Quaternized poly(4-vinylpyridine)s as model gene delivery polycations: Structure-function study by modification of side chain hydrophobicity and degree of alkylation

Bioconjugate Chemistry

Volumn 18, Issue 3, 2007, Pages 922-928

  San Juan, Aurélie ^a   Letourneur, Didier ^a   Izumrudov, Vladimir A ^b,c  

^a BICHAT HOSPITAL   (France)

^b UNIVERSITÉ PARIS 13   (France)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE QUENCHING; GENE TRANSFER; GENES; PHOSPHATASES;

DNA COMPLEX; GENE DELIVERY; GENE DELIVERY AGENTS; MOLECULAR CHARACTERISTICS; POLY(4-VINYL PYRIDINE); POLY(4-VINYLPYRIDINE); POLY4-VINYLPYRIDINE (PVP); POLYCATIONS; SIDE-CHAINS; STRUCTURE-FUNCTION STUDIES;

ALKYLATION;

ALKALINE PHOSPHATASE; ALKYL GROUP; CARBENE; DNA; ESTER DERIVATIVE; PLASMID VECTOR; POLYAMINE DERIVATIVE; POLYCATION; POLYMER; PYRIDINE DERIVATIVE; VINYL DERIVATIVE;

ACIDITY; ALKYLATION; ARTICLE; COMPLEX FORMATION; ENZYME RELEASE; FLUORESCENCE; GENETIC TRANSFECTION; NONVIRAL GENE DELIVERY SYSTEM; PHYSICAL CHEMISTRY; PROTEIN EXPRESSION; PROTON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 34347351369     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060317+     Document Type: Article

References (36)

1. Huang, L., and Viroonchatapan, E. (1999) In Non-viral vector for gene therapy (L. Huang, M.-Ch. Hung, and E. Wagner, Eds.) pp 3-22, Academic Press, New York.
2. Marxhall, J., Yew, N., Eastman, S., Jiang, C., Scheule, R., and Cheng, S. (1999) In Non-viral vector for gene therapy (L. Huang, M.-Ch. Hung, and E. Wagner, Eds.) pp 39-68, Academic Press, New York.
3. Kabanov, A. (1998) Self-assembling complexes for gene delivery: from laboratory to clinical trial. J. Wiley & Sons, New York.
4. Cho, Y. W., Kim, J. D., and Park, K. (2003) Polycation gene delivery systems: escape from endosomes to cytosol. J. Pharm. Pharmacol. 55, 721-734.
5. Behr, J.-P. (1993) Synthetic gene-transfer vectors. Acc. Chem. Res. 26, 274-278.
6. Wagner, E., and Cotten, M. (1993) Non-viral approaches to gene therapy. Curr. Opin. Biotechnol. 4, 705-710.
7. Curiel, D. (1994) High efficiency gene transfer mediated by adenovirus-polylysine-DNA complexes. Ann. N. Y. Acad. Sci. 716, 36-56.
8. Wagner, E., Cotten, M., Foisner, R., and Birnstiel, M. (1991) Transferrin-polycation DNA complexes: the effect of polycation on the structure of the complex and DNA delivery to cells. Proc. Natl. Acad. Sci. U.S.A. 88, 4255-4259.
9. Stankovitcs, J., Crane, A., Andrews, E., Wu, C. H., Wu, G., and Ledley, F. (1994) Overexpression of human methylmalonyl CoA mutase in mice after in vivo gene transfer with asialoglycoprotein/ polylysine/DNA complexes. Hum. Gene Ther. 5, 1095-1104.
10. Kabanov, A., Kiselyov, V., Chikindas, M., Astafieva, I., Glukhov, A., Gordeev, S., Izumrudov, V., Zezin, A., Levashov, A., Severin, E., and Kabanov, V. (1989) Transformation activity of plasmid DNA is enhanced by complexation with a hydrocarbon polycation. Dokl. Acad. Nauk. 306, 226-229.
11. Kabanov, A., and Kabanov, V. (1995) DNA complexes with polycations for the delivery of genetic materials into cells. Bioconjugate Chem. 4, 372-379.
12. Boussif, O., Lezoualc'h, F., Zanta, M. A., Mergny, M. D., Scherman, D., Demeneix, B., and Behr, J. P. (1995) A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine. Proc. Natl. Acad. Sci. U.S.A. 92, 7297-7301.
13. Haensler, J., and Szoka, F. (1993) Functionalization of polyamidoamine cascade polymers and their use for efficient transfection of cells in culture. Bioconjugate Chem. 4, 372-379.
14. Tang, M., Redemann, C., and Szoka, F. (1996) In vitro gene delivery by degradated polyamidoamine dendrimers. Bioconjugate Chem. 7, 703-714.
15. Remy, J.-S., Sirlin, C., Vierling, P., and Behr, J.-P. (1994) Gene transfer with a series of lipophilic DNA-binding molecules. Bioconjugate Chem. 5, 647-654.
16. Behr, J.-P. (1994) Gene transfer with synthetic cationic amphiphiles: prospects for gene therapy. Bioconjugate Chem. 5, 382-389.
17. Futaki, S., Ohashi, W., Suzuki, T., Niwa, M., Tanaka, S., Ueda, K., Harashima, H., and Sugiura, Y. (2001) Stearylated arginine-rich peptides: a new class of transfection systems. Bioconjugate Chem. 12, 1005-1011.
18. Yaroslavov, A., Sukhishvili, S., Obolsky, O., Yaroslavova, E., Kabanov, A., and Kabanov, V. (1996) DNA affinity to biological membranes is enhanced due to complexation with hydrophobized polycation. FEBS Lett. 384, 177-180.
19. Kabanov, A., Astafieva, I., Chikindas, M., Rosenblat, G., Kiselev, V., Severin, E., and Kabanov, V. (1991) DNA interpolyelectrolyte complexes as a tool for efficient cell transformation. Biopolymers 31, 1437-1443.
20. Kabanov, A., Astafieva, I., Maksimova, I., Lukandin, E., Georgiev, G., and Kabanov, V. (1993) Efficient transformation of mammalian cells using DNA interpolyelectrolyte complexes with carbon chain polycations. Bioconjugate Chem. 4, 448-454.
21. Wang, J., Huang, S.-W., Zhang, P.-C., Mao, H.-Q., and Leong, K. (2003) Effect of side-chain structures on gene transfer efficiency of biodegradable cationic polyphosphoesters. Int. J. Pharm. 265, 75-84.
22. Wakefield, D., Klein, J., Wolff, J., and Rozema, D. (2005) Membrane activity and transfection ability of amphipathic polycations as a function of alkyl group size. Bioconjugate Chem. 16, 1204-1208.
23. Waring, M. (1965) Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol. 13, 269-282.
24. Olins, D., Olins, A., and von Hippel, P. (1967) Model nuclear protein complexes: studies on the interaction of cationic homopolypeptides with DNA. J. Mol. Biol. 24, 157-176.
25. Izumrudov, V., Domashenko, N., Zhiryakova, M., and Davydova, O. (2005) Interpolyelectrolyte reactions in solutions of polycarboxybetaines, 2. Influence of alkyl spacer in the betaine moieties on complexing with polyanions. J. Phys. Chem. B 109, 17391-17399.
26. Starodubtsev, S., Kirsh, Y. E., and Kabanov, V. (1977) Solvation effects and reactivity of free pyridine residues in macromolecules of poly-4-vinylpiridine. Eur. Polym. J. 10, 739-742.
27. Bohrisch, J., Schimmel, T., Engelhardt, H., and Jaeger, W. (2002) Charge interaction of synthetic polycarboxybetaines in bulk and solution. Macromolecules 35, 4143-4149.
28. Le-Pecq, J.-B., and Paoletti, C. (1967) A fluorescent complex between ethidium bromide and nucleic acids. Physical-chemical characterization. J. Mol. Biol. 27, 87-106.
29. Izumrudov, V., Zhiryakova, M., and Kudaibergenov, S. (2000) Controllable stability of DNA-containing polyelectrolyte complexes in water-salt solutions. Biopolymers 52, 94-108.
30. Izumrudov, V., Zhiryakova, M., and Akritskaya, N. (2003) Fluorescence quenching technique for study of DNA-containing polyelectrolyte complexes. In Advanced Macromolecular and Supramolecular Materials and Processes (Geckeler, K., Ed.) pp 277-289, Kluwer Academic/Plenum Publishers, Dordrecht.
31. Nachtigal, M., Nagpal, M. L., Greenspan, P., Nachtigal, S. A., and Legrand, A. (1989) Characterization of a continuous smooth muscle cell line derived from rabbit aorta. In Vitro Cell Dev. Biol. 25, 892-898.
32. Elmadbouh, I., Rossignol, P., Meilhac, O., Vranckx, R., Pichon, C., Pouzet, B., Midoux, P., and Michel, J. B. (2004) Optimization of in vitro vascular cell transfection with non-viral vectors for in vivo applications. J. Gene Med. 6, 1112-1124.
33. Zelikin, A., Putnam, D., Shastri, P., Langer, R., and Izumrudov, V. (2002) Aliphatic ionenes as gene delivery agents: elucidation of structure-function relationship through modification of charge density and polymer length. Bioconjugate Chem. 13, 548-553.
34. Pack, D., Putnam, D., and Langer, R. (2000) Design of imidazole-containing endosomolytic biopolymers for gene delivery. Biotechnol Bioeng. 67, 217-223.
35. Kirsh, Y., Komarova, O., and Lukovkin, G. (1973) Physico-chemical study of ionic equilibria for poly-2 and poly-4-vinylpyridines in alcohol-water solutions. Eur. Polym. J. 9, 1405-1408.
36. Kabanov, V. (1994) in Macromolecular complexes in chemistry and biology (Dubin, P., Bock, J., Davies, R. M., Schulz, D. N., Thies, C., Eds.) pp 151-174, Springer-Verlag B-H, Berlin.