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Issue 5, 2011
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Glycosylated porphyrin derivatives and their photodynamic activity in cancer cells

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Abstract

The present study reports the design and synthesis of nine C2-symmetric 5,15-[bis(arayl)]-10α,20β-[bis(1,2:3,4-di-O-isopropylidene-α-D-galactopyranose-6-yl)]porphyrins (3–11) bearing electron donating or electron withdrawing substituents and a D2-symmetric 5α,10β,15α,20β-tetrakis(1,2:3,4-di-O-isopropylidene-α-D-galactopyranose-6-yl)porphyrin (12). In the system we design, the C6 of pyranose sugar is elegantly fused into the porphyrin core as mesocarbon, which renders a new type of photodynanic inducers. The biological effects of these derivatives were assessed in HeLa and HCT116 human cancer cells. In particular, the tetra-glycofused structure 12 exhibited the highest cellular uptake and photocytotoxicity. Unlike the reported sugar-porphyrin conjugates, which normally localize in mitochondria or endoplasmic reticulum, the unique glycofused porphyrins in this study were dominantly localized in lysosomes. The measurement of the dual flurorescence of annexin V-FITC/PI by flow cytometry revealed that the cell death was caused by apoptosis. Further PARP cleavage study suggested that apoptosis induced by the treatment of compound 12 was via caspase-dependent apoptotic pathway in cancer cells.

Graphical abstract: Glycosylated porphyrin derivatives and their photodynamic activity in cancer cells

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Publication details

The article was received on 02 Oct 2010, accepted on 28 Dec 2010 and first published on 11 Feb 2011


Article type: Concise Article
DOI: 10.1039/C0MD00175A
Med. Chem. Commun., 2011,2, 371-377

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    Glycosylated porphyrin derivatives and their photodynamic activity in cancer cells

    S. Vedachalam, B. Choi, K. K. Pasunooti, K. M. Ching, K. Lee, H. S. Yoon and X. Liu, Med. Chem. Commun., 2011, 2, 371
    DOI: 10.1039/C0MD00175A

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