Alkannin

Alkannin is a naphthoquinone and enantiomer of shikonin (Cay-14751) that has been found in A. tinctoria and has diverse biological activities. It inhibits tumor-specific pyruvate kinase M2 (PKM2, IC50 = 0.3 µM) with 20- and 10-fold selectivity over PKM1 and pyruvate kinase L (PKL), respectively. Alkannin inhibits proliferation of HCT116 and SW480 colorectal cancer cells with IC50 values of 2.38 and 4.53 µM, respectively. It halts the cell cycle at the G1 phase and induces apoptosis in HCT116 cells when used at a concentration of 3 µM. Alkannin (1 µM) increases levels of Hsp70 in untreated and UVB-irradiated HaCaT cells as well as inhibits UVB-induced DNA fragmentation and caspase-3 activity in HaCaT cells. It is active against methicillin-sensitive and -resistant S. aureus (MICs = 6.25 µg/ml) as well as vancomycin-sensitive and -resistant E. faecalis (MICs = 50 and 25 µg/ml, respectively). Alkannin scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH, Cay-14805) radicals in a cell-free assay (EC50 = 22 ppm).Formal Name: 5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione. CAS Number: 517-88-4. Synonyms: (-)-Alkannin, NSC 94524. Molecular Formula: C16H16O5. Formula Weight: 288.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml, Ethanol: 5 mg/ml. lambdamax: 215, 250, 279, 516, 555 nm. SMILES: OC1=C2C(C(C=C([C@H](C/C=C(C)/C)O)C2=O)=O)=C(O)C=C1. InChi Code: InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1. InChi Key: NEZONWMXZKDMKF-JTQLQIEISA-N. Origin: Plant/Arnebia sinensis.