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

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2007年 / 50卷 / 12期

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

页码：2926 / 2929

页数：4

共 50 条

[41] Phenolic analogues of amino carboxylic acid ligands for 99mTc.: V -: N-benzyl-2-(2-hydroxyphenyl) glycines (bhpg) and N-benzyl-2-(4-hydroxyphenyl) glycines (isobhpg)
Wilson, JG
Katsfis, AG
AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (07) : 583 - 587
[42] A Novel 4-Oxo-2(E)-nonenal-Derived Modification to Angiotensin II: Oxidative Decarboxylation of N-Terminal Aspartic Acid
Lee, Seon Hwa
Goto, Takaaki
Oe, Tomoyuki
CHEMICAL RESEARCH IN TOXICOLOGY, 2008, 21 (12) : 2237 - 2244
[43] Preparation of highly potent and selective non-peptide antagonists of the arginine vasopressin V1A receptor by introduction of a 2-ethyl-1H-1-imidazolyl group
Shimada, Y
Akane, H
Taniguchi, N
Matsuhisa, A
Kawano, N
Kikuchi, K
Yatsu, T
Tahara, A
Tomura, Y
Kusayama, T
Wada, K
Tsukada, J
Tsunoda, T
Tanaka, A
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (07) : 764 - 769
[44] 7-chloro-5-hydroxy-1-[2-methyl-4-(2-metaminobenzoyl]-amino)benzoyl]-2,3,4,5-5-tetrahydro-1H-1-benzazepine (OPC-41061):: A potent, orally active nonpeptide arginine vasopressin V2 receptor antagonist
Kondo, K
Ogawa, H
Yamashita, H
Miyamoto, H
Tanaka, M
Nakaya, K
Kitano, K
Yamamura, Y
Nakamura, S
Onogawa, T
Mori, T
Tominaga, M
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) : 1743 - 1754
[45] GLUTAMINE AS A PRECURSOR TO N-TERMINAL PYRROLID-2-ONE-5-CARBOXYLIC ACID IN MOUSE IMMUNOGLOBULIN LAMBDA-TYPE LIGHT-CHAINS - AMINO ACID SEQUENCE VARIABILITY AT N-TERMINAL EXTRA PIECE OF LAMBDA-TYPE LIGHT-CHAIN PRECURSORS
BURSTEIN, Y
SCHECHTER, I
BIOCHEMICAL JOURNAL, 1977, 165 (02) : 347 - 354
[46] Highly potent and orally active non-peptide arginine vasopressin antagonists for both V1A and V2 receptors:: Synthesis and pharmacological properties of 4′-[(4,4-difluoro-5-methylidene-2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl)carbonyl]-2-phenylbenzanilide derivatives
Shimada, Y
Taniguchi, N
Matsuhisa, A
Sakamoto, K
Yatsu, T
Tanaka, A
CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (11) : 1644 - 1651
[47] Synthesis and structure-activity relationships of amide derivatives of (4,4-difluoro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-ylidene)acetic acid as selective arginine vasopressin V2 receptor agonists
Tsukamoto, Issei
Koshio, Hiroyuki
Kuramochi, Takahiro
Saitoh, Chikashi
Yanai-Inamura, Hiroko
Kitada-Nozawa, Chika
Yamamoto, Eisaku
Yatsu, Takeyuki
Shimada, Yoshiaki
Sakamoto, Shuichi
Tsukamoto, Shin-ichi
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (08) : 3130 - 3141
[48] DELETION MUTAGENESIS OF N-TERMINAL AMINO-ACID-RESIDUES OF ENDONUCLEASE-V - ESSENTIAL ROLE FOR THE POSITIONING OF THE CATALYTIC-ALPHA NH2GROUP
AUGUSTINE, ML
LLOYD, RS
JOURNAL OF CELLULAR BIOCHEMISTRY, 1993, : 161 - 161
[49] PURIFICATION AND N-TERMINAL AMINO-ACID-SEQUENCE OF 2 BIRCH POLLEN ISOALLERGENS (BET-V-I AND BET-V-II) (VOL 93, PG 378, 1990)
ELSAYED
VIK
INTERNATIONAL ARCHIVES OF ALLERGY AND IMMUNOLOGY, 1993, 100 (03) : 291 - 291
[50] Synthesis and some Pharmacological Properties of Seven New Analogues of Asn-D-Tyr(Et)-Phe-Val-Asn-Abu-Pro$MI N@Arg- Arg-NH2, A Potent Linear Antagonist of V2 Receptors
Pol J Chem, 4 (552):

← 1 2 3 4 5 →