Structure-Photodynamic Effect Relationships of 24 Glycoconjugated Photosensitizers in HeLa Cells(Medicinal Chemistry)

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概要

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• The photodynamic effect of the glycoconjugated photosensitizer library containing 16 glycoconjugated 5,10,15,20-tetraphenylporphyrins and 8 glycoconjugated 5,10,15,20-tetraphenylchlorins were examined in HeLa cells, and analyzed by two approaches, namely, physiological properties (cellular uptake and reactive oxygen species (ROS)) and structural features of glycoconjugated photosensitizers. All glycoconjugated photosensitizers showed no cytotoxicity in the dark at a concentration of 5μM. The photocytotoxicity profiles poorly related to the amount of cellular uptake of the photosensitizers. Photocytotoxicities of the glycoconjugated photosensitizers were inhibited by the ROS inhibitor, sodium azide. The result clearly suggests that singlet oxygen is a dominant species in all cases. The glycoconjugated photosensitizers examined have three structural features, namely, (1) the kind of sugar moieties, (2) the kind of light-absorbing moiety and (3) the substitution position of the sugar moiety. In regard to the sugar moieties, the photosensitizers bearing D-xylose tend to show higher photocytotoxicity than other photosensitizers, while those bearing D-arabinose tend to show lower photocytotoxicity. The photocytotoxicity with respect to the light-absorbing moiety tends to increase in the order of zinc porphyrin < porphyrin < chlorin. The optical density at the Q_I band fairly explained the results. As an effect of the substitution position of the sugar moieties, the photosensitizers bearing sugar moieties at the meta-position of phenyl group showed remarkably high activity compared with para-substituted ones, and the difference could not be explained by the optical density. Confocal laser scanning microscopy revealed that the meta-substituted photosensitizers are not readily deactivated from the excited state in the cellular microenvironment, and this may explain their potent photocytotoxicity.

• 公益社団法人日本薬学会の論文
• 2008-12-01

著者

• Ohtsuki Chikara

  Department Of Crystalline Materials Science Graduate School Of Engineering Nagoya University

• Ohtsuki C

  Department Of Crystalline Materials Science Graduate School Of Engineering Nagoya University

• Ohtsuki Chikara

  Dep. Of Crystalline Materials Sci. Graduate School Engineering Nagoya Univ.

• Ohtsuki Chikara

  奈良先端科学技術大学院大学 物質創成科学研究科

• OBATA Makoto

  Division of Material Science, Graduate School of Human Culture, Nara Womens University

• Obata Makoto

  Division Of Molecular Chemistry Graduate School Of Engineering Hokkaido University

• Ohtsuki Chikara

  Graduate School Of Engineering Nagoya University

• HIROHARA Shiho

  Graduate School of Materials Science, Nara Institute of Science and Technology

• ALITOMO Hiroki

  Department of Industrial Chemistry, Osaka Prefectural College of Technology

• SHARYO Kohei

  Graduate School of Materials Science, Nara Institute of Science and Technology

• OGATA Shin-ichi

  Graduate School of Environment and Information Sciences, Yokohama National University

• YANO Shigenobu

  Endowed Research Section, Photomedical Science, Innovative Collaboration Center, Kyoto University

• ANDO Tsuyoshi

  Graduate School of Materials Science, Nara Institute of Science and Technology

• TANIHARA Masao

  Graduate School of Materials Science, Nara Institute of Science and Technology

• Ogata Shin-ichi

  Graduate School Of Environment And Information Science Yokohama National University

• Sharyo Kohei

  Graduate School Of Materials Science Nara Institute Of Science And Technology

• Ando Tsuyoshi

  Graduate School Of Materials Science Nara Institute Of Science And Technology

• Tanihara Masao

  Graduate School Of Material Science Nara Institute Of Science And Technology

• Alitomo Hiroki

  Department Of Industrial Chemistry Osaka Prefectural College Of Technology

• Hirohara Shiho

  Graduate School Of Materials Science Nara Institute Of Science And Technology

• Yano Shigenobu

  Endowed Research Section Photomedical Science Innovative Collaboration Center Kyoto University

• Yano Shigenobu

  Endowed Res. Section Photomedical Sci. Innovative Collaboration Center Kyoto Univ.

• Hirohara Shiho

  Graduate School Of Materials Sci. Nara Inst. Of Sci. And Technol.

• Ogata Shin-ichi

  Graduate School Of Enviroment And Information Science Yokohama National University

• Tanaka Mamoru

  Department Of Gastroenterology And Metabolism Nagoya City University Graduate School Of Medical Scie

• Tanihara Masao

  Department Of Gastroenterology And Metabolism Nagoya City University Graduate School Of Medical Scie

• Ogata Shin-ichi

  Graduate School Of Bioscience And Biotechnology Tokyo Institute Of Technology

• Obata Makoto

  Interdisciplinary Graduate School Of Medicine And Engineering University Of Yamanashi

• Ando Tsuyoshi

  Graduate School Of Materials Sci. Nara Inst. Of Sci. And Technol.

• Ogata Shin-ichi

  Graduate School of Biological Sciences, Nara Institute of Science and Technology

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