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Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2018-02-19 , DOI: 10.1016/j.bmc.2018.02.031
Arif Fadlan , Hiroki Tanimoto , Tatsuya Ito , Yusuke Aritomi , Maho Ueno , Masaya Tokuda , Shiho Hirohara , Makoto Obata , Tsumoru Morimoto , Kiyomi Kakiuchi

The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the d-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.



中文翻译:

TFPP-葡萄糖结合物的位置异构体的合成,光物理性质和光动力活性

本文报道了四(全氟苯基)卟啉(TFPP)-葡萄糖缀合物(1OH2OH3OH4OH6OH)的位置异构体的“完整集”的合成和表征。为了研究TFPP部分在d-葡萄糖分子上的位置对缀合物的生物学活性的影响,检查了这些缀合物的细胞摄取和光细胞毒性。一种在体外生物评价,结果这些特定的异构体对细胞摄取和细胞毒性比别人更大的影响。TFPP-葡萄糖结合物1OH3OH2OH6OH取代的异构体相比,发现4OH在几种类型的癌细胞中具有优异的光细胞毒性

更新日期:2018-02-19
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