48168-99-6Relevant academic research and scientific papers
Metabolically stable apelin-analogues, incorporating cyclohexylalanine and homoarginine, as potent apelin receptor activators
Fernandez, Kleinberg X.,Fischer, Conrad,Gheblawi, Mahmoud,Gottschalk, Samantha,Iturrioz, Xavier,Oudit, Gavin Y.,Vederas, John C.,Vu, Jennie,Wang, Wang,Llorens-Cortés, Catherine
, p. 1402 - 1413 (2021/11/11)
High blood pressure and consequential cardiovascular diseases are among the top causes of death worldwide. The apelinergic (APJ) system has emerged as a promising target for the treatment of cardiovascular issues, especially prevention of ischemia reperfusion (IR) injury after a heart attack or stroke. However, rapid degradation of the endogenous apelin peptides in vivo limits their use as therapeutic agents. Here, we study the effects of simple homologue substitutions, i.e. incorporation of non-canonical amino acids l-cyclohexylalanine (l-Cha) and l-homoarginine (l-hArg), on the proteolytic stability of pyr-1-apelin-13 and apelin-17 analogues. The modified 13-mers display up to 40 times longer plasma half-life than native apelin-13 and in preliminary in vivo assay show moderate blood pressure-lowering effects. The corresponding apelin-17 analogues show pronounced blood pressure-lowering effects and up to a 340-fold increase in plasma half-life compared to the native apelin-17 isoforms, suggesting their potential use in the design of metabolically stable apelin analogues to prevent IR injury. This journal is
Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives. I. Structure-activity relationships on the terminal peptidic moiety
Hasuoka, Atsushi,Nishikimi, Yuji,Nakayama, Yutaka,Kamiyama, Keiji,Nakao, Masafumi,Miyagawa, Ken-Ichiro,Nishimura, Osamu,Fujino, Masahiko
, p. 322 - 336 (2007/10/03)
The novel natural antibiotics pyloricidin A, B and C possess potent and highly selective antibacterial activity against Helicobacter pylori. In order to investigate the structure activity relationships for the terminal peptidic moiety, a series of pyloricidin B and pyloricidin C derivatives, bearing various amino acids in the moiety, were prepared and evaluated for their anti-H. pylori activity. The derivatives bearing α-D-, β- and γ-amino acids or peptidemimetics showed drastically decreased activity. On the other hand, the derivatives with α-L-amino acids were found to maintain the activity. Among the derivatives prepared in this work, the allyglycine derivative 2s showed the most potent anti-H. pylori activity, with an MIC value of less than 0.006 μg/ml against H. pylori NCTC11637, which is 60-fold greater than the activity of the lead compound pyloricidin C.
Rational design and synthesis of unsaturated 2,5-dioxopiperazine derivatives as potential protein tyrosine kinase inhibitors
Li, Wen-Ren,Peng, Shao-Zheng
, p. 7373 - 7376 (2007/10/03)
The first general method for the synthesis of a library of trifunctionalized (Z)-3-alkylidene-2,5-piperazinediones as potential protein tyrosine kinase inhibitors from commercially available amino compounds, α- keto acids and aldehydes using a novel cyclization/cleavage strategy on solid support is described.
Amino Acids and Peptides, 63. - Peptide Synthesis via N- or O-Activation of Amino Acids with 1,2-Dihydro-4,6-dimethyl-2-thioxo-3-pyridinecarbonitrile. - Synthesis of the 8-11 Tetrapeptide Sequence of Cyclosporin
Schmidt, Ulrich,Potzolli, Bernd
, p. 935 - 942 (2007/10/02)
Peptides and N-methyl peptides have been prepared in high yields and nearly free of racemisation via N-activation (Scheme 1) or O-activation (Scheme 2) of N-acylamino acids and N-acyl-N-methylamino acids, respectively, by 1,2-dihydro-4,6-dimethyl-2-thioxo
