title: Biological evaluation of dopamine analogues containing phenylboronic acid group as new boron carriers.
abstract: As new BNCT reagents, we designed and synthesized dopamine analogues containing phenylboronic acid group, N-3,4-dihydroxyphenethyl-4-dihydroxyborylbenzamide (dopamine-PCBA) and N-[2-(3,4-dihydroxyphenetyl)ethyl]-3-(4-dihydroxyborylphenyl)promionamide (dopamine-CEBA). The efficacies of these compounds have not been investigated for biological samples. Therefore we have carried out experiments with cultured tumor cells and tumor-bearing mice, and evaluated possibility of these compounds as boron carriers. Dopamine-PCBA and dopamine-CEBA were synthesized by coupling between p-carboxyphenylboronic acid (PCBA) or 4-(2-carboxyethyl)benzeneboronic acid (CEBA) and 3,4-(dibenzyloxy)phenethylamine hydrochloride (DBPA-HCl) followed by catalytic hydrogenation using Pd catalyst. The effect of compounds on cell vitality was determined by MTT assay in various cells. In vivo biodistribution of compounds was determined in Balb/c and DDY mice in bearing implanted CT26 cells. These results have demonstrated that dopamine-CEBA was less toxic.
authors.affiliation: Department of Chemistry, Faculty of Science, Shinshu University, Asahi, Matsumoto, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Ito
authors.forename: T
authors.initials: T
authors.lastname: Mizuno
authors.forename: K
authors.initials: K
authors.lastname: Yoshino
authors.forename: H S
authors.initials: HS
authors.lastname: Ban
authors.forename: H
authors.initials: H
authors.lastname: Nakamura
authors.forename: J
authors.initials: J
authors.lastname: Hiratsuka
authors.forename: A
authors.initials: A
authors.lastname: Ishikawa
authors.forename: H
authors.initials: H
authors.lastname: Ohki
mesh_terms: D000818:Animals; D001895:Boron / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry* / Q000493:pharmacokinetics; D045744:Cell Line, Tumor; D004298:Dopamine / Q000031:analogs & derivatives* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D051379:Mice; D008807:Mice, Inbred BALB C; D014018:Tissue Distribution
chemical_list: D001897:Boronic Acids; C010686:benzeneboronic acid; D001895:Boron; D004298:Dopamine