Design, Synthesis and Structure-Activity Relationship of New Arginine Vasopressin Analogues Containing Proline Derivatives in Position 2

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00392307" target="_blank" >RIV/61388963:_____/13:00392307 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1111/cbdd.12093" target="_blank" >http://dx.doi.org/10.1111/cbdd.12093</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1111/cbdd.12093" target="_blank" >10.1111/cbdd.12093</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Design, Synthesis and Structure-Activity Relationship of New Arginine Vasopressin Analogues Containing Proline Derivatives in Position 2

Popis výsledku v původním jazyce

In this study, we present the synthesis and pharmacological properties of new analogues of arginine vasopressin modified in the N-terminal part of the molecule with proline derivatives: indoline-2-carboxylic acid (Ica) and (2S,4R)-4-(naphthalene-2-ylmethyl)pyrrolidine-2-carboxylic acid. All the peptides were tested for pressor, antidiuretic and in vitro uterotonic activities. We also determined their binding affinity to the human oxytocin receptor. The Ica2 substitution resulted in two moderately potentand selective antioxytocic agents: [Mpa1, Ica2, D-Arg8]VP and [Mpa1,Ica2,Val4,D-Arg8]VP (pA2=7.09 and 7.50, respectively). On the other hand, peptides modified with (2S,4R)-4-(naphthalene-2-ylmethyl)pyrrolidine-2-carboxylic acid, apart from their moderate antioxytocic activity, turned out to be weak antagonists of the pressor response to arginine vasopressin. The results of this study provide useful information about the structureactivity relationship of arginine vasopressin analogues a

Název v anglickém jazyce

Design, Synthesis and Structure-Activity Relationship of New Arginine Vasopressin Analogues Containing Proline Derivatives in Position 2

Popis výsledku anglicky

In this study, we present the synthesis and pharmacological properties of new analogues of arginine vasopressin modified in the N-terminal part of the molecule with proline derivatives: indoline-2-carboxylic acid (Ica) and (2S,4R)-4-(naphthalene-2-ylmethyl)pyrrolidine-2-carboxylic acid. All the peptides were tested for pressor, antidiuretic and in vitro uterotonic activities. We also determined their binding affinity to the human oxytocin receptor. The Ica2 substitution resulted in two moderately potentand selective antioxytocic agents: [Mpa1, Ica2, D-Arg8]VP and [Mpa1,Ica2,Val4,D-Arg8]VP (pA2=7.09 and 7.50, respectively). On the other hand, peptides modified with (2S,4R)-4-(naphthalene-2-ylmethyl)pyrrolidine-2-carboxylic acid, apart from their moderate antioxytocic activity, turned out to be weak antagonists of the pressor response to arginine vasopressin. The results of this study provide useful information about the structureactivity relationship of arginine vasopressin analogues a

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemical Biology & Drug Design

ISSN

1747-0277

e-ISSN

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Svazek periodika

81

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

420-428

Kód UT WoS článku

000314985900012

EID výsledku v databázi Scopus

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