Transfection reagents
6 Assignments
0 Petitions
Accused Products
Abstract
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)1, 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 any one 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 t 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.
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Citations
101 Claims
- 1. A compound having the formula:
- 2. A compound having the formula:
- 5. A compound having the formula:
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7. The compound which is:
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8. The compound which is:
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32. A compound having the formula:
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37. A compound having the formula:
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40. A compound having the formula:
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52. A compound having the formula:
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80. A compound which is:
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N1,N4-dipalmitolyl-N1,N4-di-[2-hydroxy-3-(N-aminopropyl)]-diaminobutane; N1,N4-distearyl-N1,N4-di-[2-hydroxy-3-(N-aminopropyl)]-diaminobutane; N1,N4-dilauryl-N1,N4-di-[2-hydroxy-3-(N-aminopropyl)]-diaminobutane; N1,N2-dimyristyl-N1,N2-di-[2-hydroxy-3-(N-aminopropyl)]-diaminoethane; N1,N2-dipalmity-N1,N2-di-[2-hydroxy-3-(N-aminopropyl)]-diaminoethane; N1,N2-dipalmitolyl-N1,N2-di-[2-hydroxy-3-(N-aminopropyl)]-diaminoethane; N1,N2-distearyl-N1,N2-di-[2-hydroxy-3-(N-aminopropyl)]-diaminoethane; N1,N2-dilauryl-N1, N2-di-[2-hydroxy-3-(N-aminopropyl)]-diaminoethane; N1,N8-dimyristyl-N1,N8-di-[2-hydroxy-3-(N-aminopropyl)]-Jeffamine; N1,N8-dipalmityl-N1,N8-di-[2-hydroxy-3-(N-aminopropyl)]-Jeffamine; N1,N8-dipalmitolyl-N1,N8-di-[2-hydroxy-3-(N-aminopropyl)]-Jeffamine; N1,N8-distearyl-N1,N8-di-[2-hydroxy-3-(N-aminopropyl)]-Jeffamine; N1,N8-dilauryl-N1,N8-di-[2-hydroxy-3-(N-aminopropyl)]-Jeffamine; N1,N8-dioleyl-N1,N8-di-[2-hydroxy-3-(N-aminopropyl)]-Jeffamine; N1,N4-dimyristyl-N1,N4-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminobutane; N1,N4-dipalmityl-N1,N4-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminobutane; N1,N4-dipalmitolyl-N1,N4-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminobutane; N1,N4-distearyl-N1,N4-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminobutane; N1,N4-dilauryl-N1,N4-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminobutane; N1,N8-dimyristyl-N1,N8-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-Jeffamine; N1,N8-dipalmityl-N1,N8-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-Jeffamine; N1,N8-dipalmitolyl-N1,N8-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-Jeffamine; N1,N8-distearyl-N1,N8-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-Jeffamine; N1,N8-dilauryl-N1,N8-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-Jeffamine; N1,N8-dioleyl-N1,N8-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-Jeffamine; N1,N2-dimyristyl-N1,N2-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminoethane; N1,N2-dipalmityl-N1,N2-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminoethane; N1,N2-dipalmitolyl-N1,N2-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminoethane; N1,N2-distearyl-N1,N2-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminoethane;
orN1,N2-dilauryl-N1,N2-di-[2-hydroxy-3-(N-sperminecarboxamido)aminopropyl]-diaminoethane.
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81. A compound which is:
Specification