Issue 17, 2003
From the journal:

Organic & Biomolecular Chemistry

Conformational analysis and μ-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent

Giuliana Cardillo,*a   Luca Gentilucci,*a   Alessandra Tolomelli,a   Ahmed R. Qasem,b   Santi Spampinato*b  and  Maria Caliennib  

* Corresponding authors

a Dipartimento di Chimica “G. Ciamician”, C.S.F.M., Università di Bologna, via Selmi 2, 40126-Bologna, Italy
E-mail: cardillo@ciam.unibo.it; gentil@ciam.unibo.it
Fax: +39 0512099456

b Dipartimento di Farmacologia, Università di Bologna, via Irnerio 48, 40126-Bologna, Italy
E-mail: spampi@biocfarm.unibo.it

Abstract

Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a γ-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for μ-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.

Graphical abstract: Conformational analysis and μ-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent

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Article information

DOI
https://doi.org/10.1039/B306161M
Article type
Paper
Submitted
30 May 2003
Accepted
10 Jul 2003
First published
28 Jul 2003

Org. Biomol. Chem., 2003,1, 3010-3014

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Conformational analysis and μ-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent

G. Cardillo, L. Gentilucci, A. Tolomelli, A. R. Qasem, S. Spampinato and M. Calienni, Org. Biomol. Chem., 2003, 1, 3010 DOI: 10.1039/B306161M

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