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MedKoo Cat#: 464718 | Name: Podophyllotoxin-d6
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Podophyllotoxin-d6 is intended for use as an internal standard for the quantification of podophyllotoxin and picropodophyllotoxin by GC- or LC-MS. Podophyllotoxin is a lignan that has been found in Podophyllum and has diverse biological activities. It inhibits polymerization of isolated chicken brain tubulin (IC50 = 0.6 µM) and induces mitotic arrest at the G2/M phase in CCRF CEM lymphoblastic leukemia cells when used at concentrations ranging from 0.01 to 5 µg/ml. Podophyllotoxin (5 µM) is protective against herpes simplex virus 1 (HSV-1) infection in Vero cells. It inhibits the proliferation of several diffuse large B cell lymphoma (DLBCL) cell lines (IC50s = 0.0098-0.017 µM). Podophyllotoxin is a starting material in the semisynthesis of the anticancer compounds etoposide and teniposide. Formulations containing podophyllotoxin have been used in the treatment of external genital warts.

Chemical Structure

Podophyllotoxin-d6
Podophyllotoxin-d6
CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464718

Name: Podophyllotoxin-d6

CAS#: unknown

Chemical Formula: C22H16D6O8

Exact Mass: 420.1691

Molecular Weight: 420.45

Elemental Analysis: C, 62.85; H, 6.71; O, 30.44

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
5mg USD 1,100.00 2 Weeks
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Related CAS #
No Data
Synonym
Podophyllotoxin-d6; Podophyllotoxin d6; PPT-d6; PPT d6;
IUPAC/Chemical Name
(5R,5aR,8aR,9R)-9-hydroxy-5-(3-methoxy-4,5-bis(methoxy-d3)phenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
InChi Key
YJGVMLPVUAXIQN-UBHBGBPWSA-N
InChi Code
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/i1D3,3D3
SMILES Code
O=C1[C@@]2([C@@]([H])(C3=CC4=C(C=C3[C@H](O)[C@]2(CO1)[H])OCO4)C5=CC(OC([2H])([2H])[2H])=C(OC([2H])([2H])[2H])C(OC)=C5)[H]
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Podofilox (Podophyllotoxin) is a potent inhibitor of microtubule assembly and DNA topoisomerase II[1][2].
In vitro activity:
In this study, the inhibition of cell growth and changes in protein expression induced by podophyllotoxin were investigated in human cervical carcinoma HeLa cells. Results demonstrate that Podophyllotoxin inhibits HeLa cell growth and induces apoptosis. By using proteomic techniques, seven proteins were found to be significantly regulated by podophyllotoxin compared to the untreated control; among them, four were down-regulated and three were up-regulated. Reference: Am J Chin Med. 2013;41(1):163-75. https://pubmed.ncbi.nlm.nih.gov/23336514/
In vivo activity:
In this study, the efficacy of a more soluble and less toxic polyamidoamine (PAMAM) dendrimer-conjugated podophyllotoxin (DPODO) was evaluated against chemically induced hepatocellular carcinoma (HCC) in mice. The HCC-induced mice were treated with 10 or 20 mg per kg body weight DPODO. The DENA administration led to HCC development, characterized by anisocytosis, karyomegaly, inflammation and degenerative changes in the liver. The DPODO treatment at 10 mg and 20 mg doses significantly reduced the histopathological changes in liver tissue. The DPODO treatment also significantly lowered the levels of inflammatory markers IL-6 and NF-κB in serum and tissue, respectively. Reference: Toxicol Res (Camb). 2019 May 22;8(4):560-567. https://pubmed.ncbi.nlm.nih.gov/31367338/

Preparing Stock Solutions

The following data is based on the product molecular weight 420.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. An J, Liu Y, Duo S, Ma X, An L, Yan Y, Ji D, Yan Y, Cheng Q, Su Z. Podofilox suppresses gastric cancer cell proliferation by regulating cell cycle arrest and the c-Myc/ATG10 axis. Exp Ther Med. 2021 Nov;22(5):1203. doi: 10.3892/etm.2021.10637. Epub 2021 Aug 23. PMID: 34584548; PMCID: PMC8422391. 2. Wang B, Chen L, Zhen H, Zhou L, Shi P, Huang Z. Proteomic changes induced by podophyllotoxin in human cervical carcinoma HeLa cells. Am J Chin Med. 2013;41(1):163-75. doi: 10.1142/S0192415X13500122. PMID: 23336514. 3. Sharma S, Mehak, Chhimwal J, Patial V, Sk UH. Dendrimer-conjugated podophyllotoxin suppresses DENA-induced HCC progression by modulation of inflammatory and fibrogenic factors. Toxicol Res (Camb). 2019 May 22;8(4):560-567. doi: 10.1039/c9tx00103d. PMID: 31367338; PMCID: PMC6621132. 4. Choi JY, Cho HJ, Hwang SG, Kim WJ, Kim JI, Um HD, Park JK. Podophyllotoxin acetate enhances γ-ionizing radiation-induced apoptotic cell death by stimulating the ROS/p38/caspase pathway. Biomed Pharmacother. 2015 Mar;70:111-8. doi: 10.1016/j.biopha.2014.12.038. Epub 2015 Jan 12. PMID: 25776488.
In vitro protocol:
1. An J, Liu Y, Duo S, Ma X, An L, Yan Y, Ji D, Yan Y, Cheng Q, Su Z. Podofilox suppresses gastric cancer cell proliferation by regulating cell cycle arrest and the c-Myc/ATG10 axis. Exp Ther Med. 2021 Nov;22(5):1203. doi: 10.3892/etm.2021.10637. Epub 2021 Aug 23. PMID: 34584548; PMCID: PMC8422391. 2. Wang B, Chen L, Zhen H, Zhou L, Shi P, Huang Z. Proteomic changes induced by podophyllotoxin in human cervical carcinoma HeLa cells. Am J Chin Med. 2013;41(1):163-75. doi: 10.1142/S0192415X13500122. PMID: 23336514.
In vivo protocol:
1. Sharma S, Mehak, Chhimwal J, Patial V, Sk UH. Dendrimer-conjugated podophyllotoxin suppresses DENA-induced HCC progression by modulation of inflammatory and fibrogenic factors. Toxicol Res (Camb). 2019 May 22;8(4):560-567. doi: 10.1039/c9tx00103d. PMID: 31367338; PMCID: PMC6621132. 2. Choi JY, Cho HJ, Hwang SG, Kim WJ, Kim JI, Um HD, Park JK. Podophyllotoxin acetate enhances γ-ionizing radiation-induced apoptotic cell death by stimulating the ROS/p38/caspase pathway. Biomed Pharmacother. 2015 Mar;70:111-8. doi: 10.1016/j.biopha.2014.12.038. Epub 2015 Jan 12. PMID: 25776488.
1: Yadav P, Yadav R, Jain S, Vaidya A. Caspase-3, a primary target for natural and synthetic compounds for cancer therapy. Chem Biol Drug Des. 2021 May 8. doi: 10.1111/cbdd.13860. Epub ahead of print. PMID: 33963665. 2: Shah Z, Gohar UF, Jamshed I, Mushtaq A, Mukhtar H, Zia-Ui-Haq M, Toma SI, Manea R, Moga M, Popovici B. Podophyllotoxin: History, Recent Advances and Future Prospects. Biomolecules. 2021 Apr 19;11(4):603. doi: 10.3390/biom11040603. PMID: 33921719; PMCID: PMC8073934. 3: Banyal A, Thakur V, Thakur R, Kumar P. Endophytic Microbial Diversity: A New Hope for the Production of Novel Anti-tumor and Anti-HIV Agents as Future Therapeutics. Curr Microbiol. 2021 May;78(5):1699-1717. doi: 10.1007/s00284-021-02359-2. Epub 2021 Mar 16. PMID: 33725144. 4: Euwema MS, Swanson TJ. Deadly Single Dose Agents. 2021 Mar 16. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 28722879. 5: Adeleke BS, Babalola OO. Pharmacological Potential of Fungal Endophytes Associated with Medicinal Plants: A Review. J Fungi (Basel). 2021 Feb 17;7(2):147. doi: 10.3390/jof7020147. PMID: 33671354; PMCID: PMC7922420. 6: Ghorbani Hesari N, Tofighi Z, Shirmardi SF, Hashemi SM, Hadjiakhoondi A, Goodarzi S. Possible potential of Astrodaucus genus in development of anticancer drugs. Avicenna J Phytomed. 2021 Jan-Feb;11(1):11-21. PMID: 33628716; PMCID: PMC7885008. 7: Kalam MA, Malik AH, Ganie AH, Butt TA. Medicinal importance of Papra (Podophyllum hexandrum Royle) in Unani System of Medicine. J Complement Integr Med. 2021 Jan 29. doi: 10.1515/jcim-2020-0178. Epub ahead of print. PMID: 33544520. 8: Changxing L, Galani S, Hassan FU, Rashid Z, Naveed M, Fang D, Ashraf A, Qi W, Arif A, Saeed M, Chishti AA, Jianhua L. Biotechnological approaches to the production of plant-derived promising anticancer agents: An update and overview. Biomed Pharmacother. 2020 Dec;132:110918. doi: 10.1016/j.biopha.2020.110918. Epub 2020 Nov 1. PMID: 33254434. 9: Wang S, Wu J, Jing X, Zhang Y, Tang H, Wu J. Etoposide combined with ruxolitinib for refractory hemophagocytic lymphohistiocytosis during pregnancy: a case report and literature review. Hematology. 2019 Dec;24(1):751-756. doi: 10.1080/16078454.2020.1838708. PMID: 33138732. 10: Tissir R, Rais H, Tazi I. Lymphome plasmablastique de la muqueuse nasale isolée chez un patient immunocompétent en rémission complète après traitement multimodale: à propos d’un cas Africain et revue de la littérature [Isolated plasmablastic lymphoma of nasal mucosa in an immunocompetent patient achieving complete remission after multimodal treatment: about an African patient and literature review]. Pan Afr Med J. 2020 Sep 5;37:22. French. doi: 10.11604/pamj.2020.37.22.21352. PMID: 33062124; PMCID: PMC7532850. 11: Xiao J, Gao M, Sun Z, Diao Q, Wang P, Gao F. Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020). Eur J Med Chem. 2020 Dec 15;208:112830. doi: 10.1016/j.ejmech.2020.112830. Epub 2020 Sep 12. PMID: 32992133. 12: Oyama T, Noda T, Washio K, Shimada A. Pediatric growing teratoma syndrome of the ovary: A case report and review of the literature. Medicine (Baltimore). 2020 Sep 18;99(38):e22297. doi: 10.1097/MD.0000000000022297. PMID: 32957389; PMCID: PMC7505337. 13: Zhao W, Cong Y, Li HM, Li S, Shen Y, Qi Q, Zhang Y, Li YZ, Tang YJ. Challenges and potential for improving the druggability of podophyllotoxin- derived drugs in cancer chemotherapy. Nat Prod Rep. 2021 Mar 1;38(3):470-488. doi: 10.1039/d0np00041h. Epub 2020 Sep 8. PMID: 32895676. 14: Bridi H, de Carvalho Meirelles G, Lino von Poser G. Subtribe Hyptidinae (Lamiaceae): A promising source of bioactive metabolites. J Ethnopharmacol. 2021 Jan 10;264:113225. doi: 10.1016/j.jep.2020.113225. Epub 2020 Aug 5. PMID: 32763419; PMCID: PMC7403033. 15: Pennycook KB, McCready TA. Condyloma Acuminata. 2020 Aug 8. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 31613447. 16: Patel I, Akoluk A, Upadhyaya V, Makadia S, Douedi S, Farooq T, Flynn D, Levitt M, Hossain MA. "Do Not Ignore Musculoskeletal Pain"-Initial Presentation of a Rare Malignant Disease: Case Report and Literature Review. J Investig Med High Impact Case Rep. 2020 Jan-Dec;8:2324709620941316. doi: 10.1177/2324709620941316. PMID: 32660277; PMCID: PMC7361477. 17: Altieri B, Ronchi CL, Kroiss M, Fassnacht M. Next-generation therapies for adrenocortical carcinoma. Best Pract Res Clin Endocrinol Metab. 2020 May;34(3):101434. doi: 10.1016/j.beem.2020.101434. Epub 2020 Jun 18. PMID: 32622829. 18: Hensel A, Bauer R, Heinrich M, Spiegler V, Kayser O, Hempel G, Kraft K. Challenges at the Time of COVID-19: Opportunities and Innovations in Antivirals from Nature. Planta Med. 2020 Jul;86(10):659-664. doi: 10.1055/a-1177-4396. Epub 2020 May 20. PMID: 32434254; PMCID: PMC7356065. 19: Liu Y, Shen J, Awal Issah M, Liu T, Zhou H, Fu H. CD56-positive diffuse large B-cell lymphoma/leukemia with BCL6/MYC double-hit and multiple gene mutations: an indicator of poor prognosis? J Int Med Res. 2020 May;48(5):300060520918087. doi: 10.1177/0300060520918087. PMID: 32363958; PMCID: PMC7218936. 20: Guler Y, Ucpinar B, Erbin A. Diffuse Large B-cell Lymphoma of Testis: a Case Report and Current Literature Review. Folia Med (Plovdiv). 2020 Mar 31;62(1):200-203. doi: 10.3897/folmed.62.e47874. PMID: 32337891.