Photocytotoxicity, cellular uptake and subcellular localization of amidinophenylporphyrins as potential photodynamic therapeutic agents: An in vitro cell study

被引：28
作者：
Zhu, Sizhe [1 ]
Wu, Fengshou [1 ,2 ]
Wang, Kai [1 ]
Zheng, Yunman [2 ]
Li, Zaoying [2 ]
Zhang, Xiulan [1 ]
Wong, Wai-Kwok [3 ,4 ]
机构：
[1] Wuhan Inst Technol, Minist Educ, Key Lab Green Chem Proc, Wuhan, Peoples R China
[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[3] Hong Kong Baptist Univ, Dept Chem, Hong Kong, Peoples R China
[4] Hong Kong Baptist Univ, Inst Adv Mat, Hong Kong, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2015年 / 25卷 / 20期
关键词：
PDT; Porphyrin; Cellular uptake; Localization; SINGLET OXYGEN PHOTOGENERATION; PORPHYRINS;
D O I：
10.1016/j.bmcl.2015.08.072
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The cell-based studies of 5, 10, 15, 20-Tetrakis (4-amidinophenyl) porphyrin (Por1), its Zn complex (Por2) and amidinophenyl bisporphyrin (Por3) were carried out to examine their photocytotoxicity, cellular uptake and sub-cellular localization with human nasopharyngeal carcinoma cell (HK-1), using 5, 10, 15, 20-Tetrakis (N-methyl-4-pyridyl) porphyrin (H2TMPyP) as a reference. These porphyrins showed low dark-cytotoxicity and high photo-cytotoxicity against HK-1. The amphiphilic amidinophenyl bisporphyrin (Por3) displayed better cellular uptake than the single hydrophilic Por1, Por2 and H2TMPyP. As seen from the extent of overlapping of the fluorescence profiles, lysosomal localization of amidinophenylporphyrin Por1-Por3 and mito/lyso localization of the H2TMPyP occurred in the cells. The results suggest these porphyrins with amidine group could be used as potential agents in photodynamic therapy. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4513 / 4517
页数：5
相关论文
共 27 条
[1]  
Babudieri D. C., 1966, NATURE, V212, P1274
[2]   Internal electron-transfer reactions in cytochrome c oxidase [J].
Brzezinski, P .
BIOCHEMISTRY, 1996, 35 (18) :5611-5615
[3]   Mechanisms in photodynamic therapy: part one-photosensitizers, photochemistry and cellular localization [J].
Castano, Ana P. ;
Demidova, Tatiana N. ;
Hamblin, Michael R. .
PHOTODIAGNOSIS AND PHOTODYNAMIC THERAPY, 2004, 1 (04) :279-293
[4]   The impact of complement activation on tumor oxygenation during photodynamic therapy [J].
Cecic, Ivana ;
Minchinton, Andrew I. ;
Korbelik, Mladen .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2007, 83 (05) :1049-1055
[5]   Enhanced G4-DNA binding of 5,10,15,20 (N-propyl-4-pyridyl) porphyrin (TPrPyP4): A comparative study with TMPyP4 [J].
Cogoi, Susanna ;
Xodo, Luigi E. .
CHEMICAL COMMUNICATIONS, 2010, 46 (39) :7364-7366
[6]   The amidinium-carboxylate salt bridge as a proton-coupled interface to electron transfer pathways [J].
Deng, YQ ;
Roberts, JA ;
Peng, SM ;
Chang, CK ;
Nocera, DG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (19) :2124-2127
[7]   DIRECT EVALUATION OF ELECTRONIC COUPLING MEDIATED BY HYDROGEN-BONDS - IMPLICATIONS FOR BIOLOGICAL ELECTRON-TRANSFER [J].
DEREGE, PJF ;
WILLIAMS, SA ;
THERIEN, MJ .
SCIENCE, 1995, 269 (5229) :1409-1413
[8]   Photodynamic therapy for cancer [J].
Dolmans, DEJGJ ;
Fukumura, D ;
Jain, RK .
NATURE REVIEWS CANCER, 2003, 3 (05) :380-387
[9]   Synthesis, Light-Emitting, and Two-Photon Absorption Properties of Platinum-Containing Poly(arylene-ethynylene)s Linked by 1,3,4-Oxadiazole Units [J].
Goudreault, Thomas ;
He, Ze ;
Guo, Yank ;
Ho, Cheuk-Lam ;
Zhan, Hongmei ;
Wang, Qiwei ;
Ho, Keith Yat-Fung ;
Wong, Ka-Leung ;
Fortin, Daniel ;
Yao, Bing ;
Xie, Zhiyuan ;
Wang, Lixiang ;
Kwok, Wai-Ming ;
Harvey, Pierre D. ;
Wong, Wai-Yeung .
MACROMOLECULES, 2010, 43 (19) :7936-7949
[10]   Asymmetrically substituted cationic indole- and fluorene porphyrins inhibit tumor proliferation in small intestinal neuroendocrine tumors and medullary thyroid carcinomas [J].
Haeubl, Martin ;
Schuerz, Susanne ;
Svejda, Bernhard ;
Reith, Lorenz Michael ;
Gruber, Bernadette ;
Pfragner, Roswitha ;
Schoefberger, Wolfgang .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :760-773
123