四取代羧基酞菁锌与白蛋白共价结合物的制备与光谱性质

doi:10.3866/PKU.WHXB20100807

Abstract

Abstract:

A series of covalently bound albumin (bovine serum albumin (BSA) and human serum albumin (HSA)) conjugates of phthalocyanines functionalized with carboxyls were prepared and resulted in amide bonds. The phthalocyanines are tetra-α-(4-carboxyl phenoxy) phthalocyanine zinc (1) and tetra-α-[4-(2-carboxyl-ethyl) phenoxy] phthalocyanine zinc (3) as well as their corresponding tetra-β-substituted counterparts (compounds 2 and 4). The spectroscopic properties of these phthalocyanines and their bioconjugates in phosphate buffer saline solution (PBS) were investigated. The phthalocyanines that are covalently bound to the albumins have a more obvious monomeric absorption characteristic than the corresponding free phthalocyanines. Moreover, the spectroscopic characteristics of the phthalocyanines in the bioconjugates are not affected by solution pH. The substitution position of the carboxyl moieties on the phthalocyanine ring has an effect on the spectroscopic transformation of these macromolecules after conjugation with the albumins. Substitution at the α-position of the phthalocyanine ring leads to more prominent spectroscopic changes than that at the β-position. Both 1-albumin and 3-albumin in PBS show monomeric phthalocyanine spectra with Q-band maxima at about 697 nm and 706 nm, respectively.

Key words: Phthalocyanine, Albumin, Covalent conjugate, Spectroscopic property, Photosensitizer

MSC2000:

O644

XIAO Rong-Ping, KE Mei-Rong, HUANG Jian-Dong, ZHANG Han-Hui. Preparation and Spectroscopic Properties of Covalent Albumin Conjugates of Zinc Phthalocyanines Tetrasubstituted with Carboxyl Moieties[J].Acta Phys. -Chim. Sin., 2010, 26(08): 2274-2280.

References

[1]. Dolmans, D. E. J. G. J.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer, 2003, 3: 380
[2]. Huang, Z. Technol. Cancer Res. Treat., 2005, 4: 283
[3]. Detty, M. R.; Gibson, S. L.; Wagner, S. J. J. Med. Chem., 2004, 47 (16): 3897
[4]. Huang, J. L.; Huang, J. D.; Liu, E. S.; Chen, N. S. Acta Phys. -Chim. Sin., 2001, 17(7):662. [黄金陵, 黄剑东, 刘尔生, 陈耐生. 物理化学学报, 2001, 17(7): 662]
[5]. Yu, K. C.; Cheng, H.; Jin, L. Chinese Photograph. Sci. Photochem., 2003, 21(2):138. [俞开潮, 程红, 金玲. 感光科学与光化学, 2003, 21(2): 138]
[6]. Chen, H. W.; Chen, J. C.; Chen, N. S.; Huang, J. L.; Wang, J. D.; Huang, M. D. Prog. Biochem. Biophys., 2009, 36(9):1106. [陈宏炜, 陈锦灿, 陈耐生, 黄金陵, 王俊东, 黄明东. 生物化学与生物物理进展, 2009, 36(9): 1106]
[7]. Huang, J. L.; Chen, N. S.; Huang, J. D.; Xue, J. P.; Liu, E. S.; Yang, S. L. Sci. China Ser. B, 2001, 44(2): 113
[8]. Ke, M. R.; Huang, J. D.; Weng, S. M. J. Photochem. Photobiol., A, 2009, 201: 23
[9]. Stehle, G.; Wunder, A.; Schrenk, H. H.; Hartung, G.; Heene, D. L.; Sinn, H. Anti-Cancer Drug., 1999, 10: 785
[10]. Sharman, W. M.; van Lier, J. E.; Allen, C. M. Adv. Drug Rev., 2004, 56: 53
[11]. Lang, K.; Mosinger, J.; Wagnerova, D. M. Coord. Chem. Rev., 2004, 248: 321
[12]. Jiang, X. J.; Huang, J. D.; Zhu, Y. J.; Tang, F. X.; Ng, D. K. P.; Sun, J. C. Bioorg. Med. Chem. Lett., 2006, 16: 2450
[13]. Zhu, Y. J.; Huang, J. D.; Jiang, X. J.; Sun, J. C. Inorg. Chem. Commun., 2006, 9: 473
[14]. Huang, J. D.; Lo, P. C.; Chen, Y. M.; Lai, J. C.; Fong, W. P.; Ng, D. K. P. J. Inorg. Biochem., 2006, 100: 946
[15]. Lin, W.; Peng, Y. R.; Chen, K. Z.; Wen, J. B. Chin. J. Anal. Chem., 2006, 34(3):411. [林伟, 彭亦如, 陈奎治, 翁家宝, 徐国兴. 分析化学, 2006, 34(3): 411]
[16]. Alarcón, E.; Edwards, A. M.; Garcia, A. M.; Mu?觡oz, M.; Aspée, A.; Borsarelli, C. D.; Lissi, E. A. Photochem. Photobiol. Sci., 2009, 8 (2): 255
[17]. Wen, J. K.; Han, M. Medicinal molecular biology: theory and study technique. Beijing: Science Press, 1999:219. [温进坤, 韩梅. 医学分子生物学: 理论与研究技术. 北京: 科学出版社, 1999: 219]
[18]. Wei, J.; Huang, J. L. Macromolecules, 2005, 38: 1107
[19]. Lu, X. Q.; Shi, H. Y.; Wang, M. H. Chin. J. Immunol., 2009, 25 (3):346. [卢希勤, 施海燕, 王鸣华. 免疫学杂志, 2009, 25(3): 346]
[20]. Liu, T.; Zhang, G. F.; Zhou, W. B.; Su, Z. G. Chin. J. Anal. Chem., 2007, 35(1):43. [刘涛, 张贵锋, 周卫斌, 苏志国. 分析化学, 2007, 35(1): 43]
[21]. Mao, W. X.; Su, Y.; Tang, J. W. Chin. J. Org. Chem., 2006, 26 (5):707. [毛文学, 苏勇, 唐经武. 有机化学, 2006, 26(5): 707]
[22]. Li, X. Y.; He, X.; Ng, A.C. H.; Wu, C.; Ng, D. K. P. Macromolecules, 2000, 33: 2119
[23]. Liu, W.; Jensen, T. J.; Fronczek, F. R.; Hammer, R. P.; Smith, K. M.; Vicente, M. G. H. J. Med. Chem., 2005, 48: 1033
[24]. Jori, G. J. Photochem. Photobiol. A, 1992, 62: 371
[25]. Ng, D. K. P. C. R. Chimie, 2003, 6: 903
[26]. Huang, J. D.; Liu, E. S.; Yang, S. L.; Xue, J. P.; Chen, N. S.; Huang, J. L. Chem. J. Chin. Univ., 2002, 23(12):2287. [黄剑东, 刘尔生, 杨素苓, 薛金萍, 陈耐生, 黄金陵. 高等学校化学学报, 2002, 23(12): 2287]

Preparation and Spectroscopic Properties of Covalent Albumin Conjugates of Zinc Phthalocyanines Tetrasubstituted with Carboxyl Moieties

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