Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, Yamazaki, Noda-shi, Chiba, 278-8510, Japan.
Research Institute for Science and Technology, Tokyo University of Science, Yamazaki, Noda-shi, Chiba, 278-8510, Japan.
ChemMedChem. 2022 Feb 16;17(4):e202100636. doi: 10.1002/cmdc.202100636. Epub 2021 Dec 9.
Porphyrin selectively shows tumour accumulation and has attracted attention as a carrier molecule for drug delivery systems (DDS). Porphyrin has two functional sites termed the meso- and β-positions. In previous work, meso-porphyrin derivatives with an alkyl group were found to exhibit greater accumulation in human breast cancer cells (MCF-7). To identify the correlation between porphyrin accumulation and functional porphyrin positions of other functional groups, the accumulation of porphyrin derivatives with a phenyl group was investigated. The β-porphyrin derivative with a phenyl group showed higher accumulation in MCF-7 cells and greater affinity for albumin than the meso-porphyrin derivative. The results of density functional theory (DFT) calculations suggest that the β-porphyrin derivative with a phenyl group had higher planarity across the total structure than the meso-porphyrin derivative. It was concluded that the greater planarity of the β-porphyrin derivative with a phenyl group might lead to superior MCF-7 cell accumulation.
卟啉选择性地显示肿瘤积累，并已作为药物传递系统（DDS）的载体分子引起关注。卟啉有两个功能位点，称为中（meso-）和β-位。在以前的工作中，发现具有烷基的中卟啉衍生物在人乳腺癌细胞（MCF-7）中表现出更高的积累。为了确定卟啉积累与其他功能基团的功能卟啉位置之间的相关性，研究了具有苯基的卟啉衍生物的积累。具有苯基的β-卟啉衍生物在 MCF-7 细胞中的积累更高，并且与白蛋白的亲和力大于中卟啉衍生物。密度泛函理论（DFT）计算的结果表明，具有苯基的β-卟啉衍生物在整个结构上的平面性高于中卟啉衍生物。结论是，具有苯基的β-卟啉衍生物的更大平面性可能导致对 MCF-7 细胞的更好的积累。
