Binding of meso-Tetrakis(N-methylpyridinium-4-yl)porphyrin to AT Oligomers: Effect of Chain Length and the Location of the Porphyrin Stacking

Biophysical Journal

Volumn 86, Issue 2, 2004, Pages 1012-1017

  Kim, Jin Ok ^a   Lee, Young Ae ^a   Yun, Byeong Hwa ^a,d   Han, Sung Wook ^b   Kwag, Sam Tag ^c   Kim, Seog K ^a  

^a Yeungnam University   (South Korea)

^b Kyungwoon University   (South Korea)

^c Pukyong National University   (South Korea)

^d NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MONOMER; OLIGOMER; PORPHYRIN DERIVATIVE; PYRIDINIUM DERIVATIVE; TETRAKIS(N METHYLPYRIDINIUM 4 YL)PORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; AT RICH SEQUENCE; BASE PAIRING; BINDING SITE; CHEMICAL BINDING; CIRCULAR DICHROISM; COMPLEX FORMATION; SPECTRAL SENSITIVITY;

EID: 1142310679     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(04)74176-4     Document Type: Article

References (32)

1. Banville, D. L., L. G. Marzilli, J. A. Strickland, and W. D. Wilson. 1986. Comparison of the effects of cationic porphyrins on DNA properties: influence of GC content of native and synthetic-polymers. Biopolymers. 25:1837-1858.
2. Carvlin, M. J., N. Datta-Gupta, and R. J. Fiel. 1982. Circular dichroism spectroscopy of a cationic porphyrin bound to DNA. Biochem. Biophys. Res. Commun. 108:66-73.
3. Carvlin, M. J., and R. J. Fiel. 1983. Intercalative and nonintercalative binding of large cationic porphyrin ligands to calf thymus DNA. Nucleic Acids Res. 11:6121-6139.
4. 2+ with poly(dT*dA-dT) triplex. Ligand size effect on third-strand stabilization. Biochemistry. 36:214-223.
5. Eimer, T., and B. Nordén. 1995. Intercalative interaction of ethidium dyes with triplex structure. Bioorg. Med. Chem. 3:701-711.
6. Fiel, R. J. 1989. Porphyrin-nucleic acid interactions: a review. J. Biomol. Struct. Dyn. 6:1259-1274.
7. Gibbs, E. J., I. Tinoco, Jr., M. F. Maestre, P. A. Ellinas, and R. F. Pasternack. 1988. Self-assembly of porphyrins on nucleic acid templates. Biochem. Biophys. Res. Commun. 157:350-358.
8. Guliaev, A. B., and N. B. Leontis. 1999. Cationic 5,10,15,20-tetrakis(N-methylpyridinium-4-yl)porphyrin fully intercalates at 5′-CG-3′ steps of duplex DNA in solution. Biochemistry. 38:15425-15437.
9. Ismail, M. A., P. M. Rodger, and A. Rodger. 2000. Drug self-assembly on DNA: sequence effects with trans-bis(4-N-methylpyridiniumyl)diphenyl porphyrin and Hoechst. 33258. J. Biomol. Struct. Dyn. Conversation. 11:335-348.
10. 2] studied by CD, LD, and normal absorption. Biochemistry. 35:1187-1194.
11. Kim, S. K., and B. Nordén. 1993. Methyl green: a DNA major-groove binding drug. FEBS Lett. 315:61-64.
12. Kim, S. K., J. S. Sun, T. Garestier, C. Hélène, C. H. Nguyen, E. Bisagni, A. Rodger, and B. Nordén. 1997. Binding geometries of triple helix selective benzopyrido[4,3b]indole ligands complexed with dobble- and triple-helical polynucleotides. Biopolymers. 42:101-111.
13. Kuroda, R., and H. Tanaka. 1994. DNA-porphyrin interactions probed by induced CD spectroscopy. J. Chem. Soc. Chem. Commun. 1575-1576.
14. LeDoan, T., C. Perrouault, M. Chassignol, N. T. Thung, and C. Hélène. 1987. Sequence-targeted chemical modifications of nucleic acids by complementary oligonucleotides covalently linked to porphyrins. Nucleic Acids Res. 15:8643-8659.
15. 2TMPyP bound to various synthetic polynucleotides. Biophys. Chem. 92:35-45.
16. Lee, S., Y. A. Lee, H. M. Lee, J. Y. Lee, D. H. Kim, and S. K. Kim. 2002a. Rotation of periphery methylpyridine of meso-tetrakis(n-N-methylpyridiniumyl)porphyrin (n = 2,3,4) and its selective binding to native and synthetic DNAs. Biophys. J. 83:371-381.
17. 2] on the porphyrin-DNA interaction. J. Phys. Chem. B. 106:11351-11355.
18. Lipscomb, L. A., F. X. Zhou, S. R. Presnell, R. J. Woo, M. E. Peek, R. R. Plaskon, and L. D. Williams. 1996. Structure of a DNA-porphyrin complex. Biochemistry. 35:2818-2823.
19. Marzilli, L. G. 1990. Medical aspects of DNA-porphyrin interactions. New J. Chem. 14:409-420.
20. Marzilli, L. G., L. D. Banville, G. Zon, and W. D. Wilson. 1986. Pronounced H-I and P-31 NMR spectral changes on meso-tetrakis(N-methylpyridmium-4-yl)porphyrin binding to poly [d(G-C)]·poly [d(G-C)] and to 3-tetradecaoligodeoxyribonucleotides: evidence for symmetric, selective binding to 5′CG3′ sequences. J. Am. Chem. Soc. 108:4188-4192.
21. Marzilli, L. G., G. Pethö, M. Kin, M. S. Kim, and D. W. Dixon. 1992. Tentacle porphyrins: DNA interactions. J. Am. Chem. Soc. 114:7575-7577.
22. Mukundan, N. E., G. Pethö, D. W. Dixon, M. S. Kim, and L. G. Marzilli. 1994. Interactions of an electron-rich tetracationic, tentacle porphyrin with calf thymus DNA. Inorg. Chem. 33:4676-4687.
23. Mukundan, N. E., G. Pethö, D. W. Dixon, and L. G. Marzilli. 1995. DNA-tentacle porphyrin interactions: AT over GC selectivity exhibited by an outside binding self-stacking porphyrin. Inorg. Chem. 34:3677-3687.
24. Pastemack, R. F., C. Bustamante, P. J. Collings, A. Giannetto, and E. J. Gibbs. 1993. Porphyrin assemblies on DNA as studied by a resonance light-scattering technique. J. Am. Chem. Soc. 115:5393-5399.
25. Pastemack, R. F., S. Ewen, A. Rao, A. S. Meyer, M. A. Freedman, P. J. Collings, S. L. Frey, M. C. Ranen, and J. C. de Paula. 2001. Interaction of copper(II) porphyrins with DNA. Inorg. Chim. Acta. 317:59-71.
26. Pastemack, R. F., A. Giannetto, P. Pagano, and E. J. Gibbs. 1991. Self-assembly of porphyrin on nucleic acids and polypeptides. J. Am. Chem. Soc. 113:7799-7800.
27. Pastemack, R. F., and E. J. Gibbs. 1996. Porphyrin and metalloporphyrin interactions with nucleic acids. In Metal Ions in Biological Systems 33. Probing of Nucleic Acids by Metal Complexes of Small Molecules. A. Sigel and H. Sigel, editors. Marcel Dekker, New York. 367-397.
28. Pastemack, R. F., J. I. Goldsmith, and E. J. Gobbs. 1998. A spectroscopic and thermodynamic study of porphyrin/DNA supramolecular assemblies. Biophys. J. 75:1024-1031.
29. Schneider, H. J., and M. Wang. 1994. DNA interactions with porphyrins bearing ammonium side chains. J. Org. Chem. 59:7473-7478.
30. Sehlstedt, U., S. K. Kim, P. Carter, J. Goodisman, J. F. Vollano, B. Nordén, and J. C. Dabrowiak. 1994. Interaction of cationic porphyrins with DNA. Biochemistry. 33:417-426.
31. Strickland, J. A., L. G. Marzilli, and W. D. Wilson. 1990. Binding of mesotetrakis(N-methylpyridiniumyl)porphyrin isomers to DNA: quantitative comparison of the influence of charge distribution and copper(II) derivatization. Biopolymers. 29:1307-1323.
32. 2]. Biophys. Chem. 70:1-10.