title: Synthesis and characterization of environment-sensitive fluorescent ligands for human 5-HT1A receptors with 1-arylpiperazine structure.
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.
authors.affiliation: Dipartimento Farmaco-Chimico, Universita degli Studi di Bari, via Orabona 4, 70125 Bari, Italy.
authors.forename: Enza
authors.initials: E
authors.lastname: Lacivita
authors.forename: Marcello
authors.initials: M
authors.lastname: Leopoldo
authors.forename: Anna Carmela
authors.initials: AC
authors.lastname: Masotti
authors.forename: Carmela
authors.initials: C
authors.lastname: Inglese
authors.forename: Francesco
authors.initials: F
authors.lastname: Berardi
authors.forename: Roberto
authors.initials: R
authors.lastname: Perrone
authors.forename: Sourav
authors.initials: S
authors.lastname: Ganguly
authors.forename: Md
authors.initials: M
authors.lastname: Jafurulla
authors.forename: Amitabha
authors.initials: A
authors.lastname: Chattopadhyay
mesh_terms: D000818:Animals; D002021:Buffers; D016466:CHO Cells; D002462:Cell Membrane / Q000378:metabolism; D006224:Cricetinae; D003412:Cricetulus; D015195:Drug Design; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D005786:Gene Expression Regulation; D006801:Humans; D008737:Methyl Chloride / Q000737:chemistry; D008856:Microscopy, Fluorescence; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D044282:Receptor, Serotonin, 5-HT1A / Q000378:metabolism*
chemical_list: D002021:Buffers; D005456:Fluorescent Dyes; D010879:Piperazines; D044282:Receptor, Serotonin, 5-HT1A; D008737:Methyl Chloride