Tricationic pyridium porphyrins appending different peripheral substituents: Experimental and DFT studies on their interactions with DNA

Biophysical Chemistry

Volumn 135, Issue 1-3, 2008, Pages 102-109

  Zhao, Ping ^a   Xu, Lian Cai ^a   Huang, Jin Wang ^a   Zheng, Kang Cheng ^a   Fu, Bo ^a   Yu, Han Cheng ^a   Ji, Liang Nian ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

Cationic porphyrin; DFT; DNA binding; Photocleavage

Indexed keywords

5,10,15,20 TETRAKIS(1 METHYLPYRIDINIUM 4 YL)PORPHYRIN; DNA; PORPHYRIN DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; BINDING AFFINITY; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DNA CLEAVAGE; DNA DENATURATION; FLUORESCENCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; VISCOSITY;

BINDING, COMPETITIVE; CIRCULAR DICHROISM; COMPUTER SIMULATION; DNA; MOLECULAR STRUCTURE; NUCLEIC ACID DENATURATION; PHOTOLYSIS; PORPHYRINS; PYRIDINES; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE; TEMPERATURE; VISCOSITY;

EID: 43049148987     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2008.03.013     Document Type: Article

References (50)

1. Hambright P., and Fleicher E.B. The acid-base equilibria, kinetics of copper ion incorporation, and acid-catalyzed zinc ion displacement from the water-soluble porphyrin α, β, γ, δ-tetra(4-N-methylpyridyl)porphine. Inorg. Chem. 9 (1970) 1757-1761
2. Fiel R.J., Howard J.C., Mark E.H., and Gupta N.D. Interaction of DNA with a porphyrin ligand: evidence for intercalation. Nucleic Acids Res. 6 (1979) 3093-3118
3. Mauro E.D., Saladino R., Tagliatesta P., Sanctis V.D., and Negri R. Manganese water-soluble porphyrin senses DNA conformation. J. Mol. Biol. 282 (1998) 43-57
4. Pogozelski W.K., and Tullius T.D. Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98 (1998) 1089-1108
5. Burrows C.J., and Muller J.G. Oxidative strand scission of nucleic acids: routes initiated by hydrogen abstraction from the sugar moiety. Chem. Rev. 98 (1998) 1109-1152
6. Sirish M., and Scheider H.J. Porphyrin derivatives as water-soluble receptors for peptides. Chem. Commun. 10 (1999) 907-908
7. Haq I., Trent J.O., Chowdhry B.Z., and Jenkins T.C. Intercalative G-tetraplex stabilization of telomeric DNA by a cationic Porphyrin. J. Am. Chem. Soc. 121 (1999) 1768-1779
8. Hurley L.H., Wheelhouse R.T., Sun D., Kerwin S.M., Salazar M., Fedoroff O.Y., Han F.X., Han H., Izbicka E., and Von Hoff D.D. G-quadruplexes as targets for drug design. Pharmacol. Ther. 85 (2000) 141-158
9. Pasternack R.F., Gibbs E.J., Gaudemer A., Antebi A., Bassner S., Poy L.D., Turner D.H., Williams A., Laplace F., Lansard M.H., Merienne C., and Fauvet M.P. Molecular complexes of nucleosides and nucleotides with a monomeric cationic porphyrin and some of its metal derivatives. J. Am. Chem. Soc. 107 (1985) 8179-8186
10. Uno T., Hamasaki K., Tanigawa M., and Shimabayashi S. Binding of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin to double helical RNA and DNA / RNA hybrids. Inorg. Chem. 36 (1997) 1676-1683
11. Armitage B. Photocleavage of nucleic acids. Chem. Rev. 98 (1998) 1171-1200
12. Guliaev A.B., and Leontis N.B. 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 (1999) 15425-15437
13. Ohyama T., Mita H., and Yamamoto Y. Binding of 5,10,15,20-tetrakis(N-methylpyridinium-4-yl)-21H,23H-porphyrin to an AT-Rich Region of a Duplex DNA. Biophys. Chemist. 113 (2005) 53-59
14. Pasternack R.F., Gibbs E.J., and Villafrancas J.J. Interactions of porphyrins with nucleic acids. Biochemistry 22 (1983) 2406-2414
15. Ishkava Y., Yamashita A., and Uno T. Efficient photocleavage of DNA by cationic porphyrin-acridine hybrids with the effective length of diamino alkyl linkage. Chem. Pharm. Bull. 49 3 (2001) 287-293
16. Deng Y., Chang C.K., and Nocera D.G. Facile synthesis of β-derivatized porphyrins-structural characterization of a β ± β-bis-porphyrin. Angew. Chem., Int. Ed. 39 (2000) 1066-1068
17. Kim J.O., Lee Y.A., Jin B., Park T., Song R., and Kim S.K. Binding mode of cationic monomer and dimer porphyrin with native and synthetic polynucleotides studied by polarized light spectroscopy. Biophys. Chem. 111 (2004) 63-71
18. Wu S., Li Z., Ren L.G., Chen B., Liang F., Zhou X., Jia T., and Cao X.P. Dicationic pyridium porphyrins appending different peripheral substituents: synthesis and studies for their interactions with DNA. Bioorg. Med. Chem. 14 (2006) 2956-2965
19. Li H.D., Fedorova O.S., Grachev A.N., Trumble W.R., Bohach G.A., and Czuchajowski L. A series of meso-tris N-methyl-pyridiniumyl-4-alkylamidophenyl porphyrins: synthesis, interaction with DNA and antibacterial activity. Biochim. Biophys. Acta 1354 (1997) 252-260
20. Jia T., Jiang Z.X., Wang K., and Li Z.Y. Binding and photocleavage of cationic porphyrin-phenylpiperazine hybrids to DNA. Biophys. Chem. 119 (2006) 295-302
21. Zhao P., Xu L.C., Huang J.W., Zheng K.C., Liu J., Yu H.C., and Ji L.N. DNA binding and photocleavage properties of a novel cationic porphyrin-anthraquinone hybrid. Biophys. Chem. 134 (2008) 72-83
22. Kurita N., and Kobayashi K. Density functional MO calculation for stacked DNA base-pairs with backbones. Comput. Chem. 24 (2000) 351-357
23. 2+ with DFT method. J. Phys. Chem., A. 105 (2001) 10899-10905
24. 2L](L = o-hpip, m-hpip and p-hpip). Dalton Trans. 7 (2003) 1352-1359
25. 2,OH,H and F). J. Mol. Struct. (Theochem) 637 (2003) 195-203
26. Xu H., Zheng K.C., Deng H., Lin L.J., Zhang Q.L., and Ji L.N. Effects of the ancillary ligands of polypyridyl ruthenium(II) complexes on the DNA-binding behaviors. New J. Chem. 27 (2003) 1255-1263
27. Adler A.D., Longo F.R., Finarelli J.D., Goldmacher J., and Assour K.J. A simplified synthesis for meso-tetraphenylporphine. J. Org. Chem. 32 (1967) 476-477
28. Reichmann M.E., Rice S.A., Thomas C.A., and Doty P. A further examination of the molecular weight and size of desoxypentose nucleic acid. J. Am. Chem. Soc. 76 (1954) 3047-3053
29. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision D.01 (2005), Gaussian, Inc., Wallingford CT
30. Masaaki T., Ashish K.S., and Elvis N. Enhanced conformational changes in DNA in the presence of mercury(II), cadmium(II) and lead(II) porphyrins. J. Inorg. Biochem. 94 (2003) 50-58
31. Sari M.A., Battioni J.P., Dupre D., Mansuy D., and Lepecq J.B. Interaction of cationic porphyrins with DNA: importance of the number and position of the charges and minimum structural requirements for intercalation. Biochemistry 29 (1990) 4205-4215
32. Mukundan N.E., Petho G., Dixon D.W., Kim M.S., and Marzilli L.G. Interactions of an electron-rich tetracationic tentacle porphyrin with calf thymus DNA. Inorg. Chem. 33 (1994) 4676-4687
33. Nyarko E., Hanada N., Habib A., and Tabata M. Fluorescence and phosphorescence spectra of Au(III), Pt(II) and Pd(II) porphyrins with DNA at room temperature. Inorg. Chim. Acta 357 (2004) 739-745
34. Masaaki T., Ashish K.S., and Elvis N. Enhanced conformational changes in DNA in the presence of mercury(II), cadmium(II) and lead(II) porphyrins. J. Inorg. Biochem. 94 (2003) 50-58
35. Kelly J.M., Tossi A.B., McConell D.J., and OhUigin C. A study of the interactions of some polypyridylruthenium(II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation. Nucl. Acids Res. 13 (1985) 6017-6034
36. Uno T., Hamasaki K., Tanigawa M., and Shinabayashi S. Binding of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin to double helical RNA and DNA•RNA hybrids. Inorg. Chem. 36 (1997) 1676-1683
37. Kuroda R. H. Tanaka. DNA-porphyrin interactions probed by induced CD spectroscopy. J. Chem. Soc., Chem. Commun. 13 (1994) 1575-1576
38. Nyarko E., and Tabata M. Interactions of tetracationic mercury(II), cadmium(II) and lead(II) porphyrins with DNA and their effects on DNA cleavage. J. Porphyr. Phthalocyanines 5 (2001) 873-880
39. Daryono H.T., Shunsuke M., Takehiro A., Naoki Y., and Hidenari I. Interaction of metallopyrazoliumylporphyrins with calf thymus DNA. J. Inorg. Biochem. 85 (2001) 219-228
40. Satyanarayana S., Dabrowiak J.C., and Chaires J.B. Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: mode and specificity of binding. Biochemistry 32 (1993) 2573-2584
41. In: Bloomfield V.A., Crothers D.M., and Tinoko Jr. I. (Eds). Nucleic Acids: Structures, Properties, and Functions (2000), University Science Books, California 535-596 Chapter 11
42. Fleming I. Frontier Orbital and Organic Chemical Reaction (1976), Wiley, New York
43. Barton J.K., and Raphael A.L. Photoactivated stereospecific cleavage of double-helical DNA by cobalt(III) complexes. J. Am. Chem. Soc. 106 (1984) 2466-2468
44. Dougherty T.J., Gomer C.J., Henderson B.W., Jori G., Kessel D., Korbelik M., Moan J., and Peng Q. Photodynamic therapy. J Natl Cancer Inst. 90 (1998) 889-905
45. Sternberg E.D., Dolphin D., and Bruckner C. Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron 54 (1998) 4151-4202
46. Bonnett R. Chemical Aspects of Photodynamic Therapy (2000), Gordon and Breach Science, Amsterdam
47. Mettath S., Munson B.R., and Pandey R.K. DNA interaction and photocleavage properties of porphyrins containing cationic substituents at the peripheral position. Bioconjug. Chem. 10 (1999) 94-102
48. Armitage B. Photocleavage of nucleic acids. Chem. Rev. 98 (1998) 1171-1200
49. Chatterjee S.R., Srivastava T.S., Kamat J.P., and Devasagayam T.P.A. Photocleavage of plasmid pBR322 DNA by some anionic porphyrins. J. Porphyr. Phthalocyanines 2 (1998) 337-343
50. Taima H., Okubo A., Yoshioka N., and Inoue H. DNA-binding properties and photocleavage activity of cationic water-soluble chlorophyll derivatives. Chem. Eur. J. 12 (2006) 6331-6340