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

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	Letters in Peptide Science
Volume	5
Issue number	5-6
DOIs	https://doi.org/10.1007/BF02443502
State	Published - 1998
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry

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10.1007/BF02443502

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@article{8899f717e5f94f19a7fda2b84c45b83b,

title = "Consequences of cis-amide bond simulation in opioid peptides",

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

author = "Jacek Olczak and Krzysztof Kaczmarek and Iwona Maszczy{\'n}ska and Marek Lisowski and Dagmar Stropova and Hruby, {Victor J.} and Yamamura, {Henry I.} and Lipkowski, {Andrzej W.} and Janusz Zabrocki",

year = "1998",

doi = "10.1007/BF02443502",

language = "English (US)",

volume = "5",

pages = "437--440",

journal = "Letters in Peptide Science",

issn = "0929-5666",

publisher = "Springer Science and Business Media B.V.",

number = "5-6",

}

TY - JOUR

T1 - Consequences of cis-amide bond simulation in opioid peptides

AU - Olczak, Jacek

AU - Kaczmarek, Krzysztof

AU - Maszczyńska, Iwona

AU - Lisowski, Marek

AU - Stropova, Dagmar

AU - Hruby, Victor J.

AU - Yamamura, Henry I.

AU - Lipkowski, Andrzej W.

AU - Zabrocki, Janusz

PY - 1998

Y1 - 1998

N2 - 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.

AB - 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.

KW - 1,5-disubstituted tetrazole ring

KW - Leu-enkephalin

KW - cis peptide bond conformation

UR - http://www.scopus.com/inward/record.url?scp=0000178624&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000178624&partnerID=8YFLogxK

U2 - 10.1007/BF02443502

DO - 10.1007/BF02443502

M3 - Article

AN - SCOPUS:0000178624

SN - 0929-5666

VL - 5

SP - 437

EP - 440

JO - Letters in Peptide Science

JF - Letters in Peptide Science

IS - 5-6

ER -

Consequences of cis-amide bond simulation in opioid peptides

Abstract

Keywords

ASJC Scopus subject areas

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