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J Med Chem. 2009 Dec 10;52(23):7892-6. doi: 10.1021/jm900706d.

Synthesis and characterization of environment-sensitive fluorescent ligands for human 5-HT1A receptors with 1-arylpiperazine structure.

Author information

1
Dipartimento Farmaco-Chimico, Universita degli Studi di Bari, via Orabona 4, 70125 Bari, Italy.

Abstract

A series of "long-chain" 1-(2-methoxyphenyl)piperazine derivatives containing an environment-sensitive fluorescent moiety (4-amino-1,8-naphthalimide, 4-dimethylaminophthalimide, dansyl) was synthesized. The compounds displayed very high to moderate 5-HT(1A) receptor affinity and good fluorescence properties. 6-Amino-2-[5-[4-(2-methoxyphenyl)-1-piperazinyl]pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione (4) combined very high 5-HT(1A) receptor affinity (K(i) = 0.67 nM), high fluorescence emission in CHCl(3), and undetectable fluorescence emission in aqueous solution. It was evaluated for its ability to visualize 5-HT(1A) receptors overexpressed in CHO cells by fluorescence microscopy.

PMID:
19705871
DOI:
10.1021/jm900706d
[Indexed for MEDLINE]

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