Study on Photosensitive Oxidation Ability of Metallophthalocyanines on Tryptophan

doi:10.7517/j.issn.1674-0475.2012.02.124

Abstract

Abstract: Phthalocyanines are promising photosensitizers for application in PDT. The mechanism of the therapeutic and biological effects induced by them has been the hot topic of research on PDT. Tryptophan was choosed as a target molecule which reacted with metallophthalocyanines substituted with quinolinoxy groups, to discuss the relationship between structure and photosensitive oxidation ability. The results show that photo-oxidizing ability of phthalocyanines was influenced by the central metal ion, the structure of substitutional group, the substituent position and the number of substitutional group. Phthalocyanines with closed-shell electronic structure central metallic ion, rich substituents and substituted in α position, exibit higher photosensitive oxidation ability. This study can offer some guidance for the design of new photosensitizers.

Key words: quinolinoxy, metallophthalocyanines, photosensitive oxidation, tryptophan

CLC Number:

O611
O614

LIU Hong, ZHENG Ke, LI Jun, CAI Li-xuan, FANG Yu-ting, XUE Jin-ping. Study on Photosensitive Oxidation Ability of Metallophthalocyanines on Tryptophan[J]. Imaging Science and Photochemistry, 2012, 30(2): 124-128.

References

[1] Serra A, Pineiro M, Pereira N, et al. A look at clinical applications and developments of photodynamic therapy[J]. Oncol.Rev., 2008, 2(4):235-249.
[2] Rosenthal I, Kriahna C M, et al. The role of molecular oxygen in the photodynamic effect of phthalocyanines[J]. Radiat. Res., 1986, 107(1):136-142.
[3] Tang N L, Peng J Y. Determination of proteins with tetracarboxy manganese(II) phthalocyanine by resonance light scattering technique[J]. Spectrochim Acta A, 2008, 71(4):1246-1249.
[4] Zhong H, Wang K, Chen H Y. Protein analysis with tetra-substituted sulfonated cobalt phthalocyanine by the technique of rayleigh light scattering[J].Anal. Biochem., 2004, 330(1):37-42.
[5] a. Langlots R, Ali H, van Lier J E, et al. Biological activities of phthalocyanines-IV. type II sensitized photooxidation of L-tryptophan and cholesterol by sulfonated metallo phthalocyanines[J]. Photochem. Photobiol.,1986, 44(2): 117-123. b. Wagner J R, Ali H, Langlois R, et al. Biological activities of phthalocyanines VI:photooxidation of L-tryptophan by selectively sulfonated gallium phthalocyanines:singlet oxygen yields and effect of aggregation[J]. Photochem. Photobiol., 1987,45(5): 587-594.
[6] 董润安,邱勇,宋心琦.磺化铝酞菁对甘氨酰-L-色氨酸的光敏化氧化[J].科学通报,1997,42(22):2402-2405. Dong R A, Qiu Y, Song X Q. Photosensitive oxidation of sulphonated aluminum phthalocyanine on glycyl -L- tryptophan [J].Chinese Science Bulletin, 1997, 42(22):2402-2405.
[7] 魏彦,陈伟,王玉,等. 两亲性酞菁锌对人体肝癌细胞的光灭活作用[J].影像科学与光化学,2010, 28(5): 362-367. Wei Y, Chen W, Wang Y, et al. Photoinhibition on liver cancer cell of amphiphilic phthalocyanine zinc[J]. Imaging Science and Photochemistry, 2010, 28(5): 362-367.
[8] 吴世康,汪鹏飞. 有机-过渡金属配合物的三重态发光问题[J].影像科学与光化学,2011, 29(2): 81-98. Wu S K, Wang P F. The organic-transition metal complex and the emission of triplet states[J]. Imaging Science and Photochemistry, 2011, 29(2): 81-98.
[9] 沈淑引,刘恺,张先付,周庆复,许慧君.烷氧基取代金属酞菁的合成和在有机溶液中聚集性质的研究[J].感光科学与光化学,1993,11(4):366-370. Shen S Y, Liu K, Zhang X F, Zhou Q F, Xu H J. Aggregation of copper-phthalocyanines with different alkoxy chains in organic solution[J].Photographic Science and Photochemistry,1993,11(4):366-370.
[10] 黄金陵,黄剑东,刘尔生,等.酞菁配合物的结构与其光动力抗癌活性[J]. 物理化学学报,2001,17(7):662-671. Huang J L, Huang J D, Liu E S, et al.Some relationships between structures and photodynamic anti-cancer activities of phthalocyanines[J]. Acta Phys.Chim.Sin., 2001, 17(7):662-671.
[11] Ogunsipe A, Nyokong T. Effects of central metal on the photophysical and photochemical properties of non-transition metal sulfophthalocyanine[J].J. Porphyrins Phthalocyanines, 2005, 9(2):121-129.