4'-Demethylepipodophyllotoxin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526338

CAS#: 6559-91-7

Description: 4'-Demethylepipodophyllotoxin is a potent inhibitor of microtubule assembly.


Price and Availability

Size
Price

250mg
USD 190
2g
USD 1050
Size
Price

500mg
USD 350
5g
USD 1650
Size
Price

1g
USD 650

4'-Demethylepipodophyllotoxin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526338
Name: 4'-Demethylepipodophyllotoxin
CAS#: 6559-91-7
Chemical Formula: C21H20O8
Exact Mass: 400.1158
Molecular Weight: 400.383
Elemental Analysis: C, 63.00; H, 5.04; O, 31.97


Synonym: 4'-Demethylepipodophyllotoxin

IUPAC/Chemical Name: (5R-(5alpha,5abeta,8aalpha,9beta))-5,8,8a,9-Tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one

InChi Key: YVCVYCSAAZQOJI-JHQYFNNDSA-N

InChi Code: 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

SMILES Code: O=C1OC[C@]2([H])[C@H](O)C3=C(C=C4OCOC4=C3)[C@@H](C5=CC(OC)=C(O)C(OC)=C5)[C@]21[H]


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Zhou M, Li J, Li C, Guo L, Wang X, He Q, Fu Y, Zhang Z. Tertiary amine mediated targeted therapy against metastatic lung cancer. J Control Release. 2016 Nov 10;241:81-93. doi: 10.1016/j.jconrel.2016.09.013. Epub 2016 Sep 14. PubMed PMID: 27639682.

2: Tang ZB, Chen YZ, Zhao J, Guan XW, Bo YX, Chen SW, Hui L. Conjugates of podophyllotoxin and norcantharidin as dual inhibitors of topoisomeraseⅡ and protein phosphatase 2A. Eur J Med Chem. 2016 Nov 10;123:568-76. doi: 10.1016/j.ejmech.2016.07.031. Epub 2016 Jul 18. PubMed PMID: 27517805.

3: Li JL, Zhao W, Zhou C, Zhang YX, Li HM, Tang YL, Liang XH, Chen T, Tang YJ. Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: 4β-S-aromatic heterocyclic podophyllum derivatives display antitumor activity. Sci Rep. 2015 Oct 7;5:14814. doi: 10.1038/srep14814. PubMed PMID: 26443888; PubMed Central PMCID: PMC4595834.

4: Zi CT, Yang D, Dong FW, Li GT, Li Y, Ding ZT, Zhou J, Jiang ZH, Hu JM. Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives. Bioorg Med Chem. 2015 Apr 1;23(7):1437-46. doi: 10.1016/j.bmc.2015.02.021. Epub 2015 Feb 24. PubMed PMID: 25744190.

5: Kuo YC, Lee CH. Inhibition against growth of glioblastoma multiforme in vitro using etoposide-loaded solid lipid nanoparticles with p-aminophenyl-α-D-manno-pyranoside and folic acid. J Pharm Sci. 2015 May;104(5):1804-14. doi: 10.1002/jps.24388. Epub 2015 Feb 18. PubMed PMID: 25694089.

6: Xiao L, Zhao W, Li HM, Wan DJ, Li DS, Chen T, Tang YJ. Design and synthesis of the novel DNA topoisomerase II inhibitors: esterification and amination substituted 4'-demethylepipodophyllotoxin derivates exhibiting anti-tumor activity by activating ATM/ATR signaling pathways. Eur J Med Chem. 2014 Jun 10;80:267-77. doi: 10.1016/j.ejmech.2014.03.082. Epub 2014 Mar 30. PubMed PMID: 24793877.

7: Zhao W, Chen L, Li HM, Wang DJ, Li DS, Chen T, Yuan ZP, Tang YJ. A rational design strategy of the novel topoisomerase II inhibitors for the synthesis of the 4-O-(2-pyrazinecarboxylic)-4'-demethylepipodophyllotoxin with antitumor activity by diminishing the relaxation reaction of topoisomerase II-DNA decatenation. Bioorg Med Chem. 2014 Jun 1;22(11):2998-3007. doi: 10.1016/j.bmc.2014.03.048. Epub 2014 Apr 13. PubMed PMID: 24775914.

8: Zhi X, Yu X, Yang C, Ding G, Chen H, Xu H. Synthesis of 4β-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker. Bioorg Med Chem Lett. 2014 Feb 1;24(3):765-72. doi: 10.1016/j.bmcl.2013.12.105. Epub 2014 Jan 3. PubMed PMID: 24412075.

9: Sang CY, Liu JF, Qin WW, Zhao J, Hui L, Jin YX, Chen SW. Synthesis and evaluation of the apoptosis inducing and CT DNA interaction properties of a series of 4β-carbamoyl 4'-O-demethylepipodophyllotoxins. Eur J Med Chem. 2013;70:59-67. doi: 10.1016/j.ejmech.2013.09.053. Epub 2013 Oct 6. PubMed PMID: 24140948.

10: Li WQ, Wang XL, Qian K, Liu YQ, Wang CY, Yang L, Tian J, Morris-Natschke SL, Zhou XW, Lee KH. Design, synthesis and potent cytotoxic activity of novel podophyllotoxin derivatives. Bioorg Med Chem. 2013 Apr 15;21(8):2363-9. doi: 10.1016/j.bmc.2013.01.069. Epub 2013 Feb 17. PubMed PMID: 23490151.

11: Zhang F, Koh GY, Hollingsworth J, Russo PS, Stout RW, Liu Z. Reformulation of etoposide with solubility-enhancing rubusoside. Int J Pharm. 2012 Sep 15;434(1-2):453-9. doi: 10.1016/j.ijpharm.2012.06.013. Epub 2012 Jun 12. PubMed PMID: 22698860.

12: Bai JK, Zhao W, Li HM, Tang YJ. Novel biotransformation process of podophyllotoxin to 4 β-sulfur-substituted podophyllum derivates with anti-tumor activity by Penicillium purpurogenum Y.J. Tang. Curr Med Chem. 2012;19(6):927-36. PubMed PMID: 22214458.

13: Zhao W, Li HM, Wan DJ, Tang YJ. Manipulation of heterogeneity product in 4'-demethylepipodophyllotoxin biotransformation process by using yeast extract as nitrogen source. Appl Microbiol Biotechnol. 2012 Jan;93(1):107-15. doi: 10.1007/s00253-011-3424-y. Epub 2011 Jun 25. PubMed PMID: 21706170.

14: 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. doi: 10.1128/AEM.03047-10. Epub 2011 Mar 11. PubMed PMID: 21398491; PubMed Central PMCID: PMC3126428.

15: Zhang JQ, Zhang ZW, Hui L, Chen SW, Tian X. Novel semisynthetic spin-labeled derivatives of podophyllotoxin with cytotoxic and antioxidative activity. Bioorg Med Chem Lett. 2010 Feb 1;20(3):983-6. doi: 10.1016/j.bmcl.2009.12.048. Epub 2009 Dec 22. PubMed PMID: 20053564.

16: Li X, Choi JS. Effects of quercetin on the pharmacokinetics of Etoposide after oral or intravenous administration of etoposide in rats. Anticancer Res. 2009 Apr;29(4):1411-5. PubMed PMID: 19414395.

17: Tang YJ, Xu XL, Zhong JJ. A novel biotransformation process of 4'-demethylepipodophyllotoxin to 4'-demethylepipodophyllic acid by Bacillus fusiformis CICC 20463, Part II: process optimization. Bioprocess Biosyst Eng. 2010 Feb;33(2):237-46. doi: 10.1007/s00449-009-0317-x. Epub 2009 Apr 25. PubMed PMID: 19396467.

18: Chen SW, Xiang R, Liu J, Tian X. Synthesis and biological evaluation of novel conjugates of podophyllotoxin and 5-FU as antineoplastic agents. Bioorg Med Chem. 2009 Apr 15;17(8):3111-7. doi: 10.1016/j.bmc.2009.03.009. Epub 2009 Mar 12. PubMed PMID: 19324555.

19: Bender RP, Jablonksy MJ, Shadid M, Romaine I, Dunlap N, Anklin C, Graves DE, Osheroff N. Substituents on etoposide that interact with human topoisomerase IIalpha in the binary enzyme-drug complex: contributions to etoposide binding and activity. Biochemistry. 2008 Apr 15;47(15):4501-9. doi: 10.1021/bi702019z. Epub 2008 Mar 21. PubMed PMID: 18355043; PubMed Central PMCID: PMC2737519.

20: Yang TM, Guo SF, Chen CR, Zhang XY, Li WG. Anti-osteosarcoma effects and mechanisms of 4-O-amino-phenol-4'-demethylepipodophyllotoxin ether. J Pharm Pharmacol. 2008 Feb;60(2):179-88. doi: 10.1211/jpp.60.2.0006. PubMed PMID: 18237465.