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1 September 2004 Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells
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Abstract

Thirty-two glycoconjugated porphyrins were synthesized by a modification of Lindsey method in the presence of Zn(OAc)2·2H2O as a template. The Zn2 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-(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/cm2. 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.

Shiho Hirohara, Makoto Obata, Atsuhiro Saito, Shin-ichi Ogata, Chikara Ohtsuki, Suguru Higashida, Shun-ichiro Ogura, Ichiro Okura, Yuko Sugai, Yuji Mikata, Masao Tanihara, and Shigenobu Yano "Cellular Uptake and Photocytotoxicity of Glycoconjugated Porphyrins in HeLa Cells," Photochemistry and Photobiology 80(2), 301-308, (1 September 2004). https://doi.org/10.1562/2004-03-07-RA-103.1
Received: 7 March 2004; Accepted: 1 June 2004; Published: 1 September 2004
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