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US 6,399,663 B1Granted
Highly packed polycationic ammonium, sulfonium and phosphonium lipids
AssigneeInvitrogen Corporation
InventorsAlberto Haces, Valentina C. Ciccarone
Life of this patent
Estimating the term…
Abstract
The present invention discloses highly packed polycationic ammonium, sulfonium and phosphonium lipid compounds useful for making lipid aggregates for delivery of macromolecules and other compounds into cells. They are especially useful for the DNA-dependent transformation of cells. Methods for their preparation and use as intracellular delivery agents are also disclosed.
Claims52
A compound according to the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 1 to about 10;
- ni, where i=1 to x, are independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 or 0 and N is positively charged when r is 1;
- RA and RB, independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH, SH, NH2 or amine groups within about 3 carbon atoms of the bond between A1 or A2 and N.
5 more elements
A compound having the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 1 to about 20;
- ni, where i=1 to x, are, independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 and N is positively charged;
- RA and RB, independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to about 6 carbon atoms;
- R1 and RB, independently of one another, are selected from the group consisting of alkyl groups having from 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH within about 3 carbon atoms of the bond between A1 or A2 and N.
6 more elements
A compound having the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 2 to 5;
- ni, where i=1 to x, are, independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 or 0 and N is positively charged when r is 1;
- RA and RB , independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to about 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having from 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH within about 3 carbon atoms of the bond between A1 or A2 and N.
6 more elements
A lipid aggregate which comprises one or more compounds having the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 1 to about 20;
- ni, where i=1 to x, are, independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 or 0, with N being positively charged when r is 1;
- RA and RB, independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to about 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having from 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH, SH, NH2 or amine groups within about 3 carbon atoms of the bond between A1 or A2 and N.
6 more elements
A composition for transfecting a cell which comprises one or more compounds having the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 1 to about 20;
- ni, where i=1 to x, are, independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 or 0 with N being positively charged when r is 1;
- RA and RB, independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to about 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having from 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH, SH, NH2 or amine groups within about 3 carbon atoms of the bond between A1 or A2 and N.
6 more elements
A kit for preparing a lipid aggregate comprising one or more compounds having the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 1 to about 20;
- ni, where i=1 to x, are, independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 or 0 with N being positively charged when r is 1;
- RA and RB, independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to about 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having from 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH, SH, NH2 or amine groups within about 3 carbon atoms of the bond between A1 or A2 and N.
6 more elements
A method for delivery of a macromolecule to a cell comprising the step of contacting the cell with a composition which comprises the macromolecule and one or more having the formula:
- and salts thereof where:
- X is N;
- x is an integer ranging from 1 to about 20;
- ni, where i=1 to x, are, independently of one another, integers that have values ranging from 1 to about 6;
- r is 1 or 0, with N being positively charged when r is 1;
- RA and RB, independently of one another, are selected from the group consisting of hydrogen, an alkyl, a hydroxyalkyl and a thiol-substituted alkyl group having from 1 to about 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having from 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of straight-chain or branched alkyl groups substituted with one or two OH, SH, NH2 or amine groups within about 3 carbon atoms of the bond between A1 or A2 and N.
6 more elements
Dependencies are inferred from the claim text.