title: Oxoisoaporphine alkaloid derivatives: synthesis, DNA binding affinity and cytotoxicity.
abstract: A series of novel oxoisoaporphine alkaloid derivatives, 9-aminoalkanamido-1-azabenzanthrone (general formula Ar-NHCO(CH(2))(n)NR(2), Ar=1-azabenzanthrone, n=1, 2 or 3), had been synthesized. Compared with 1-azabenzanthrone, the derivatives had significantly higher DNA binding affinity with calf thymus DNA, and higher potent cytotoxicity against different tumor cell lines. The cytotoxicity and the structure-activity relationship of the prepared compounds were studied. The derivatives with two methylene groups (n=2), and piperidine or ethanolamine functional group in the side chain exhibited highest DNA binding affinity and cytotoxicity.
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China.
authors.forename: Huang
authors.initials: H
authors.lastname: Tang
authors.forename: Xiao-Dong
authors.initials: XD
authors.lastname: Wang
authors.forename: Yong-Biao
authors.initials: YB
authors.lastname: Wei
authors.forename: Shi-Liang
authors.initials: SL
authors.lastname: Huang
authors.forename: Zhi-Shu
authors.initials: ZS
authors.lastname: Huang
authors.forename: Jia-Heng
authors.initials: JH
authors.lastname: Tan
authors.forename: Lin-Kun
authors.initials: LK
authors.lastname: An
authors.forename: Jian-Yong
authors.initials: JY
authors.lastname: Wu
authors.forename: Albert Sun-Chi
authors.initials: AS
authors.lastname: Chan
authors.forename: Lian-Quan
authors.initials: LQ
authors.lastname: Gu
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001060:Aporphines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004247:DNA / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D051379:Mice; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001060:Aporphines; D004247:DNA