Synthesis and biological evaluation of the disulfide form of the glutathione analogue gamma-(L-glutamyl)-L-cysteinyl-L-aspartyl-L-cysteine.
By using the chain to chain mode of cyclization the title glutathione analogue (4), containing the 11-membered disulfide ring replacing the native -Cys-Gly fragment, has been synthesized and characterized together with its reduced dithiol form gamma-Glu-Cys-Asp-Cys (5). The activity of (4) with gamma-glutamyl-transferase and glutathione reductase has been evaluated and compared with those of the two conformationally restricted glutathione analogues (2) and (3) previously reported.
Cacciatore
Ivana
I
Dipartimento di Scienze del Farmaco, Università "G D'Annunzio," Via dei Vestini 31, Chieti 66100, Italy.
Di Stefano
Antonio
A
Duprè
Silvestro
S
Morera
Enrico
E
Pinnen
Francesco
F
Spirito
Alessandra
A
D000818:Animals; D002417:Cattle; D004220:Disulfides / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005978:Glutathione / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D005980:Glutathione Reductase / Q000037:antagonists & inhibitors; D007668:Kidney / Q000201:enzymology; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013329:Structure-Activity Relationship; D013552:Swine; D005723:gamma-Glutamyltransferase / Q000037:antagonists & inhibitors
D004220:Disulfides; D004791:Enzyme Inhibitors; D009842:Oligopeptides; C480314:gamma-glutamyl-cysteinyl-aspartyl-cysteine; D005980:Glutathione Reductase; D005723:gamma-Glutamyltransferase; D005978:Glutathione