title: Computer-based de novo design, synthesis, and evaluation of boronic acid-based artificial receptors for selective recognition of dopamine.
abstract: Dopamine is an important neurotransmitter that plays important roles in various physiological and pathological processes, such as Parkinson's disease. Chemosensors for dopamine have a number of potential applications. On the basis both of the strong and reversible complexation between the boronic acid moiety and a diol functional group and computational chemistry studies, we have designed a series of four compounds for selective three-point recognition of dopamine, which include boronic acid-diol complexation, aromatic-hydrophobic interactions, and ionic interactions between a carboxylate and a protonated amino group. These compounds were synthesized in seven or eight linear steps and showed dopamine selectivity of up to tenfold over epinephrine. NMR spectroscopy experiments were conducted to probe the structures of the receptor-dopamine complexes. These receptors are the first to show such significant selectivity for dopamine over epinephrine in aqueous solution under near physiological conditions.
authors.affiliation: Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-4098, USA.
authors.forename: Shan
authors.initials: S
authors.lastname: Jin
authors.forename: Minyong
authors.initials: M
authors.lastname: Li
authors.forename: Chunyuan
authors.initials: C
authors.lastname: Zhu
authors.forename: ViLinh
authors.initials: V
authors.lastname: Tran
authors.forename: Binghe
authors.initials: B
authors.lastname: Wang
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D017076:Computer-Aided Design; D004298:Dopamine / Q000032:analysis* / Q000378:metabolism; D015195:Drug Design; D004837:Epinephrine / Q000378:metabolism; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy; D012680:Sensitivity and Specificity; D014867:Water / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D014867:Water; D004298:Dopamine; D004837:Epinephrine