Etoposide

Catalog No.S1225

Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity.

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Etoposide Chemical Structure

Etoposide Chemical Structure
Molecular Weight: 588.56

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Product Information

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Product Description

Biological Activity

Description Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity.
Targets Topo II [2]
(Cell-free assay)
In vitro Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA, which induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. [1] Etoposide inhibits the growth of murine angiosarcoma cell line (ISOS-1) in a 5 days-period with IC50 of 0.25 μg/mL. Cell growth of normal murine microvascular endothelial cells (mECs) is less sensitive to Etoposide with IC50 of 10 μg/mL). [2] Etoposide treated for 6 hr inhibits colonies of tetraploid variant of the human leukemic lymphoblast line CCRF-CEM with IC50 of 0.6 μM. [3] Etoposide treated for 2 hr inhibits growth of human pancreatic cancer cell line Y1, Y3, Y5, Y19, YM. YS, and YT with IC50s of 300 μg/mL, 300 μg/mL, 300 μg/mL, 91 μg/mL, 0.68 μg/mL, 300 μg/mL, 300 μg/mL, and 260 μg/mL, respectively. [4] Etoposide exposed for 1 hr inhibits growth of human glioma cell lines CL5, G142, G152, G111, and G5 with IC50 of 8, 9, 9.8, 10, and 15.8 μg/mL respectively for 12 days. Under same condition, the IC90 value is attained in cell lines CL5, G152, G142, and G111 at 26, 27, 32, and 33 μg/mL. Etoposide inhibition of topoisomerase II is homogeneous for each cell. The average inhibition rates are 15%, 21.8%, 31.8%, 41.5%, and 49.5% for 1, 2, 4, 8, and 16 μg Etoposide, respectively. [5]
Cell Data
Cell LinesAssay TypeConcentrationIncubation TimeFormulationActivity DescriptionPMID
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A549MV;Hdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?MYG0POKhcA>?MX3EUXNQyqB?NYTTW5p2UUN3ME2yOFEvQcLiwsJCpFMyNjJ|wrFOwG0>NWPtO4NHOjR7OU[xN|Y>
MCF7NFmweZFIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NXPySVd7PDkEoHi=NI\k[|VFVVORwrC=MV;JR|UxRThzLkC5xsDDucLiMUSuNlHDqM7:TR?=M13yWFI1QTl4MUO2
HL-60 M3XGc2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7MnrlO|LDqGh?NF;5NWxKSzVyPUCuNVLjiIYQvF2=NGDZN|QzPDl7M{CxOC=>
HL-60[R]NUDW[opTT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=MlfYO|LDqGh?MULJR|UxRTNwMUNihKXPxE1?NV\BdXM1OjR7OUOwNVQ>
MIAPACANGf1SYVIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=M{fzc2dKPTB;MT6zJOKyKDBwMEOg{txOM2C5RVI1QTV|OEKx
MCF-7NF3WRYRIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=MV;HTVUxRTBwMkWgxtEhOC5zIN88US=>NI\TbY0zPDl3M{iyNS=>
HeLaNGLhc2JIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NHXqXZdIUTVyPUCuOlQhyrFiMD60JO69VQ>?M3jEOFI1QTV|OEKx
MO59K M2XMb2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7MVO3JIQ>M3Xzd2lEPTB;MD6xO-KBjc7:TR?=MlHCNlQ6PTN3NkG=
MO59JNVjoR41WT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=MmSxO{BlM3rjV2lEPTB;MD6x5qCG|ryPM4OxXVI1QTV|NU[x
ME 180M3jDNGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7MYG0POKhcMLiMWfJR|UxRThwOdMgxtHDqDBwM,MAie69VQ>?NWDyWWJYOjR7NUOwNlc>
MCF-7MYLHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?Ml\FOFjDqGkEoB?=MWjJR|UxRTJ|LkmgxtEhOC5|4pEF{txOMnfxNlQ6PTNyMke=
HeLaMlr0S5Jwf3SqIFnubIljcXSrb36gRZN{[Xl?MX[0POKhcMLiMXnJR|UxRTRwN{GgxtEhOS524pEF{txOMmnGNlQ6PTNyMke=
MDA-MB-453M2KzUGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7NX3aeG9ZPDkEoHlCpC=>NHLjZ5NKSzVyPUGyMlUhyrFiMD64OgKBjc7:TR?=M4nNfVI1QTV|MEK3
MDA-MB-231M3TX[mdzd3e2aDDJcohq[mm2aX;uJGF{e2G7NECzV3I1QMLiaNMgNV7QenhzUUN3ME2yOE4zOiEEsTCyMlk16oDHzszNMWiyOFk2OzB{Nx?=
PC-3NEDjPFRIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NHrTZos1QMLiaNMgMUDJR|UxRTF2LkSgxtEhOy5{M,MAie69VQ>?MUiyOFk2OzB{Nx?=
HT-29M3nmUGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7NEXiWVY1QMLiaNMgNXzkeIFJUUN3ME2yNU41PSEEsTCzMlg46oDHzszNMmK4NlQ6PTNyMke=
BGC-823MWjHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?MlHROFjDqGkEoB?=NWj2ZWNUUUN3ME20N{44PCEEsTC1MlE{6oDHzszNMV:yOFc6Ozh5Nx?=
HeLaM4rDe2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7M1:0ZVQ5yqCqwrC=NULsWHR5UUN3ME2yNFkvQTBiwsGgNVMvPDJi4pEF{txONXjaOIlrOjR5OUO4O|c>
A549MkDKS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl?MnXhOFjDqGkEoB?=MnjpTWM2OD1zM{muOVQhyrFiNz6wOgKBjc7:TR?=MY[yOFc6Ozh5Nx?=
HK-2NGfmOIJIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NHLhfFg1QMLiaNMgNI\xOY9KSzVyPUmuNVchyrFiMT61PQKBjc7:TR?=M1;obVI1Pzl|OEe3

... Click to View More Cell Line Experimental Data

In vivo Etoposide administrated as a single agent is found to been ineffective in many xenografts growth, such as Heterotransplanted Hepatoblastoma NMHB1, and NMHB 2, [6] human neuroblastoma xenograft, [7] and human gastrointestinal cancer xenograft, [8] while the dose of 10 mg/kg i.p. Etoposide inhibits murine angiosarcoma cell ISOS-1 tumors in 36% of controls. [2] Etoposide induces tumor immunity in Lewis lung cancer. A single administration of 50 mg/kg Etoposide i.p., induces a 60% survival of C57B1/6 mice injected with Lewis lung cancer cell (3LL) over 60 days. About 40% of these surviving mice reject a subsequent challenge with 3LL, while none of control mice survive beyond 30 days. 3LL cells which have survived an 90% lethal concentration of Etoposide in vitro kill 75% of recipient mice, but 60% surviving mice reject challenge with 3LL. Splenocytes harvested from tumor rejecting mice protect naive mice injected with 3LL. [9]
Features

Protocol(Only for Reference)

Kinase Assay: [5]

Topoisomerase II activity assay Nuclear extracts are prepared, and nuclei are isolated. The activity of topoisomerase II is calculated from the percentage of decatenation obtained. Tritiated kinoplast DNA (KDNA 0.22 μg) is used as a substrate. Etoposide and topoisomerase II are incubated for 30 min at 37 ℃ and are stopped with 1% sodium dodecyl sulfate (SDS) and proteinase K (100 μg/mL). The percentages of decatenation and inhibition of topoisomerase II by Etoposide are obtained.

Cell Assay: [5]

Cell lines Human glioma cell lines CL5
Concentrations 80 μg/mL
Incubation Time 1 hour
Method After the Etoposide treatment, cells are removed from the dish with phosphate-buffered saline (PBS) containing 0.03% trypsin and 0.27 mM ethylenediaminetetraacetic acid (EDTA) and are diluted into culture dishes in appropriate numbers to yield between 20 and 200 colonies. After 12 days, cultures are fixed with methanol-acetic acid, stained with crystal violet, and scored for colonies containing more than 50 cells. The standard errors are typically less than 15% of the mean value unless otherwise stated.

Animal Study: [2]

Animal Models Murine angiosarcoma xenografts ISOS-1
Formulation Saline
Dosages 10 mg/kg
Administration i.p. every day for 5 days from day 7

Conversion of different model animals based on BSA (Value based on data from FDA Draft Guidelines)

SpeciesMouseRatRabbitGuinea pigHamsterDog
Weight (kg)0.020.151.80.40.0810
Body Surface Area (m2)0.0070.0250.150.050.020.5
Km factor36128520
Animal A (mg/kg) = Animal B (mg/kg) multiplied by  Animal B Km
Animal A Km

For example, to modify the dose of resveratrol used for a mouse (22.4 mg/kg) to a dose based on the BSA for a rat, multiply 22.4 mg/kg by the Km factor for a mouse and then divide by the Km factor for a rat. This calculation results in a rat equivalent dose for resveratrol of 11.2 mg/kg.

Rat dose (mg/kg) = mouse dose (22.4 mg/kg) ×  mouse Km(3)  = 11.2 mg/kg
rat Km(6)
1

References

[1] van Maanen JM et al, J Natl Cancer Inst, 1988, 80(19), 1526-1533.

[2] Ma G, et al. J Dermatol Sci, 2000, 24(2), 126-133.

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Clinical Trial Information( data from http://clinicaltrials.gov, updated on 2016-05-07)

NCT Number Recruitment Conditions Sponsor
/Collaborators
Start Date Phases
NCT02722369 Not yet recruiting Small Cell Lung Cancer University College, London August 2016 Phase 2
NCT02538926 Not yet recruiting B Acute Lymphoblastic Leukemia|B Lymphoblastic Lymphoma|Recurrent Adult Acute Lymphoblastic Leukemia|Recurrent B Lymphoblastic Lymphoma|Recurrent T  ...more B Acute Lymphoblastic Leukemia|B Lymphoblastic Lymphoma|Recurrent Adult Acute Lymphoblastic Leukemia|Recurrent B Lymphoblastic Lymphoma|Recurrent T Lymphoblastic Leukemia/Lymphoma|Refractory B Lymphoblastic Lymphoma|Refractory T Lymphoblastic Lymphoma|T Acute Lymphoblastic Leukemia|T Lymphoblastic Lymphoma University of Washington|National Cancer Institute (NCI) August 2016 Phase 2
NCT02703272 Not yet recruiting Lymphoma, Non-Hodgkin Janssen Research & Development, LLC June 2016 Phase 3
NCT02763579 Not yet recruiting Small Cell Lung Cancer Hoffmann-La Roche May 2016 Phase 3
NCT02658214 Recruiting Small Cell Lung Carcinoma|Carcinoma, Squamous Cell of Head and Neck|Stomach Neoplasms|Triple Negative Breast Neoplasms|Ovarian Neoplasms|Fallopian  ...more Small Cell Lung Carcinoma|Carcinoma, Squamous Cell of Head and Neck|Stomach Neoplasms|Triple Negative Breast Neoplasms|Ovarian Neoplasms|Fallopian Tube Neoplasms|Peritoneal Neoplasms|Esophagogastric Junction Neoplasms AstraZeneca April 2016 Phase 1

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Chemical Information

Download Etoposide SDF
Molecular Weight (MW) 588.56
Formula

C29H32O13

CAS No. 33419-42-0
Storage 3 years -20℃powder
6 months-80℃in solvent
Synonyms VP-16, VP-16213
Solubility (25°C) * In vitro DMSO 100 mg/mL (169.9 mM)
Water <1 mg/mL (<1 mM)
Ethanol <1 mg/mL (<1 mM)
In vivo 30% propylene glycol, 5% Tween 80, 65% D5W 30 mg/mL
* <1 mg/ml means slightly soluble or insoluble.
* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.
Chemical Name Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5α,5aβ,8aα,9β(R*)]]-

Customer Product Validation (2)


Click to enlarge
Rating
Source Leukemia, 2015, 29: 1702–1712. Etoposide purchased from Selleck
Method Cell Viability Analysis
Cell Lines Riva、U2932 & MYC-BCL2 cells
Concentrations
Incubation Time 24 h
Results Etoposide and cytarabine are the key components of DLBCL salvage regimens RICE43 and R-DHAP respectively. These drugs behaved nearly identically to doxorubicin and dinaciclib in combination studies with ABT-199.

Click to enlarge
Rating
Source BMC Cancer 2014 14, 483. Etoposide purchased from Selleck
Method Immunoblotting
Cell Lines HT29 cells
Concentrations 59 uM
Incubation Time 18 h
Results V158411 reduced Cdc2 Y15 and CDK2 T160 phosphorylation following gemcitabine, camptothecin, doxorubicin and etoposide treatment. Changes to histone H3 phosphorylation were chemotherapeutic agent dependent as were the changes to Chk2 phosphorylation. Increased apoptosis, as measured by cleavage of caspase-2 and -3, has been suggested to be a potential biomarker of Chk1 inhibitor induced chemosensitization. Increases in PARP, caspase-2 and caspase-3 cleavage was observed following treatment of HT29 cells with gemcitabine, camptothecin, cisplatin, oxaliplatin and doxorubicin but not etoposide in combination with V158411 compared to cytotoxic treatment alone.

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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