Polyacetals comprising a recurring units represented by a formula selected from the group consisting of formula (I) and (II): wherein A comprises at least one acetal group; B is selected from the group consisting of--CH--,--CH(CH3)--, CH 2CH--,--CH2C(CH3)--,--CH(CH3)CH--, and--CHCH(CH3)CH(CH3)--
Polyacetals comprising a recurring units represented by a formula selected from the group consisting of formula (I) and (II): wherein A comprises at least one acetal group; B is selected from the group consisting of--CH--,--CH(CH3)--, CH 2CH--,--CH2C(CH3)--,--CH(CH3)CH--, and--CHCH(CH3)CH(CH3)--; Z is selected from the group consisting of C(O)OR1, C(O)SR1, C(O)NR1R 2, and VU; V is a linker group; U is selected from the group consisting of poly(ethyleneimine), poly(propyleneimine), poly(lysine), PAMAM dendrimer, octaamine dendrimer, hexadecaamine dendrimer, enhancer, and targeting receptor; R1 and R2 are each individually selected from the group consisting of hydrogen, C1 to C10 alkyl, and C6 to C10 aryl; D is a linkage selected from the group consisting of carboxylic amide, carboxylic ester, urea, and urethane; and G is selected from the group consisting of C4 to C20 alkyl, C6-C10 aryl, and--(OCH2 CH2)n--, where n is in the range of 1 to about 250, are useful in nucleic acid delivery applications. In preferred embodiments, complexes formed between polyacetals of the formulae (I) or (II) and polynucleotides are useful as transfection reagents.
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What is claimed is: 1. A polymer comprising a recurring unit represented by a formula selected from the group consisting of formula (I) and (II): wherein A comprises at least one acetal group; wherein B is selected from the group consisting of--CH--,--CH(CH3)--, CH2CH--,--CH2C(CH3)--,--CH(CH3)CH-
What is claimed is: 1. A polymer comprising a recurring unit represented by a formula selected from the group consisting of formula (I) and (II): wherein A comprises at least one acetal group; wherein B is selected from the group consisting of--CH--,--CH(CH3)--, CH2CH--,--CH2C(CH3)--,--CH(CH3)CH--, and--CHCH(CH3)CH(CH3)--; wherein Z is selected from the group consisting of C(O)OR 1, C(O)SR1, C(O)NR1R2, and VU; wherein V is a linker group; wherein U is selected from the group consisting of poly(ethyleneimine), poly(propyleneimine), poly(lysine), PAMAM dendrimer, octaamine dendrimer, hexadecaamine dendrimer, enhancer, and targeting receptor; wherein R1 and R2 are each individually selected from the group consisting of hydrogen, C1 to C10 alkyl, and C6 to C10 aryl; wherein D is a linkage selected from the group consisting of carboxylic amide, carboxylic ester, urea, and urethane; and wherein G is selected from the group consisting of C4 to C20 alkyl, C6-C10 aryl, and--(OCH 2CH2)n--, where n is in the range of 1 to about 250. 2. The polymer of claim 1 in which U is poly(ethyleneimine). 3. The polymer of claim 2 in which the poly(ethyleneimine) has a molecular weight in the range of about 200 to about 100,000 Daltons. 4. The polymer of claim 1 in which U is poly(lysine). 5. The polymer of claim 4 in which the poly(lysine) has a molecular weight in the range of about 200 to about 50,000 Daltons. 6. The polymer of claim 1 in which Z is VU. 7. The polymer of claim 2 in which V is--C(O)NH--. 8. The polymer of claim 1 in which U is selected from the group consisting of poly(ethyleneimine), enhancer, and targeting receptor. 9. The polymer of claim 8 in which U is a poly(ethylenimine) having a molecular weight in the range of about 200 to about 100,000 Daltons. 10. The polymer of claim 8 in which U is an enhancer selected from the group consisting of lipid, cholesterol, lipoprotein, fatty acid, lysosomotrophic agent, and fusogenic agent. 11. The polymer of claim 8 in which U is a targeting receptor selected from the group consisting of transferrin, antibody, antibody fragment, galactose, and mannose. 12. A method for making the polymer of claim 1, comprising reacting a monomer represented by a formula selected from the group consisting of formula (III) and formula (IV) with a comonomer having a formula represented by formula (V): wherein A, B, Z and G have the same meanings as set forth in claim 1; wherein E is selected from the group consisting of--OH,--NH2, and--NH(CH3); and wherein C is selected from the group consisting of isocyanate, NHS-ester, carboxylic acid, carboxylic ester, carboxylic acid chloride and anhydride. 13. A method for making the polymer of claim 7, comprising reacting a compound represented by the formula H2NU with a polymer comprising a recurring unit represented by a formula selected from the group consisting of formula (VII) and (VIII): wherein U, A, B, D and G have the same meanings as set forth in claim 1; and wherein R3, R4 and R5 are each individually selected from the group consisting of hydrogen, C1 to C10 alkyl, and C6 to C10 aryl. 14. A complex comprising the polymer of claim 6 and a polynucleotide. 15. A method for making the complex of claim 14, comprising intermixing the polymer of claim 6 and the polynucleotide. 16. The method of claim 15 in which the intermixing is conducted by adding a solution comprising the polymer of claim 6 to a second solution comprising the polynucleotide. 17. The method of claim 16 in which the V in the polymer of claim 6 is--C(O)NH--. 18. A method for transfecting a cell, comprising contacting the cell with the complex of claim 14. 19. The method of claim 18 in which the V in the polymer of claim 6 is--C(O)NH--. 20. The method of claim 19 in which the U in the polymer of claim 6 is poly(ethyleneimine). 21. The polymer of claim 1 in which the recurring unit is represented by a formula selected from the group consisting of formula (IX) and formula (X): wherein Z has the same meaning as set forth in claim 1; wherein R6, R7 and R8 are each individually selected from the group consisting of H and--CH3; wherein X is selected from the group consisting of--CH 2CH2--,--CH2CH2CH2CH2--,--CH2CH2OCH2CH2--, and--CH 2CH2OCH2CH2OCH2CH2--; and wherein Y is selected from the group consisting of linear or branched C4H8, C5H10, C6H 12, C7H14, C8H16, C10 H20, and C12H24. 22. The polymer of claim 21 in which U is poly(ethylenimine). 23. The polymer of claim 22 in which the poly(ethylenimine) has a molecular weight in the range of about 200 to about 100,000 Daltons. 24. The polymer of claim 21 in which U is poly(lysine). 25. The polymer of claim 24 in which the poly(lysine) has a molecular weight in the range of about 200 to about 50,000 Daltons. 26. The polymer of claim 21 in which Z is VU. 27. The polymer of claim 26 in which V is--C(O)NH--. 28. The polymer of claim 21 in which U is selected from the group consisting of poly(ethylenimine), an enhancer, and targeting receptor. 29. The polymer of claim 28 in which U is poly(ethylenimine) having a molecular weight in the range of about 200 to about 100,000 Daltons. 30. The polymer of claim 28 in which U is an enhancer selected from the group consisting of lipid, cholesterol, lipoprotein, fatty acid, lysosomotrophic agent, and fusogenic agent. 31. The polymer of claim 28 in which U is a targeting receptor selected from the group consisting of transferrin, antibody, antibody fragment, galactose, and mannose. 32. A method for making the polymer of claim 21, comprising reacting a monomer represented by a formula selected from the group consisting of formula (XI) and formula (XII) with a comonomer represented by the formula (XIII): wherein X, Y and Z have the same meanings as set forth in claim 21. 33. A method for making the polymer of claim 27, comprising reacting a poly(ethyleneimine) with a polymer comprising a recurring unit represented by a formula selected from the group consisting of formula (XIV) and formula (XV): wherein X and Y have the same meanings as set forth in claim 27. 34. A complex comprising the polymer of claim 26 and a polynucleotide wherein the polynucleotide is selected from the group consisting of plasmid DNA, antisense DNA, DNA oligomer, and siRNA. 35. A method for making the complex of claim 34, comprising intermixing the polymer of claim 26 and the polynucleotide. 36. The method of claim 35 in which the intermixing is conducted by adding a solution comprising the polymer of claim 26 to a second solution comprising the polynucleotide. 37. The method of claim 36 in which the V in the polymer of claim 26 is--C(O)NH--. 38. A method for transfecting a cell, comprising contacting the cell with the complex of claim 34. 39. The method of claim 38 in which the V in the polymer of claim 26 is--C(O)NH--. 40. The method of claim 39 in which the Z in the polymer of claim 26 is poly(ethyleneimine). 41. A monomer represented by a formula selected from the group consisting of formula (XI) and formula (XII): wherein X is selected from the group consisting of--CH 2CH2--,--CH2CH2CH2CH2--,--CH2CH2OCH2CH2--, and--CH 2CH2OCH2CH2OCH2CH2--; and wherein Z is selected from the group consisting of C(O)OR 1, C(O)SR1, and C(O)NR1R2, where R1 and R2 are each individually selected from the group consisting of hydrogen, C1 to C20 alkyl, and C6-C10 aryl. 42. A method for making the monomer of claim 41, comprising reacting a divinyl ether represented by formula (XVI) with about two equivalents of a compound represented by formula (XVII), in the presence of an acid in a non-alcoholic organic solvent: wherein X is selected from the group consisting of--CH 2CH2--,--CH2CH2CH2CH2--,--CH2CH2OCH2CH2--, and--CH 2CH2OCH2CH2OCH2CH2--; wherein Z is selected from the group consisting of C(O)OR 1, C(O)SR1, and C(O)NR1R2, where R1 and R2 are each individually selected from the group consisting of hydrogen, C1 to C20 alkyl, and C6-C10 aryl; wherein M is a protecting group selected from the group consisting of 9-fluorenylmethyl carbamate, activated amide, and cyclic imide; and wherein R is methyl or hydrogen and wherein n is 1 or 2.
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이 특허에 인용된 특허 (3)
Papisov Mikhail I., Biodegradable polyacetal polymers and methods for their formation and use.
Yurkovetskiy, Aleksandr; Yin, Mao; Lowinger, Timothy B.; Cabral, Carolina B.; Hammond, Charles E.; Stevenson, Cheri A., Modified polymers for delivery of polynucleotides, method of manufacture, and methods of use thereof.
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