Nga N. Chung

Novel µ opioid antagonists derived from the µ opioid agonists endomorphin and [Dmt1]DALDA (H‐Dmt‐D‐Arg‐Phe‐Lys‐NH2)

Saijian Shi, Jian Xu, Lingling Feng, Xin Dong Fan et autres

Abstract Hybrid analogues of the µ opioid agonists endomorphin and [Dmt1]DALDA (H‐Dmt‐D‐Arg‐Phe‐Lys‐NH2, Dmt = 2′,6′‐dimethyltyrosine) containing cis‐4‐amino‐Pro, trans‐4‐amino‐Pro, cis‐4‐aminoethyl‐Pro or cis‐4‐guanidinylethyl‐Pro in the 2 position of the peptide sequence were synthesized. None of the compounds retained high µ opioid agonist activity and, …

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Solid-Phase Azopeptide Diels–Alder Chemistry for Aza-pipecolyl Residue Synthesis To Study Peptide Conformation

Ramesh M. Chingle, Mukandila Mulumba, Nga N. Chung, Thi M.‐D. Nguyen et autres

Solid-phase chemistry for the synthesis and Diels-Alder reaction of Fmoc-protected azopeptides has been developed and used to construct aza-pipecolyl (azaPip) peptides. Considering their ability to induce electronic and structural constraints that favor cis-amide isomer geometry and type VI β-turn conformation in model …

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Corrigendum to “Chemical space screening around Phe3 in opioid peptides: Modulating µ versus δ agonism by Suzuki-Miyaura cross-couplings” [Bioorg. Med. Chem. Lett. 28(13) (2018) 2320–2323]

Tom Willemse, Émilie Eiselt, Charlie Hollanders, Wim B. G. Schepens et autres

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Equipotent enantiomers of cyclic opioid peptides at μ opioid receptor

Grazyna Weltrowska, Thi M.‐D. Nguyen, Nga N. Chung, Brian C. Wilkes et autres

Abstract Head‐to‐tail cyclized analogs of the µ opioid receptor (MOR) agonist tetrapeptides DALDA (H‐Tyr‐D‐Arg‐Phe‐Lys‐NH2and [Dmt1]DALDA (H‐Dmt‐D‐Arg‐Phe‐Lys‐NH2; Dmt = 2′,6′‐dimethyltyrosine) and their enantiomers (mirror‐image isomers) were synthesized and pharmacologically characterized in vitro. Three pairs of enantiomeric cyclic peptides with both mirror‐image isomers having …

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Chemical space screening around Phe3 in opioid peptides: Modulating µ versus δ agonism by Suzuki-Miyaura cross-couplings

Tom Willemse, Émilie Eiselt, Charlie Hollanders, Wim B. G. Schepens et autres

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χ-Space Screening of Dermorphin-Based Tetrapeptides through Use of Constrained Arylazepinone and Quinolinone Scaffolds

Olivier Van der Poorten, Robin Van Den Hauwe, Émilie Eiselt, Cecilia Betti et autres

Herein, the synthesis of novel conformationally constrained amino acids, 4-amino-8-bromo-2-benzazepin-3-one (8-Br-Aba), 3-amino-3,4-dihydroquinolin-2-one, and regioisomeric 4-amino-naphthoazepinones (1- and 2-Ana), is described. Introduction of these constricted scaffolds into the N -terminal tetrapeptide of dermorphin (i.e., H-Tyr- d -Ala-Phe-Gly-NH 2 ) induced significant shifts in …

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Analgesic Properties of Opioid/NK1 Multitarget Ligands with Distinct in Vitro Profiles in Naive and Chronic Constriction Injury Mice

Joanna Starnowska-Sokół, Roberto Costante, Karel Guillemyn, Katarzyna Popiołek-Barczyk et autres

The lower efficacy of opioids in neuropathic pain may be due to the increased activity of pronociceptive systems such as substance P. We present evidence to support this hypothesis in this work from the spinal cord in a neuropathic pain model in …

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A Cyclic Tetrapeptide (“Cyclodal”) and Its Mirror-Image Isomer Are Both High-Affinity μ Opioid Receptor Antagonists

Grazyna Weltrowska, Thi M.‐D. Nguyen, Nga N. Chung, JodiAnne T. Wood et autres

Head-to-tail cyclization of the μ opioid receptor (MOR) agonist [Dmt 1 ]DALDA (H-Dmt- d -Arg-Phe-Lys-NH 2 ( 9; Dmt = 2′,6′-dimethyltyrosine) resulted in a highly active, selective MOR antagonist, c[- d -Arg-Phe-Lys-Dmt-] ( 1 ) (“cyclodal”), with subnanomolar binding affinity. A docking …

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[Dmt1]DALDA analogues modified with tyrosine analogues at position 1

Yunxin Cai, Dandan Lu, Zhen Chen, Yi Ding et autres

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Bifunctional Peptide-Based Opioid Agonist–Nociceptin Antagonist Ligands for Dual Treatment of Acute and Neuropathic Pain

Karel Guillemyn, Joanna Starnowska-Sokół, Camille Lagard, Jolanta Dyniewicz et autres

Drugs able to treat both nociceptive and neuropathic pain effectively without major side effects are lacking. We developed a bifunctional peptide-based hybrid (KGNOP1) that structurally combines a mu-opioid receptor agonist (KGOP1) with antinociceptive activity and a weak nociceptin receptor antagonist (KGNOP3) with …

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Dual Alleviation of Acute and Neuropathic Pain by Fused Opioid Agonist-Neurokinin 1 Antagonist Peptidomimetics

Cecilia Betti, Joanna Starnowska-Sokół, Joanna Mika, Jolanta Dyniewicz et autres

Herein, the synthesis and biological evaluation of dual opioid agonists-neurokinin 1 receptor (NK1R) antagonists is described. In these multitarget ligands, the two pharmacophores do not overlap, and this allowed maintaining high NK1R affinity and antagonist potency in compounds 12 and 13. Although …

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Synthesis and biological evaluation of compact, conformationally constrained bifunctional opioid agonist – Neurokinin-1 antagonist peptidomimetics

Karel Guillemyn, Patrycja Kleczkowska, Anna Katharina Lesniak, Jolanta Dyniewicz et autres

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