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5-S-GAD, a novel radical scavenging compound, prevents lens opacity development.

Abstract
The ability of N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine (5-S-GAD)-a novel catechol derivative isolated from an insect as an antibacterial substance-to scavenge free radicals and prevent cataract progression was examined. 5-S-GAD scavenged 1,1-diphenylpicrylhydrazyl (DPPH) and superoxide anions (O(2)(*)(-)), and inhibited lipid peroxidation. It also significantly inhibited the onset of glucocorticoid-induced lens opacification in chick embryos. These effects of 5-S-GAD were stronger than those of N-acetylcarnosine and TEMPOL, which are reported to be effective radical scavengers in the prevention of cataract progression. 5-S-GAD clearly delayed the maturation of cataracts induced by diamide in cultured lenses of rats. Daily instillation of 5-S-GAD retarded the development of lens opacity in galactose-fed rats. Biochemical analysis of the lenses revealed that 20-kDa proteins, presumably consisting of alpha-crystallin, were the most susceptible to oxidative stress, which leads to the carbonylation of the side chains of these proteins. alpha-Crystallin carbonylation induced by diamide or galactose was notably inhibited by 5-S-GAD in a dose-dependent manner. Our results show that 5-S-GAD prevents acute lens opacification in these short-term experimental models, possibly in part by virtue of its antioxidative property, and 5-S-GAD is expected to have long-term pharmaceutical effects.
AuthorsNobuko Akiyama, Izumi O Umeda, Shunji Sogo, Hideo Nishigori, Masafumi Tsujimoto, Shunji Natori
JournalFree radical biology & medicine (Free Radic Biol Med) Vol. 46 Issue 4 Pg. 511-9 (Feb 15 2009) ISSN: 1873-4596 [Electronic] United States
PMID19084592 (Publication Type: Comparative Study, Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Biphenyl Compounds
  • Cyclic N-Oxides
  • Free Radical Scavengers
  • Glucocorticoids
  • N-beta-alanyl-5-S-glutathionyl-3,4-dihydroxyphenylalanine
  • Picrates
  • Spin Labels
  • alpha-Crystallins
  • N-acetylcarnosine
  • Diamide
  • Superoxides
  • Dihydroxyphenylalanine
  • Carnosine
  • 1,1-diphenyl-2-picrylhydrazyl
  • Glutathione
  • tempol
  • Galactose
Topics
  • Animals
  • Biphenyl Compounds (metabolism)
  • Carnosine (analogs & derivatives, pharmacology)
  • Cataract (chemically induced, physiopathology, prevention & control)
  • Cells, Cultured
  • Chick Embryo
  • Cyclic N-Oxides (pharmacology)
  • Diamide (toxicity)
  • Dihydroxyphenylalanine (analogs & derivatives, pharmacology)
  • Disease Progression
  • Dose-Response Relationship, Drug
  • Free Radical Scavengers (pharmacology)
  • Galactose (administration & dosage, toxicity)
  • Glucocorticoids (administration & dosage, toxicity)
  • Glutathione (analogs & derivatives, pharmacology)
  • Insecta
  • Lens, Crystalline (drug effects, metabolism, pathology)
  • Lipid Peroxidation (drug effects, physiology)
  • Male
  • Oxidative Stress (physiology)
  • Picrates (metabolism)
  • Protein Carbonylation (drug effects, physiology)
  • Rats
  • Rats, Sprague-Dawley
  • Spin Labels
  • Superoxides (chemistry, metabolism)
  • alpha-Crystallins (metabolism)

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