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Synthesis, Photophysical Properties and DNA-Binding Studies of p-Hydroxy and m-Hydroxy Amphiphilic Porphyrins
Corresponding Author(s) : Jie Zhang
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
Three p-hydroxy and m-hydroxy amphiphilic porphyrins had been synthesized and fully characterized by 1H NMR, IR and FAB-MS. Their photophysical properties were also determined. Furthermore, the UV-visible absorption and fluorescence emission titration experiments indicate that porphyrins and DNA existed an outside binding mode. In addition, the DNA binding constant of 4pOH-TPP, 3pOH-TPP and 4mOH-TPP were determined.
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References
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(a) I. Banerjee, M.P. Douaisi, D. Mondal and R.S. Kane, Nanotechnology, 23, 105101 (2012); doi:10.1088/0957-4484/23/10/105101.; (b) H.T. Guo, X.B. Pan, R.C. Mao, X. Zhang, L. Wang, X. Lu, J. Chang, J.-T. Guo, S. Passic, F.C. Krebs, B. Wigdahl, T.K. Warren, C.J. Retterer, S. Bavari, X. Xu, A. Cuconati and T.M. Block, Antimicrob. Agents Chemother., 55, 478 (2011); doi:10.1128/AAC.00989-10.; (c) K. Watanabe, S. Negi, Y. Sugiura, A. Kiriyama, A. Honbo, K. Iga, E.N. Kodama, T. Naitoh, M. Matsuoka and K. Kano, Chem. Asian J., 5, 825 (2010); doi:10.1002/asia.200900465.
(a) G.M. Yang, L.B. Liu, Q. Yang and S. Wang, Chem. Asian J., 6, 1147 (2011); doi:10.1002/asia.201000892.; (b) R.W.Y. Sun, C.K.L. Li, D.L. Ma, J.J. Yan, C.-N. Lok, C.-H. Leung, N. Zhu and C.-M. Che, Chemistry, 16, 3097 (2010); doi:10.1002/chem.200902741.
(a) M.T. Whited, P.I. Djurovich, S.T. Roberts, A.C. Durrell, C.W. Schlenker, S.E. Bradforth and M.E. Thompson, J. Am. Chem. Soc., 133, 88 (2011); doi:10.1021/ja108493b.; (b) J.R. Sommer, A.H. Shelton, A. Parthasarathy, I. Ghiviriga, J.R. Reynolds and K.S. Schanze, Chem. Mater., 23, 5296 (2011); doi:10.1021/cm202241e.; (c) S.M. Borisov, D.B. Papkovsky, G.V. Ponomarev, A.S. DeToma, R. Saf and I. Klimant, J. Photochem. Photobiol. A, 206, 87 (2009); doi:10.1016/j.jphotochem.2009.05.018.
(a) H. Imahori, S. Kang, H. Hayashi, M. Haruta, H. Kurata, S. Isoda, S.E. Canton, Y. Infahsaeng, A. Kathiravan, T. Pascher, P. Chábera, A.P. Yartsev and V. Sundström, J. Phys. Chem. A, 115, 3679 (2011); doi:10.1021/jp103747t.; (b) F. Werner, J.F. Gnichwitz, R. Marczak, E. Palomares, W. Peukert, A. Hirsch and D.M. Guldi, J. Phys. Chem. B, 114, 14671 (2010); doi:10.1021/jp102737a.; (c) P. Silviya Reeta, J. Kandhadi and G. Lingamallu, J. Kandhadi and G. Lingamallu, Tetrahedron Lett., 51, 2865 (2010); doi:10.1016/j.tetlet.2010.03.088.; (d) R.R. Lunt and V. Bulovic, Appl. Phys. Lett., 98, 113305 (2011); doi:10.1063/1.3567516.
(a) K. Andrews and D.R. McMillin, Biochemistry, 47, 1117 (2008); doi:10.1021/bi7018755.; (b) Y. Ikawa, S. Moriyama, H. Harada and H. Furuta, Org. Biomol. Chem., 6, 4157 (2008); doi:10.1039/b810171j.; (c) P. Poddutoori, P.K. Poddutoori and B.G. Maiya, J. Porphyr. Phthalocyan., 10, 1 (2006); doi:10.1142/S1088424606000028.
(a) J.S. Trommel and L.G. Marzilli, Inorg. Chem., 40, 4374 (2001); doi:10.1021/ic010232e.; (b) D.R. McMillin, A.H. Shelton, S.A. Bejune, P.E. Fanwick and R.K. Wall, Coord. Chem. Rev., 249, 1451 (2005); doi:10.1016/j.ccr.2004.11.016.
L.W. Ma, J. Moan and K. Berg, Lasers Med. Sci., 9, 127 (1994); doi:10.1007/BF02590361.
Y. Ishikawa, A. Yamashita and T. Uno, Chem. Pharm. Bull. (Tokyo), 49, 287 (2001); doi:10.1248/cpb.49.287.
(a) J.Z. Lu, W.J. Pan, R.W. He, S. Jin, X. Liao, B. Wu, P. Zhao and H. Guo, Transition Metal Chem., 37, 497 (2012); doi:10.1007/s11243-012-9615-2.; (b) P. Zhao, L.C. Xu, J.W. Huang, K.-C. Zheng, J. Liu, H.-C. Yu and L.-N. Ji, Biophys. Chem., 134, 72 (2008); doi:10.1016/j.bpc.2008.01.009.