Synthesis and antitumor activity of 1,8-diaminoanthraquinone derivatives.
Continuing our ongoing studies on cytotoxic substances, a series of regioisomeric disubstituted aminoanthraquinone (DAAQ) derivatives have been synthesized as cytotoxic activity based on a proposed bioactive amino conformation. To assess the biological activity of amino-substitution in the side-chains of anthraquinone located at positions 1 and 8 of the anthraquinone ring system. The aim of the study was to determine if members of the anthraquinone family could be used as adjuncts to increase the growth inhibiting effect of anticancer agents in rat glioma C6 cells, human hepatoma G2 cells and 2.2.15 cells. In vitro cytotoxicity data is reported for the compounds and some indications of structure--activity relationships have been discerned. A number of compounds were found to have good cytotoxicity against proliferation in these three cell lines. This has led to the discovery some of the DAAQ as a conformationally constrained structure possessing anticancer properties that displays cytotoxicity for these above cell lines and is being investigated further.
Huang
Hsu-Shan
HS
School of Pharmacy, National Defense Medical Center, Neihu, Taipei 11490, Taiwan, R.O.C. huanghs@ndmctsgh.edu.tw
Chiu
Hui-Fen
HF
Lu
Wei-Chih
WC
Yuan
Chun-Lung
CL
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002855:Chromatography, Thin Layer; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013778:Tetrazolium Salts
C505013:1,8-diaminoanthraquinone; D000880:Anthraquinones; D000972:Antineoplastic Agents, Phytogenic; D013778:Tetrazolium Salts; C059087:2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-5-((phenylamino)carbonyl)-2H-tetrazolium hydroxide