Abstract
5,15-Diazaporphyrin appended with D -mannose moieties was prepared through Suzuki–Miyaura crosscoupling reaction and SN 2 alkylation. The resultant diazaporphyrin was hydrophilic enough to exhibit sufficient solubility in aqueous media. Because of the photosensitizing ability of diazaporphyrins, the in vitro activity of the D -mannose-appended diazaporphyrin in photodynamic therapy (PDT) was investigated. The specific internalization of the functionalized diazaporphyrin into human breast adeno-carcinoma (MDA-MB-231) cells through mannose receptors was confirmed by confocal microscopy imaging. We also demonstrated the strong PDT activity of the functionalized diazaporphyrin at a nanomolar level with short light irradiation time.