Antioxidant activities of 5-hydroxyoxindole and its 3-hydroxy-3-phenacyl derivatives: the suppression of lipid peroxidation and intracellular oxidative stress.

Abstract	The antioxidant activities of 5-hydroxyoxindole (1) and newly synthesized 3,5-dihydroxy-3-phenacyl-2-oxindole derivatives against rat liver microsome/tert-butylhydroperoxide system-induced lipid peroxidation and hydrogen peroxide-induced intracellular oxidative stress were investigated. Compound 1 and its derivatives showed significant suppression of lipid peroxidation and an intracellular oxidative stress. The effects of the more lipophilic derivatives tended to be greater than that of the original compound 1. The cytotoxicity of all of the oxindole derivatives on human promyelocytic leukemia HL60 cells was lower than that of 2,6-di(tert-butyl)-4-hydroxytoluene (BHT), a widely used phenolic antioxidant. These results show that compound 1 and its 3-substituted derivatives could be good lead candidates for future novel antioxidant therapeutics.
Authors	Daisuke Yasuda, Kyoko Takahashi, Tomoyuki Ohe, Shigeo Nakamura, Tadahiko Mashino
Journal	Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 21 Issue 24 Pg. 7709-14 (Dec 15 2013) ISSN: 1464-3391 [Electronic] England
PMID	24216095 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Copyright	Copyright © 2013 Elsevier Ltd. All rights reserved.
Chemical References	5-hydroxyoxindole Antineoplastic Agents Antioxidants Indoles Oxindoles 3-hydroxy-3-phenacyloxindole tert-Butylhydroperoxide Hydrogen Peroxide
Topics	Animals Antineoplastic Agents (chemical synthesis, chemistry, pharmacology) Antioxidants (chemical synthesis, chemistry, pharmacology) Cell Proliferation (drug effects) Dose-Response Relationship, Drug Drug Screening Assays, Antitumor HL-60 Cells Humans Hydrogen Peroxide (antagonists & inhibitors, pharmacology) Indoles (chemical synthesis, chemistry, pharmacology) Lipid Peroxidation (drug effects) Microsomes, Liver (drug effects, metabolism) Molecular Structure Oxidative Stress (drug effects) Oxindoles Rats Structure-Activity Relationship Tumor Cells, Cultured tert-Butylhydroperoxide (antagonists & inhibitors, pharmacology)

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