Binding of cationic bis-porphyrins linked with p- or m-xylylenediamine and their zinc(II) complexes to duplex DNA

Molecules

Volumn 13, Issue 12, 2008, Pages 3117-3128

  Ishikawa, Yoshinobu ^a   Yamakawa, Naoki ^b   Uno, Tadayuki ^c  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

Binding mode; Circular dichroism; Distamycin; DNA; Molecular docking simulation; Porphyrin; Viscometry; Zinc, titration

Indexed keywords

1,3 XYLENEDIAMINE; 1,3-XYLENEDIAMINE; CATION; HETERODUPLEX; METALLOPORPHYRIN; XYLENE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; SPECTROSCOPY; VISCOSITY;

CATIONS; CIRCULAR DICHROISM; METALLOPORPHYRINS; MODELS, MOLECULAR; NUCLEIC ACID HETERODUPLEXES; SPECTRUM ANALYSIS; VISCOSITY; XYLENES; ZINC;

EID: 58149229450     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13123117     Document Type: Article

References (24)

1. Pasternack, R.F.; Gibbs, E.J. Porphyrin and metalloporphyrin interactions with nucleic acids. Met Ions Biol. Syst. 1996, 33, 367-397.
2. Pratviel, G.; Bernadou, J.; Meunier, B. Selective DNA cleavage by metalloporphyrin derivatives. Met. Ions Biol. Syst. 1996, 33, 399-426.
3. Uno, T.; Hamasaki, K.; Tanigawa, M.; Shimabayashi, S. Binding of meso-Tetrakis(N-methylpyridinium-4-yl)porphyrin to Double Helical RNA and DNA·;RNA Hybrids. Inorg. Chem. 1997, 36, 1676-1683.
4. Kim, J.O.; Lee, Y.A.; Yun. B.H.; Han, S.W.; Kwag, S.T.; Kim, S.K. Binding of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin to AT oligomers: effect of chain length and the location of the porphyrin stacking. Biophys. J. 2004, 86, 1012-1017.
5. Evans, S.E.; Mendez, M.A.; Turner, K.B.; Keating, L.R.; Grimes, R.T.; Melchoir, S.; Szalai, V.A. End-stacking of copper cationic porphyrins on parallel-stranded guanine quadruplexes. J. Biol. Inorg. Chem. 2007, 12, 1235-1249.
6. Han, H.; Langley, D.R.; Rangan, A.; Hurley, L.H. Selective interactions of cationic porphyrins with G-quadruplex structures. J. Am. Chem. Soc. 2001, 123, 8902-1893.
7. Yamashita, T.; Uno, T.; Ishikawa, Y. Stabilization of guanine quadruplex DNA by the binding of porphyrins with cationic side arms. Bioorg. Med. Chem. 2005, 13, 2423-2430.
8. Seenisamy, J.; Rezler, E.M.; Powell, T.J.; Tye, D.; Gokhale, V.; Joshi, C.S.; Siddiqui-Jain, A.; Hurley, L.H. The dynamic character of the G-quadruplex element in the c-MYC promoter and modification by TMPyP4. J. Am. Chem. Soc. 2004, 126, 8702-8709.
9. Ohyama, T.; Mita, H.; 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. Chem. 2005, 113, 53-59.
10. Park, T.G.; Ko, J.H.; Ryoo, A.Y.; Kim, J.M.; Cho, D.W.; Kim, S.K. Binding modes of V(=O)meso-tetrakis(N-methylpyridinium-4-yl)porphyrin to various synthetic DNAs studied by polarized spectroscopy. Biochim. Biophys. Acta 2006, 1760, 388-394.
11. 10. Biopolymers 2007, 85, 349-358.
12. Uno, T.; Aoki, K.; Shikimi, T.; Hiranuma, Y.; Tomisugi, Y.; Ishikawa, Y. Copper insertion facilitates water-soluble porphyrin binding to rA·rU and rA·dT base pairs in duplex RNA and RNA·DNA hybrids. Biochemistry 2002, 41, 13059-13066.
13. Ishikawa, Y.; Yamashita, A.; Uno, T. Efficient photocleavage of DNA by cationic porphyrinacridine hybrids with the effective length of diamino alkyl linkage. Chem. Pharm. Bull. 2001, 49, 287-293.
14. Yamakawa, N.; Ishikawa, Y.; Uno, T. Solution properties and photonuclease activity of cationic bis-porphyrins linked with a series of aliphatic diamines. Chem. Pharm. Bull. 2001, 49, 1531-1540.
15. Ishikawa, Y.; Yamakawa, N.; Uno, T. Potent DNA photocleavage by zinc(II) complexes of cationic bis-porphyrins linked with aliphatic diamine. Bioorg. Med. Chem. 2002, 10, 1953-1960.
16. Aoki, K.; Ishikawa, Y.; Oyama, M.; Tomisugi, Y.; Uno, T. Self-aggregation inhibits the photonuclease activity of porphyrins. Chem. Pharm. Bull. 2003, 51, 899-903.
17. Villanueva, A.; Caggiari, L.; Jori, G.; Milanesi, C. Morphological aspects of an experimental tumour photosensitized with a meso-substituted cationic porphyrin. J. Photochem. Photobiol. B. 1994, 23, 49-56.
18. Mikami-Terao, Y.; Akiyama, M.; Yuza, Y.; Yanagisawa,T.; Yamada, O.; Yamada, H. Antitumor activity of G-quadruplex-interactive agent TMPyP4 in K562 leukemic cells. Cancer Lett. 2008, 261, 226-234.
19. Ishikawa, Y.; Yamakawa, N.; Uno, T. Synthetic control of interchromophoric interaction in cationic bis-porphyrins toward efficient DNA photocleavage and singlet oxygen production in aqueous solution. Bioorg. Med. Chem. 2007, 15, 5230-5238.
20. Coll, M.; Frederick, C.A.; Wang, A.H.; Rich, A. A bifurcated hydrogen-bonded conformation in the d(A·T) base pairs of the DNA dodecamer d(CGCAAATTTGCG) and its complex with distamycin. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8385-8389.
21. MOE (Molecular Operating Environment), version 2005.04; Chemical Computing Group Inc.: Montreal, Quebec, Canada, 2005.
22. Tjahjono, D.H.; Akutsu, T.; Yoshioka, N.; Inoue, H. Cationic porphyrins bearing diazolium rings: synthesis and their interaction with calf thymus DNA. Biochim. Biophys. Acta 1999, 1472, 333-343.
23. Kuroda, R.; Tanaka, H. DNA-porphyrin interactions probed by induced CD spectroscopy. J. Chem. Soc. Chem Commun. 1994, 13, 1575-1576.
24. Pabo, C.O.; Sauer, R.T. Protein-DNA recognition. Annu. Rev. Biochem. 1984, 53, 293-321.