Binding and photocleavage of cationic porphyrin-phenylpiperazine hybrids to DNA

Biophysical Chemistry

Volumn 119, Issue 3, 2006, Pages 295-302

  Jia, Tao ^a   Jiang, Zhong Xing ^a   Wang, Kai ^a,b   Li, Zao Ying ^a  

^a WUHAN UNIVERSITY   (China)

^b WUHAN INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Apparent affinity binding constant; Cationic porphyrin; Intercalation; Phenylpiperazine; Photocleavage

Indexed keywords

5 (4 CARBOXYPHENYL) 10,15,20 TRIS(4 PYRIDYL)PORPHYRIN; 5 (4 METHOXYCARBONYLPHENYL) 10,15,20 TRIS(4 PYRIDYL)PORPHYRIN; 5,10 BIS(4 CARBOXYPHENYL) 15,20 BIS(4 PYRIDYL)PORPHYRIN; 5,10 BIS(4 METHOXYCARBONYLPHENYL) 15,20 BIS(4 PYRIDYL)PORPHYRIN; CATION; DNA; ETHIDIUM BROMIDE; PHENYLPIPERAZINE; PIPERAZINE DERIVATIVE; PLASMID DNA; PORPHYRIN DERIVATIVE; SODIUM AZIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL INTERACTION; DNA BINDING; DNA CLEAVAGE; INTERCALATION COMPLEX; PHOTODEGRADATION; PRIORITY JOURNAL;

ANIMALS; BINDING, COMPETITIVE; CATIONS; CATTLE; CHIMERA; CIRCULAR DICHROISM; DNA; ETHIDIUM; FLUORESCENCE; INDICATORS AND REAGENTS; INTERCALATING AGENTS; KINETICS; LIGHT; MOLECULAR STRUCTURE; PIPERAZINES; PLASMIDS; PORPHYRINS; SODIUM AZIDE; SPECTROMETRY, FLUORESCENCE; ULTRAVIOLET RAYS;

EID: 32044475065     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2005.09.025     Document Type: Article

References (24)

1. L.G. Marzilli Medical aspects of DNA-porphyrin interaction New J. Chem. 14 1990 409 420
2. T. Uno, K. Hamasaki, M. Tannigawa, and S. Shimabayashi Binding of meso-tetrakis(N-methylpyridinium-4-yl) porphyrin to double helical RNA and DNA • RNA hybrids Inorg. Chem. 36 1997 1676 1683
3. R.F. Pasternack, E.J. Gibbs, and J.J. Villafranca Interactions of porphyrins with nucleic acids Biochemistry 22 1983 2406 2414
4. T. Ohyama, H. Mita, and Y. Yamamoto 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
5. J.-O. Kim, Y.-A. Lee, B. Jin, T. Park, R. Song, and S.K. Kim Binding mode of cationic monomer and dimer porphyrin with native and synthetic polynucleotides studied by polarized light spectroscopy Biophys. Chemist. 111 2004 63 71
6. Y. Ishikawa, A. Yamashita, and T. Uno Efficient photocleavage of DNA by cationic porphyrin-acridine hybrids with the effective length of diamino alkyl linkage Chem. Pharm. Bull. 49 2001 287 293
7. L. Ding, C. Casas, G. Etemad-Moghadam, and B. Meunier Synthesis of water-soluble, cationic functionalized metalloporphyrins having a cytotoxic activity New J. Chem. 14 1990 421 431
8. G.R. Clark, C.J. Squire, E.J. Gray, W. Leupin, and S. Neidle Designer DNA-binding drugs: the crystal structure of a meta-hydroxy analog of Hoechst 33258 bound to d(CGCGAATTCGCG)2 Nucleic Acids Res. 24 1996 4882 4889
9. A.L. Satz, C.M. White, T.A. Beerman, and T.C. Bruice Double-stranded DNA binding characteristics and subcellular distribution of a minor groove binding diphenyl ether bisbenzimidazole Biochemistry 40 2001 6465 6474
10. T.D. Ros, G. Spalluto, A.S. Boutorine, R.V. Bensasson, and M. Prato DNA-photocleavage agents Curr. Pharm. Des. 7 2001 1781 1821
11. M.A. Sari, J.P. Battioni, D. Dupre, D. Mansuy, and J.B. Lepecq 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
12. B.H. Yun, S.H. Jeon, T.-S. Cho, S.Y. Yi, U. Sehlstedt, and S.K. Kim Binding mode of porphyrins to poly[d(A-T)] and poly[d(G-C)] Biophys. Chemist. 70 1998 1 10
13. A.D. Adler, F.R. Longo, J.D. Finarelli, J. Goldmacher, and K.J. Assour A simplified synthesis for meso-tetraphenylporphine J. Org. Chem. 32 1967 476
14. J.B. LePecq, and C. Paoletti A fluorescent complex between ethidium bromide and nucleic acids, physical-chemical characterization J. Mol. Biol. 27 1967 87 106
15. S. Mashiko, N. Suzuki, S. Koga, M. Nakano, T. Goto, T. Ashino, I. Muzumoto, and H. Inaba Measurement of rate constants for quenching singlet oxygen with a Cypridina luciferin analog (2-methyl-6-[p-methylphenyl]- 3,7-dihydroimidazo[1,2-al]pyrazin-3-one) and sodium azide J. Biolumin. Chemilumin. 6 1991 69 72
16. S.R. Chatterjee, S.J. Shetty, T.P.A. Devasagayam, and T.S. Srivastava Photocleavage of plasmid DNA by the porphyrin meso-tetrakis[4- (carboxymethyleneoxy)phenyl]porphyrin J. Photochem. Photobiol., B Biol. 41 1997 128 135
17. R.J. Fiel, J.C. Howard, E.H. Mark, and N.D. Gupta Interaction of DNA with a porphyrin ligand: evidence for intercalation Nucleic Acids Res. 6 1979 3093 3118
18. G. Dougherty, J.R. Pilbrow, A. Skorobogaty, and T.D. Smith Electron spin resonance spectroscopic and spectrophotometric investigation of the binding of tetracationic porphyrins and porphyrazines with calf thymus DNA J. Chem. Soc., Faraday Trans. 2 81 1985 1739 1759
19. M.J. Carvlin, and R.J. Fiel Intercalative and nonintercalative binding of large cationic porphyrin ligands to calf thymus DNA Nucleic Acids Res. 11 1983 6121 6139
20. X.-D. Chen, and M.H. Liu Induced chirality of binary aggregates of oppositely charged water-soluble porphyrins on DNA matrix J. Inorg. Biochem. 94 2003 106 113
21. S. Lee, S.H. Jeon, B.-J. Kim, S.W. Han, H.G. Jang, and S.K. Kim Classification of CD and absorption spectra in the Soret band of H2TMPyP bound to various synthetic polynucleotides Biophys. Chemist. 92 2001 35 45
22. T. Masaaki, K.S. Ashish, and N. Elvis Enhanced conformational changes in DNA in the presence of mercury(II), cadmium(II) and lead(II) porphyrins J. Inorg. Biochem. 94 2003 50 58
23. U. Sehlstedt, S.K. Kim, P. Carter, J. Goodisman, J.F. Vollano, B. Norden, and J.C. Dabrowiak Interactions of cationic porphyrins with DNA Biochemistry 33 1994 417 426
24. C. OhUigin, D.J. McConnell, J.M. Kelly, and W.J.M. Van Der Putten Methylene blue photosensitized strand cleavage of DNA: effects of dye binding and oxygen Nucleic Acid Res. 15 1987 7411 7427