Anthraflavic Acid

Anthraflavic acid is a polyketide synthase-derived anthraquinone that has been found in Rhei Rhizoma and has diverse biological activities. It inhibits alpha-amylase in a cell-free assay (IC50 = 198.3 nM) and cytochrome P450 activity induced by a mixture of polychlorinated biphenyls (PCBs) in rat hepatic microsomes. Anthraflavic acid binds to estrogen receptor alpha (ERalpha) and ERbeta (Kis = 0.31 and 0.69 µM, respectively). It is cytotoxic against a panel of six breast cancer cell lines (IC50s = 156-241 µg/ml). Anthraflavic acid (50 µM) inhibits mutagenicity induced by the carcinogen 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1) in the Ames test using S. typhimurium. Topical application of anthraflavic acid (3 µmol/animal) reduces the number of tumors per mouse and the number of mice with tumors in a model of two-stage carcinogenesis initiated by 7,12-dimethylbenz[a]anthracene (DMBA, Cay-30383) and promoted by 12-O-tetradecanoylphorbol-13-acetate (TPA, Cay-10008014). Anthraflavic acid has been used as an anolyte in redox flow batteries.Formal Name: 2,6-dihydroxy-9,10-anthracenedione. CAS Number: 84-60-6. Synonyms: 2,6-Dihydroxyanthraquinone, 2,6-DHAQ, NSC 33531. Molecular Formula: C14H8O4. Formula Weight: 240.2. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Acetonitrile: Slightly soluble, Water: Slightly soluble. SMILES: O=C1C2=CC=C(C=C2C(C3=CC=C(C=C13)O)=O)O. InChi Code: InChI=1S/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16H. InChi Key: APAJFZPFBHMFQR-UHFFFAOYSA-N. Origin: Synthetic.