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Titolo:
IODINATED 2-AMINOTETRALINS AND 3-AMINO-1-BENZOPYRANS - LIGANDS FOR DOPAMINE D2 AND D3 RECEPTORS
Autore:
CHUMPRADIT S; KUNG MP; VESSOTSKIE J; FOULON C; MU M; KUNG HF;
Indirizzi:
UNIV PENN,DEPT RADIOL,3700 MARKET ST,ROOM 305 PHILADELPHIA PA 19104 UNIV PENN,DEPT RADIOL PHILADELPHIA PA 19104 UNIV PENN,DEPT PHARMACOL PHILADELPHIA PA 19104
Titolo Testata:
Journal of medicinal chemistry
fascicolo: 24, volume: 37, anno: 1994,
pagine: 4245 - 4250
SICI:
0022-2623(1994)37:24<4245:I2A3-L>2.0.ZU;2-4
Fonte:
ISI
Lingua:
ENG
Soggetto:
AUTORECEPTOR SELECTIVITY; STRUCTURAL REQUIREMENTS; D3-DOPAMINE RECEPTOR; STIMULATING ACTIVITY; AGONISTS; SERIES; MONOHYDROXYAMINOTETRALINS; MICRODIALYSIS; DERIVATIVES; EXPRESSION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
40
Recensione:
Indirizzi per estratti:
Citazione:
S. Chumpradit et al., "IODINATED 2-AMINOTETRALINS AND 3-AMINO-1-BENZOPYRANS - LIGANDS FOR DOPAMINE D2 AND D3 RECEPTORS", Journal of medicinal chemistry, 37(24), 1994, pp. 4245-4250

Abstract

In developing selective ligands for dopamine D2 and D3 receptors, several iodinated 2-aminotetralins and 3-amino-1-benzopyrans, 7-hydroxy-2-[N-(3'-iodo-2'-propenyl)amino]tetralin (1), -2-[N-propyl-N-(3'-iodo-2'-propenyl)amino]tetralin (7-, 5-, and 6-OH-PIPAT) (2, 3, and 4), and pyl-N-(3'-iodo-2'-propenyl)-amino]-2H-1-benzopyran (6- and 8-OH-benzopyrans) (5 and 6), were prepared. These compounds were evaluated for their binding profiles in several membrane preparations: Spodoptera frugiperda (Sf9) cells expressing dopamine D2 (non-GTP coupled, low-affinity states) and D3 receptors, HEK293 cells expressing dopamine D2 receptors in high-affinity states (D2H), rat hippocampal homogenates for 5-HT1A receptors, and cerebellar homogenates for sigma receptors. The mono-N-alkylated 2-aminotetralin, 1, displayed high sigma binding (K-i =1.68 nM) with a moderate D3 binding (K-i = 30.2 nM). Derivatives withone N-propyl and one N-(3'-iodo-2'-propeny) group generally displayedhigh to moderate affinity to D3 receptors (K-i = 2.90, 1.85, 0.99, 2.20, 31.4, and 6.69 nM for 7-OH-DPAT [7-hydroxy-2-(N,N-di-n-propylamino)tetralin], 2, 3, 4, 5, and 6, respectively). It is interesting to note that all of the active D3 ligands also displayed comparable binding to the high affinity states of D2 receptors in HEK293 cells (K-i = 6.6, 3.6, 9.7, and 10.8 nM for 2, 3, 4, and 6, respectively). Among all of the tetralin derivatives tested, 5-OH-PIPAT, 3, showed the highest binding affinity to D3 receptors (K-i = 0.99 nM) and better selectivity(K-iD2H/K-iD3, K-iD2/K-iD3, K-i5-HT1A/K-iD3 and K-i sigma/K-iD3 = 3.64, 327, 48.4, and 1250 nM, respectively), making it the best ligand for studying dopamine D2H and D3 receptors.

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Documento generato il 19/01/20 alle ore 07:05:35