ChemInform Abstract: SYNTHESIS AND BIOLOGICAL ACTIVITIES OF ARGININE‐VASOPRESSIN ANALOGUES DESIGNED FROM A CONFORMATION‐ACTIVITY APPROACH

Botos, C. R.; Smith, Clark W.; Chan, Y. L.; Walter, R.

doi:10.1002/chin.198016311

Cited by 3 publications

(3 citation statements)

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“…All peptides were coded arbitrarily, so the substance tested was unknown to the observer. The Kimbrough et al, 1963Botos et al, 1979Berde et al, 1964Gillessen and du Vigneaud, 1970Gillessen and du Vigneaud, 1970Chan and du Vigneaud, 1962Smith et al, 1980Fenier et al, 1965Walter et al, 1976Sawyer et al, 1974Botos et al, 1979Manning et al, 1984Bankowski et al, 1978Kruszynski et al, 1980 late Dr. Roderich Walter and the late Dr. Vincent du Vigneaud, Cornell the Spearman's rank-difference correlation method (Guilford, 1956). Universitv.…”

Section: Methodsmentioning

confidence: 99%

A V1-like receptor mediates vasopressin-induced flank marking behavior in hamster hypothalamus

Albers¹,

Pollock²,

Simmons³

et al. 1986

J. Neurosci.

110

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A vasopressin-sensitive mechanism within the medial preoptic area-anterior hypothalamus (MPOA-AH) appears to be essential for expression of a complex behavior involved in olfactory communication in Golden hamsters called flank marking. The present study investigated whether the induction of flank marking by arginine-vasopressin (AVP) within the MPOA-AH is mediated by a receptor that is more similar to the vasopressor (Vl) or the antidiurectic (V2) AVP receptor. Adult male hamsters were anesthetized and implanted with a 26 gauge guide cannula stereotaxically aimed at the MPOA-AH and then microinjected with analogs of vasopressin, oxytocin, and selective Vl and V2 antagonists. Hamsters were tested for flank-marking behavior during a 5 or 10 min observation period following the injection of peptlde in a vehicle of 100 nl of saline. None of the 15 analogs of AVP and oxytocin produced more flank marking than the 50.8 + 16.2 and 76.8 f 4.4 (mean f SEW, II = 4) flank marks observed following injection of AVP at the 1 or 10 ng dose, respectively. The number of flank marks produced by each analog was found to be highly related to the pressor activity of that analog at both the 1 ng (p = +0.74, p < 0.01) and 10 ng (p = +0.82, p < 0.01) doses. In contrast, no statistically reliable relationship between flank marking and the antidiuretic activity of these analogs was found at either dose (1 ng: p = +O.O7,p > 0.05; 10 ng: p = +O.lO,p > 0.05). In a second series of studies, microinjection of 2 different Vl antagonists into the MPOA-AH significantly (p < 0.005) inhibited flank marking in response to AVP. However, microinjection of a V2 antagonist or saline did not inhibit flank marking. These data indicate that the receptors mediating the induction of 'flank marking within the MPOA-AH are more similiar to Vl (pressor) receptors than to V2 (antidiuretic) receptors. Scent marking is a major form of communication in mammals.Odors deposited in the environment can serve a variety of social functions from attracting mates to repelling competitors (Yahr, 1984). In the Golden hamster (Mesocricetus auratus), one form of scent marking, termed flank gland marking, is accomplished by rubbing a dorsal flank gland against vertical objects in the environment. Flank gland marking is commonly observed in both male and female hamsters and can be elicited by the odors of other hamsters and aggression during social encounters (Johnston, 1975).Several lines of evidence now indicate that neurons within the medial preoptic area-anterior hypothalamus (MPOA-AH) Received Dec. 2, 1985; revised Jan. 20, 1986; accepted Jan. 22, 1986. We wish to thank Professor Maurice Manning for providing several vasopressin analogs and for his comments on the manuscript. This work was supported by NIH Grants (to H.E.A.) and HD-18022 (to C.F.F. are critical for the expression of scent marking behavior. Lesions that destroy the MPOA-AH severely reduce scent-marking behavior in several mammalian species (Hart, 1974;Hart and Voith, 1978;Yahr, 1984). Implants of testoster...

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Section: Methodsmentioning

confidence: 99%

A V1-like receptor mediates vasopressin-induced flank marking behavior in hamster hypothalamus

Albers¹,

Pollock²,

Simmons³

et al. 1986

J. Neurosci.

110

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“…Glomerular filtration rate might then be expected to decrease. This explanation has also been proposed for the reduction in GFR elicited by a substitution-analogue of vasopressin (Botos, Smith, Chan & Walter, 1979).…”

Section: Discussionmentioning

confidence: 89%

Effects of vasopressin-glycine and vasopressin-glycine-lysine-arginine on renal function in the rat

Lote¹,

McVicar²,

Smyth³

1986

Journal of Endocrinology

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The peptides vasopressin-Gly and vasopressin-Gly-Lys-Arg occur as part of the sequence of the vasopressin-neurophysin precursor molecule and may be released from the hypothalamus and/or pituitary. [8-Lysine]-vasopressin-Gly (LVP-Gly) and [8-lysine]-vasopressin-Gly-Lys-Arg were administered i.v. to conscious, water-diuretic rats. The renal effects of the peptides were assessed by comparison with the actions of [8-lysine]-vasopressin (LVP) which was administered to separate groups of rats. LVP-Gly and LVP-Gly-Lys-Arg were weakly antidiuretic. LVP-Gly-Lys-Arg was the more potent of the two peptides, but on a molar basis it only had about 10% of the antidiuretic activity of LVP. LVP-Gly and LVP-Gly-Lys-Arg at 10 pmol/h per 100 g body weight (equivalent to the maximal antidiuretic dose of LVP) slightly decreased (P less than 0.001) urine flow without causing significant changes in urine osmolality. LVP (10 pmol/h per 100 g body weight) promoted a marked natriuresis (P less than 0.001) but LVP-Gly and LVP-Gly-Lys-Arg were not natriuretic, even at the dose which was markedly antidiuretic (100 pmol/h per 100 g body weight). Osmolal output decreased at all doses during administration of the extended peptides, but was not significantly changed in the control group or by LVP. Inulin clearance was decreased by about 30% during administration of both LVP and LVP-Gly-Lys-Arg at 100 pmol/h per 100 g body weight.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…Several papers reported the biological and structural effects of the replacement of the residue at position 7 in AVP. When this residue was replaced with 3,4-dehydroproline the biological activity of the analogue became high [33]. However, replacement with D-proline, glycine [34] or valine yielded compounds of low activity.…”

Section: Introductionmentioning

confidence: 99%

Conformational solution studies of [Sar⁷]desamino‐ and [MeAla⁷]desamino‐ vasopressin analogues using NMR spectroscopy

Rodziewicz‐Motowidło

Zhukov

Kasprzykowski

et al. 2002

Journal of Peptide Science

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Solution structures of two analogues of vasopressin with an amino acid sequence of c[Mpa1-Tyr2-Phe3-Gln4-Asn5-Cys6]-Xaa7-Arg8-Gly9-NH2 (Xaa = Sar [I] or MeAla [II]) were established using ROE and the 3J(HNH alpha) couplings. Each of the peptides was found to exist in two stable isomers, pertaining to the cis or trans status of the Cys6-Xaa7 peptide bond, thus giving rise to four study objects. Two methods for studies of the conformational properties of the structures were compared. In the first, the algorithm consisted of three steps: (i) An Electrostatically Driven Monte-Carlo (EDMC) search for low-energy conformations. (ii) Simulations of the NOESY spectra and the vicinal couplings for these conformations. (iii) Determination of the statistical weights of the conformations with the ANALYZE package, so as to meet the best fit of the averaged NOE intensities and couplings to the experimental data. In the second method, the distance constraints and the torsion angles were used as the usual constraints in the Distance Geometry and Simulated Annealing algorithms. The flexibility of the pressin ring and the C-terminus was characterized by a large number of families of conformations. The presence of the beta-turn at position 4,5 was confirmed for all low energy structures found. The use of the EDMC method for the elaboration of the NMR data for small flexible peptides yielded an adequate description of their conformational diversity and is the method of choice for the analysis of their solution structures.

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ChemInform Abstract: SYNTHESIS AND BIOLOGICAL ACTIVITIES OF ARGININE‐VASOPRESSIN ANALOGUES DESIGNED FROM A CONFORMATION‐ACTIVITY APPROACH

Cited by 3 publications

References 1 publication

A V1-like receptor mediates vasopressin-induced flank marking behavior in hamster hypothalamus

A V1-like receptor mediates vasopressin-induced flank marking behavior in hamster hypothalamus

Effects of vasopressin-glycine and vasopressin-glycine-lysine-arginine on renal function in the rat

Conformational solution studies of [Sar⁷]desamino‐ and [MeAla⁷]desamino‐ vasopressin analogues using NMR spectroscopy

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ChemInform Abstract: SYNTHESIS AND BIOLOGICAL ACTIVITIES OF ARGININE‐VASOPRESSIN ANALOGUES DESIGNED FROM A CONFORMATION‐ACTIVITY APPROACH

Cited by 3 publications

References 1 publication

A V1-like receptor mediates vasopressin-induced flank marking behavior in hamster hypothalamus

A V1-like receptor mediates vasopressin-induced flank marking behavior in hamster hypothalamus

Effects of vasopressin-glycine and vasopressin-glycine-lysine-arginine on renal function in the rat

Conformational solution studies of [Sar7]desamino‐ and [MeAla7]desamino‐ vasopressin analogues using NMR spectroscopy

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Conformational solution studies of [Sar⁷]desamino‐ and [MeAla⁷]desamino‐ vasopressin analogues using NMR spectroscopy