Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: UNIPROT:P01185 (vasopressin)
 23,126 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

1 Synthetic analogues of oxytocin and of lysine-vasopressin with an hydroxyl group in either the L ro D configuration replacing the primary amino group have been tested for biological activity.2 [1-(L-2-Hydroxy-3-mercaptopropanoic acid)] oxytocin ([L-Hmp(1)]oxytocin) was 1.5 to 2 times more potent than oxytocin on the rat uterus in situ, the rat mammary strip and the rat mammary gland in situ and 3 times more potent on the rat isolated uterus.3 The pressor activity of [1-(L-2-hydroxy-3-mercaptopropanoic acid)-8-lysine]vasopressin ([L-Hmp(1), Lys(8)] vasopressin) was 2.2 and the antidiuretic activity 2.1 times that of lysine-vasopressin.4 The [D-Hmp(1)] analogues of oxytocin and vasopressin were much less potent than the [L-Hmp(1)] analogues.5 The responses to oxytocin and its hydroxy analogues in vivo were qualitatively indistinguishable but the pressor and antidiuretic responses to the hydroxy analogues of lysine-vasopressin were prolonged compared with those to the parent hormone.6 The hydroxy analogues of oxytocin and lysine-vasopressin were not inactivated by pregnancy plasma oxytocinase.7 The results are discussed in relation to the importance of the primary amino group for the biological activity and metabolism of the neurohypophysial hormones.
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PMID:Hydroxy analogues of oxytocin and of lysine-vasopressin. 51 8

[1-(L-2-Hdroxy-3-mercaptopropanic acid)]arginine-vasopressin (hydroxy-AVP), [1-(L-2-hydroxy-3-mercaptopropanoic acid),8-D-arginine]vasopressin (hydroxy-DAVP), and [1-(L-2-hydroxy-3-mercaptopropanoic acid),4-valine,8-D-arginine]vasopressin (hydroxy-VDAVP) were synthesized by a combination of the solid-phase and solution methods of peptide synthesis. Protected octapeptides synthesized by the solid-phase method were further acylated by 1 + 8 couplings in solution to furnish the key intermediates. Hydroxy-AVP has antidiuretic potency of 470 units/mg and activity in the rat vasopressor assay of 550 units/mg, representing a small enhancement of activity over that of arginine-vasopressin (AVP) in each case. Hydroxy-DAVP and hydroxy-VDAVP have essentially the same high antidiuretic activity (900 units/mg) and very low vasopressor potencies (0.9 and less than 0.02 units/mg, respectively). Hydroxy-AVP, hydroxy-DAVP, and hydroxy-VDAVP thus have antidiuretic-pressor selectivity (A/P) of 1, 1000, and greater than 45 000, respectively. These data are compared with those of other vasopressin analogues. Hydroxy-VDAVP is a highly specific antidiuretic peptids and may be useful in pharmacological studies of antidiuresis.
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PMID:[1-(L-2-hydroxy-3-mercaptopropanoic acid)] analogues of arginine-vasopressin, [8-D-arginine]vasopressin, and [4-valine,8-D-arginine]vasopressin. 92 17

In an attempt to determine some of the structural features in position 1 that account for antivasopressor activity, eight new 1-(beta, beta-dialkyl-substituted) analogues of 1-(3-mercaptopropanoic acid)-8-arginine-vasopressin and 1-(3-mercaptopropanoic acid)-2-O-methyltyrosine-8-arginine-vasopressin have been designed and synthesized. The protected precursors required for these peptides were obtained by a combination of solid-phase and solutions methods. Some of the reported analogues, namely 1-(1-mercapto-4-methylcyclohexaneacetic acid)-8-arginine-vasopressin, 1-(1-mercapto-4-methylcyclohexaneacetic acid)-2-O-methyltryosine-8-arginine-vasopressin, 1-(4-tert-butyl-1-mercaptocyclohexaneacetic acid)-2-O-methyltyrosine-8-arginine- vasopressin, 1-(1-mercapto-4-phenylcyclohexaneacetic acid)-8-arginine-vasopressin and 1-(1-mercapto-4-phenylcyclohexaneacetic acid)-2-O-methyltyrosine-8-arginine- vasopressin, are among the most potent and selective antagonists of the vasopressor response to arginine-vasopressin reported to date.
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PMID:Synthesis of arginine-vasopressins, modified in positions 1 and 2, as antagonists of the vasopressor response to the parent hormone. 334 76

We synthesized a series of analogs of arginine vasotocin by systematically substituting each residue, and we then evaluated the anovulatory activity of these compounds in the rat, investigating the correlation between molecular structure and anovulatory, pressor, and antidiuretic activities. Substitution of the N-terminus cysteine with 3-mercaptopropanoic acid in arginine vasotocin and arginine vasopressin produced a 3- to 4-fold increase in both anovulatory and antidiuretic activity and only a 10% change in pressor activity. A similar substitution with lysine vasopressin produced no significant change in either anovulatory or antidiuretic potency; however, the pressor activity was reduced by half. Substitution of this cysteine in arginine vasotocin with 2-hydroxy-3-mercaptopropanoic acid produced an analog more potent in anovulatory activity than arginine vasotocin but less potent than [1-(3-mercaptopropanoic acid)]-arginine vasotocin. The most potent anovulatory analog synthesized was [1-(3-mercaptopropanoic acid)]-8-ornithine vasotocin, which gave a 10-fold increase in anovulatory activity, a 4-fold reduction in antidiuretic activity, and only a 10% increase in pressor potency when compared with arginine vasotocin. These data suggest that different receptors are involved in the anovulatory and antidiuretic responses, but that the anovulatory and pressor effects may be mediated through similar receptors. Further work is necessary to produce a peptide that possesses specific anovulatory activity.
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PMID:Anovulatory effect of synthetic analogs of arginine vasotocin in the rat. 684 22