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.
Dipartimento di Scienze del Farmaco, Università "G D'Annunzio," Via dei Vestini 31, Chieti 66100, Italy.
Ivana
I
Cacciatore
Antonio
A
Di Stefano
Silvestro
S
Duprè
Enrico
E
Morera
Francesco
F
Pinnen
Alessandra
A
Spirito
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