The effects of N-terminal part modification of arginine vasopressin analogues with 2-aminoindane-2-carboxylic acid:: A highly potent V2 agonist

被引:16
|
作者
Kowalczyk, Wioleta
Sobolewski, Dariusz
Prahl, Adam
Derdowska, Izabela
Borovickova, Lenka
Slaninova, Jirina
Lammek, Bernard
机构
[1] Univ Gdansk, Fac Chem, PL-80952 Gdansk, Poland
[2] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague, Czech Republic
关键词
D O I
10.1021/jm070174s
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In this study we present the synthesis and some pharmacological properties of nine new analogues of arginine vasopressin modified in the N-terminal part of the molecule with 2-aminoindane-2-carboxylic acid (Aic). The peptides were tested for their in vitro uterotonic and in vivo pressor and antidiuretic activities. One of the new peptides, [Mpa(1),Aic(2),Val(4),D-Arg(8)]VP, exhibited an antidiuretic activity similar to that of [Mpa(1),D-Arg(8)]VP, thus being one of the most potent antidiuretic vasopressin analogues reported to date.
引用
收藏
页码:2926 / 2929
页数:4
相关论文
共 50 条
  • [31] Influence of (2S,4R)-4-(2-naphthylmethyl)-pyrro lidine2-carboxylic acid replacing position 2 of Arginine Vasopressin (AVP) and its analogues on their pharmacological properties
    Kwiatkowska, Anna
    Derdowska, Izabela
    Prahl, Adam
    Sobolewski, Dariusz
    Slaninova, Jirina
    Lammek, Bernard
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 94 - 94
  • [32] Position 4 analogues of [deamino-Cys1] arginine vasopressin exhibit striking species differences for human and rat V2/V1b receptor selectivity
    Guillon, G
    Pena, A
    Murat, B
    Derick, S
    Trueba, M
    Ventura, MA
    Szeto, HH
    Wo, N
    Stoev, S
    Cheng, LL
    Manning, M
    JOURNAL OF PEPTIDE SCIENCE, 2006, 12 (03) : 190 - 198
  • [33] Synthesis and structure-activity relationships (SAR) of pyrrolobenzodiazepines related to the potent selective orally active nonpeptide vasopressin V2 receptor agonist VNA-932.
    Ashwell, MA
    Bagli, JF
    Caggiano, TJ
    Chan, PS
    Dusza, JP
    Dushin, RG
    Failli, AA
    Molinari, AJ
    Park, CH
    Rodgers, JF
    Shumsky, JS
    Trybulski, EJ
    Williams, DK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U38 - U38
  • [34] [1-(BETA-MERCAPTO-BETA,BETA-CYCLOPENTAMETHYLENEPROPIONIC ACID),2-(O-METHYL)TYROSINE]ARGININE-VASOPRESSIN AND [1-(BETA-MERCAPTO-BETA,BETA-CYCLOPENTAMETHYLENEPROPIONIC ACID)]ARGININE-VASOPRESSIN, 2 HIGHLY POTENT ANTAGONISTS OF THE VASOPRESSOR RESPONSE TO ARGININE-VASOPRESSIN
    KRUSZYNSKI, M
    LAMMEK, B
    MANNING, M
    SETO, J
    HALDAR, J
    SAWYER, WH
    JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (04) : 364 - 368
  • [35] Effects of N-terminal modification of recombinant human cytochrome P450 1A2 on catalytic activity
    Kim, H.-J.
    Lee, S.-B.
    Guengerich, F. P.
    Park, Y. I.
    Dong, M.-S.
    XENOBIOTICA, 2007, 37 (04) : 356 - 365
  • [36] Effects of the β-agonist, isoprenaline, on the down-regulation, functional responsiveness and trafficking of β2-adrenergic receptors with N-terminal polymorphisms
    Koryakina, Yulia
    Jones, Stacie M.
    Cornett, Lawrence E.
    Seely, Kathryn
    Brents, Lisa
    Prather, Paul L.
    Kofman, Alexander
    Kurten, Richard C.
    CELL BIOLOGY INTERNATIONAL, 2012, 36 (12) : 1171 - 1183
  • [37] CITATION CLASSIC - [1-(BETA-MERCAPTO-BETA,BETA-CYCLOPENTAMETHYLENEPROPIONIC ACID),2-(O-METHYL)TYROSINE]ARGININE-VASOPRESSIN AND [1-(BETA-MERCAPTO-BETA,BETA-CYCLOPENTAMETHYLENEPROPIONIC ACID)]ARGININE-VASOPRESSIN, 2 HIGHLY POTENT ANTAGONISTS OF THE VASOPRESSOR RESPONSE TO ARGININE-VASOPRESSIN
    MANNING, M
    SAWYER, WH
    CURRENT CONTENTS/LIFE SCIENCES, 1988, (38): : 20 - 20
  • [38] CITATION CLASSIC - [1-(BETA-MERCAPTO-BETA,BETA-CYCLOPENTAMETHYLENEPROPIONIC ACID),2-(O-METHYL)TRYOSINE]ARGININE-VASOPRESSIN AND [1-(BETA-MERCAPTO-BETA,BETA-CYCLOPENTAMETHYLENEPROPIONIC ACID)]ARGININE-VASOPRESSIN, 2 HIGHLY POTENT ANTAGONISTS OF THE VASOPRESSOR RESPONSE TO ARGININE-VASOPRESSIN
    MANNING, M
    SAWYER, WH
    CURRENT CONTENTS/CLINICAL MEDICINE, 1988, (38) : 20 - 20
  • [39] Involvement of arginine 878 together with Ca2+ in mouse aminopeptidase A substrate specificity for N-terminal acidic amino-acid residues
    Couvineau, Pierre
    de Almeida, Hugo
    Maigret, Bernard
    Llorens-Cortes, Catherine
    Iturrioz, Xavier
    PLOS ONE, 2017, 12 (09):
  • [40] The cardiovascular and renal effects of a highly potent μ-opioid receptor agonist, cyclo[Nε,Nβ-carbonyl-D-Lys2,Dap 5]enkephalinamide
    Gutkowska, J
    Jankowski, M
    Pawlak, D
    Mukaddam-Daher, S
    Izdebski, J
    EUROPEAN JOURNAL OF PHARMACOLOGY, 2004, 496 (1-3) : 167 - 174