Synthesis of cardiolipin analogues and uses thereof

Details Synthesis of cardiolipin analogues and uses thereof Synthesis of cardiolipin analogues and uses thereof

C - Chemistry, Metallurgy

07

F

C07F 9/02 (2006.01)

Patent

CA 2587103

The invention provides novel synthetic methodologies for preparing cardiolipin, migrated caridiolipin (1,2-positional isomer of cardiolipin) and their analogues having varying fatty acids and/or alkyl chains with varying length and degrees of saturation/unsaturation. The method comprises (a) reacting an optically pure 1,2-O-dialkyl-sn-glycerol or 1,2-O-dialkyl-sn- glycerol with one or more phosphoramidite reagent(s), wherein a phosphite triester is produced; (b) coupling the product of (a) with glycerol, wherein a protected cardiolipin is produced; and (c) deprotecting the protected cardiolipin, such that cardiolipin is prepared. The cardiolipins and analogues thereof, prepared by the present methods, can be incorporated into liposomes, which can also include active agents such as hydrophobic or hydrophilic drugs, antisense nucleotides or diagnostic agents. Such liposomes can be used to treat diseases or can be used in diagnostic and/or analytical assays.

L'invention concerne de nouvelles méthodes de synthèse de cardiolipine et de variantes de cardiolipine (isomère de cardiolipine en position 1,2) et leurs produits analogues comportant des chaînes d'acides gras et/ou d'alkyles variables, à longueur et degrés de saturation/insaturation variables. Une de ces méthodes consiste (a) à faire réagir un 1,2-O-diacyl-sn-glycérol ou un 1, 2-O-dialkyl-sn-glycérol optiquement pur avec un ou plusieurs réactifs de phosphoramidite, pour produire un triester de phosphite ; (b) à coupler le produit obtenu en (a) avec du glycérol, pour produire une cardiolipine protégée ; et (c) à enlever la protection de la cardiolipine protégée pour obtenir de la cardiolipine. Les cardiolipines et leurs produits analogues préparés à l'aide desdites méthodes, peuvent être introduits dans des liposomes, des nucléotides antisens ou des agents de diagnostic. Ces liposomes peuvent ensuite être utilisés pour le traitement de maladies ou peuvent être utilisés dans des essais diagnostiques et/ou analytiques.

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