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Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in Hela Cells. ¶
Author(s) -
Hirohara Shiho,
Obata Makoto,
Salto Atsuhiro,
Ogata Shinichi,
Ohtsuki Chikara,
Higashida Suguru,
Ogura Shunichiro,
Okura Ichiro,
Sugal Yuko,
Mikata Yuji,
Tanihara Masao,
Yano Shigenobu
Publication year - 2004
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2004.tb00087.x
Subject(s) - porphyrin , hela , photodynamic therapy , tetraphenylporphyrin , chemistry , cytotoxicity , free base , yield (engineering) , photosensitizer , combinatorial chemistry , selectivity , nuclear chemistry , photochemistry , in vitro , organic chemistry , biochemistry , materials science , catalysis , salt (chemistry) , metallurgy
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 HCI. 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‐(β‐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‐(β‐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.