4-[omega-[4-arylpiperazin-1-yl]alkoxy]phenyl)imidazo[1,2-a]pyridine derivatives: fluorescent high-affinity dopamine D3 receptor ligands as potential probes for receptor visualization.
Sixteen long-chain arylpiperazines bearing the fluorescent moiety 2-phenylimidazo[1,2-a]pyridine were synthesized as fluorescent dopamine D3 receptors ligands (385 nM < Ki < 0.72 nM). The most potent D3 compounds 15a and 19a (Ki = 1.6 and 0.72 nM, respectively) showed good Stokes shift and high quantum yield in ethanol (Phi = 0.74 and 0.66, respectively). In the first attempt, 15a was unable to visualize D3 receptors expressed in CHO cells by epifluorescence microscopy.
Leopoldo
Marcello
M
Dipartimento Farmaco-Chimico, Università degli Studi di Bari, Via Orabona, 4, 70125 Bari, Italy.
Lacivita
Enza
E
Passafiume
Elena
E
Contino
Marialessandra
M
Colabufo
Nicola A
NA
Berardi
Francesco
F
Perrone
Roberto
R
D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D050637:Receptors, Dopamine D3 / Q000378:metabolism*
C524190:(4-(3-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)phenyl)imidazo(1,2-a)pyridine; C524189:(4-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)phenyl)imidazo(1,2-a)pyridine; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005456:Fluorescent Dyes; D007093:Imidazoles; D008024:Ligands; D010879:Piperazines; D011725:Pyridines; D050637:Receptors, Dopamine D3