Document Detail


Photoreactivity of amino acids: tryptophan-induced photochemical events via reactive oxygen species generation.
MedLine Citation:
PMID:  17690425     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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 (t(0.5): 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.
Authors:
Naoko Igarashi; Satomi Onoue; Yoshiko Tsuda
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Analytical sciences : the international journal of the Japan Society for Analytical Chemistry     Volume:  23     ISSN:  0910-6340     ISO Abbreviation:  Anal Sci     Publication Date:  2007 Aug 
Date Detail:
Created Date:  2007-08-10     Completed Date:  2007-10-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8511078     Medline TA:  Anal Sci     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  943-8     Citation Subset:  IM    
Affiliation:
Analytical Research and Development, Pfizer Global Research and Development, Nagoya Laboratories, Pfizer Japan Inc., Taketoyo, Aichi, Japan. n-igarashi@optfiber.net
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / chemistry,  radiation effects
Photochemistry
Reactive Oxygen Species / chemistry*
Tryptophan / chemistry,  radiation effects*
Ultraviolet Rays*
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Reactive Oxygen Species; 73-22-3/Tryptophan

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