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

doi:10.1016/j.bmc.2013.10.021

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

18 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 language	English
Pages (from-to)	7709-7714
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	24
DOIs	https://doi.org/10.1016/j.bmc.2013.10.021
Publication status	Published - 2013 Dec 15

Keywords

5-Hydroxyoxindole
Antioxidant
Lipophilicity
Oxidative stress
Radical scavenging activity

ASJC Scopus subject areas

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

Access to Document

10.1016/j.bmc.2013.10.021

Cite this

@article{e4451b0fc6e84623a9d8bcd5c8707cb7,

title = "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.",

keywords = "5-Hydroxyoxindole, Antioxidant, Lipophilicity, Oxidative stress, Radical scavenging activity",

author = "Daisuke Yasuda and Kyoko Takahashi and Tomoyuki Ohe and Shigeo Nakamura and Tadahiko Mashino",

note = "Funding Information: This work was supported by Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT), 2012–2016, Strategic Research Foundation at Private Universities of the MEXT, 2011–2015 and Graduate School Doctoral Student Grant-in-Aid Program 2011 and 2012 from Keio University. ",

year = "2013",

month = dec,

day = "15",

doi = "10.1016/j.bmc.2013.10.021",

language = "English",

volume = "21",

pages = "7709--7714",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "24",

}

TY - JOUR

T1 - Antioxidant activities of 5-hydroxyoxindole and its 3-hydroxy-3-phenacyl derivatives

T2 - The suppression of lipid peroxidation and intracellular oxidative stress

AU - Yasuda, Daisuke

AU - Takahashi, Kyoko

AU - Ohe, Tomoyuki

AU - Nakamura, Shigeo

AU - Mashino, Tadahiko

N1 - Funding Information: This work was supported by Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT), 2012–2016, Strategic Research Foundation at Private Universities of the MEXT, 2011–2015 and Graduate School Doctoral Student Grant-in-Aid Program 2011 and 2012 from Keio University.

PY - 2013/12/15

Y1 - 2013/12/15

N2 - 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.

AB - 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.

KW - 5-Hydroxyoxindole

KW - Antioxidant

KW - Lipophilicity

KW - Oxidative stress

KW - Radical scavenging activity

UR - http://www.scopus.com/inward/record.url?scp=84888438928&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84888438928&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2013.10.021

DO - 10.1016/j.bmc.2013.10.021

M3 - Article

C2 - 24216095

AN - SCOPUS:84888438928

SN - 0968-0896

VL - 21

SP - 7709

EP - 7714

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 24

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this