Antioxidant activities of 5-hydroxyoxindole and its 3-hydroxy-3-phenacyl derivatives

The suppression of lipid peroxidation and intracellular oxidative stress

Daisuke Yasuda, Kyoko Takahashi, Tomoyuki Ohe, Shigeo Nakamura, Tadahiko Mashino

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7709-7714
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume21
Issue number24
DOIs
Publication statusPublished - 2013 Dec 15

Fingerprint

Oxidative stress
Lipid Peroxidation
Oxidative Stress
Antioxidants
Derivatives
Lipids
tert-Butylhydroperoxide
Lipid Peroxides
HL-60 Cells
Liver Microsomes
Hydrogen Peroxide
Leukemia
Cytotoxicity
Liver
Rats
5-hydroxyoxindole
Therapeutics

Keywords

  • 5-Hydroxyoxindole
  • Antioxidant
  • Lipophilicity
  • Oxidative stress
  • Radical scavenging activity

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

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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.",
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T2 - The suppression of lipid peroxidation and intracellular oxidative stress

AU - Yasuda, Daisuke

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AU - Ohe, Tomoyuki

AU - Nakamura, Shigeo

AU - Mashino, Tadahiko

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KW - Oxidative stress

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