139059-75-9Relevant academic research and scientific papers
Evaluation of functional groups on amino acids in cyclic tetrapeptides in histone deacetylase inhibition
Islam, Md. Shahidul,Bhuiyan, Mohammed P. I.,Islam, Md. Nurul,Nsiama, Tienabe Kipassa,Oishi, Naoto,Kato, Tamaki,Nishino, Norikazu,Ito, Akihiro,Yoshida, Minoru
, p. 2103 - 2110 (2012/08/29)
The naturally occurring cyclic tetrapeptide, chlamydocin, originally isolated from fungus Diheterospora chlamydosphoria, consists of α-aminoisobutyric acid, l-phenylalanine, d-proline and an unusual amino acid (S)-2-amino-8-((S)-oxiran-2-yl)-8-oxooctanoic acid (Aoe) and inhibits the histone deacetylases (HDACs), a class of regulatory enzymes. The epoxyketone moiety of Aoe is the key functional group for inhibition. The cyclic tetrapeptide scaffold is supposed to play important role for effective binding to the surface of enzymes. In place of the epoxyketone group, hydroxamic acid and sulfhydryl group have been applied to design inhibitor ligands to zinc atom in catalytic site of HDACs. In the research for more potent HDAC inhibitors, we replaced the epoxyketone moiety of Aoe with different functional groups and synthesized a series of chlamydocin analogs as HDAC inhibitors. Among the functional groups, methoxymethylketone moiety showed as potent inhibition as the hydroxamic acid. On the contrary, we confirmed that borate, trifruoromethylketone, and 2-aminoanilide are almost inactive in HDAC inhibition.
Synthesis of new cytotoxic cyclopeptide analogs of Chlamodycin
Bernardi, Elisabeth,Cros, Suzy,Viallefont, Philippe,Lazaro, Rene
, p. 944 - 948 (2007/10/02)
With the aim of discovering new antitumoral compounds, analogs of Chlamodycin and HC toxin containing biologically active groups have been designed and synthesized.Interesting preliminary results concerning the in vitro cytotoxic activity of some of these
