Reactions of some cyclopentenones with selected cysteine derivatives and biological activities of the product thioethers.
The conjugate addition reaction between glutathione, N-Boc-cysteine methyl ester, N-acetyl cysteine methyl ester and N-acetyl cysteine and several substituted cyclopentenones is described. The reversibility of this process was demonstrated by thio-adduct metathesis on treatment of the adduct with a different cysteinyl derivative. The levels at which these compounds inhibit the function of nuclear factor kappa B (NF-kappaB) and potentiate heat shock factor (HSF) are reported and the possible relevance of these studies concerning the antiviral and anti-inflammatory activities of the cyclopentenone prostanoids is discussed.
Bickley
Jamie F
JF
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK.
Ciucci
Alessandra
A
Evans
Paul
P
Roberts
Stanley M
SM
Ross
Nicolette
N
Santoro
M Gabriella
MG
D003517:Cyclopentanes / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D005786:Gene Expression Regulation / Q000187:drug effects; D005978:Glutathione / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007928:Lethal Dose 50; D008738:Methyl Ethers / Q000737:chemistry; D015394:Molecular Structure; D013440:Sulfides / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity
D003517:Cyclopentanes; D008738:Methyl Ethers; D013440:Sulfides; D005978:Glutathione; D003545:Cysteine; C013905:cyclopentenone