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Consequences of Cis-amide Bond Simulation in Opioid Peptides |
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| Authors: | Jacek Olczak Krzysztof Kaczmarek Iwona Maszczyska Marek Lisowski Dagmar Stropova Victor J. Hruby Henry I. Yamamura Andrzej W. Lipkowski Janusz Zabrocki |
| Affiliation: | (1) Institute of Organic Chemistry, Technical University of !["Lstrok"]("/content/t6136948170um025/xlarge321.gif") ód!["zacute"]("/content/t6136948170um025/xlarge378.gif") , Zwirki Str. 36, PL-90-924 ód, Poland;(2) Medical Research Centre, Polish Academy of Sciences, PL-00-784 Warsaw, Poland;(3) Institute of Chemistry, University of Wroc!["lstrok"]("/content/t6136948170um025/xlarge322.gif") aw, PL-50-383 Wrocaw, Poland;(4) University of Arizona, Tucson, AZ, 85721, U.S.A.;(5) Department of Pharmacology, University of Arizona, Tucson, AZ, 85721, U.S.A. |
| Abstract: | Six analogs of leucine-enkephalin were synthesized in which a 1,5-disubstituted tetrazole ring was incorporated in order to lock selected peptide bonds in cis geometry. The obtained compounds were examined based on their biological effects in vivo and in vitro. Only one analog was completely inactive in binding assays being very weakly active in the antinociceptive test. The remaining five compounds displayed at least weak receptor affinity and in vivo activity. |
| Keywords: | cis peptide bond conformation 1,5-disubstituted tetrazole ring Leu-enkephalin |
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