Ashley, Gary W.; MacDonald, Robert C.; Shida, Miho;

Cationic phospholipids for transfection

A novel class of cationic phospholipids and novel method for their synthesis are disclosed. The class of phospholipids comprises phosphotriester derivatives of phosphoglycerides and sphingolipids. It has been unexpectedly found that liposomes comprising one or more of these cationic phospholipids are effective in the lipofection of nucleic acids. These novel phospholipids are particularly attractive because of they are not only effective in lipofection, but are extremely cheap and easy to make.

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We claim:

1. A method for synthesizing the cationic lipid having the structure ##STR11## wherein R.sup.4 is a C.sub.1 to about C.sub.24 straight or branched alkyl, a C.sub.2 to about C.sub.24 straight or branched alkenyl, or alkynyl chain optionally substituted with dansyl, NBD, DPH, carbocyclic aromatic, or heterocyclic moiety or R.sup.4 is a C.sub.1 to about C.sub.6 straight or branched chain ester, aldehyde, ketone, ether, haloalkyl, azidoalkyl, or a C.sub.4 to about C.sub.6 tetraalkylammonium, and

R.sup.5 is H or C.sub.1 to about C.sub.24 straight or branched alkyl, a C.sub.2 to about C.sub.24 straight or branched alkenyl, or alkynyl chains optionally substituted with dansyl, NBD, DPH carbocyclic aromatics, or heterocyclic moiety,

comprising contacting a parent compound having the structure: ##STR12## with a substituted triflate in a solvent.

2. A method according to claim 1 wherein the solvent is diethyl ether.

3. A method according to claim 1 wherein the substituted triflate is R.sup.4 -triflate, and R.sup.4 is C.sub.1 to about C.sub.24 straight or branched alkyl, a C.sub.2 to about C.sub.24 straight or branched alkenyl, or alkynyl chains optionally substituted with dansyl, NBD, DPH, carbocylclic aromatics, or heterocyclic moieties or a C.sub.1 to about C.sub.6, straight or branched chain ester, aldehyde, ketone, ether, haloalkyl, azidoalkyl, or a C.sub.4 to about C.sub.6 tetraalkylammonium.

4. A method according to claim 1 wherein the parent compound is a sphingomyelin.