Cellular uptake and photocytotoxicity of glycoconjugated porphyrins in HeLa cells

Photochemistry and Photobiology
Shiho HiroharaShigenobu Yano

Abstract

Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)(2).2H(2)O as a template. The Zn(2+) ion template strategy improved the yield about three-fold in the case of meta-substituted tetraphenylporphyrins. In addition, free-base porphyrins were obtained almost quantitatively by demetalation with 4 M HCl. Sixteen deacetylated glycoconjugated porphyrins were tested as candidate photodynamic therapy (PDT) drugs using HeLa cells. Most of the deacetylated glycoconjugated porphyrins showed higher cellular uptake than tetraphenylporphyrin tetrasulfonic acid (TPPS), and 5,10,15,20-tetrakis[4-(beta-D-arabinopyranosyloxy)phenyl]porphyrin (p-5d) in particular showed 18.5-fold higher uptake than TPPS. The photocytotoxicity of 5,10,15,20-tetrakis[4-(beta-D-glucopyranosyloxy)phenyl]porphyrin (p-5a), p-5d and TPPS was examined with HeLa cells, using a light dose of 16 J/cm(2). These photosensitizers had no cytotoxicity in the dark, but their photocytotoxicity increased in the order of TPPS < p-5a < p-5d. These results suggest p-5d is a good candidate for a PDT drug.

Citations

May 19, 2012·Photodiagnosis and Photodynamic Therapy·Mathias O Senge
Aug 15, 2009·Journal of Photochemistry and Photobiology. B, Biology·Shiho HiroharaShigenobu Yano
Jan 5, 2005·Journal of Photochemistry and Photobiology. B, Biology·Shiho HiroharaShigenobu Yano
Mar 8, 2006·Journal of Photochemistry and Photobiology. B, Biology·Shiho HiroharaShigenobu Yano
Jun 5, 2016·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Md Lutful AminSeJin Kim

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