Arginine-vasopressin analogues containing D-3-(3′-pyridyl)-alanine residue in position 2

Two analogues of arginine-vasopressin: [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 7-sarcosine, 8-arginine]vasopressin and [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 7-N-methylalanine, 8-arginine]vasopressin were synthesized by solid-phase peptide synthesis method. Both peptides exhibit antioxytocic, antivasopressor and antiglycogenolytic activities, and on the other hand they are weak antidiuretic agonists. The binding affinities of both analogues to oxytocic receptor (guinea pig myometrium membranes) and to hepatic V1 receptor (rat liver membranes) are practically the same as for the parent hormones, whereas the binding affinities to renal V2 receptor (bovine kidney membranes) are 60-90 times lower than for vasopressin.

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The Effects of N-Terminal Part Modification of Arginine Vasopressin Analogues with 2-Aminoindane-2-carboxylic Acid: A Highly Potent V2Agonist

Journal of Medicinal Chemistry ◽

10.1021/jm070174s ◽

2007 ◽

Vol 50 (12) ◽

pp. 2926-2929 ◽

Cited By ~ 9

Author(s):

Wioleta Kowalczyk ◽

Dariusz Sobolewski ◽

Adam Prahl ◽

Izabela Derdowska ◽

Lenka Borovičková ◽

...

Keyword(s):

Carboxylic Acid ◽

Arginine Vasopressin ◽

Terminal Part ◽

Vasopressin Analogues

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Cross-reactivity of vasopressin analogues with porcine antibodies to [8-arginine]vasopressin

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19772266 ◽

1977 ◽

Vol 42 (7) ◽

pp. 2266-2271 ◽

Cited By ~ 1

Author(s):

J. Slaninová ◽

T. Barth ◽

I. Rychlík

Keyword(s):

Arginine Vasopressin ◽

Cross Reactivity ◽

Vasopressin Analogues

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

Chemischer Informationsdienst ◽

10.1002/chin.198016311 ◽

1980 ◽

Vol 11 (16) ◽

Author(s):

C. R. BOTOS ◽

C. W. SMITH ◽

Y.-L. CHAN ◽

R. WALTER

Keyword(s):

Arginine Vasopressin ◽

Biological Activities ◽

Vasopressin Analogues

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cAMP and extrarenal vasopressin V2 receptors in dogs

AJP Heart and Circulatory Physiology ◽

10.1152/ajpheart.1992.263.6.h1888 ◽

1992 ◽

Vol 263 (6) ◽

pp. H1888-H1891 ◽

Cited By ~ 1

Author(s):

J. F. Liard

Keyword(s):

Arginine Vasopressin ◽

Plasma Catecholamines ◽

Isotonic Saline ◽

Vena Cava ◽

Electromagnetic Flowmeter ◽

Conscious Dogs ◽

Plasma Camp ◽

Arterial Plasma ◽

V2 Antagonist ◽

Vasopressin Analogues

The effect of vasopressin analogues on plasma adenosine 3',5'-cyclic monophosphate (cAMP) concentration was examined in a group of five conscious dogs instrumented for the measurement of arterial pressure and cardiac output (electromagnetic flowmeter). These dogs were infused for 20 min with a selective antidiuretic (V2) agonist, desamino-8-D-arginine vasopressin (DDAVP, 10 ng.kg-1 x min-1). This infusion was repeated on another day in the presence of the combined V1-V2 antagonist d(CH2)5-D-Tyr(Et)-4-valine,8-arginine vasopressin. The dogs also received an infusion of the selective V1 agonist 2-phenylalanine,8-ornithine oxytocin (Phe-OrnOT) at a rate of 10 ng.kg-1 x min-1. The effect of these infusions was compared with those of an isotonic saline infusion. Plasma cAMP measured in the aorta remained unchanged during all infusions but that of the selective V2 agonist DDAVP alone, during which it increased significantly from 22.4 +/- 0.8 to 32.6 +/- 4.6 and 37.0 +/- 4.1 pmol/ml after 10 and 20 min, respectively. In the plasma sampled from the inferior vena cava caudal to the renal veins, cAMP increased during DDAVP infusion from 22.2 +/- 2.5 to 39.2 +/- 3.8 and 36.0 +/- 4.0 pmol/ml after 10 and 20 min, respectively. The infusion of DDAVP was later given to the same dogs under anesthesia after bilateral nephrectomy, which did not modify the effect of DDAVP on arterial plasma cAMP. In another group of four conscious dogs, infusion of DDAVP at the same rate did not induce significant changes in plasma catecholamines.(ABSTRACT TRUNCATED AT 250 WORDS)

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ChemInform Abstract: Arginine-Vasopressin Analogues with High Antidiuretic/Vasopressor Selectivity.

Chemischer Informationsdienst ◽

10.1002/chin.198620332 ◽

1986 ◽

Vol 17 (20) ◽

Author(s):

Z. GRZONKA ◽

F. KASPRZYKOWSKI ◽

E. KOJRO ◽

K. DARLAK ◽

P. MELIN ◽

...

Keyword(s):

Arginine Vasopressin ◽

Vasopressin Analogues

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Tryptic splitting of vasopressin analogues containing homologues of lysine or arginine in position 8

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19792451 ◽

1979 ◽

Vol 44 (8) ◽

pp. 2451-2454

Author(s):

Anastasia Dimeli ◽

Tomislav Barth

Keyword(s):

Amino Acid ◽

Arginine Vasopressin ◽

Basic Amino Acid ◽

Peptide Bond ◽

Peptide Chain ◽

Side Chain ◽

Lysine Vasopressin ◽

Vasopressin Analogues

Vasopressin analogues containing an amino acid with a shorter side chain in position 8 of the peptide chain were more resistant to tryptic splitting of the peptide bond formed by the basic amino acid and terminal glycine amide. In the lysine vasopressin series, analogues with ornithine or lower homologues of lysine in position 8 were not hydrolyzed. In the arginine vasopressin series, the analogue containing 3-guanidino-2-aminopropionic acid in position 8 was completely resistant to the action of trypsin. The vasopressin analogue with norarginine in position 8 was split at a lower rate than natural arginine vasopressin.

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