Photoreactivity of Amino Acids: Tryptophan-induced Photochemical Events via Reactive Oxygen Species Generation

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  • IGARASHI Naoko
    Analytical Research and Development, Pfizer Global Research and Development, Nagoya Laboratories, Pfizer Japan Inc. Graduate School of Pharmaceutical Sciences, Chiba University
  • ONOUE Satomi
    Analytical Research and Development, Pfizer Global Research and Development, Nagoya Laboratories, Pfizer Japan Inc.
  • TSUDA Yoshiko
    Analytical Research and Development, Pfizer Global Research and Development, Nagoya Laboratories, Pfizer Japan Inc.

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説明

Tryptophan (Trp), an aromatic amino acid, is a constituent of peptides/proteins and is also a precursor of serotonin, kynurenine derivatives, and nicotinamide adenine dinucleotides. There have been a number of reports on photochemical reactions involving peptides/proteins which contain Trp that showed significant photodegradation, dimerization, and photoionization. The photochemical properties of Trp have not been fully elucidated, and this would provide novel insight into the handling of Trp-containing peptides/proteins. Consequently, we have been trying to evaluate the photochemical properties of Trp, as well as other essential amino acids, focusing on their photosensitivity, photodegradation, and their ability to induce lipid peroxidation. Among all the essential amino acids tested, Trp exhibited the maximal level of superoxide anion generation under 18 h of light exposure (30000 lux). UV spectral analysis of Trp suggested the absorbability of UVA/B light, and exposure of Trp, in both solid and solution states, to UVA/B light resulted in significant photodegradation (t0.5: 18 h) and gradual color changes. In addition, photoirradiated Trp generated lipoperoxidant, a causative agent of photoirritation, and this might be associated with ROS generation.

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  • Analytical Sciences

    Analytical Sciences 23 (8), 943-948, 2007

    社団法人 日本分析化学会

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