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|Title:||Novel opioid peptide derived antagonists containing (2S)-2-methyl-3-(2,6- dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp]|
|Authors:||Ghosh, A. |
|Citation:||Ghosh, A., Luo, J., Liu, C., Weltrowska, G., Lemieux, C., Chung, N.N., Lu, Y., Schiller, P.W. (2008-09-25). Novel opioid peptide derived antagonists containing (2S)-2-methyl-3-(2,6- dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp]. Journal of Medicinal Chemistry 51 (18) : 5866-5870. ScholarBank@NUS Repository. https://doi.org/10.1021/jm8004702|
|Abstract:||A synthesis of the novel tyrosine analogue (2S)-2-methyl-3-(2,6-dimethyl-4- carbamoylphenyl)propanoic acid [(2S)-Mdcp] (15) was developed. In (2S)-Mdcp, the amino and hydroxyl groups of 2′,6′-dimethyltyrosine are replaced by a methyl and a carbamoyl group, respectively, and its substitution for Tyr 1 in opioid agonist peptides resulted in compounds showing antagonism at all three opioid receptors. The cyclic peptide (2S)-Mdcp-c[D-Cys-Gly- Phe(pNO2)-D-Cys]NH2 (1) was a potent and selective μ antagonist, whereas (2S)-Mdcp-c[D-Pen-Gly-Phe(pF)-Pen]-Phe-OH (3) showed subnanomolar δ antagonist activity and extraordinary δ selectivity. © 2008 American Chemical Society.|
|Source Title:||Journal of Medicinal Chemistry|
|Appears in Collections:||Staff Publications|
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