Synthesis and characterization of environment-sensitive fluorescent ligands for human 5-HT1A receptors with 1-arylpiperazine structure.
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.
Lacivita
Enza
E
Dipartimento Farmaco-Chimico, Universita degli Studi di Bari, via Orabona 4, 70125 Bari, Italy.
Leopoldo
Marcello
M
Masotti
Anna Carmela
AC
Inglese
Carmela
C
Berardi
Francesco
F
Perrone
Roberto
R
Ganguly
Sourav
S
Jafurulla
Md
M
Chattopadhyay
Amitabha
A
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*
D002021:Buffers; D005456:Fluorescent Dyes; D010879:Piperazines; D044282:Receptor, Serotonin, 5-HT1A; D008737:Methyl Chloride