Temozolomide

For research use only. Not for use in humans.

Catalog No.S1237 Synonyms: CCRG81045, NSC 362856

45 publications

Temozolomide Chemical Structure

Molecular Weight(MW): 194.15

Temozolomide is a monofunctional SN-1 alkylating agent that can modify nitrogen atoms in the DNA ring and the extracyclic oxygen group, chemically converted to MTIC and degrades to methyldiazonium cation, which transfers methyl groups to DNA at physiologic pH. A DNA damage inducer in L-1210 and L-1210/BCNU cells.

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Selleck's Temozolomide has been cited by 45 publications

Purity & Quality Control

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Biological Activity

Description Temozolomide is a monofunctional SN-1 alkylating agent that can modify nitrogen atoms in the DNA ring and the extracyclic oxygen group, chemically converted to MTIC and degrades to methyldiazonium cation, which transfers methyl groups to DNA at physiologic pH. A DNA damage inducer in L-1210 and L-1210/BCNU cells.
Features Methazolastone is a second-generation alkylating agent.
Targets
DNA replication [1]
(L-1210, L-1210/BCNU cells)
In vitro

Methazolastone causes formation of DNA alkali-labile sites which are present in similar amounts and repaired at a similar rate in L-1210 and L-1210/BCNU cell lines. In L-1210 but not in L-1210/BCNU methazolastone induces an arrest of cells in SL-G2-M phases.[1] Methazolastone sensitivity of both chemo-sensitive and resistant cells (D54-R and U87-R) is enhanced significantly under hyperoxia. Both Methazolastone and hyperoxia are associated with increased phosphorylation of ERK p44/42 MAPK (Erk1/2), but to a lesser extent in D54-R cells, suggesting that Erk1/2 activity may be involved in regulation of hyperoxia and Methazolastone-mediated cell death. Hyperoxia enhances Methazolastone toxicity in GBM cells by induction of apoptosis, possibly via MAPK-related pathways. [2] Methazolastone induces in monocytes the DNA damage response pathways ATM-Chk2 and ATR-Chk1 resulting in p53 activation. [3] Chronic Methazolastone exposure results in acquired Methazolastone-resistance and elevates miR-21 expression. [4] Methazolastone treatment triggers endoplasmic reticula (ER) stress with increased expression of GADD153 and GRP78 proteins, and deceases pro-caspase 12 protein. Methazolastone induces autophagy through mitochondrial damage- and ER stress-dependent mechanisms to protect glioma cells. [5]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
Kelly NUTFSnJtT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NFvkcog1QCCq NWCzWHNTUUN3ME2xN|kvOjEkgJpCtgKBkTVwOUWg{txO NFPw[IozPTl4MEK4Ni=>
KellyCis83 MkDLS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NYixflQ4PDhiaB?= MnvyTWM2OD1{NUGuNFDjiIoEsfMAjVE2Njd3IN88US=> NXPrVoNEOjV7NkCyPFI>
SK-N-AS NVzG[ZRJT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= Ml;FOFghcA>? NEf4OYZKSzVyPUKyO{44OOLCidMx5qCKOjJwMUWg{txO MW[yOVk3ODJ6Mh?=
SK-N-ASCis24 NEfpbHVIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NGj2ZXY1QCCq MWrJR|UxRTR6MD62NQKBkcLz4pEJNVAyNjF3IN88US=> M3i2OlI2QTZyMkiy
CHP-212 NVr2b|lvT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= M33ocVQ5KGh? M{nSUWlEPTB;Nz65O-KBkcLz4pEJNE43QSEQvF2= Ml\aNlU6PjB{OEK=
CHP-212Cis100 MoTpS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NFPGVZM1QCCq MoHOTWM2OD17LkW15qCKyrIkgJmwMlg5KM7:TR?= NH7nWGMzPTl4MEK4Ni=>
U87  M{jiSmZ2dmO2aX;uJGF{e2G7 NGXjcIYyODBizszN NUfuWY9ROjRvN{KgbC=> NUTOXFhrcW6mdXPld{BF[1JzIHX4dJJme3Orb36= MkHkNlU5ODh6Nki=
LN229 MXXHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? M1n6fFAuPTBizszN MXnJR|UxRTF4IN88US=> MWKyOVc2ODJ5Mx?=
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U251MG NHzYcYRCeG:ydH;zbZMhSXO|YYm= NFPmS3IyODEEoN88US=> Mm\DOFghcA>? M2m1UnBDWw>? MXnpcoR2[2W|IHHwc5B1d3Orcx?= Mk\5NlU3QDB2NkS=
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U251 NWPR[VhrT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NUD2VW5[OTByLUSwNEDPxE1? MnX5O|IwQTZiaB?= M1TENpRp\SCjboTpMZBzd2yrZnXyZZRqfmViZX\m[YN1KGOjbjDi[UBmdmijbnPl[EBjgSCpb4PzfZBwdCCnbnjhcoNm\CEEoB?= NWTEcXM3OjV|N{WyO|E>
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U251 NGLubpVHfW6ldHnvckBCe3OjeR?= MWiyNFAh|ryP MVe0PEBp MljwbY5kemWjc3XzJJRp\SCneIDy[ZN{cW:wIH;mJGJTS0FzLDDCVmNCOixiUlHEOVEh[W6mIF\BUmNFOg>? NGfjR5IzPTN|N{eyNS=>
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U251  NHjCfWpCeG:ydH;zbZMhSXO|YYm= NXfJdlNrOTByIN88US=> NF7iWIw1QCCq NIjDWVhFVVOR NX30NYRxcW6lcnXhd4V{KHSqZTDjZZNx[XOnLUOvO{Bi[3Srdnn0fS=> Mk\vNlQ1QDF3OE[=
U251 MVXHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MYeyOEBp MkflTWM2OD16Nj6yPgKBkcLz4pEJNU42QCEQvF2= NFraSVYzPDN{Nkm1OC=>
U251 MX7Hdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MYi0PEBp NVnEXJRrUUN3ME23OU4{POLCidMx5qCKOS5yMjFOwG0> NY\ydGNlOjR|Mk[5OVQ>
U251 NGTCNWhIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MXy3NkBp Mo\JTWM2OD15Mj60NwKBkcLz4pEJNU41PSEQvF2= MXGyOFMzPjl3NB?=
U251 MYfHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NXXCb5FiQTZiaB?= NFfKT3NKSzVyPU[5Mlgz6oDLwsJihKk{NjB2IN88US=> M1rlelI1OzJ4OUW0
T98G NX73fppIT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NYTCXXVFOC15NUCg{txO NH6weWc4Oi97NjDo NFvudXpqdmirYnn0d{Bk\WyuII\pZYJqdGm2eTDpckBiKGSxc3Wg[IVx\W6mZX70JI1idm6nch?= NXT6WIhMOjR|MkSwPFA>
U251-MG MmjuS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NUX1Z|NnOC16MECg{txO M2nkfFczKGh? M2\yXolvcGmkaYTzJINmdGxidnnhZoltcXS7IHnuJIEh\G:|ZTDk[ZBmdmSnboSgcYFvdmW{ NWCz[lNXOjRyOUO2N|A>
D54-MG MUjHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MYSwMVgxOCEQvF2= NHvWc|g4OiCq MWDpcohq[mm2czDj[YxtKH[rYXLpcIl1gSCrbjDhJIRwe2ViZHXw[Y5l\W62IH3hco5meg>? M4j3U|I1ODl|NkOw
SHG-44 NVfNXIw3T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MVOxNE0zODBizszN M4jxNlk3KGh? MVfJR|UxRTlwN{OgxtEhOi5zMjFOwG0> NF7uNVEzPDB4NUW2PS=>
U373  MVnHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MoW0NVAuOjByIN88US=> NVjVVmsxQTZiaB?= NHvSZ2xKSzVyPUGwMlE{KMLzIEGuNFIh|ryP MoDoNlQxPjV3Nkm=
HT-29  NUPmbmVtTnWwY4Tpc44hSXO|YYm= NGnpb282ODBizszN MXqyOE81QCCq NYTxSnNs\W6qYX7j[ZMhfGinIHzleoVteyCxZjFOt{1JOkG[wrC= MY[yOFA{QDB4OB?=
PC-3  MoTIS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? M{HjNFAuOjVizszN M{HKfVQ5KGh? M3joZ4lvcGmkaYTzJINmdGxiZ4Lve5RpKHeqaXPoJINidiCkZTDwc5RmdnSrYYTl[EBjgSCueXPvdIVv\Q>? NEHRRmozOzd2NkmzOC=>
PC-3  NF\OVnhCeG:ydH;zbZMhSXO|YYm= NXrnbG9qOjVizszN MVO0PEBp NYTsXoVlcW6mdXPld{BieG:ydH;zbZMhf2irY3igZ4FvKGKnIIDveIVvfGmjdHXkJIJ6KGy7Y3;w[Y5m M3Xm[|I{PzR4OUO0
T98G NEfW[YRIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MYS1NE01ODBizszN NFPJeW0yPDRiaB?= M17tW4lvcGmkaYTzJINmdGxidnnhZoltcXS7IHnuJIEh\G:|ZTDk[ZBmdmSnboSgcYFvdmW{ NGK3O5czOzdzNUS5PS=>
U87-MG MVPHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NIHCbo4yODBiwsXN MoTuO|IhcA>? MkW2bY5pcWKrdIOgZ4VtdCCpcn;3eIghf2irY3igZ4FvKGKnIHXubIFv[2WmIHL5JGdVSg>? M2n3V|I{Pjl4N{i4
U251-MG Mom1S5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? NGnscHAyODBiwsXN MmDhO|IhcA>? M36yXYlvcGmkaYTzJINmdGxiZ4Lve5RpKHeqaXPoJINidiCkZTDlcohidmOnZDDifUBIXEJ? NXj6XHdlOjN4OU[3PFg>
LNT-229 MUXHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? NYjLO|FvOy1zMECg{txO MmWxNlQhcA>? MWrpcohq[mm2czDjcI9vd2enbnnjJJN2en[rdnHsJIlvKGFiZH;z[U1l\XCnbnTlcpQhdWGwbnXy Mlj4NlM3Pjd4M{K=
T98G NYnrSpVxT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MlXJNVAuPzByIN88US=> NYnMWVl[OjRiaB?= M3PiZolvcGmkaYTzJINtd26xZ3XubYMhe3W{dnn2ZYwhcW5iYTDkc5NmNWSncHXu[IVvfCCvYX7u[ZI> NYHmTGN2OjN4Nke2N|I>
U87  NVKwc2VZTnWwY4Tpc44hSXO|YYm= MXixNFAhyrWP MUSzJIg> MmPn[YxmfmG2ZYOgeIhmKGyndnXsd{Bw\iCyQ3jrNUBidmRicFPob|I> M4m1RlI{PjZ5NE[5
HCT116 MnnhSpVv[3Srb36gRZN{[Xl? NIPsdo4yODBiwsXN Mk\SN{Bp NWWxWoZGcW6mdXPld{B1cGViQ3jrNUBRcG:|cHjvdplt[XSrb36= NV76[WtlOjN4Nke0Olk>
HCT3-6 MkOySpVv[3Srb36gRZN{[Xl? M3n4TFExOCEEtV2= NVPyU5gzOyCq NXX0ZnZUcW6mdXPld{B1cGViQ3jrNUBRcG:|cHjvdplt[XSrb36= NXjBZY5IOjN4Nke0Olk>
U-87  MXLHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MVmwMVQxKM7:TR?= MnnONVIh\A>? MWjpcohq[mm2czDj[YxtKGe{b4f0bEBqdiCjIHTvd4Uu\GWyZX7k[Y51KG2jbn7ldi=> NXHZOoNpOjN4NEW3Nlk>
U-87  Mlj6RZBweHSxc3nzJGF{e2G7 NUOzflN1OC12MDFOwG0> NX3X[pJGOy94IHS= Mo\EbY5lfWOnczDhdI9xfG:|aYOgbY4h[m:2aDDkc5NmNSCjbnSgeIlu\S2mZYDlcoRmdnRibXHucoVz NGXmRpMzOzZ2NUeyPS=>
U-87  MorNSpVv[3Srb36gRZN{[Xl? M1:yN|AuPDBizszN NELK[Gs{NzZiZB?= NGDx[HpqdmS3Y3XzJIF2fG:yaHHnfUBqdiCkb4ToJIRwe2VvIHHu[EB1cW2nLXTldIVv\GWwdDDtZY5v\XJ? MkTYNlM3PDV5Mkm=
GB-SCC010 NEPzUmxIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NH;OcpM1KGR? M3fjNmlEPTB;MkK2JO69VQ>? MWKyN|YyOjd3NR?=
GB-SCC026 NFv1eVFIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= NGLpZ2k1KGR? MkHwTWM2OD13Mz6xJO69VQ>? M4frZVI{PjF{N{W1
GB-SCC028 NYrI[XdpT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NG\Db2I1KGR? NYLZeXozUUN3ME2xOlch|ryP Mn\3NlM3OTJ5NUW=
U87 NVGw[4VmT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NUf4VHpwPCCm NInTOHBKSzVyPUS1MlIh|ryP NYX1NWJ6OjN4MUK3OVU>
U87 stem cell NWLEOWtKT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= MonmOEBl MY\JR|UxRTZ4Lkeg{txO NEPkT4MzOzZzMke1OS=>

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
pERK / ERK / p-p38 / p38; 

PubMed: 24436439     


Cells were treated with TMZ (0.5 mM) time dependently, and Western blotting was used to analyze for phosphorylated ERK and p38 MAPK expression.

DR5 / c-FLIP / Survivin / XIAP; 

PubMed: 24436439     


Western blot analysis showing expressions in DR5 and antiapoptotic proteins (c-FLIP, survivin, and XIAP) in glioma cells treated with increasing doses of TMZ (0–2 mM) for 24 hours. 

24436439
Growth inhibition assay
Cell viability; 

PubMed: 25751281     


Distinct temozolomide-resistance for MGMT-expressing (SF767) and MGMT-negative (U87) GBM cells was assessed.

25751281
Immunofluorescence
Phalloidin / Phospho-H2A.X; 

PubMed: 27375225     


Immunofluorescence analysis of the level of phospho-H2A.X in nucleus which can reflect DNA damage response increased significantly at day 6, peaked during days 7-10 and decreased significantly at day 12 after treatment temozolomide (200 μM). 

cleaved caspase-3; 

PubMed: 25663820     


Representative Photomicrographs of cleaved caspase-3 immunoreactivity in control (DMSO treated) and treated group of U87 cells. Base line immunofluorescence was detected in control group. Significant Increase in immunofluorescence is detected in all treated groups with the highest observed intensity in combination treatment group (NA-2 + TMZ).

27375225 25663820
In vivo After a daily i.p. dose of 40 mg/kg for 5 consecutive days (days 1-5 after tumor transplant), methazolastone increases life-span by 86% in L-1210 and 22% in L-1210/BCNU. In L-1210/BCNU no effect is seen after 100 μM or 200 μM treatment; only 400 μM methazolastone produced an accumulation of cells in premitotic phase but much less than in L-1210. In L-1210/BCNU the maximum accumulation of cells in SL-G2-M is, after 48 hours-72 hours, approximately 30% as compared to 23% in untreated cells. Cells accumulates in SL-G2-M occurred too when L- 1210 leukemia-bearing mice are treated i.v. with methazola stone (40 mg/kg). No such effect is seen on L-1210/BCNU cells from mice given the same drug dose. [1]

Protocol

Cell Research:

[1]

- Collapse
  • Cell lines: L-1210 and L-1210/BCNU cells
  • Concentrations: 0 μM -100 μM
  • Incubation Time: l hours
  • Method:

    L-1210 and L-1210/BCNU cells are seeded at 0.2 × 104 cells/mL and incubated for 24 hours. The cultures are treated with Methazolastone for l hours at 37oC, then washed twice in PBS by centrifugation and resuspended in fresh medium. Controls and treated samples are diluted in fresh medium 1:4 at 48 hours and 1:2 at 96 hours. Using these dilutions cell concentrations throughout the experiments are between 3 × 105 and 8 × 105/mL. Control growth is logarithmic in this range.


    (Only for Reference)
Animal Research:

[1]

- Collapse
  • Animal Models: DBA/2 mice with L-1210 and L-1210/BCNU cells
  • Formulation: 95% ethanol
  • Dosages: 40 mg/kg
  • Administration: Administered via i.v.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 38 mg/mL (195.72 mM)
Water Insoluble
Ethanol Insoluble
In vivo Add solvents to the product individually and in order(Data is from Selleck tests instead of citations):
5% DMSO+30% PEG 300+ddH2O
For best results, use promptly after mixing.
2mg/mL

* 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 Information

Molecular Weight 194.15
Formula

C6H6N6O2

CAS No. 85622-93-1
Storage powder
in solvent
Synonyms CCRG81045, NSC 362856
Smiles CN1N=NC2=C(N=C[N]2C1=O)C(N)=O

Bio Calculators

Molarity Calculator

Molarity Calculator

Calculate the mass, volume or concentration required for a solution. The Selleck molarity calculator is based on the following equation:

Mass (mg) = Concentration (mM) × Volume (mL) × Molecular Weight (g/mol)

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*When preparing stock solutions, please always use the batch-specific molecular weight of the product found on the via label and MSDS / COA (available on product pages).

Dilution Calculator

Dilution Calculator

Calculate the dilution required to prepare a stock solution. The Selleck dilution calculator is based on the following equation:

Concentration (start) x Volume (start) = Concentration (final) x Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2 ( Input Output )

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* When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and MSDS / COA (available online).

The Serial Dilution Calculator Equation

  • Serial Dilutions

  • Computed Result

  • C1=C0/X C1: LOG(C1):
    C2=C1/X C2: LOG(C2):
    C3=C2/X C3: LOG(C3):
    C4=C3/X C4: LOG(C4):
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    C8=C7/X C8: LOG(C8):
Molecular Weight Calculator

Molecular Weight Calculator

Enter the chemical formula of a compound to calculate its molar mass and elemental composition:

Total Molecular Weight: g/mol

Tip: Chemical formula is case sensitive. C10H16N2O2 c10h16n2o2

Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter its chemical formula and click 'Calculate'.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Molarity Calculator

Mass Concentration Volume Molecular Weight

Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04091503 Not yet recruiting Drug: Intranasal Modified Temozolomide Glioma Malignant|Gliosarcoma|Astrocytoma of Brain Center Trials & Treatment Europe December 10 2019 Phase 1
NCT03796507 Not yet recruiting Drug: Temozolomide Glioma of Brain University of Rochester|National Institutes of Health (NIH) November 1 2019 Early Phase 1
NCT03932981 Recruiting Drug: Temozolomide Adult Brainstem Glioma Assistance Publique - Hôpitaux de Paris July 26 2019 Phase 2
NCT03709680 Recruiting Drug: Palbociclib|Drug: Temozolomide|Drug: Irinotecan Solid Tumors|Ewing Sarcoma|Rhabdoid Tumor|Rhabdomyosarcoma|Neuroblastoma|Medulloblastoma|Diffuse Intrinsic Pontine Glioma Pfizer May 24 2019 Phase 1
NCT03832621 Recruiting Drug: Temozolomide|Drug: Nivolumab|Drug: Ipilimumab Metastatic Colorectal Cancer Fondazione IRCCS Istituto Nazionale dei Tumori Milano March 25 2019 Phase 2

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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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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID