Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing b2-tryptophan analogues.

Rositsa Zamfirova; Nikola Pavlov; Petar Todorov; Polina Mateeva; Jean Martinez; Monique Calmes; Emilia Naydenova

doi:10.1016/j.bmcl.2013.05.064

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Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing b2-tryptophan analogues.

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Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing b2-tryptophan analogues.

Rositsa Zamfirova, Nikola Pavlov, Petar Todorov, Polina Mateeva, Jean Martinez, Monique Calmes and Emilia Naydenova

Bioorganic and Medicinal Chemistry Letters, Vol.23, pp.4052-4055

28/05/2013

DOI: https://doi.org/10.1016/j.bmcl.2013.05.064

Abstract

Nociceptin analogue

Nociceptin/orphanin FQ-NOP receptor

b-Tryptophan analogues

Rat vas deferens

We report the synthesis and the biological activity of new analogues of Ac-RFMWMK-NH2 and Ac- RYYRWK-NH2, modified in position 4 and 5, respectively, with incorporation of newly synthesized b2- tryptophan analogues. Trp was substituted by the (S)-2-(1-methyl-1H-indol-3-yl)propionic residue or by (S)-2-(5-methoxy-1H-indol-3-yl)propionic residue. The biological activity (pEC50 and Emax) of these compounds was tested on electrically stimulated preparations of rat vas deferens. The 5-methoxy b-tryptophan group reverses the affinity of the compounds.

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Title: Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing b2-tryptophan analogues.
Creators - without role: Rositsa Zamfirova - Institute of Neurobiology
Nikola Pavlov - University of Chemical Technology and Metallurgy
Petar Todorov - Department of Organic Chemistry
Polina Mateeva - Institute of Neurobiology
Jean Martinez - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Monique Calmes - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Emilia Naydenova - University of Chemical Technology and Metallurgy
Publication Details: Bioorganic and Medicinal Chemistry Letters, Vol.23, pp.4052-4055
Grant note: Grant DTK_02/61 of the National Research Fund, Bulgaria.
Identifiers: 9935949809311
Academic Unit: Institut des Biomolécules Max Mousseron - IBMM
Language: English
Resource Type: Journal article
Local Fields: hal-00969102