Home DNA Damage/DNA Repair DNA/RNA Synthesis chemical - Autophagy activator - Apoptosis related activator TMZ(Temozolomide) For research use only.

TMZ(Temozolomide)

Synonyms: NSC 362856,CCRG 81045,Methazolastone

TMZ(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. Temozolomide induces apoptosis and exhibits antitumor activity.

TMZ(Temozolomide) Chemical Structure

TMZ(Temozolomide) Chemical Structure

CAS No. 85622-93-1

Purity & Quality Control

TMZ(Temozolomide) Related Products

Signaling Pathway

DNA/RNA Synthesis Signaling Pathways

DNA/RNA Synthesis Signaling Pathway

Cell Data

Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
Kelly Growth Inhibition Assay 48 h IC50=139.20 ± 5.95 μM 25960282
KellyCis83 Growth Inhibition Assay 48 h IC50=251.00 ± 15.75 μM 25960282
SK-N-AS Growth Inhibition Assay 48 h IC50=227.70 ± 22.15 μM 25960282
SK-N-ASCis24 Growth Inhibition Assay 48 h IC50=480.60 ± 101.15 μM 25960282
CHP-212 Growth Inhibition Assay 48 h IC50=7.97 ± 0.69 μM 25960282
CHP-212Cis100 Growth Inhibition Assay 48 h IC50=9.55 ± 0.88 μM 25960282
U87  Function Assay 100 μM 24-72 h induces DcR1 expression 25808868
LN229 Growth Inhibition Assay 0-50 μM IC50=16 μM 25750273
TR-LN229 Growth Inhibition Assay 0-50 μM IC50=77 μM 25750273
U87  Apoptosis Assay 0–200 µM 24 h enhances CQ induced apoptosis 25681668
U251MG Apoptosis Assay 100 μM 48 h PBS induces apoptosis 25680464
U87MG Apoptosis Assay 100 μM 48 h PBS induces apoptosis 25680464
U87 Growth Inhibition Assay 50-350 μM 48 h  inhibits cell growth slightly 25554223
U118  Growth Inhibition Assay 50-350 μM 48 h  inhibits cell growth slightly 25554223
U87 Function Assay 250/350 μM 48 h  enhances TMX-induced p-PKC-pan decrease 25554223
U118  Function Assay 250/350 μM 48 h  enhances TMX-induced p-PKC-pan decrease 25554223
U87 Growth Inhibition Assay 250/350 μM 48 h  increases the percentage of cells in S and G2/M cotreated with TMX 25554223
A375 Growth Inhibition Assay 48 h  IC50=265 μM 25524552
A2058 Growth Inhibition Assay 48 h  IC50=12 μM 25524552
M238 Growth Inhibition Assay 48 h  IC50=40 μM 25524552
M249 Growth Inhibition Assay 48 h  IC50=254 μM 25524552
M21 Growth Inhibition Assay 48 h  IC50=221 μM 25524552
U251 Cytotoxity Assay 20 μM  48 h  reduceds the percentages of colonies formed 25434381
LN229 Cytotoxity Assay 20 μM  48 h  reduceds the percentages of colonies formed 25434381
U373MG-LUC Growth Inhibition Assay 72 h IC50>600 μM 25431953
U87  Growth Inhibition Assay 25-200 μM 48 h  inhibits cell growth in a dose-dependent manner 25400745
U251 Growth Inhibition Assay 25-200 μM 48 h  inhibits cell growth in a dose-dependent manner 25400745
U251 Growth Inhibition Assay 100-400 μM 72/96 h the anti-proliferative effect can be enhanced by gossypol enhanced   25375271
U373 Growth Inhibition Assay 100-400 μM 72/96 h the anti-proliferative effect can be enhanced by gossypol enhanced   25375271
U343 Growth Inhibition Assay 100-400 μM 72/96 h the anti-proliferative effect can be enhanced by gossypol enhanced   25375271
U87MG-luc2 Growth Inhibition Assay 100-400 μM 72/96 h the anti-proliferative effect can be enhanced by gossypol enhanced   25375271
U87 Function Assay 200 μM 48 h increases BRCC3 mRNA expression 25337721
U251 Function Assay 200 μM 48 h increases BRCC3 mRNA expression 25337721
A172 Function Assay 200 μM 48 h increases BRCC3 mRNA expression 25337721
U251 Function Assay 200 μM 48 h increases the expression of BRCA1, BRCA2, RAD51 and FANCD2 25337721
A172 Function Assay 200 μM 48 h increases the expression of BRCA1, BRCA2, RAD51 and FANCD2 25337721
U87 Function Assay 200 μM 24/72/120 h increases γH2AX foci formation time-dependently 25337721
U251 Function Assay 200 μM 24/72/120 h increases γH2AX foci formation time-dependently 25337721
A172 Function Assay 200 μM 24/72/120 h increases γH2AX foci formation time-dependently 25337721
SNB19V Growth Inhibition Assay 7 d DMSO GI50=35.7±12 μM 25277441
SNB19M Growth Inhibition Assay 7 d DMSO GI50=469.9±88 μM 25277441
SNB19VR Growth Inhibition Assay 7 d DMSO GI50=280.2±18 μM 25277441
U373V Growth Inhibition Assay 7 d DMSO GI50=68.0±32 μM 25277441
U373M Growth Inhibition Assay 7 d DMSO GI50=368.7±86 μM 25277441
U373VR Growth Inhibition Assay 7 d DMSO GI50=288.8±33 μM 25277441
U87MG Growth Inhibition Assay 7 d DMSO GI50=38.3±20 μM 25277441
HCT116 Growth Inhibition Assay 7 d DMSO GI50=579.9±32 μM 25277441
DLD1 Growth Inhibition Assay 7 d DMSO GI50=501.4±93 μM 25277441
MRC5 Growth Inhibition Assay 7 d DMSO GI50=449.4±8 μM 25277441
SNB19V  Function Assay 100 μM TMZ 0-72 h increases γH2AX expression between 16 and 72 h 25277441
T98G  Growth Inhibition Assay 5/10/15 μM 24 h induces cell death dose-dependently after concomitant-temozolomide with NPe6-PDT 25262961
U251  Growth Inhibition Assay 5/10/15 μM 24 h induces cell death dose-dependently after concomitant-temozolomide with NPe6-PDT 25262961
T98G  Function Assay 15 μM 24 h increases DNA-fragmentation in NPe6-PDT treated glioma cells 25262961
U251  Function Assay 15 μM 24 h increases DNA-fragmentation in NPe6-PDT treated glioma cells 25262961
U-87 MG Growth Inhibition Assay 72 h IC50=0.93 mM  25245332
U-118 MG Growth Inhibition Assay 72 h IC50=1.05 mM  25245332
U87 Growth Inhibition Assay 24 h IC50=260.34 μM  25173233
U87 GSLCs Growth Inhibition Assay 24 h IC50=766.11 μM  25173233
U87MG Growth Inhibition Assay 72 h IC50=15.625 μM  25050915
U251 Growth Inhibition Assay 100-400 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
U87 Growth Inhibition Assay 100-400 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
MDA-MB-231-br Growth Inhibition Assay 0-10 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
HCC-1937 Growth Inhibition Assay 0-300 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
MDA-MB-231 Growth Inhibition Assay 0-40 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
MDA-MB-468 Growth Inhibition Assay 0-500 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
T47D Growth Inhibition Assay 0-100 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
MCF7 Growth Inhibition Assay 0-1000 μM 48 h DMSO inhibits cell growth in a dose-dependent manner 24623736
Hs683 Growth Inhibition Assay 0-1000 μM 96 h IC50=128.9 μM 24495907
U87 Growth Inhibition Assay 0-1000 μM 96 h IC50=18.45 μM 24495907
LNZ308 Growth Inhibition Assay 0-1000 μM 96 h IC50=326.7 μM 24495907
U87 Apoptosis Assay 100 μM 48 h DMSO increases the caspase-3/7 activity 24481586
U251  Apoptosis Assay 100 μM 48 h DMSO increases the caspase-3/7 activity 24481586
U251 Growth Inhibition Assay 24 h IC50=86.29 ± 1.58 μM 24326954
U251 Growth Inhibition Assay 48 h IC50=75.34 ± 1.02 μM 24326954
U251 Growth Inhibition Assay 72 h IC50=72.42 ± 1.45 μM 24326954
U251 Growth Inhibition Assay 96 h IC50=69.82 ± 3.04 μM 24326954
T98G Growth Inhibition Assay 0-750 μM 72/96 h inhibits cell viability in a dose dependent manner 24324080
U251-MG Growth Inhibition Assay 0-800 μM 72 h inhibits cell viability in a dose dependent manner 24093630
D54-MG Growth Inhibition Assay 0-800 μM 72 h inhibits cell viability in a dose dependent manner 24093630
SHG-44 Growth Inhibition Assay 10-200 μM 96 h IC50=9.73 ± 2.12 μM 24065569
U373  Growth Inhibition Assay 10-200 μM 96 h IC50=10.13 ± 1.02 μM 24065569
HT-29  Function Assay 500 μM 24/48 h enhances the levels of γ-H2AX  24038068
PC-3  Growth Inhibition Assay 0-25 μM 48 h inhibits cell growth which can be potentiated by lycopene 23746934
PC-3  Apoptosis Assay 25 μM 48 h induces apoptosis which can be potentiated by lycopene 23746934
T98G Growth Inhibition Assay 50-400 μM 144 h inhibits cell viability in a dose dependent manner 23715499
U87-MG Growth Inhibition Assay 100 µM 72 h inhibits cell growth which can be enhanced by GTB 23696788
U251-MG Growth Inhibition Assay 100 µM 72 h inhibits cell growth which can be enhanced by GTB 23696788
LNT-229 Growth Inhibition Assay 3-100 μM 24 h inhibits clonogenic survival in a dose-dependent manner 23667632
T98G Growth Inhibition Assay 10-700 μM 24 h inhibits clonogenic survival in a dose-dependent manner 23667632
U87  Function Assay 100 µM 3 h elevates the levels of pChk1 and pChk2 23667469
HCT116 Function Assay 100 µM 3 h induces the Chk1 Phosphorylation 23667469
HCT3-6 Function Assay 100 µM 3 h induces the Chk1 Phosphorylation 23667469
U-87  Growth Inhibition Assay 0-40 μM 12 d inhibits cell growth in a dose-dependent manner 23645729
U-87  Apoptosis Assay 0-40 μM 3/6 d induces apoptosis in both dose- and time-dependent manner 23645729
U-87  Function Assay 0-40 μM 3/6 d induces autophagy in both dose- and time-dependent manner 23645729
GB-SCC010 Growth Inhibition Assay 4 d IC50=226 μM 23612755
GB-SCC026 Growth Inhibition Assay 4 d IC50=53.1 μM 23612755
GB-SCC028 Growth Inhibition Assay 4 d IC50=167 μM 23612755
U87 Growth Inhibition Assay 4 d IC50=45.2 μM 23612755
U87 stem cell Growth Inhibition Assay 4 d IC50=66.7 μM 23612755
TLX5 lymphoma Cytotoxicity assay IC50 = 5 μM 7739008
GM892 A Cytotoxicity assay IC50 = 7.6 μM 7739008
TLX5 lymphoma Cytotoxicity assay IC50 = 5 μM 12459014
HCT116 Cytotoxicity assay 4 days IC50 = 4.34 μM 19800803
SNB75 Antiproliferative assay 10 uM 24 hrs Antiproliferative activity against human SNB75 cells at 10 uM after 24 hrs by SRB assay 22268526
C6 Antiproliferative assay 100 uM 48 hrs Antiproliferative activity against rat C6 cells at 100 uM after 48 hrs by neutral red incorporation assay 22268526
SF295 Antiproliferative assay 10 uM 24 hrs Antiproliferative activity against human SF295 cells at 10 uM after 24 hrs by SRB assay 22268526
U87 Antiproliferative assay 5 days IC50 = 49 μM 22608389
U138MG Cytotoxicity assay 48 hrs IC50 = 26 μM 23069682
C6 Cytotoxicity assay 48 hrs IC50 = 34 μM 23069682
A2780 Antitumor assay 5 days IC50 = 8.5 μM 23895620
A2058 Antitumor assay 5 days IC50 = 35.5 μM 23895620
SNB19 Antitumor assay 5 days IC50 = 37 μM 23895620
M8 Apoptosis assay 50 to 100 uM 48 hrs Induction of apoptosis in human M8 cells assessed as apoptotic/necrotic cells at 50 to 100 uM after 48 hrs by APC-labeled annexin V and 7-AAD staining-based flow cytometric analysis 24125877
SK-MEL-30 Apoptosis assay 100 uM 48 hrs Induction of apoptosis in human SK-MEL-30 cells assessed as apoptotic/necrotic cells at 100 uM after 48 hrs by APC-labeled annexin V and 7-AAD staining-based flow cytometric analysis relative to control 24125877
SK-MEL-30 Apoptosis assay 50 uM 48 hrs Induction of apoptosis in human SK-MEL-30 cells assessed as apoptotic/necrotic cells at 50 uM after 48 hrs by APC-labeled annexin V and 7-AAD staining-based flow cytometric analysis relative to control 24125877
MNT1 Apoptosis assay 100 uM 48 hrs Induction of apoptosis in human MNT1 cells assessed as apoptotic/necrotic cells at 100 uM after 48 hrs by APC-labeled annexin V and 7-AAD staining-based flow cytometric analysis relative to control 24125877
MNT1 Apoptosis assay 50 uM 48 hrs Induction of apoptosis in human MNT1 cells assessed as apoptotic/necrotic cells at 50 uM after 48 hrs by APC-labeled annexin V and 7-AAD staining-based flow cytometric analysis relative to control 24125877
A2780 Cytotoxicity assay 5 days Cytotoxicity against human A2780 cells after 5 days by MTT assay 24900418
A2780/CP70 Cytotoxicity assay 5 days Cytotoxicity against MMR-deficient human A2780/CP70 cells after 5 days by MTT assay 24900418
GBM 047T Antitumor assay 20 uM 1 to 2 weeks Tumoricidal effect in patient derived GBM 047T cells assessed as reduction in neurosphere formation at 20 uM after 1 to 2 weeks by 3D tumor clonogenic assay 26355532
GBM 464T Antitumor assay 20 uM 1 to 2 weeks Tumoricidal effect in patient derived GBM 464T cells assessed as reduction in neurosphere formation at 20 uM after 1 to 2 weeks by 3D tumor clonogenic assay 26355532
U87MG Function assay 3 hrs Induction of DNA alkylation in human U87MG cells assessed as increase in N7-MedG formation after 3 hrs by LC-MS/MS analysis 27614414
U87MG Antitumor assay Antitumor activity against human U87MG cells orthotopically xenografted in Harlan nude mouse brain assessed as induction of slow tumor growth at 50 umol/kg, iv administered once daily for 5 days 27614414
U87MG Antitumor assay Antitumor activity against human U87MG cells orthotopically xenografted in Harlan nude mouse brain assessed as increase in mouse survival at 50 umol/kg, iv administered once daily for 5 days 27614414
MDCK Cytotoxicity assay 24 hrs Cytotoxicity against MDCK cells expressing carbonic anhydrase 9 assessed as reduction in cell viability incubated for 24 hrs measured after 7 days under normoxic condition by methylene blue staining based clonogenic survival assay 27823879
MDCK Cytotoxicity assay 24 hrs Cytotoxicity against MDCK cells expressing carbonic anhydrase 9 assessed as reduction in cell viability incubated for 24 hrs measured after 7 days under hypoxic condition by methylene blue staining based clonogenic survival assay 27823879
NB-EBc1 qHTS assay qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells 29435139
C6 Cytotoxicity assay 4 days EC50 = 16.5 μM ChEMBL
U87 Cytotoxicity assay 72 hrs IC50 = 19.38 μM ChEMBL
SNB19 Growth inhibition assay 7 days GI50 = 35.7 μM ChEMBL
SNB19 Growth inhibition assay 7 days GI50 = 45.6 μM ChEMBL
U373 Function assay 100 uM 72 hrs Induction of double stranded DNA break in empty vector transfected human U373 cells assessed as increase in gamma-H2AX level at 100 uM after 72 hrs by flow cytometry ChEMBL
Glioma Antitumor assay Antitumor activity against Homo sapiens (human) Glioma cells xenografted in transgenic mouse assessed as mouse survival ChEMBL
Click to View More Cell Line Experimental Data

Biological Activity

Description TMZ(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. Temozolomide induces apoptosis and exhibits antitumor activity.
Features Methazolastone is a second-generation alkylating agent.
Targets
DNA replication [1]
(L-1210, L-1210/BCNU cells)
In vitro
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 Research 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.
Experimental Result Images Methods Biomarkers Images PMID
Western blot DR5 / c-FLIP / Survivin / XIAP pERK / ERK / p-p38 / p38 24436439
Growth inhibition assay Cell viability 25751281
Immunofluorescence Phalloidin / Phospho-H2A.X cleaved caspase-3 27375225
In Vivo
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]
Animal Research Animal Models DBA/2 mice with L-1210 and L-1210/BCNU cells
Dosages 40 mg/kg
Administration Administered via i.v.
NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT05128734 Not yet recruiting
Breast Cancer Triple Negative
AHS Cancer Control Alberta
 July 1 2024 Phase 2
NCT06161974 Not yet recruiting
High Grade Glioma|Astrocytoma|Astrocytoma Grade III|Astrocytoma Grade IV|Diffuse Intrinsic Pontine Glioma|WHO Grade III Glioma|WHO Grade IV Glioma|Metastatic Brain Tumor|Diffuse Midline Glioma H3 K27M-Mutant|Thalamus Tumor|Spinal Tumor|IDH1 Mutation|IDH1 R132|IDH1 R132C|IDH1 R132H|IDH1 R132S|IDH1 R132G|IDH1 R132L|Oligodendroglioma
Rigel Pharmaceuticals|Nationwide Children''s Hospital
 June 2024 Phase 2
NCT04967690 Not yet recruiting
Newly Diagnosed Glioblastoma
Double Bond Pharmaceutical AB
 January 2024 Phase 1
NCT05698524 Recruiting
Recurrent High Grade Glioma|Anaplastic Astrocytoma|Anaplastic Oligodendroglioma|Glioblastoma|Gliosarcoma
University of Nebraska|Xynomic Pharmaceuticals Inc.
 June 26 2023 Phase 1
NCT04945148 Not yet recruiting
Glioblastoma IDH-wildtype
Hopital Foch|National Cancer Institute France
 May 2023 Phase 2

Chemical Information & Solubility

Molecular Weight 194.15 Formula

C6H6N6O2
CAS No. 85622-93-1 SDF Download TMZ(Temozolomide) SDF
Smiles CN1C(=O)N2C=NC(=C2N=N1)C(=O)N
Storage (From the date of receipt) 3 years-20°C （in the dark）powder

In vitro
Batch:

DMSO : 39 mg/mL ( (200.87 mM) Moisture-absorbing DMSO reduces solubility. Please use fresh DMSO.)

Water : 7 mg/mL

Ethanol : Insoluble


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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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