4/'-Demethylepipodophyllotoxin

• CAT Number: I004472
• CAS Number: 6559-91-7
• Molecular Formula: C21H20O8
• Molecular Weight: 400.38
• Purity: ≥95%
• Synonyms: 6-oxo-1H-pyrazine-3-carboxylic acid
• Target: Topoisomerase
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• IC50: 0.31uM(EC5 0in HL60 cell, MTT assay, 48h); 0.37uM(EC50 in HepG2 cell, MTT assay, 48h)
• IUPAC Name: (5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• InChI: InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
• InChIKey: YVCVYCSAAZQOJI-JHQYFNNDSA-N
• SMILES: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O

4′-Demethylepipodophyllotoxin (Cat No.:I004472) is a crucial intermediate compound utilized in the synthesis of podophyllotoxin-type anticancer drugs. It exhibits potent inhibitory effects on microtubule assembly, a process crucial for cell division. By interfering with microtubule formation, 4′-DMEP disrupts the normal progression of the cell cycle and inhibits the growth of cancer cells. Due to its structural similarity to podophyllotoxin, it serves as an important building block in the development of novel chemotherapeutic agents for the treatment of various types of cancers.

Reference

[1]. Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4/’-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011 May;77(9):3023-34.

[2]. Dhawan D, Balasubramanian S, Amonkar AJ, Chemopreventive effect of 4/’-demethyl epipodophyllotoxin on DMBA/TPA-induced mouse skin carcinogenesis. Carcinogenesis. 1999 Jun;20(6):997-1003.