Synthesis and biological activity profile of new analogues of the cyclic opioid peptide H-Tyr-c[D-Cys-Gly-Phe(pNO2)-D-Cys]-NH2 containing (S)-alpha-hydroxymethylcysteine in place of cysteine. |
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Authors: | Renata Witkowska Nga N Chung Peter W Schiller Janusz Zabrocki |
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Affiliation: | Institute of Organic Chemistry, Technical University of ?ód?, ?ód?, Poland. |
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Abstract: | To examine the effect on biological activity of replacing D-Cys in the opioid peptide H-Tyr-c[D-Cys-Gly-Phe(pNO(2))-D-Cys]-NH(2) in position 2 or/and 5 with alpha-hydroxymethylcysteine (alpha-Hmc), three analogues were synthesized. These compounds exhibit agonist activity at both mu and delta receptors. However, the most active analogue, with (S)-alpha-Hmc residue in position 5, was 3360- and 2190-fold less active than the parent peptide in the GPI and MVD assays, respectively. |
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Keywords: | α‐hydroxymethylamino acids α‐hydroxymethylcysteine opioid activity opioid peptides |
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