Inhibition of dipeptidyl peptidase IV (DPP IV) by 2-(2-amino-1-fluoro-propylidene)-cyclopentanecarbonitrile, a fluoroolefin containing peptidomimetic
| Autor: | Kake Zhao, Dong Sung Lim, John T. Welch, Takashi Funaki |
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| Rok vydání: | 2003 |
| Předmět: |
Nitrile
Peptidomimetic Stereochemistry Isostere Dipeptidyl Peptidase 4 Placenta Clinical Biochemistry Pharmaceutical Science Peptide Binding Competitive Biochemistry Chemical synthesis Dipeptidyl peptidase chemistry.chemical_compound Drug Stability Biomimetic Materials Pregnancy Nitriles Drug Discovery Humans Protease Inhibitors Molecular Biology chemistry.chemical_classification biology Chemistry Organic Chemistry Stereoisomerism Hydrogen-Ion Concentration Enzyme Enzyme inhibitor biology.protein Molecular Medicine Female Peptides |
| Zdroj: | Bioorganic & Medicinal Chemistry. 11:207-215 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/s0968-0896(02)00384-x |
| Popis: | Novel, potent inhibitors of dipeptidyl peptidase IV (DPP IV, EC 3.4.14.5, CD26), containing the fluoroolefin peptide isostere psi [CFz.dbnd6;C], have been prepared via the intermediacy of the Peterson fluoroolefination reaction. The nitrile containing inhibitors were found to inhibit dipeptidyl peptidase IV competitively with K(i) values for the l-3 and u-3 inhibitors of 7.69 and 6.03 microM, respectively. In contrast to earlier reported fluoroolefin containing inhibitors, the nitriles underwent no detectable degradation at pH 7.6 under buffered conditions. |
| Databáze: | OpenAIRE |
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