Etoposide
Supplier: MP BIOMEDICALS (FKA ICN BIOMED
Synonyms:
(5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methylhexahydropyrano[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, 4'-Demethylepipodophyllotoxin 9-(4,6-O-Ethylidene-beta-D-glucopyranoside)
Etoposide is an important chemotherapeutic agent that is used to treat a wide spectrum of human cancers. It also belongs to the drug type plant alkaloid.
- Regulates DNA
- Removes knots from genome
- Inhibits DNA synthesis
- pKa=9.8 (Lit.)
- Physical form: White powder
The primary cytotoxic target for etoposide is topoisomerase II
Etoposide is an antitumor agent that complexes with topoisomerase II and DNA to enhance double-strand and single-strand cleavage of DNA and reversibly inhibit religation. Blocks the cell cycle in S-phase and G2-phase of the cell cycle; induces apoptosis in normal and tumor cell lines; inhibits synthesis of the oncoprotein Mdm2 and induces apoptosis in tumor lines that overexpress Mdm2.
Etoposide inhibits DNA synthesis and is very active against cells in the late S and G2 phases of the cell cycle. Etoposide was reported to be used to serum starve Saos-2 M5(p53−/−) cells which were transfected by electroporation with indicated expression plasmids for flag-E2F1 and myc-EBNA3C for selection of colony forming units, thus studying the blocking effect of EBV Nuclear Antigen 3C on E2F1 Mediated Apoptosis Induced by the DNA Damage Response.
This ubiquitous enzyme regulates DNA under- and overwinding, and removes knots and tangles from the genome by generating transient double-stranded breaks in the double helix. Etoposide kills cells by stabilizing a covalent enzyme-cleaved DNA complex (known as the cleavage complex) that is a transient intermediate in the catalytic cycle of topoisomerase II.
Absorbance: λmax (methanol) 283 ± 3 nm
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Formula:
C₂₉H₃₂O₁₃ MW: 588.56 g/mol Melting Pt: 236…251 °C (lit.) Storage Temperature: Ambient |
MDL Number:
MFCD00869325 CAS Number: 33419-42-0 |
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