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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)437-440
Number of pages4
JournalLetters in Peptide Science
Volume5
Issue number5-6
StatePublished - 1998

Fingerprint

Leucine Enkephalin
Opioid Peptides
Amides
Peptides
Assays
Geometry
1H-tetrazole
In Vitro Techniques

Keywords

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

ASJC Scopus subject areas

  • Biochemistry

Cite this

Olczak, J., Kaczmarek, K., Maszczyńska, I., Lisowski, M., Stropova, D., Hruby, V. J., ... Zabrocki, J. (1998). Consequences of cis-amide bond simulation in opioid peptides. Letters in Peptide Science, 5(5-6), 437-440.

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: Letters in Peptide Science, Vol. 5, No. 5-6, 1998, p. 437-440.

Research output: Contribution to journalArticle

Olczak, J, Kaczmarek, K, Maszczyńska, I, Lisowski, M, Stropova, D, Hruby, VJ, Yamamura, HI, Lipkowski, AW & Zabrocki, J 1998, 'Consequences of cis-amide bond simulation in opioid peptides', Letters in Peptide Science, vol. 5, no. 5-6, pp. 437-440.
Olczak J, Kaczmarek K, Maszczyńska I, Lisowski M, Stropova D, Hruby VJ et al. Consequences of cis-amide bond simulation in opioid peptides. Letters in Peptide Science. 1998;5(5-6):437-440.
Olczak, Jacek ; Kaczmarek, Krzysztof ; Maszczyńska, Iwona ; Lisowski, Marek ; Stropova, Dagmar ; Hruby, Victor J ; Yamamura, Henry I. ; Lipkowski, Andrzej W. ; Zabrocki, Janusz. / Consequences of cis-amide bond simulation in opioid peptides. In: Letters in Peptide Science. 1998 ; Vol. 5, No. 5-6. pp. 437-440.
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