Synthesis and some of the pharmacological properties of [4-leucine]-8-lysine-vasopressin and [1-deamino,4-leucine]-8-lysine-vasopressin

Dyckes, Douglas F.; Ferger, Martha F.; Vigneaud, Vincent du; Çhan, W. Y.

doi:10.1021/jm00265a022

Cited by 14 publications

(17 citation statements)

References 8 publications

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“…The dissociation of behavioral and endocrine effects is also supported by results with [Leu4]LVP, which is effective in memory retention (Fig. 2) while exhibiting low agonistic or inhibitory endocrine activities (32). An even more active LVP derivative in terms of memory retention is [tri-Gly]LVP (Fig.…”

Section: Methodssupporting

confidence: 52%

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Walter¹,

Hoffman²,

Flexner³

et al. 1975

Proc. Natl. Acad. Sci. U.S.A.

100

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Neurohypophyseal hormones and several of their analogs as well as N-terminal and C-terminal fragments, have been studied for their ability to attenuate puromycin-induced amnesia in mice. arginine]vasopressin, and the analogs des--0lycinamide{8-lysine]vasopressin, [1-p-mercaptopropionic acid, 8-lysinelvasopressin, [1,6-aminosuberic acid, 8-lysine vasopressin, [4-leu- Gly-NH2, as well as its derivatives D-Leu-Gly-NH2 and the diketopiperazine, cyclo(-Leu-Gly-).Peptides possessing behavioral and electrophysiological activities are the focus of increasing attention (1-9). Among these peptides are the antidiuretic hormone of pig, [8-ly-sine]vasopressin (LVP) (for primary structures see Fig. 1), and des-9-glycinamide-LVP (DGLVP), which was isolated from hog pituitary (6). The peptides delay extinction of active avoidance behavior in intact rats (10)(11)(12) and restore the ability of hypophysectomized rats to acquire a conditioned avoidance response (3,5

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Section: Methodssupporting

confidence: 52%

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Walter¹,

Hoffman²,

Flexner³

et al. 1975

Proc. Natl. Acad. Sci. U.S.A.

100

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“…It was subsequently shown that both peptides 1 and 2 are also highly selective for human V 1b receptors (86). It bears noting that d[Leu 4 ,Lys 8 ]VP had been reported to be a weak antidiuretic V 2 agonist/weak vasopressor agonist in the rat (87), 30 years before the V 1b receptor was first predicted and/or cloned (88). The selective V 1b agonists d[Cha 4 ]AVP and d[Leu 4 ,Lys 8 ]VP have been used as a research tool in a number of studies (1, 20, 62, 73, 89, 90).…”

Section: V1b Receptor Agonists (Table 5)mentioning

confidence: 99%

Oxytocin and Vasopressin Agonists and Antagonists as Research Tools and Potential Therapeutics

Manning

Misicka

Olma

et al. 2012

J Neuroendocrinology

379

348

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We recently reviewed the status of peptide and nonpeptide agonists and antagonists for the V1a, V1b and V2 receptors for arginine vasopressin (AVP) and the oxytocin receptor for oxytocin (OT). In the present review, we update the status of peptides and nonpeptides as: (i) research tools and (ii) therapeutic agents. We also present our recent findings on the design of fluorescent ligands for V1b receptor localisation and for OT receptor dimerisation. We note the exciting discoveries regarding two novel naturally occurring analogues of OT. Recent reports of a selective VP V1a agonist and a selective OT agonist point to the continued therapeutic potential of peptides in this field. To date, only two nonpeptides, the V2/V1a antagonist, conivaptan and the V2 antagonist tolvaptan have received Food and Drug Administration approval for clinical use. The development of nonpeptide AVP V1a, V1b and V2 antagonists and OT agonists and antagonists has recently been abandoned by Merck, Sanofi and Pfizer. A promising OT antagonist, Retosiban, developed at Glaxo SmithKline is currently in a Phase II clinical trial for the prevention of premature labour. A number of the nonpeptide ligands that were not successful in clinical trials are proving to be valuable as research tools. Peptide agonists and antagonists continue to be very widely used as research tools in this field. In this regard, we present receptor data on some of the most widely used peptide and nonpeptide ligands, as a guide for their use, especially with regard to receptor selectivity and species differences.

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“…The Boc-7- aminoheptanoic acid (BOC-Aha) was from Bachem, (Torrance, CA). Peptide d[Leu 4 ,Lys 8 ]VP 20 ( A ) was resynthesized as previously described 3,19 . Peptide [HO 1 ]Leu 4 ,Lys 8 ]VP ( B ) was synthesized specifically for this study by the Merrifield solid-phase method 46,47 with modifications previously described 48,49,3,19 as shown in Solid-Phase Synthesis Procedures below.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Pharmacological Characterization of Fluorescent Peptides for Imaging Human V1b Vasopressin or Oxytocin Receptors

et al. 2011

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Among the four known vasopressin and oxytocin receptors, the specific localization of the V1b isoform is poorly described due to the lack of selective pharmacological tools. In an attempt to address this need, we decided to design, synthesize and characterize fluorescent selective V1b analogues. Starting with the selective V1b agonist, [deamino-Cys1, Leu4, Lys8]vasopressin (d[Leu4,Lys8]VP) synthesized earlier, we added blue, green or red fluorophores to the lysine residue at position 8, either directly or by the use of linkers of different lengths. Among the nine analogues synthesized, two exhibited very promising properties. These are d[Leu4, Lys (Alexa 647)8]VP (3) and d[Leu4, Lys (11-aminoundecanoyl-Alexa 647)8]VP (9). They remained full V1b agonists with nanomolar affinity and specifically decorated the plasma membrane of CHO cells stably transfected with the human V1b receptor. These new selective fluorescent peptides will allow the cellular localisation of V1b or OT receptor isoforms in native tissues.

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Synthesis and some of the pharmacological properties of [4-leucine]-8-lysine-vasopressin and [1-deamino,4-leucine]-8-lysine-vasopressin

Cited by 14 publications

References 8 publications

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Neurohypophyseal hormones, analogs, and fragments: their effect on puromycin-induced amnesia.

Oxytocin and Vasopressin Agonists and Antagonists as Research Tools and Potential Therapeutics

Design, Synthesis, and Pharmacological Characterization of Fluorescent Peptides for Imaging Human V1b Vasopressin or Oxytocin Receptors

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