title: Cellular uptake and photocytotoxicity of glycoconjugated porphyrins in HeLa cells.
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.
authors.affiliation: Division of Material Science, Graduate School of Human Culture, Nara Women's University, Nara 630-8560, Japan.
authors.forename: Shiho
authors.initials: S
authors.lastname: Hirohara
authors.forename: Makoto
authors.initials: M
authors.lastname: Obata
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Saito
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Ogata
authors.forename: Chikara
authors.initials: C
authors.lastname: Ohtsuki
authors.forename: Suguru
authors.initials: S
authors.lastname: Higashida
authors.forename: Shun-ichiro
authors.initials: S
authors.lastname: Ogura
authors.forename: Ichiro
authors.initials: I
authors.lastname: Okura
authors.forename: Yuko
authors.initials: Y
authors.lastname: Sugai
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mikata
authors.forename: Masao
authors.initials: M
authors.lastname: Tanihara
authors.forename: Shigenobu
authors.initials: S
authors.lastname: Yano
mesh_terms: D001692:Biological Transport; D002470:Cell Survival / Q000187:drug effects / Q000528:radiation effects; D006031:Glycosylation; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000097:blood / Q000138:chemical synthesis / Q000378:metabolism / Q000633:toxicity; D011166:Porphyrins / Q000097:blood / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity*
chemical_list: D017319:Photosensitizing Agents; D011166:Porphyrins