65365-16-4Relevant articles and documents
Synthesis and biological activity of peptide proline-boronic acids as proteasome inhibitors
Han, Liqiang,Wen, Yanzhao,Li, Ridong,Xu, Bo,Ge, Zemei,Wang, Xin,Cheng, Tieming,Cui, Jingrong,Li, Runtao
, p. 4031 - 4044 (2017/07/05)
On the basis of the application of proline-boronic acid as pharmacophore in the kinase inhibitors and our previous research results, using proline-boronic acid as warhead, two series of peptide proline-boronic acids, dipeptide proline-boronic acids (I) and tripeptide proline-boronic acids (II), were designed and synthesized. All the synthesized compounds were first evaluated for their biological activity against MGC803 cell, and then, the best compound II-7 was selected to test its anti-tumor spectrum on six human tumor cell lines and proteasome inhibition against three subunits. The results indicated that series II have much better biological activities than series I. The compound II-7 exhibited not only excellent biological activities with IC50 values of nM level in both cell and proteasome models, but also much better subunit selectivity. Thus, proline-boronic acid as warhead is reasonable in the design of proteasome inhibitors.
Synthesis and Conformation of Aromatic Cyclic Dipeptides. Cyclo(phenylalanyl)2, Cyclo(1-naphthylalanyl)2, and Cyclo(2-naphthylalanyl)2
Egusa, Syun,Takagi, Jun,Sisido, Masahiko,Imanishi, Yukio
, p. 2195 - 2202 (2007/10/02)
Cyclic dipeptides of aromatic amino acids, cyclo(L-phenylalanyl)2, cyclo(L-1-naphthylalanyl)2, and cyclo(L-2-naphthylalanyl)2 were synthesized and subjected to spectroscopic analyses using 1H NMR, absorption, circular dichroism (CD), fluorescence, and fluoroscence-detected circular dichroism (FDCD).The 1H NMR data suggested that the 2,5-piperazinedione rings of the three cyclic dipeptides are in planar or nearly planar bowsplitboat-type conformation.The aromatic side groups of cyclo(1- and 2-naphthylalanyl)2's were found to take asymmetric configurations, one naphthyl group being folded onto the 2,5-piperazinedione ring, the order being unfolded.Strong exciton couplet was observed in CD spectra of the three compounds.The signs of the exciton splitting were opposite in the two naphthyl cyclic dipeptides.Fluorescence spectra of the two naphthyl cyclic dipeptides showed no excimer emission.The absence of strong interchromophoric interaction in the lowest excited state was also suggested by the virtual coincidence of CD spectrum with FDCD spectrum.From the above spectroscopic data, probable conformations were proposed for the naphthyl cyclic dipeptides.
