Synthesis and structure–activity investigation of novel vasopressin hypotensive peptide agonists

@article{Manning1999SynthesisAS,
  title={Synthesis and structure–activity investigation of novel vasopressin hypotensive peptide agonists},
  author={Maurice Manning and Stoytcho Stoev and L L Cheng and Nga Ching Wo and W. Y. Chan},
  journal={Journal of Peptide Science},
  year={1999},
  volume={5}
}
We report the solid phase synthesis and vasodepressor potencies of the novel hypotensive peptide [1(‐β‐mercapto‐β,β‐pentamethylene propionic acid)‐2‐O‐ethyl‐D‐tyrosine, 3‐arginine, 4‐valine] arginine vasopressin, d(CH2)5[D‐Tyr(Et)2, Arg3, Val4]AVP (A), its related Lys3 (B), Tyr‐NH29 (C), [Lys3, Tyr‐NH29] (D) analogs and in a preliminary structure–activity study of positions 2–4 and 7–9, 24 analogs (1–24) of A–C. Peptides 1–6, 9–14 have the following single substituents at positions 2, 3, 4, 8… 
Design and synthesis of potent, highly selective vasopressin hypotensive agonists
TLDR
The solid‐phase synthesis and vasodepressor potencies of a new lead vasopressin (VP) hypotensive peptide and d(CH2)5[D‐Tyr(Et)2, Arg3, Val4, Lys7, Eda9]LVP (C) and 21 analogues of C were found to exhibit no or negligible activities in these assays.
A comparison between haemodynamic effects of vasopressin analogues
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Functional and Binding Characterizations of Urotensin II-Related Peptides in Human and Rat Urotensin II-Receptor Assay
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A structure-to-function analysis of Urotensin II demonstrated the minor contribution of the N-terminal segment and the essential role of the cyclic structure and three residues within the loop are required for receptor recognition and activation.
Discovery and design of novel and selective vasopressin and oxytocin agonists and antagonists: the role of bioassays
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Bioassay characterisations of Peptide I show that its vasodepressor action is independent of the peripheral autonomic, bradykinin, nitric oxide and prostaglandin systems and is not mediated by the known classical oxytocin and vasopressin receptors.
The Role of the Merrifield Solid Phase Method in the Discovery and Exploration of a New Class of Selective Vasopressin Hypotensive Agonists
TLDR
These findings offer promising clues to the design of more potent VP hypotensive agonists and of critically needed antagonists of the putative VP vasodilating receptor.
Impact of the Merrifield solid phase method on the design and synthesis of selective agonists and antagonists of oxytocin and vasopressin: A historical perspective
This tribute to Bruce Merrifield traces the author's fortuitous path in 1964 from Vincent du Vigneaud's laboratory to the laboratory of D. W. Woolley to learn the solid phase method and then to his

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This presentation will trace the serendipitous discovery of novel vasopressin (VP) hypotensive agonists d(CH2)5[D-Tyr(Et)2,X3]VAVP (where X = Arg, Lys) to lead to the development of a new class of therapeutically useful antihypertensives.
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