[1-β-Mercaptopropionic acid, 8-α,γ-diaminobutyric acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-ornithine]vasopressin. Synthesis and biological effects

Zaoral, M.; Brtník, F.; Barth, Tomislav; Machová, Alena

doi:10.1135/cccc19762088

Cited by 7 publications

(8 citation statements)

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“…73,74 For the Dab 8 and Dap 8 analogues, the values are strikingly lower than the original values. 75,76 We have no explanation for these striking differences in antidiuretic activities. The vasopressor activities of the resynthesized position 8 analogues of dAVP are in general much closer to the values in the original publications [73][74][75][76] (Table 1).…”

Section: Resultsmentioning

confidence: 92%

“…These two peptides and indeed peptide D are clearly far more potent antidiuretic agonists than AVP (antidiuretic activity ) 332 units/ mg). 86 These findings on the contrasting effects on antidiuretic activities of the Lys 8 , Orn 8 , Dab 8 , and Dap 8 substitutions in dAVP [73][74][75][76] 4 ]AVP (B), closely mirror the effects on vasopressor activities of these four substituents at position 8 in dAVP [73][74][75][76] (Table 1). Thus, there is no correlation between the number of carbons in the side chain at position 8 and the vasopressor potency of the resultant analogue.…”

Section: Effects Of Position 8 Modifications Of Peptides A-d On Antid...mentioning

confidence: 87%

“…The purity of the free peptides 1 − 13 (Table ) was checked by thin-layer chromatography (TLC), high performance liquid chromatography (HPLC), and mass spectrometry. The four previously published position 8 analogues of dAVP, d[Lys 8 ]VP, d[Orn 8 ]VP, d[Dab 8 ]VP, and d[Dap 8 ]VP 76 (Table ), were resynthesized by the solid-phase method as described for dAVP . They were purified and analyzed as described for peptides 1 − 13 .…”

Section: Peptide Synthesismentioning

confidence: 99%

“…We thus selected the basic amino acids, Lys, ornithine (Orn), diaminobutyric acid (Dab), and diaminopropionic acid (Dap), which have, respectively, 4, 3, 2, and 1 methylene groups in their side chains. These four amino acids had previously been incorporated in dAVP 72 to give, respectively, d[Lys 8 ]VP, d[Orn 8 ]VP, d[Dab 8 ]VP, and d[Dap 8 ]VP . These four position 8 analogues of dAVP were resynthesized for this study.…”

Section: Introductionmentioning

confidence: 99%

“…d Original synthesis and data reported in ref . e Original synthesis and data reported in ref . f Original synthesis and data reported in ref .…”

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V_1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

et al. 2007

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The neurohypophyseal peptides arginine vasopressin (AVP) and oxytocin (OT) mediate a wide variety of peripheral and central physiological and behavioral effects by acting on four different G-protein coupled receptors, termed V1a (vascular), V1b (pituitary), V2 (renal), and OT (uterine). We recently reported that d[Cha4]AVP (A), d[Leu4]AVP (B), d[Orn4]AVP (C), and d[Arg4]AVP (D) have high affinity and are selective agonists for the human V1b receptor. However, peptides A-D were subsequently shown to be potent antidiuretic agonists in the rat and are, thus, not selective V1b agonists in the rat. Peptides A-D served as leads for the studies reported here. They were modified at position 8 by Lys, ornithine (Orn), diaminobutyric acid (Dab), and diaminopropionic acid (Dap) to give d[Cha4,Lys8]VP (1), d[Cha4,Orn8]VP (2), d[Cha4,Dab8]VP (3), d[Cha4,Dap8]VP (4), d[Leu4,Lys8]VP (5), d[Leu4,Orn8]VP (6), d[Leu4,Dab8]VP (7), d[Leu4,Dap8]VP (8), d[Orn4,Lys8]VP (9), d[Orn4,Orn8]VP (10), d[Arg4,Lys8]VP (11), d[Arg4,Orn8]VP (12), and d[Arg4,Dab8]VP (13). All peptides were synthesized by the Merrifield solid-phase method. Their binding and functional properties were evaluated in rat AVP V1a, V1b, and V2 receptors and on the rat OT receptor expressed either in native tissues or in stably transfected cells. They were also examined in rat vasopressor, antidiuretic, and in in vitro (no Mg++) oxytocic assays. Functional studies performed on chinese hamster ovary cells expressing the different AVP/OT receptors confirm that d[Cha4,Lys8]VP (1), d[Cha4,Dab8]VP (3), d[Leu4,Lys8]VP (5), and d[Leu4,Dap8]VP (8) are the first selective agonists for the rat V1b receptor. These selective V1b agonists are promising new tools for studies of the role of the V1b receptor in the rat.

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Section: Resultsmentioning

confidence: 92%

Section: Effects Of Position 8 Modifications Of Peptides A-d On Antid...mentioning

confidence: 87%

Section: Peptide Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…d Original synthesis and data reported in ref . e Original synthesis and data reported in ref . f Original synthesis and data reported in ref .…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V_1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

et al. 2007

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ChemInform Abstract: AMINO ACIDS AND PEPTIDES. CXXXIV. (1‐β‐MERCAPTOPROPIONIC ACID, 8‐α,Γ‐DIAMINOBUTYRIC ACID)VASOPRESSIN AND (1‐β‐MERCAPTOPROPIONIC ACID, 8‐D‐ORNITHINE)VASOPRESSIN. SYNTHESIS AND BIOLOGICAL EFFECTS

Zaoral¹,

Brtník²,

Barth³

et al. 1976

Chemischer Informationsdienst

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Durch Kondensation der Komponenten (I) und (II) nach üblicher Methode, Entfernung der Schutzgruppen, oxidativen Disulfid‐ ringschluß und elektrophoretische Reinigung werden die Vasopressin (IIIa)‐Analogen (IIIb) und (IIIc) synthetisiert, die hohe biologische Aktivität aufweisen: Der antidiuretische Effekt von (IIIb) ist um ein Mehrfaches höher als der von Desamino‐ [8‐Lysin]‐Vasopressin, die Pressor‐Aktivität von (IIIb) entspricht der von [8‐Arginin]‐ Vasopressin.

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V

Elks¹,

Ganellin²

1990

Dictionary of Drugs

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[1-β-Mercaptopropionic acid, 8-α,γ-diaminobutyric acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-ornithine]vasopressin. Synthesis and biological effects

Cited by 7 publications

References 0 publications

Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V_1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V_1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

ChemInform Abstract: AMINO ACIDS AND PEPTIDES. CXXXIV. (1‐β‐MERCAPTOPROPIONIC ACID, 8‐α,Γ‐DIAMINOBUTYRIC ACID)VASOPRESSIN AND (1‐β‐MERCAPTOPROPIONIC ACID, 8‐D‐ORNITHINE)VASOPRESSIN. SYNTHESIS AND BIOLOGICAL EFFECTS

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[1-β-Mercaptopropionic acid, 8-α,γ-diaminobutyric acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-ornithine]vasopressin. Synthesis and biological effects

Cited by 7 publications

References 0 publications

Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

ChemInform Abstract: AMINO ACIDS AND PEPTIDES. CXXXIV. (1‐β‐MERCAPTOPROPIONIC ACID, 8‐α,Γ‐DIAMINOBUTYRIC ACID)VASOPRESSIN AND (1‐β‐MERCAPTOPROPIONIC ACID, 8‐D‐ORNITHINE)VASOPRESSIN. SYNTHESIS AND BIOLOGICAL EFFECTS

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Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V_1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8

Design and Synthesis of the First Selective Agonists for the Rat Vasopressin V_1bReceptor: Based on Modifications of Deamino-[Cys]arginine Vasopressin at Positions 4 and 8