Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells

Xinyu Wang; Salomon Stavchansky; Phillip D. Bowman; Sean M. Kerwin

Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells

Xinyu Wang, Salomon Stavchansky, Phillip D. Bowman, Sean M. Kerwin

Department of Pharmaceutical Sciences

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

Abstract

Caffeic acid phenethyl ester (CAPE), a natural polyphenolic compound with many biological activities, has been shown to be protective against ischemia-reperfusion injury. We have synthesized six new catechol ring-fluorinated CAPE derivatives and evaluated their cytotoxic and cytoprotective effects against menadione-induced cytotoxicity in human umbilical vein endothelial cells. These results provide some insights into the structural basis of CAPE cytoprotection in this assay, which does not appear to be based solely on direct antioxidant properties.

Original language	American English
Journal	Bioorganic & medicinal chemistry
Volume	14
State	Published - Jan 1 2006

Keywords

Antioxidants/chemical synthesis/chemistry/pharmacology
Caffeic Acids/chemical synthesis/chemistry/pharmacology
Cells
Cultured
Cytoprotection/drug effects
Drug Evaluation
Endothelial Cells/drug effects/metabolism
Fluorine/chemistry
Humans
Oxidative Stress/drug effects
Phenylethyl Alcohol/analogs & derivatives/chemical synthesis/chemistry/pharmacology
Preclinical
Structure-Activity Relationship
Vitamin K 3/toxicity

Disciplines

Pharmacy and Pharmaceutical Sciences

Cite this

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title = "Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells",

abstract = " Caffeic acid phenethyl ester (CAPE), a natural polyphenolic compound with many biological activities, has been shown to be protective against ischemia-reperfusion injury. We have synthesized six new catechol ring-fluorinated CAPE derivatives and evaluated their cytotoxic and cytoprotective effects against menadione-induced cytotoxicity in human umbilical vein endothelial cells. These results provide some insights into the structural basis of CAPE cytoprotection in this assay, which does not appear to be based solely on direct antioxidant properties.",

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author = "Xinyu Wang and Salomon Stavchansky and Bowman, {Phillip D.} and Kerwin, {Sean M.}",

year = "2006",

month = jan,

day = "1",

language = "American English",

volume = "14",

journal = "Bioorganic & medicinal chemistry",

}

TY - JOUR

T1 - Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells

AU - Wang, Xinyu

AU - Stavchansky, Salomon

AU - Bowman, Phillip D.

AU - Kerwin, Sean M.

PY - 2006/1/1

Y1 - 2006/1/1

N2 - Caffeic acid phenethyl ester (CAPE), a natural polyphenolic compound with many biological activities, has been shown to be protective against ischemia-reperfusion injury. We have synthesized six new catechol ring-fluorinated CAPE derivatives and evaluated their cytotoxic and cytoprotective effects against menadione-induced cytotoxicity in human umbilical vein endothelial cells. These results provide some insights into the structural basis of CAPE cytoprotection in this assay, which does not appear to be based solely on direct antioxidant properties.

AB - Caffeic acid phenethyl ester (CAPE), a natural polyphenolic compound with many biological activities, has been shown to be protective against ischemia-reperfusion injury. We have synthesized six new catechol ring-fluorinated CAPE derivatives and evaluated their cytotoxic and cytoprotective effects against menadione-induced cytotoxicity in human umbilical vein endothelial cells. These results provide some insights into the structural basis of CAPE cytoprotection in this assay, which does not appear to be based solely on direct antioxidant properties.

KW - Antioxidants/chemical synthesis/chemistry/pharmacology

KW - Caffeic Acids/chemical synthesis/chemistry/pharmacology

KW - Cells

KW - Cultured

KW - Cytoprotection/drug effects

KW - Drug Evaluation

KW - Endothelial Cells/drug effects/metabolism

KW - Fluorine/chemistry

KW - Humans

KW - Oxidative Stress/drug effects

KW - Phenylethyl Alcohol/analogs & derivatives/chemical synthesis/chemistry/pharmacology

KW - Preclinical

KW - Structure-Activity Relationship

KW - Vitamin K 3/toxicity

UR - https://digitalcommons.pcom.edu/scholarly_papers/441

M3 - Article

VL - 14

JO - Bioorganic & medicinal chemistry

JF - Bioorganic & medicinal chemistry

ER -

Cytoprotective effect of caffeic acid phenethyl ester (CAPE) and catechol ring-fluorinated CAPE derivatives against menadione-induced oxidative stress in human endothelial cells

Abstract

Keywords

Disciplines

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