Consequences of cis-amide bond simulation in opioid peptides

Jacek Olczak; Krzysztof Kaczmarek; Iwona Maszczyńska; Marek Lisowski; Dagmar Stropova; Victor J. Hruby; Henry I. Yamamura; Andrzej W. Lipkowski; Janusz Zabrocki

doi:10.1007/BF02443502

Consequences of cis-amide bond simulation in opioid peptides

Jacek Olczak, Krzysztof Kaczmarek, Iwona Maszczyńska, Marek Lisowski, Dagmar Stropova, Victor J. Hruby, Henry I. Yamamura, Andrzej W. Lipkowski, Janusz Zabrocki

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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.

Original language	English (US)
Pages (from-to)	437-440
Number of pages	4
Journal	International Journal of Peptide Research and Therapeutics
Volume	5
Issue number	5-6
DOIs	https://doi.org/10.1007/BF02443502
State	Published - Jan 1 1998

Keywords

1,5-disubstituted tetrazole ring
Cis peptide bond conformation
Leu-enkephalin

ASJC Scopus subject areas

Analytical Chemistry
Bioengineering
Biochemistry
Molecular Medicine
Drug Discovery

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10.1007/BF02443502

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Consequences of cis-amide bond simulation in opioid peptides. / Olczak, Jacek; Kaczmarek, Krzysztof; Maszczyńska, Iwona; Lisowski, Marek; Stropova, Dagmar; Hruby, Victor J.; Yamamura, Henry I.; Lipkowski, Andrzej W.; Zabrocki, Janusz.

In: International Journal of Peptide Research and Therapeutics, Vol. 5, No. 5-6, 01.01.1998, p. 437-440.

Research output: Contribution to journal › Article › peer-review

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