RESUMEN
Porphyrin, which shows selective accumulation in cancer cells, has attracted attention as a drug carrier. The influences of the functional porphyrin positions (ß- and meso-positions) on porphyrin accumulation must be understood. In this work, we focused on the investigation of the phenyl functional group whose ß-position influences cancer cell accumulation through direct membrane permeation and endocytosis. The endocytic pathway, in particular, is influenced by both clathrin-dependent and caveolae-dependent endocytosis.
Asunto(s)
Neoplasias , Porfirinas , Humanos , Membrana Celular , Neoplasias/tratamiento farmacológico , Portadores de Fármacos , Endocitosis , Porfirinas/farmacologíaRESUMEN
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 ß-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 ß-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 ß-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 ß-porphyrin derivative with a phenyl group might lead to superior MCF-7â cell accumulation.