Amide-based cationic lipids

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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562561, 562563, 564159, 564197, C07C23305

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active

060205261

ABSTRACT:
The present invention provides novel amide-based cationic lipids of the general structure: ##STR1## or a salt, or solvate, or enantiomers thereof wherein; (a) Y is a direct link or an alkylene of 1 to about 20 carbon atoms; (b) R.sub.1 is H or a lipophilic moiety; (c) R.sub.2, R.sub.3, and R.sub.4 are positively charged moieties, or at least one but not all of R.sub.2, R.sub.3, or R.sub.4 is a positive moiety and the remaining are independently selected from H, an alkyl moiety of 1 to about 6 carbon atoms, or a heterocyclic moiety of about 5 to about 10 carbon atoms; (d) n and p are independently selected integers from 0 to 8, such that the sum of n and o is from 1 to 16; (e) X.sup.- is an anion or polyanion and (f) m is an integer from 0 to a number equivalent to the positive charge(s) present on the lipid; provided that if Y is a direct link and the sum of n and p is 1 then one of either R.sub.3 or R.sub.4 must have an alkyl moiety of at least 10 carbon atoms.
The present invention further provides compositions of these lipids with polyanionic macromolecules, methods for interfering with protein expression in a cell utilizing these compositions and a kit for preparing the same.

REFERENCES:
patent: 4897355 (1990-01-01), Eppstein et al.
patent: 5171678 (1992-12-01), Beher et al.
patent: 5264618 (1993-11-01), Felgner et al.
patent: 5334761 (1994-08-01), Gebeyehu et al.
Felgner et al., "Lipofection: A highly efficient, lipid-mediated DNA-transfection procedure," Proc. Natl. Acad. Sci. USA 84:7413-7414 (1987).
Remy et.al., Bioconjugate chem, vol. 5, pp. 647-654, 1994.

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