Podophyllotoxin

• CAT Number: I003874
• CAS Number: 518-28-5
• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.41
• Purity: ≥95%
• Target: Topoisomerase
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1
• InChIKey: YJGVMLPVUAXIQN-XVVDYKMHSA-N
• SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O

Podophyllotoxin (Cat.No:I003874) is a naturally occurring lignan derived from the roots of certain plants, including the Mayapple. It exhibits antiviral and antitumor properties. Podophyllotoxin and its derivatives, such as etoposide and teniposide, have been developed as chemotherapy drugs for the treatment of various cancers, including lung, testicular, and ovarian cancers.

Reference

1:One-pot synthesis and biological evaluation of N-(aminosulfonyl)-4-podophyllotoxin carbamates as potential anticancer agents. Xu XH, Guan XW, Feng SL, Ma YZ, Chen SW, Hui L.Bioorg Med Chem Lett. 2017 Apr 27. pii: S0960-894X(17)30469-9. doi: 10.1016/j.bmcl.2017.04.082. [Epub ahead of print] PMID: 28512026 2:Antigiardial Activity of Podophyllotoxin-Type Lignans from Bursera fagaroides var. fagaroides. Gutiérrez-Gutiérrez F, Puebla-Pérez AM, González-Pozos S, Hernández-Hernández JM, Pérez-Rangel A, Alvarez LP, Tapia-Pastrana G, Castillo-Romero A.Molecules. 2017 May 13;22(5). pii: E799. doi: 10.3390/molecules22050799. PMID: 28505094 Free Article3:The Catalytically Lignan-Activation-Based Approach for the Synthesis of (epi)-Podophyllotoxin Derivatives. Wan JH, Hu Y, Liu H, Tu YH, He ZY, Sun JS.J Org Chem. 2017 May 15. doi: 10.1021/acs.joc.7b00485. [Epub ahead of print] PMID: 28504515 4:Supramolecular system of podophyllotoxin and hydroxypropyl-β-cyclodextrin: Characterization, inclusion mode, docking calculation, solubilization, stability and cytotoxic activity. Yang LJ, Wang SH, Zhou SY, Zhao F, Chang Q, Li MY, Chen W, Yang XD.Mater Sci Eng C Mater Biol Appl. 2017 Jul 1;76:1136-1145. doi: 10.1016/j.msec.2017.03.197. Epub 2017 Mar 22. PMID: 28482478 5:Comparison of Tumor Penetration of Podophyllotoxin-Carboxymethylcellulose Conjugates with Various Chemical Compositions in Tumor Spheroid Culture and In Vivo Solid Tumor. Yang Y, Roy A, Zhao Y, Undzys E, Li SD.Bioconjug Chem. 2017 May 17;28(5):1505-1518. doi: 10.1021/acs.bioconjchem.7b00165. Epub 2017 Apr 28. PMID: 28437080 6:Synthesis and Antiproliferative Activity of Novel All-Trans-Retinoic Acid-Podophyllotoxin Conjugate towards Human Gastric Cancer Cells. Zhang L, Wang J, Liu L, Zheng C, Wang Y.Molecules. 2017 Apr 17;22(4). pii: E628. doi: 10.3390/molecules22040628. PMID: 28420180 Free Article7:Biotechnological approaches for production of anti-cancerous compounds resveratrol, podophyllotoxin and zerumbone. Nandagopal K, Halder M, Dash B, Nayak S, Jha S.Curr Med Chem. 2017 Apr 4. doi: 10.2174/0929867324666170404145656. [Epub ahead of print] PMID: 28393691 8:Induction of apoptotic DNA fragmentation mediated by mitochondrial pathway with caspase-3-dependent BID cleavage in human gastric cancer cells by a new nitroxyl spin-labeled derivative of podophyllotoxin. Yang YJ, Qi SN, Shi RY, Yao J, Wang LS, Yuan HQ, Jing YX.Biomed Pharmacother. 2017 Jun;90:131-138. doi: 10.1016/j.biopha.2017.03.048. Epub 2017 Mar 26. PMID: 28347917 9:Synthesis and biological evaluation of novel podophyllotoxin-NSAIDs conjugates as multifunctional anti-MDR agents against resistant human hepatocellular carcinoma Bel-7402/5-FU cells. Zhang L, Liu L, Zheng C, Wang Y, Nie X, Shi D, Chen Y, Wei G, Wang J.Eur J Med Chem. 2017 May 5;131:81-91. doi: 10.1016/j.ejmech.2017.03.011. Epub 2017 Mar 8. PMID: 28301815 10:In vitro polyploidy induction: changes in morphology, podophyllotoxin biosynthesis, and expression of the related genes in Linum album (Linaceae). Javadian N, Karimzadeh G, Sharifi M, Moieni A, Behmanesh M.Planta. 2017 Jun;245(6):1165-1178. doi: 10.1007/s00425-017-2671-2. Epub 2017 Mar 14. PMID: 28293732