An internal standard for the quantification of podophyllotoxin and picropodophyllotoxin
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Unlabeled Version(s)
19575Podophyllotoxin
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Podophyllotoxin-d6

Item No. 33547

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,5aR,8aR,9R)-5,8,8a,9-tetrahydro-9-hydroxy-5-(3-methoxy-4,5-bis(methoxy-d3)phenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
Synonyms
  • PPT-d6
Molecular Formula
C22H16D6O8
Formula Weight
420.4
Purity
≥99% deuterated forms (d1-d6)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: solubleDMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1[C@]2([H])[C@@](C3=CC(OC([2H])([2H])[2H])=C(C(OC)=C3)OC([2H])([2H])[2H])([H])C4=CC(OCO5)=C5C=C4[C@@H]([C@@]2([H])CO1)O
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
InChi Key
YJGVMLPVUAXIQN-UBHBGBPWSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $134

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    1 mg

    $253

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    5 mg

    $994

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    Cayman Chemical
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    Product Description

    Podophyllotoxin-d6 is intended for use as an internal standard for the quantification of podophyllotoxin (Item No. 19575) and picropodophyllotoxin (Item No. 17329) by GC- or LC-MS. Podophyllotoxin is a lignan that has been found in Podophyllum and has diverse biological activities.1,2,3,4,5 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.2,3 Podophyllotoxin (5 µM) is protective against herpes simplex virus 1 (HSV-1) infection in Vero cells.4 It inhibits the proliferation of several diffuse large B cell lymphoma (DLBCL) cell lines (IC50s = 0.0098-0.017 µM).5 Podophyllotoxin is a starting material in the semisynthesis of the anticancer compounds etoposide (Item No. 12092) and teniposide (Item No. 14425).6 Formulations containing podophyllotoxin have been used in the treatment of external genital warts.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Imbert, T.F. Discovery of podophyllotoxins. Biochimie 80(3), 207-222 (1998).

    2. Loike, J.D., Brewer, C.F., Sternlicht, H., et al. Structure-activity study of the inhibition of microtubule assembly in vitro by podophyllotoxin and its congeners. Cancer Res. 38(9), 2688-2693 (1978).

    3. Krishan, A., Paika, K., and Frei, E., III Cytofluorometric studies on the action of podophyllotoxin and epipodophyllotoxins (VM-26, VP-16-213) on the cell cycle traverse of human lymphoblasts. J. Cell Biol. 66(3), 521-530 (1975).

    4. Hammonds, T.R., Denyer, S.P., Jackson, D.E., et al. Studies to show that with podophyllotoxin the early replicative stages of herpes simplex virus type 1 depend upon functional cytoplasmic microtubules. J. Med. Microbiol. 45(3), 167-172 (1996).

    5. Strömberg, T., Feng, X., Delforoush, M., et al. Picropodophyllin inhibits proliferation and survival of diffuse large B-cell lymphoma cells. Med. Oncol. 32(7), 188 (2015).

    6. Xu, H., Lv, M., and Tian, X. A review on hemisynthesis, biosynthesis, biological activities, mode of action, and structure-activity relationship of podophyllotoxins: 2003-2007. Curr. Med. Chem. 16(3), 327-349 (2009).