behaviour in reductive media and gene transfection activity

Aurore Fraix; Tony Le Gall; Mathieu Berchel; Caroline Denis; Pierre Lehn; Tristan Montier; Paul-Alain Jaffres

doi:10.1039/C3OB27261C

Cationic lipophosphoramidates with two disulfide motifs: synthesis, behaviour in reductive media and gene transfection activity

Aurore Fraix ¹ Tony Le Gall ^{2, 3} Mathieu Berchel ^{1, 2} Caroline Denis ^{3, 2} Pierre Lehn ^{3, 2} Tristan Montier ^{3, 2} Paul-Alain Jaffres ^{1, 2}

1 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique

2 IBISA " SynNanoVect " platform

3 INSERM U613, IFR148

Abstract : Lipophosphoramidates have previously been identified as efficient vectors for gene delivery. The incorporation of functional groups that respond to a physiological stimulus is hypothesised to further improve the efficacy of this type of vector and eventually reduce its cytotoxicity. In the present work, we report the effects of the incorporation of two disulfide motifs into the hydrophobic domain, close to the phosphoramidate group. Three cationic vectors possessing such a red/ox sensitive function were synthesised. The capability of one of them (5b) to compact DNA is reported jointly with its ability to release that DNA in the presence of a reducing agent. Finally, compound 5b was tested as a vector for gene delivery into human cells in vitro and its cytotoxicity was also evaluated

Type de document :

Article dans une revue

Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2013, 11 (10), 〈http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob27261c#!divAbstract〉. 〈10.1039/C3OB27261C〉

Domaine :

Chimie / Chimie organique

Chimie

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https://hal.univ-brest.fr/hal-01555861
Contributeur : Nicolas Renard <>
Soumis le : mardi 4 juillet 2017 - 15:07:38
Dernière modification le : jeudi 29 novembre 2018 - 16:09:12

Cationic lipophosphoramidates with two disulfide motifs: synthesis, behaviour in reductive media and gene transfection activity

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