A topoisomerase II poison
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Teniposide

Item No. 14425

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,5aR,8aR,9S)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-β-D-glucopyranosyl]oxy]-furo[3’,4’:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
CAS Number
29767-20-2
Synonyms
  • NSC 122819
  • VM-26
Molecular Formula
C32H32O13S
Formula Weight
656.7
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
284 nm
SMILES
[H][C@@]12O[C@H](C3=CC=CS3)OC[C@@]1([H])O[C@](O[C@@H]4C(C=C(OCO5)C5=C6)=C6[C@@H](C7=CC(OC)=C(O)C(OC)=C7)[C@]8([H])[C@]4([H])COC8=O)([H])[C@H](O)[C@H]2O
InChi Code
InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+
InChi Key
NRUKOCRGYNPUPR-QBPJDGROSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Cayman Chemical
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    Product Description

    Teniposide is a topoisomerase II poison.1,2,3,4 It promotes calf thymus topoisomerase II-mediated DNA cleavage when used at concentrations ranging from 0.04 to 40 µg/ml.1 Teniposide induces single- and double-stranded DNA breaks in a concentration-dependent manner.2 It inhibits the proliferation of A549 lung cancer cells (IC50 = 0.7 µM). Teniposide induces cell cycle arrest at the S phase and apoptosis in Tca8113 tongue squamous cell carcinoma cells when used at a concentration of 5 mg/L and induces cell cycle arrest at the G2/M phase when used at 0.15 mg/L.3 It reduces tumor growth and inhibits metastasis in a 3LL murine Lewis lung carcinoma model when administered at a dose of 6.5 mg/kg.4 Formulations containing teniposide have been used in combination therapy in the treatment of refractory childhood acute lymphoblastic leukemia.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ross, W., Rowe, T., Glisson, B., et al. Role of topoisomerase II in mediating epipodophyllotoxin-induced DNA cleavage. Cancer Res. 44(12 Pt. 1), 5857-5860 (1984).

    2. Long, B.H., Musial, S.T., and Brattain, M.G. Single- and double-strand DNA breakage and repair in human lung adenocarcinoma cells exposed to etoposide and teniposide. Cancer Res. 45(7), 3106-3112 (1985).

    3. Li, J., Chen, W., Zhang, P., et al. Topoisomerase II trapping agent teniposide induces apoptosis and G2/M or S phase arrest of oral squamous cell carcinoma. World J. Surg. Oncol. 4(1), 41 (2006).

    4. Colombo, T., Broggini, M., Vaghi, M., et al. Comparison between VP 16 and VM 26 in Lewis lung carcinoma of the mouse. Eur. J. Cancer Clin. Oncol. 22(2), 173-179 (1986).