Issue 5, 2011

Glycosylated porphyrin derivatives and their photodynamic activity in cancer cells

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

Supplementary files

Article information

Article type
Concise Article
Submitted
02 Oct 2010
Accepted
28 Dec 2010
First published
11 Feb 2011

Med. Chem. Commun., 2011,2, 371-377

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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