Disclosed are compounds capable of facilitating transport of biologically active agents or substances into cells having the general structure: wherein Q is selected from the group consisting of N, O and S; L is any bivalent organic radical capable of linking each Q, such as C, CH, (CH2)l, or {(C
Disclosed are compounds capable of facilitating transport of biologically active agents or substances into cells having the general structure: wherein Q is selected from the group consisting of N, O and S; L is any bivalent organic radical capable of linking each Q, such as C, CH, (CH2)l, or {(CH2)i-Y--(CH2)j}k, wherein Y is selected from the group consisting of CH2, an ether, a polyether, an amide, a polyamide, an ester, a sulfide, a urea, a thiourea, a guanidyl, a carbamoyl, a carbonate, a phosphate, a sulfate, a sulfoxide, an imine, a carbonyl, and a secondary amino group and wherein Y is optionally substituted by--X1-L'-X2-Z or-Z; R1-R6, independently of one another, are selected from the group consisting of H,--(CH2)p-D-Z, an alkyl, an alkenyl, an aryl, and an alkyl or alkyl ether optionally substituted by one or more of an alcohol, an aminoalcohol, an amine, an amide, an ether, a polyether, a polyamide, an ester, a mercaptan, an alkylthio, a urea, a thiourea, a guanidyl, or a carbamoyl group, and wherein at least one of R1, R3, R4 and R6 is a straight chain or branched, cyclic, alkyl, alkenyl, alkynyl or aryl group; and anyone of R1, R3, R4 and/or R6 may optionally be covalently linked with each other, with Y or with L when L is C or CH to form a cyclic moiety; Z is selected from the group consisting of amine, spermiyl, carboxyspermiyl, guanidyl, spermidinyl, putricinyl, diaminoalkyl, pyridyl, piperidinyl, pyrrolidinyl, polyamine, amino acid, peptide, and protein; X1 and X2, independently of one another, are selected from the group consisting of NH, O, S, alkylene, and arylene; L' is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, alkylene ether, and polyether; D is Q or a bond; A1 and A2, independently of one another, are selected from the group consisting of CH2O, CH2S, CH2NH, C(O), C{NH), C(S) and (CH2)t; X is a physiologically acceptable anion; m, n, r, s, u, v, w and y are 0 or 1, with the proviso that when both m and n are 0 at least one of r, s, u and y is other than 0; i, j, k, l, p and are integers from 0 to about 100; q is an integer from 1 to about 1000; and a is the number of positive charge divided by the valence of the anion.
대표청구항▼
What is claimed is: 1. A method for introducing a nucleic acid into a cell, comprising the steps of contacting the nucleic acid with a polycation, thereby forming a complex; and incubating the complex with the cell, wherein the polycation has the formula: where: Q is N; L is [(CH2)i--Y--(CH2)j ]
What is claimed is: 1. A method for introducing a nucleic acid into a cell, comprising the steps of contacting the nucleic acid with a polycation, thereby forming a complex; and incubating the complex with the cell, wherein the polycation has the formula: where: Q is N; L is [(CH2)i--Y--(CH2)j ]k, where Y is a CH2, an ether, an amide, a thiourea, an imine, a carbonyl, or a secondary amino group; R1, R3, R4, and R6, independently of one another, are selected from H, alkyl, alkenyl, or alkynyl; R2 and R5, independently of one another, are--(CH2)p-D-Z, wherein (CH2)p is optionally substituted with--OH; D is a bond or Q; Z is an amine, a polyamine or a diaminoalkyl optionally substituted with--OH; X- is a physiologically acceptable anion; a is the number of positive charges divided by the valence of the anion; m and n are 1; r, s, u, and y are 1; i and j are independently an integer from 0 to about 100; k is an integer from 1 to about 100; p is an integer from 1 to about 100; q is an integer from 1 to about 100, and wherein, i) R1, R3, R4, and R6 are optionally substituted by one or more of an alcohol, an amino alcohol, or an amine; and ii) any two or more of R1, R3, R4 and R6 are covalently linked with each other thereby forming a cyclic moiety. 2. The method of claim 1, wherein Y is CH2. 3. The method of claim 1, wherein D is a bond. 4. The method of claim 1, wherein p and k independently are integers from 1 to 25, and i and j independently are integers from 0 to 25. 5. The method of claim 1, wherein p and k independently are integers from 1 to 10, and i and j independently are integers from 0 to 10. 6. The method of claim 1, wherein p and k independently are integers from 1 to 4, i and j independently are integers from 0 to 4, and q is 1. 7. The method of claim 2, wherein R2 and R5 are (CH2)p-D-Z, wherein (CH2) )p is substituted with an--OH. 8. The method of claim 7, wherein p and k independently are integers from 1 to 4, i and j independently are integers from 0 to 4, and q is 1. 9. The method of claim 7, wherein Z is a diaminoalkyl optionally substituted with--OH. 10. The method of claim 7, wherein D is a bond. 11. The method of claim 1, wherein R1, R3, R1, and R6, independent of one another, are selected from H or an alkyl group. 12. The method of claim 1, wherein R2 and R5 are an amino alcohol group. 13. The method of claim 1, wherein R2 and R5 are independently an aminoalcohol selected from aminoethanol, aminopropanol, or aminobutanol. 14. The method of claim 13, wherein the amino alcohol group has the structure 15. The method of claim 1, wherein the nucleic acid is DNA. 16. The method of claim 1, wherein the nucleic acid is RNA. 17. The method of claim 1, wherein the nucleic acid inhibits expression of nucleic acids in the cell. 18. The method of claim 1, wherein the nucleic acid catalyzes reactions. 19. The method of claim 1, wherein the complex formed is a liposome. 20. The method of claim 1, wherein the complex is a liposome and wherein the method further comprises the step of forming liposomes after contacting the nucleic acid with the polycation. 21. The method of claim 1, wherein a mixture of the polycation and a neutral lipid is formed and the nucleic acid is contacted with the mixture to form the complex. 22. The method of claim 1, wherein a mixture of the polycation and a neutral lipid selected from DOPE, DOPC or cholesterol is formed and the nucleic acid is contacted with the mixture to form the complex. 23. The method of claim 1, wherein a mixture of the nucleic acid and a peptide or a protein is formed and the polycation is contacted with the mixture to form the complex. 24. A method of making a compound having the structure wherein L is [(CH2)i--Y--(CH2)j]k, where Y is a CH2, an ether, an amide, a carbonyl, or a secondary amino group; i and j are independently an integer from 0 to about 100; k is an integer from 1 to about 100and R1 and R4 are independently C1 to C8 alkyl covalently linked with each other thereby forming a cyclic moiety; wherein the method comprises alkylating a cyclic diamine having the structure with an epoxyalkyl phthalimide reagent, followed by admixing the resulting compound with a reducing agent. 25. The method of claim 24. wherein epoxyalkyl phthalimide reagent is epoxypropyl phthalimide and the reducing agent is hydrazine. 26. A compound for introducing a nucleic acid into a cell having the formula where: Q is N; L is [(CH2)i--Y--(CH2)j]k, where Y is a CH2, an ether, an amide, a thiourea, an imine, a carbonyl, or a secondary amino group; R1, R3, R4, and R6, independently of one another, are selected from H, alkyl, alkenyl, or alkynyl; R2 and R5, independently of one another, are--(CH2)p-D-Z, wherein (CH2)p is optionally substituted with OH; D is a bond or Q; Z is an amine, a polyamine or a diaminoalkyl optionally substituted with--OH; X- is a physiologically acceptable anion; a is the number of positive charges divided by the valence of the anion; m and n are 1; r, s, u, andy are 1; i and j are independently an integer from 0 to about 100; k is an integer from 1 to about 100; p is an integer from 1 about 100; q is an integer from 1 to about 100, and wherein, i) R1, R3, R4, and R6 are optionally substituted by one or more of an alcohol, an amino alcohol, or an amine; and ii) any two or more of R1, R3, R4 and R6 are covalently linked with each other thereby forming a cyclic moiety, provided that when two of R1, R3, R4, and R6 are covalently linked with each other thereby forming a cyclic moiety, at least one of R1, R3, R4, and R6 not forming the cyclic moiety is not alkyl. 27. The compound of claim 26, wherein Y is CH2. 28. The compound of claim 26, wherein D is a bond. 29. The compound of claim 26, wherein p and k independently are integers from 1 to 4, i and j independently are integers from 0 to 4, and q is 1. 30. The compound of claim 27, wherein R2 and R5 are (CH2)p-D-Z, wherein (CH2)p is substituted with an--OH. 31. The compound of claim 30, wherein p and k independently are integers from 1 to 4, i and j independently are integers from 0 to 4, and q is 1. 32. The compound of claim 30, wherein Z is a diaminoalkyl optionally substituted with--OH. 33. The compound of claim 30, wherein D is a bond. 34. The compound of claim 26, wherein R1, R3, R4, and R6, independent of one another, are selected from H or an alkyl group. 35. The compound of claim 26, wherein R2 and R5 are an amino alcohol group. 36. The compound of claim 35, wherein R2 and R5 are independently an aminoalcohol group selected from aminoethanol, aminopropanol, or aminobutanol. 37. The compound of claim 35, wherein the amino alcohol group has the structure 38. The method of claim 8, wherein Z is a diaminoalkyl optionally substituted with--OH. 39. The compound of claim 31, wherein Z is a diaminoalkyl optionally substituted with--OH. 40. The method of claim 8, wherein i is 0 and j is 1. 41. The method of claim 40, wherein k is 1. 42. The method of claim 41, wherein p is 3. 43. The compound of claim 31, wherein i is 0 and j is 1. 44. The compound of claim 43, wherein k is 1. 45. The compound of claim 44, wherein p is 3. 46. The method of claim 6, wherein k is 1. 47. The compound of claim 29, wherein k is 1.
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