Teniposide
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MedKoo CAT#: 100820

CAS#: 29767-20-2

Description: Teniposide is a semisynthetic derivative of podophyllotoxin with antineoplastic activity. Teniposide forms a ternary complex with the enzyme topoisomerase II and DNA, resulting in dose-dependent single- and double-stranded breaks in DNA, DNA: protein cross-links, inhibition of DNA strand religation, and cytotoxicity. This agent acts in the late S or early G phase of the cell cycle.


Chemical Structure

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Teniposide
CAS# 29767-20-2

Theoretical Analysis

MedKoo Cat#: 100820
Name: Teniposide
CAS#: 29767-20-2
Chemical Formula: C32H32O13S
Exact Mass: 656.15636
Molecular Weight: 656.65
Elemental Analysis: C, 58.53; H, 4.91; O, 31.67; S, 4.88

Price and Availability

Size Price Availability Quantity
5.0mg USD 90.0 Ready to ship
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
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Synonym: NSC-122819; NSC 122819; NSC122819; VM26; VM-26; VM 26; HSDB 6546; HSDB6546; HSDB-6546; CCRIS 2058. Brand name: Vumon; Vehem. Abbreviations: EPT; PTG.

IUPAC/Chemical Name: (5S,5aR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

InChi Key: NRUKOCRGYNPUPR-DKQCQWADSA-N

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+,31+,32-/m0/s1

SMILES Code: O=C1OC[C@]2([H])[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@]4([H])O[C@H](C5=CC=CS5)OC[C@@]4([H])O3)C6=C(C=C7OCOC7=C6)[C@H](C8=CC(OC)=C(O)C(OC)=C8)[C@]21[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: Soluble in DMSO, not in water

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).

HS Tariff Code: 2934.99.9001

Biological target: Teniposide is a podophyllotoxin derivative and acts as a topoisomerase II inhibitor.
In vitro activity: The IC50 of teniposide (VM-26) against Tca8113 cells was 0.35 mg/l and that of CDDP was 1.1 mg/l. The morphological changes of Tca8113 cells were observed with fluorescence microscope and TEM. Apoptotic morphological feature could be found in the nucleus. Apoptotic rate of Tca8113 cells incubated with 5.0 mg/l of VM-26 for 72 hours was 81.67% and cells were arrested at S phase. However, when exposed to 0.15 mg/l of VM-26 for 72 hours, G2/M phase increased from 12.75% to 98.71%, while the apoptotic rate was 17.38%, which was lower than that exposed to 5.0 mg/l of VM-26. Reference: World J Surg Oncol. 2006 Jul 6;4:41. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/16822322/
In vivo activity: Teniposide at a dose of 0.5 mg/kg significantly increased the frequency of MNPCE. Additionally, teniposide significantly decreased the percent PCE, indicating a reduction in erythroblast proliferation most likely by mitotic arrest. A total of 148 MN from teniposide-treatment group were analysed by FISH and 69 (46.62%) MN of these were double labelled with centromere and telomere probes, indicating that they were formed by lagging chromosomes and reflecting an aneugenic activity of teniposide. Similarly, 77 (53.38%) of the induced MN were centromere negative, indicating that they were formed by acentric fragments and reflecting the clastogenic activity of teniposide. Since the centromere probe labelled mitotic chromosomes at both chromatids, it can be concluded that equal proportions of MN contained single chromatids (chromosome loss) and biarmed chromosomes (non-disjunction). Reference: Mutagenesis. 2012 Jan;27(1):31-9. https://academic.oup.com/mutage/article-lookup/doi/10.1093/mutage/ger051

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 45.69

Preparing Stock Solutions

The following data is based on the product molecular weight 656.65 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
In vitro protocol: 1. Li J, Chen W, Zhang P, Li N. Topoisomerase II trapping agent teniposide induces apoptosis and G2/M or S phase arrest of oral squamous cell carcinoma. World J Surg Oncol. 2006 Jul 6;4:41. doi: 10.1186/1477-7819-4-41. PMID: 16822322; PMCID: PMC1543631.
In vivo protocol: 1. Attia SM. Molecular cytogenetic evaluation of the aneugenic effects of teniposide in somatic and germinal cells of male mice. Mutagenesis. 2012 Jan;27(1):31-9. doi: 10.1093/mutage/ger051. Epub 2011 Aug 6. PMID: 21821840.

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1: He S, Yang H, Zhang R, Li Y, Duan L. Preparation and in vitro-in vivo evaluation of teniposide nanosuspensions. Int J Pharm. 2014 Nov 13;478(1):131-137. doi: 10.1016/j.ijpharm.2014.11.020. [Epub ahead of print] PubMed PMID: 25448575.

2: Nguyen TT, Jung SJ, Kang HK, Kim YM, Moon YH, Kim M, Kim D. Production of rubusoside from stevioside by using a thermostable lactase from Thermus thermophilus and solubility enhancement of liquiritin and teniposide. Enzyme Microb Technol. 2014 Oct;64-65:38-43. doi: 10.1016/j.enzmictec.2014.07.001. Epub 2014 Jul 11. PubMed PMID: 25152415.

3: Sun YC, Wang J, Guo CC, Sai K, Wang J, Chen FR, Yang QY, Chen YS, Wang J, To TS, Zhang ZP, Mu YG, Chen ZP. MiR-181b sensitizes glioma cells to teniposide by targeting MDM2. BMC Cancer. 2014 Aug 25;14:611. doi: 10.1186/1471-2407-14-611. PubMed PMID: 25151861; PubMed Central PMCID: PMC4155117.

4: Wu JJ, Wang XH, Li L, Li X, Zhang L, Sun ZC, Fu XR, Ma W, Chang Y, Zhang XD, Han LJ, Zhang MZ. Fotemustine, teniposide and dexamethasone in treating patients with CNS lymphoma. Asian Pac J Cancer Prev. 2014;15(11):4733-8. PubMed PMID: 24969912.

5: Mack F, Schäfer N, Kebir S, Stuplich M, Schaub C, Niessen M, Scheffler B, Herrlinger U, Glas M. Carmustine (BCNU) plus Teniposide (VM26) in recurrent malignant glioma. Oncology. 2014;86(5-6):369-72. doi: 10.1159/000360295. Epub 2014 Jun 18. PubMed PMID: 24942787.

6: Li WQ, Yu HY, Li YM, Wang X, He J, Yan HZ, Yang DH, Wu XJ, Hou LJ, Liu HM, Xia CY, Lu YC. Higher LRRFIP1 expression in glioblastoma multiforme is associated with better response to teniposide, a type II topoisomerase inhibitor. Biochem Biophys Res Commun. 2014 Apr 18;446(4):1261-7. doi: 10.1016/j.bbrc.2014.03.105. Epub 2014 Mar 29. PubMed PMID: 24690174.

7: Thiepold AL, Lemercier S, Franz K, Atta J, Sulzbacher A, Steinbach JP, Rieger J. Prophylactic use of pegfilgrastim in patients treated with a nitrosourea and teniposide for recurrent glioma. Pharmacotherapy. 2014 Jun;34(6):633-42. doi: 10.1002/phar.1409. Epub 2014 Mar 11. PubMed PMID: 24619825.

8: Zhang Z, Ma L, Jiang S, Liu Z, Huang J, Chen L, Yu H, Li Y. A self-assembled nanocarrier loading teniposide improves the oral delivery and drug concentration in tumor. J Control Release. 2013 Feb 28;166(1):30-7. doi: 10.1016/j.jconrel.2012.12.018. Epub 2012 Dec 20. PubMed PMID: 23266449.

9: Mo L, Hou L, Guo D, Xiao X, Mao P, Yang X. Preparation and characterization of teniposide PLGA nanoparticles and their uptake in human glioblastoma U87MG cells. Int J Pharm. 2012 Oct 15;436(1-2):815-24. doi: 10.1016/j.ijpharm.2012.07.050. Epub 2012 Jul 28. PubMed PMID: 22846410.

10: He S, Cui Z, Mei D, Zhang H, Wang X, Dai W, Zhang Q. A cremophor-free self-microemulsified delivery system for intravenous injection of teniposide: evaluation in vitro and in vivo. AAPS PharmSciTech. 2012 Sep;13(3):846-52. doi: 10.1208/s12249-012-9809-0. Epub 2012 May 30. PubMed PMID: 22644709; PubMed Central PMCID: PMC3429691.



Additional Information

CLINICAL PHARMACOLOGY
Teniposide is a phase-specific cytotoxic drug, acting in the late S or early G2 phase of the cell cycle, thus preventing cells from entering mitosis. Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA-protein cross-links. The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate. Teniposide has a broad spectrum of in vivo antitumor activity against murine tumors, including hematologic malignancies and various solid tumors. Notably, teniposide is active against sublines of certain murine leukemias with acquired resistance to cisplatin, doxorubicin, amsacrine, daunorubicin, mitoxantrone, or vincristine.
 
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