Hybrid phosphoinositide phospholipids: compositions and uses

Details Hybrid phosphoinositide phospholipids: compositions and uses Hybrid phosphoinositide phospholipids: compositions and uses

C - Chemistry, Metallurgy

07

F

C07F 9/117 (2006.01) C07F 9/653 (2006.01) C07F 9/655 (2006.01) C12Q 1/00 (2006.01) C12Q 1/42 (2006.01) C12Q 1/44 (2006.01) C12Q 1/48 (2006.01) G01N 33/50 (2006.01) G01N 33/53 (2006.01) G01N 33/543 (2006.01) G01N 33/92 (2006.01)

Patent

CA 2480170

The methods and compositions disclosed synthesis of a novel class of "two- headed" phospholipid-phosphoinositide hybrids possessing a carbon backbone, such as 2,3-diacylthreitol, erythritol or a synthetic module. The second phospholipid head group allows introduction of a biochemical or chemical moiety in a position orthogonal in space to those occupied by the phosphoinositide head group and the two acyl chains. The diacyl moieties allow for the incorporation of Pea-PIP2 into a lipid bilayer, while the Ptdlns(4,5)P2 moiety in the aqueous layer is specifically recognized by lipid binding proteins. In alternative embodiments of the invention, reporters, for example biotin, fluorophores and/or spin labels, are attached to the free amino group of the head groups of such molecules to specifically target the reporters to the lipid-water interface. Figure (1) illustrates (at c) an exemplary hybrid lipid of the present invention that possess a phosphatidylethanolamine (PE, or Pea) head group at the 1-position and a Ptdlns(4, 5)P2 head group at the 4-position.

L'invention concerne des compositions et des procédés relatifs à la synthèse d'une nouvelle classe d'hybrides phosphoinositides-phospholipides "à deux têtes" possédant un squelette carboné, tel que le 2,3-diacylthreitol, l'érythritol ou un module synthétique. Le second groupe de tête phospholipidique permet l'introduction d'une fraction biochimique ou chimique dans une position dans l'espace perpendiculaire à celles occupées par le groupe de tête phosphoinositidique et les deux chaînes acyle. Les fractions diacyle permettent l'incorporation de Pea-PIP¿2? dans une bicouche lipidique, tandis que la fraction Ptdlns(4,5)P¿2? dans la couche aqueuse est reconnue spécifiquement par des protéines se liant aux lipides. Dans d'autres modes de réalisation de l'invention, des rapporteurs, par exemple la biotine, des fluorophores et/ou des marqueurs de spin, sont liés au groupe amino libre des groupes de tête de ces molécules pour diriger spécifiquement ces rapporteurs sur l'interface lipide-eau.

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