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Cat. No. Name Size Price Add Cart
KI0395VP-16100 mg$112
VP-16500 mg$448

Chemical Characteristic

Product NameVP-16
SynonymsEtoposide, NSC-141540
CAS No.33419-42-0
Molecular Weight 588.56
FormulaC29H32O13
Chemical NameFuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-?-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5?,5a?,8a?,9?(R*)]]-
SmilesO1COc2c1cc1c(c2)[C@H]([C@H]2COC(=O)[C@@H]2[C@@H]1c1cc(c(c(c1)OC)O)OC)OC1[C@@H]([C@H]([C@@H]2O[C@@H](OC[C@H]2O1)C)O)O
Chemical Structure

Biological activities

Etoposide is known as an inhibitor of the enzyme topoisomerase II that controls and alters the topologic states of DNA during transcription. [1] Etoposide preferentially interacts with the topo IIα isoform, while topo IIβ is the preferred target for amsacrine. Etoposide inhibits MDA-parental cells and MDA-VP cells with IC50s of 3.3 and 45.6 μM, respectively. Etoposide induces 70% depletion of topo IIα protein and 10% depletion of topo IIβ protein. [2] Etoposide showes a generally high efficiency against C6, F98 and 9L cells with IC50s of 25.2, 46.5 and 58.2 μM.[3] The cytotoxic effect of etoposide is via targeting topoisomeraseII, specifically by both stabilizing and increasing the concentration of the topoisomerase II??NA cleavage complex. Etoposide acts by interacting with topoisomerase II, the cellular processes and genetic variation associated with sensitivity to etoposide. The median of the etoposide concentration required to inhibit 50% cellular growth (IC50) for all 321 cell lines following treatment with etoposide for 72 hours is 0.4 µM. [1] Etoposide inhibits DNA synthesis in meiosis and causes single strand and double strand breakage in DNA. In vitro, etoposide has a strong effect on diplotene-diakinesis I cells harvested 1 day after exposure, and a significant effect also on late pachytene cells harvested 3 days after exposure. The highest induction is obtained 1 day after treatment with etoposide dose 10 mg/kg, 34.5/1,000 early spermatids. 1 day after treatment with 5 mg/kg etoposide can reduce type A3 spermatogonia in the 2C+S peak at stage I. Eighteen days after treatment by 10 mg/kg etoposide can also significantly reduce the number of elongated spermatids. Etoposide causes a specific type of inhibition of topoisomerase II function before the meiotic divisions at late pachytene and diplotene-diakinesis. [4] Etoposide increases Topo II-mediated DNA breakage primarily by inhibiting the ability of the enzyme to religate cleaved nucleic acid molecules. Etoposide induces also the activation of the S-phase specific checkpoint pathway identified by ATR, Rad9-containing clamps and downstream Chk1 kinase. Etoposide induces the formation of apoptosis-associated heterochromatin foci (AAHF) and gene silencing. Etoposide induces apoptosis mainly through the cytochrome c/Apaf-1/caspase-9 pathway. After treatment of exponentially growing HL60 cells with etoposide, the number of apoptotic cells increases rapidly between 3 and 4 hours in parallel with the appearance of DNA fragmentation and proteolysis of the enzyme poly(ADP-ribose)-polymerase (PARP), two biochemical hallmarks of apoptosis. [5] In vivo, a single administration of sub-lethal doses of etoposide together with Ad.survivin-AS exerts a maximum antitumor effect, resulting in complete suppression of tumor growth even beyond the 28th day following treatment. After infection with an Ad.survivin-AS MOI of 20, etoposide inhibits DU145 Cells growth with the IC50 decreasing from 10.90 (uninfected) to 2.73 mM. [6] In rats, chronic treatment with etoposide causes damage to spermatogenic cells. [4]

Protocols

10 mg etoposide is dissolved in neutral oil prior to all the preparation steps. [3]

References

[1] Bleibel WK, et al. Identification of genomic regions contributing to etoposide-induced cytotoxicity. Hum Genet. 2009, 125(2): 173-180.
[2] Zhou Z, et al. Enhanced etoposide sensitivity following adenovirus-mediated human topoisomerase II alpha gene transfer is independent of topoisomerase IIbeta. Br J Cancer. 2001, 85(5): 747-751.
[3] Lamprecht A, et al. Etoposide nanocarriers suppress glioma cell growth by intracellular drug delivery and simultaneous P-glycoprotein inhibition. J Control Release. 2006, 112(2): 208-213.
[4] L?hdetie J, et al. Etoposide (VP-16) Is a Potent Inducer of Micronuclei in Male Rat Meiosis: Spermatid Micronucleus Test and DNA Flow Cytometry After Etoposide Treatment. Enviro Mol Mutagen. 1994, 24 (3) :192-202.
[5] Montecucco A, et al. Cellular response to etoposide treatment. Cancer Lett. 2007, 252(1): 9-18.
[6] Hayashi N, et al. Adenoviral infection of survivin antisense sensitizes prostate cancer cells to etoposide in vivo. Prostate. 2005, 65(1):10-9.

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