title: Relationship between electronic structure and cytotoxic activity of dopamine and 3-benzazepine derivatives.
abstract: A structure-activity relationship of dopamine and 3-benzazepine derivatives is discussed, using theoretically calculated results. In order to clearly divide dopamines and 3-benzazepines into a strongly active and a weakly active group, the CC50, two different dipole moments (microESP-G and microESP-W) and heat of formation (deltaHf) of dopamine [1-13] and 3-benzazepine derivatives [14-23] were separately calculated in two states of gas-phase and water-solution by the COSMO/PM3 method. It was found that ten derivatives [1-3, 9, 12-13 and 20-23] (CC50: 0.056 to 2.5 mM) showed the strongest cytotoxic activity with small delta(deltaHf) values, whereas thirteen derivatives [4-8, 10-11, 14-19] (CC50: > 3.6 mM) showed the weakest cytotoxic activity with large delta(deltaHf) values.
authors.affiliation: Department of Chemistry, Faculty of Science, Josai University, Sakado, Saitama Japan. tkuri@josai.ac.jp
authors.forename: Teruo
authors.initials: T
authors.lastname: Kurihara
authors.forename: Tomoya
authors.initials: T
authors.lastname: Yamada
authors.forename: Ayako
authors.initials: A
authors.lastname: Yamamoto
authors.forename: Masami
authors.initials: M
authors.lastname: Kawase
authors.forename: Noboru
authors.initials: N
authors.lastname: Motohashi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.forename: Joseph
authors.initials: J
authors.lastname: Molnár
mesh_terms: D001552:Benzazepines / Q000737:chemistry / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D004298:Dopamine / Q000031:analogs & derivatives / Q000737:chemistry / Q000633:toxicity; D004305:Dose-Response Relationship, Drug; D004563:Electrochemistry; D018922:HL-60 Cells / Q000187:drug effects; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
chemical_list: D001552:Benzazepines; D004298:Dopamine