吩噻嗪-Corrole 镓(III)配合物的合成、荧光及其光断裂DNA性质

doi:10.3866/PKU.WHXB201111291

Abstract

Abstract: Phenothiazine (PTZ)-corrole dyads 1-3 and their gallium(III) complexes 4-6 have been synthesized and characterized. The steady-state absorption and emission spectra and the time-resolved fluorescence decay profiles have been measured in toluene. The radiative and nonradiative rate constants have been obtained from the fluorescence quantum yields and monoexponential fluorescence lifetimes. The absorption spectra revealed that the gallium(III) corrole dyads exhibit stronger Soret bands and Q bands than free base corrole dyads. The fluorescence quantum yields of 1-3 are 0.156, 0.134, and 0.139, and the radiative rate constants are 4.02×10⁷, 3.47×10⁷, and 2.89×10⁷ s^-1, respectively. The fluorescence quantum yields of 4-6 are 0.502, 0.443, and 0.494, and the radiative rate constants are 20.9×10⁷, 16.78×10⁷, and 21.11×10⁷ s^-1, which are obviously higher than those of the corresponding free base corroles. The lifetimes of 4-6 are 2.40, 2.64, and 2.34 ns, respectively, which are somewhat shorter than those of the corresponding free base corroles. Agarose gel electrophoresis shows that these gallium(III) corrole dyads could cleave supercoiled DNA (form I) to give nicked-circular DNA (form II) under irradiation.

Key words: Corrole, Phenothiazine, Gallium(III), Fluorescence, DNA

MSC2000:

O644

SHI Lei, JIANG Huan-Feng, YIN Wei, WANG Hua-Hua, WANG Hui, ZHANG Lei, JI Liang-Nian, LIU Hai-Yang. Synthesis, Fluorescence and DNA Photocleavage Activity of Phenothiazine-Corrole Gallium(III) Complexes[J].Acta Phys. -Chim. Sin., 2012, 28(02): 465-469.

References

(1) Fang, H. F.; Ling, Z.; Brothers, J. P.; Fu, X. F. Chem. Commun. 2011, 47, 11677.

(2) Nigel-Etinger, I.; Mahammed, A.; Gross, Z. Catal. Sci. Technology 2011, 1 (4), 578.
(3) Zhai, Q. Q.; Xu, L.; Ge, Y. S.; Tian, T.;Wu,W. D.; Yan, S. Y.; Zhou, Y. Y.; Deng, M. G.; Liu, Y.; Zhou, X. Chem. Eur. J. 2011, 17 (32), 8890.
(4) Aviv, I.; Gross, Z. Chem. Commun. 2007, 1987 and references therein.
(5) Liu, H. Y.; Yam, F.; Xie, Y. T.; Li, X. Y.; Chang, C. K. J. Am. Chem. Soc. 2009, 131, 12890.

(6) Flamigni, L.; Gryko, D. T. Chem. Soc. Rev. 2009, 38, 1635.

(7) Botoshansky, M.; Palmer, J. H.; Durrell, A. C.; Gray, H. B.; Gross, Z. J. Am. Chem. Soc. 2011, 133 (33), 12899.
(8) Tasior, M.; Gryko, D. T.; Cembor, M.; Jaworski, J. S.; Venturac B.; Flamigni L. New J. Chem. 2007, 31, 247.

(9) Tasior, M.; Gryko, D. T.; Shen, J.; Kadish, K. M.; Becherer, T.; Venturac, B.; Flamigni, L. J. Phys. Chem. C 2008, 112, 19699.

(10) He, C. L.; Ren, F. L.; Zhang, X. B.; Han, Z. X. Talanta 2006, 70, 364.

(11) Ghosh, A.; Jynge, K. Chem. Eur. J. 1997, 3, 823.

(12) Simkhovich, L.; Goldberg, I.; Gross, Z. J. Inorg. Biochem. 2000, 80 (3-4), 235.
(13) Bendix, J.; Dmochowski, I. J.; Gray, H. B.; Mahammed, A.; Simkhovich, L.; Gross, Z. Angew. Chem. Int. Edit. 2000, 39 (22), 4048.
(14) Liu, X.; Mahammed, A.; Tripathy, U.; Gross, Z.; Steer, R. P. Chem. Phys. Lett. 2008, 459 (1-6), 113.
(15) Saltsman, I.; Mahammed, A.; Goldberg, I.; Tkachenko, E.; Botoshansky, M.; Gross, Z. J. Am. Chem. Soc. 2002, 124 (25), 7411.
(16) Sorasaenee, K.; Taqavi, P.; Henling, L. M.; Gray, H. B.; Tkachenko, E.; Mahammed, A.; Gross, Z. J. Porphyr. Phthalocyanines 2007, 11 (3-4), 189.
(17) Mahammed, A.; Gray, H. B.;Weaver, J. J.; Sorasaenee, K.; Gross, Z. Bioconjugate Chem. 2004, 15 (4), 738.
(18) Agadjanian, H.; Ma, J.; Rentsendorj, A.; Valluripalli, V.; Hwang, J. Y.; Mahammed, A.; Farkas, D. L.; Gray, H. B.; Gross, Z.; Medina-Kauwe, L. K. Proc. Nat. Acad. Sci. U. S. A. 2009, 106 (15), 6105.
(19) Motohashi, N. Antitumor Activities of Phenothiaiznes. In Phenothiazines and 1,4-Benzothiazines. Chemical and Biological Aspects. Bioactive Molecules. Gupta, R. R. Ed.; Elsevier: Amsterdam, 1988; Vol. 4, pp 705-770.
(20) Viola, G.; Dall'Acqua, F. Current Drug Targets 2006, 7, 1135.

(21) Shi, L.; Liu, H. Y.; Peng, K. M.;Wang, X. L.; You, L. L.; Zhang, L.;Wang, H.; Ji, L. N.; Jiang, H. F. Tetrahedron Lett. 2010, 51, 3439.

(22) Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32 (2), 476.
(23) Ghosh, A.;Wondimagegn, T.; Parusel, A. B. J. J. Am. Chem. Soc. 2000, 122, 5100.

(24) Peng, K. M.; Shao,W. L.;Wang, H. H.; Ying, X.;Wang, H.; Ji, L. N.; Liu, H. Y. Acta Phys. -Chim. Sin. 2011, 27, 199. [彭开美, 邵文莉, 汪华华, 应晓, 王惠, 计亮年, 刘海洋. 物理化学学报, 2011, 27, 199.]
(25) Gross, Z.; Galili, N.; Simkhovich, L.; Saltsman, I.; Botoshansky, M.; Bläser, D.; Boese, R.; Goldberg, I. Org. Lett. 1999, 1, 599.

(26) Kowalska, D.; Liu, X.; Tripathy, U.; Mahammed, A.; Gross, Z.; Hirayama, S.; Steer, R. P. Inorg. Chem. 2009, 48 (6), 2670.

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Synthesis, Fluorescence and DNA Photocleavage Activity of Phenothiazine-Corrole Gallium(III) Complexes

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