Moeno S, Krause R W M, Ermilov E A, Kuzyniak W, Höpfner M
Department of Oral Biological Sciences, School of Oral Health Sciences, Faculty of Health Sciences, University of the Witwatersrand, Johannesburg, South Africa.
Photochem Photobiol Sci. 2014 Jun;13(6):963-70. doi: 10.1039/c3pp50393c.
Two novel zinc phthalocyanines (Pcs): tetramethyl tetrakis-2,(3)-[(4-methyl-2-pyridyloxy)phthalocyaninato] zinc(II) (4) and (the negatively charged form) tetrakis-2,(3)-[(3-carboxylicacid-6-sulfanylpyridine)phthalocyaninato] zinc(II) (5), water soluble by virtue of their ionic substituent groups were synthesized. The spectroscopic properties of both compounds were determined and their photodynamic activities were investigated in a human tumor cell model. In aqueous media the two peripherally substituted water soluble Pcs are highly aggregated. The phototoxic activity of the two novel Pcs (Pc 4 and Pc 5; 0-20 μM) was shown to be time- and dose-dependent in human pancreatic carcinoid BON cells, leading to a reduction of tumor cells of >80% compared to the controls. The effectiveness of the treatment appeared to be attenuated by the aggregation of Pcs under aqueous conditions. Interestingly, even those cells that were not immediately killed by the photoactivated photosensitizer seemed to be affected by the Pc photodynamic activity, as a single PDT induced long-lasting effects on cell survival. Even 4 days after PDT, the number of surviving cells did not re-increase or still dropped, as compared to control cells. The underlying mechanism of this observation has to be deciphered in future investigations.
合成了两种新型锌酞菁（Pcs）：四甲基四 - 2，（3） - [（4 - 甲基 - 2 - 吡啶氧基）酞菁锌（II）]（4）和（带负电荷形式）四 - 2，（3） - [（3 - 羧酸 - 6 - 巯基吡啶）酞菁锌（II）]（5），它们因其离子取代基团而具有水溶性。测定了这两种化合物的光谱性质，并在人肿瘤细胞模型中研究了它们的光动力活性。在水性介质中，这两种周边取代的水溶性Pcs高度聚集。两种新型Pcs（Pc 4和Pc 5；0 - 20 μM）在人胰腺类癌BON细胞中的光毒性活性表现出时间和剂量依赖性，与对照组相比，导致肿瘤细胞减少>80%。在水性条件下，Pcs的聚集似乎减弱了治疗效果。有趣的是，即使那些没有被光活化的光敏剂立即杀死的细胞似乎也受到Pc光动力活性的影响，因为单次光动力疗法（PDT）对细胞存活产生了持久影响。与对照细胞相比，即使在PDT后4天，存活细胞数量也没有重新增加或仍在下降。这一观察结果的潜在机制有待未来研究破译。
