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US 2009/0317908 A1Published application
Highly packed polycationic ammonium, sulfonium and phosphonium lipids
AssigneeLife Technologies Corporation
InventorsAlberto Haces, Valentina Ciccarone
Life of this patent
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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.
Claims11
A compound or polycation having the formula:
- or salt thereof where:
- x is an integer ranging from 1 to about 20;
- 1 is an integer ranging from 1 to about 6;
- r and s, independently of one another, are 0 or 1, wherein when r is 1, the N bonded to R1 and A1 has a positive charge, and when s is 1, the N bonded to R2 and A2 has a positive charge;
- RA and RB, independently of one another, are selected from the group consisting of H, or an alkyl, hydroalkyl or thiol-substituted alkyl group having from 1 to 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of a —CH(D-L)2 and a —C(D-L)3 group wherein D is selected from the group consisting of —CO—, —CO2—, —O—C—O—, —CO—N—, —O—CO—N—, —O—, and —S—, and L is selected from the group consisting of:
- (a) a straight chain or branched alkyl, alkenyl, or alkynyl group having from 2 to about 22 carbon atoms wherein one or more non-neighboring—CH2— groups can be replaced with an O or S atom;
- (b) a substituted straight chain or branched alkyl, alkenyl, or alkynyl group having from 2 to about 22 carbon atoms wherein the substituent is an aromatic, alicyclic heterocyclic or polycyclic ring and wherein one or more of the non-neighboring neighboring —CH2— groups of said alkyl, alkenyl or alkynyl group can be substituted with an O or S atom;
- and
- (c) an aromatic, alicyclic, heterocyclic and a polycyclic ring moiety.
9 more elements
A compound or polycation having the formula:
- or salt thereof where:
- x is an integer ranging from 1 to about 20;
- 1 is an integer ranging from 1 to about 6;
- r and s, independently of one another, are 0 or 1, wherein when r is 1, the N bonded to R1 and A1 has a positive charge, and when s is 1, the N bonded to R2 and A2 has a positive charge;
- RA and RB, independently of one another, are selected from the group consisting of H, or an alkyl, hydroalkyl or thiol-substituted alkyl group having from 1 to 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of a B-L group wherein B is selected from the group consisting of —CO—, —CO2—, —O—C—O—, —CO—N—, —O—CO—N—, —O—CH2—, —S—CH2—, —CH2—S—, and —CH2— and L is selected from the group consisting of:
- (a) a straight chain or branched alkyl, alkenyl, or alkynyl group having from 2 to about 22 carbon atoms wherein one or more non-neighboring—CH2— groups can be replaced with an O or S atom;
- (b) a substituted straight chain or branched alkyl, alkenyl, or alkynyl group having from 2 to about 22 carbon atoms wherein the substituent is an aromatic, alicyclic heterocyclic or polycyclic ring and wherein one or more of the non-neighboring neighboring —CH2— groups of said alkyl, alkenyl or alkynyl group can be substituted with an O or S atom;
- and
- (c) an aromatic, alicyclic, heterocyclic and a polycyclic ring moiety.
9 more elements
A compound or polycation having the formula:
- or salt thereof where:
- x is an integer ranging from 1 to about 20;
- 1 is an integer ranging from 1 to about 6;
- r and s, independently of one another, are 0 or 1, wherein when r is 1, the N bonded to R1 and A1 has a positive charge, and when s is 1, the N bonded to R2 and A2 has a positive charge;
- RA and RB, independently of one another, are selected from the group consisting of H, or an alkyl, hydroalkyl or thiol-substituted alkyl group having from 1 to 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of a substituted straight chain or branched alkyl, alkenyl, or alkynyl group having from 2 to about 22 carbon atoms wherein the substituent is an aromatic, alicyclic heterocyclic or polycyclic ring and wherein one or more of the non-neighboring neighboring —CH2— groups of said alkyl, alkenyl or alkynyl group can be substituted with an O or S atom.
5 more elements
A compound or polycation having the formula:
- or salt thereof where:
- x is an integer ranging from 1 to about 20;
- 1 is an integer ranging from 1 to about 6;
- r and s, independently of one another, are 0 or 1, wherein when r is 1, the N bonded to R1 and A1 has a positive charge, and when s is 1, the N bonded to R2 and A2 has a positive charge;
- RA and RB, independently of one another, are selected from the group consisting of H, or an alkyl, hydroalkyl or thiol-substituted alkyl group having from 1 to 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of a straight chain or branched alkyl, alkenyl, or alkynyl group having from 2 to about 22 carbon atoms wherein one or more of the non-neighboring neighboring —CH2— groups of said alkyl, alkenyl or alkynyl group can be substituted with an O or S atom.
5 more elements
A compound or polycation having the formula:
- or salt thereof where:
- x is an integer ranging from 1 to about 20;
- 1 is an integer ranging from 1 to about 6;
- r and s, independently of one another, are 0 or 1, wherein when r is 1, the N bonded to R1 and A1 has a positive charge, and when s is 1, the N bonded to R2 and A2 has a positive charge;
- RA and RB, independently of one another, are selected from the group consisting of H, or an alkyl, hydroalkyl or thiol-substituted alkyl group having from 1 to 6 carbon atoms;
- R1 and R2, independently of one another, are selected from the group consisting of alkyl groups having 1 to about 6 carbon atoms;
- and
- A1 and A2, independently of other A1 and A2 groups, are selected from the group consisting of a straight chain or branched alkyl group substituted with one or two SH groups within about 3 carbon atoms of the bond between A1 or A2 and N.
5 more elements
Dependencies are inferred from the claim text.