Porphyrin-fullerene C60 dyads with high ability to form photoinduced charge-separated state as novel sensitizers for photodynamic therapy
Porphyrin-fullerene C60 dyads with high ability to form photoinduced charge-separated state as novel sensitizers for photodynamic therapy
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DOI：
10.1562/2005-01-24-ra-426r.1
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发表时间：
2005-07-01
影响因子：
3.3
通讯作者：
Durantini, EN
中科院分区：
文献类型：
--
作者：
Milanesio, ME;Alvarez, MG;Durantini, EN
本文比较了5-（4-乙酰氨基苯基）-10,15,20-三（4-甲氧基苯基）卟啉（P- c -60）及其与锌（II）的金属配合物（ZnP-C-60）在均质光氧化介质和体外对hep -2人喉癌细胞系的光动力学活性。这项研究首次评估了具有形成光诱导电荷分离状态的高容量的二元体，作为光动力疗法（PDT）灭活细胞的药物。对甲苯和N，N-二甲基甲酰胺（DMF）进行了吸收和荧光光谱研究。二偶体中卟啉部分的发射被附着的富勒烯C-60部分强烈猝灭。单线态分子氧，O-2((1)Delta(g))，产物（Phi(Delta)）用9,10-二甲基蒽（DMA）测定。（Phi(Delta)）的值与溶剂的极性密切相关。在甲苯中发现二分体和P的Phi（Delta）值相当，而DMF中二分体的O-2(（1)Delta(g)）产量显著减少。在极性较强的溶剂中，电荷转移态发生稳定，降低了卟啉三态形成的效率。此外，这两个双体光敏分解l -色氨酸在DMF。在生物培养基中，使用增敏剂浓度未观察到暗细胞毒性
The photodynamic activities of a porphyrin-C-60 dyad (P-C-60) and its metal complex with Zn(II) (ZnP-C-60) were compared with 5-(4-acetamidophenyl)-10,15,20-tris(4-methoxyphenyl)porphyrin (P), both in homogeneous medium-bearing photooxidizable substrates and in vitro on the Hep-2-human-larynx-carcinoma cell line. This study represents the first evaluation of dyads, with a high capacity to form a photoinduced charge-separated state, to act as agents to inactivate cells by photodynamic therapy (PDT). Absorption and fluorescence spectroscopic studies were performed in toluene and N,N-dimethylformamide (DMF). The emission of the porphyrin moiety in the dyads is strongly quenched by the attached fullerene C-60 moiety. The singlet molecular oxygen, O-2((1)Delta(g)), productions (Phi(Delta)) were determined using 9,10-dimethylanthracene (DMA). The values Of (Phi(Delta) were strongly dependent on the solvent's polarity. Comparable Phi(Delta) values were found for dyads and P in toluene, while O-2((1)Delta(g)) production was significantly diminished for the dyads in DMF. In more polar solvent, the stabilization of charge-transfer state takes place, decreasing the efficiency of porphyrin triplet-state formation. Also, both dyads photosensitize the decomposition of L-tryptophan in DMF. In biological medium, no dark cytotoxicity was observed using sensitizer concentrations