Temozolomide (CCRG 81045) - Moligand™, 10mM in DMSO , DNA inhibitor, CAS No.85622-93-1, DNA inhibitor

CAS: 85622-93-1 Cat. No.: T408143 Molecular Weight: 194.15 EC Number: 630-358-9 PubChem CID: 5394

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

NSC 362856,TMZ | 3,​4-​dihydro-​3-​methyl-​4-​oxo-imidazo[5,​1-​d]​-​1,​2,​3,​5-​tetrazine-​8-​carboxamide

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Temozolomide (CCRG81045, NSC 362856, TMZ) 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 methy
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. 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. Methazolastone induces in monocytes the DNA damage response pathways ATM-Chk2 and ATR-Chk1 resulting in p53 activation. Chronic Methazolastone exposure results in acquired Methazolastone-resistance and elevates miR-21 expression. 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.

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.
Cell Data

cell lines：

Concentrations：0 μM -100 μM

Incubation Time：l hours

Powder Purity:≥99%

Specifications

Synonyms

NSC 362856, TMZ | 3, ​4-​dihydro-​3-​methyl-​4-​oxo-imidazo[5, ​1-​d]​-​1, ​2, ​3, ​5-​tetrazine-​8-​carboxamide

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Temozolomide (CCRG81045, NSC 362856, TMZ) 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 methy

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

DNA inhibitor

Product Properties

• ALogP: -1.1

Names and Identifiers

• Isomeric SMILES: CN1C(=O)N2C=NC(=C2N=N1)C(=O)N
• WGK Germany: 3
• RTECS: NJ5927050
• PubChem CID: 5394
• Molecular Weight: 194.15
• Reaxy-Rn: 5547136

Chemical and Physical Properties

• Melt Point(°C): 206 °C(dec.)

References

1. Songlei Zhou, Fenfen Ma, Jianing Gong, Yukun Huang, Yu Chen, Shiqiang Tong, Zheng Cheng, Yinzhe Sun, Xiaoying Xie, Tongtong Zhang, Xin Luan, Huiping Lu, Hongzhuan Chen, Jun Chen.  (2025)  Immuno-Initiator Rectifies Immunodeficiency to Restore Immune Function and Potentiate Immunotherapy against IDH Mutant Glioma.  ACS Nano,      [PMID:40679872] [10.1021/acsnano.5c09310]

2. Jiang Chenrui, Chen Feifei, Chen Yue, Sun Yu, He Hua, Dramou Pierre, Xu Tao, Xu Hongbin.  (2025)  Self-assembled aggregation-induced emission supramolecular probe for sensitive temozolomide detection and intracellular imaging.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:40804284] [10.1007/s00216-025-06045-1]

3. Huanqi Zhang, Ziyan Liu, Jing Cheng, Yiming Jiang, Xiaoli Zheng, Chong Zhang, Yangling Li.  (2025)  HTR1D regulates the PI3K/Akt signaling pathway to impact glioblastoma development and resistance to temozolomide.  CHEMICO-BIOLOGICAL INTERACTIONS,      [PMID:40972861] [10.1016/j.cbi.2025.111748]

4. Yechun Jiang, Yu Jin, Chengcheng Feng, Yayun Wu, Weinan Zhang, Liang Xiao, Zhaoyou Chu, Benjin Chen, Yan Ma, Haisheng Qian, Lingling Xu.  (2023)  Engineering Hyaluronic Acid Microneedles Loaded with Mn2+ and Temozolomide for Topical Precision Therapy of Melanoma.  Advanced Healthcare Materials,      [PMID:38112062] [10.1002/adhm.202303215]

5. Li Yatian, Gao Zhenyue, Wang Yuhong, Pang Bo, Zhang Binbin, Hu Ruxin, Wang Yuqing, Liu Chao, Zhang Xuebin, Yang Jingxuan, Mei Mei, Wang Yongzhi, Zhou Xuan, Li Min, Ren Yu.  (2023)  Lysine methylation promotes NFAT5 activation and determines temozolomide efficacy in glioblastoma.  Nature Communications,  14  (1): (1-19).  [PMID:37429858] [10.1038/s41467-023-39845-z]

6. Yajing Wang, Ziwei Ding, Shiqun Lv, Jie Liu, Jie Pan, Yingcong Yu, Jun Gao, Xianfeng Huang.  (2023)  Development of tLyP-1 functionalized nanoliposomes with tunable internal water phase for glioma targeting.  JOURNAL OF LIPOSOME RESEARCH,      [PMID:36974836] [10.1080/08982104.2023.2191718]

7. Hou Xiaoying, Du Hongzhi, Deng Yufei, Wang Haiping, Liu Jinmi, Qiao Jialu, Liu Wei, Shu Xiji, Sun Binlian, Liu Yuchen.  (2023)  Gut microbiota mediated the individualized efficacy of Temozolomide via immunomodulation in glioma.  Journal of Translational Medicine,  21  (1): (1-15).  [PMID:36927689] [10.1186/s12967-023-04042-5]

8. Xiaoyi Shi, Meng Li, Qiming Huang, Liuming Xie, Zhibing Huang.  (2023)  Monacolin K Induces Apoptosis of Human Glioma U251 Cells by Triggering ROS-Mediated Oxidative Damage and Regulating MAPKs and NF-κB Pathways.  ACS Chemical Neuroscience,      [PMID:36917811] [10.1021/acschemneuro.3c00104]

9. Su Jie, Yin Wei, Huo Mengmeng, Yao Qing, Ding Liqiong.  (2023)  Induction of apoptosis in glioma cells by lycorine via reactive oxygen species generation and regulation of NF-κB pathways.  NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY,  396  (6): (1247-1255).  [PMID:36715733] [10.1007/s00210-023-02384-x]

10. Zhou Songlei, Huang Yukun, Chen Yu, Liu Yipu, Xie Laozhi, You Yang, Tong Shiqiang, Xu Jianpei, Jiang Gan, Song Qingxiang, Mei Ni, Ma Fenfen, Gao Xiaoling, Chen Hongzhuan, Chen Jun.  (2023)  Reprogramming systemic and local immune function to empower immunotherapy against glioblastoma.  Nature Communications,  14  (1): (1-20).  [PMID:36702831] [10.1038/s41467-023-35957-8]

11. Chen Bo, Li Xiaoli, Wu Lihong, Zhou Duanfang, Song Yi, Zhang Limei, Wu Qiuya, He Qichen, Wang Gang, Liu Xu, Hu Hui, Zhou Weiying.  (2022)  Quercetin Suppresses Human Glioblastoma Migration and Invasion via GSK3β/β-catenin/ZEB1 Signaling Pathway.  Frontiers in Pharmacology,      [PMID:36386155] [10.3389/fphar.2022.963614]

12. Chunyan Liao, Xiang Wang, Xueying Zhou, Dequan Wang, Ziyin Zhang, Yan Liu, Xiao Wu, Ying Chen, Yifeng Tan, Xin Dai, Pei Jing, Jie Pang, Xiao Xiao, Jie Liu, Xiaoming Liao, Shiyong Zhang.  (2022)  Dietary Antioxidant-Constructed Nanodrugs Can High-Efficiently Kill Cancer Cells while Protecting Noncancer Cells.  ACS Applied Materials & Interfaces,      [PMID:36315104] [10.1021/acsami.2c12043]

13. Hu Keqi, Zhou Daquan, Rao Linlin, Wang Peng, Xiang Chunxiang, Chen Feng.  (2021)  A Multifunctional AIE Nanoprobe as a Drug Delivery Bioimaging and Cancer Treatment System.  Frontiers in Bioengineering and Biotechnology,      [PMID:34820365] [10.3389/fbioe.2021.766470]

14. Mingming Sun, Hao Sheng, Tingfeng Wu, Jiaqi Song, Huanran Sun, Yingzhi Wang, Jiyan Wang, Zhen Li, Huifang Zhao, Junzhen Tan, Yanping Li, Guo Chen, Qingrong Huang, Yuan Zhang, Bei Lan, Shuangping Liu, Changliang Shan, Shuai Zhang.  (2021)  PIKE-A promotes glioblastoma growth by driving PPP flux through increasing G6PD expression mediated by phosphorylation of STAT3.  BIOCHEMICAL PHARMACOLOGY,      [PMID:34411567] [10.1016/j.bcp.2021.114736]

15. Man Xu, Guangmeng Li, Haoxiang Zhang, Xiaoming Chen, Yi Li, Qianming Yao, Maobin Xie.  (2020)  Sequential delivery of dual drugs with nanostructured lipid carriers for improving synergistic tumor treatment effect.  DRUG DELIVERY,      [PMID:32611218] [10.1080/10717544.2020.1785581]

16. Zeng Xiaofan, Wang Qi, Tan Xuan, Jia Le, Li Yuwei, Hu Mingdi, Zhang Zhijie, Bai Xicheng, Zhu Yanhong, Yang Xiangliang.  (2019)  Mild thermotherapy and hyperbaric oxygen enhance sensitivity of TMZ/PSi nanoparticles via decreasing the stemness in glioma.  JOURNAL OF NANOBIOTECHNOLOGY,  17  (1): (1-12).  [PMID:30935403] [10.1186/s12951-019-0483-1]

17. Yuanyuan Xie, Xiaofan Zeng, Xian Wu, Jun Hu, Yanhong Zhu, Xiangliang Yang.  (2018)  Hyperbaric oxygen as an adjuvant to temozolomide nanoparticle inhibits glioma growth by inducing G2/M phase arrest.  Nanomedicine,      [PMID:29473458] [10.2217/nnm-2017-0395]

18. Bin Du, Changqing Hong, Xinghong Zhang, Jiazhi Wang, Qiang Qu.  (2018)  Preparation and mechanical behaviors of SiOC-modified carbon-bonded carbon fiber composite with in-situ growth of three-dimensional SiC nanowires.  JOURNAL OF THE EUROPEAN CERAMIC SOCIETY,      [PMID:] [10.1016/j.jeurceramsoc.2018.01.002]

19. Yao‑Dong Chen, Yu Zhang, Tian‑Xiu Dong, Yu‑Tong Xu, Wei Zhang, Ting‑Ting An, Peng‑Fei Liu, Xiu‑Hua Yang.  (2017)  Hyperthermia with different temperatures inhibits proliferation and promotes apoptosis through the EGFR/STAT3 pathway in C6 rat glioma cells.  Molecular Medicine Reports,  16  (6): (9401-9408).  [PMID:29039593] [10.3892/mmr.2017.7769]

20. Qicheng Chen, Li Ye, Jiajun Fan, Xuyao Zhang, Huan Wang, Siyang Liao, Ping Song, Ziyu Wang, Shaofei Wang, Yubin Li, Jingyun Luan, Yichen Wang, Wei Chen, Wenjing Zai, Ping Yang, Zhonglian Cao, Dianwen Ju.  (2017)  Autophagy suppression potentiates the anti-glioblastoma effect of asparaginase in vitro and in vivo.  Oncotarget,      [PMID:29207624] [10.18632/oncotarget.19409]

21. Nan Wang, Pei Sun, Mingming Lv, Gangsheng Tong, Xin Jin, Xinyuan Zhu.  (2017)  Mustard-inspired delivery shuttle for enhanced blood–brain barrier penetration and effective drug delivery in glioma therapy.  Biomaterials Science,  5  (5): (1041-1050).  [PMID:28378865] [10.1039/C7BM00133A]

22. Xiang Zhang, Zhixing Long, Zixu Qin, Hongyan Ran, Sha Wu, Muxin Gong, Jing Li.  (2024)  A detailed evaluation of the advantages among extracellular vesicles from three cell origins for targeting delivery of celastrol and treatment of glioblastoma.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:39608584] [10.1016/j.ijpharm.2024.125005]

23. Taosha Jin, Haiyang Wang, Ihsan Ullah, Wenjiao Xie, Taian Lin, Qiaoling Tan, Xiaoyu Pan, Youyong Yuan.  (2025)  A Wireless Operated Flexible Bioelectronic Microneedle Patch for Actively Controlled Transdermal Drug Delivery.  ADVANCED MATERIALS,      [PMID:39906918] [10.1002/adma.202417136]

24. Zhipeng Yang, Haoyuan Li, Biao Yang, Yanjie Liu.  (2024)  Albumin-Based Microneedles for Spatiotemporal Delivery of Temozolomide and Niclosamide to Resistant Glioblastoma.  ACS Applied Materials & Interfaces,      [PMID:39145481] [10.1021/acsami.4c09394]

25. Jiamei Song, Jiaqi Zeng, Xi Chen, Jiayu Wang, Ying Zhang, Yuhao Gao, Ruiqi Wang, Nan Jiang, Yuhui Lin, Rui Li.  (2025)  Anti-neuroinflammatory agent rhein lysinate-based self-assembled injectable hydrogel loaded with ZL006 for promoting post-stroke functional recovery.  BIOMATERIALS,      [PMID:39884131] [10.1016/j.biomaterials.2025.123124]

26. Pinxin Lv, Zhanfeng Wang, Xinghui Si, Jing Su, Zhifei Yu, Hongquan Yu, Guofeng Ji, Wantong Song.  (2024)  Biopolymer Immune Implants co-loaded with TMZ, R848 and IOX1 for Perioperative Therapy of Glioblastoma.  Acta Biomaterialia,      [PMID:39368721] [10.1016/j.actbio.2024.09.053]

27. Li Ting, Chen Lin, Xue Yunxin, Xiao Xiangyu, Dai Wenjun, Tan Kaiyuan, Chen Tiantian, Tao Yingfang, Mao Chun, Shen Jian, Wan Mimi.  (2024)  Chemotactic nanomotor for multimodal combined therapy of glioblastoma.  Science China-Chemistry,      [PMID:] [10.1007/s11426-023-1837-7]

28. Mengyue Li, Junfeng Wu, Na Li, Junjian Zhou, Wen Cheng, Anhua Wu, Lianqing Liu, Niandong Jiao.  (2024)  Cross-Scale Drug Delivery of Diatom Microrobots Based on A Magnetic Continuum Robot for Combined Chemical and Photodynamic Therapy of Glioblastoma.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202402333]

29. Lei Jiaming, Zhou Hong, Cheng Shijiao, Yu Wenwen, Yang Meiting, Lin Li.  (2024)  Daphnoretin inhibits glioblastoma cell proliferation and metastasis via PI3K/AKT signaling pathway inactivation.  Journal of Cancer,  15  (17): (5810-5827).  [PMID:39308674] [10.7150/jca.98915]

30. Lili Li, Lin Jing, Zijun Tang, Jingguo Du, Yonglong Zhong, Xu Liu, Mingqing Yuan.  (2024)  Dual-targeting liposomes modified with BTP-7 and pHA for combined delivery of TCPP and TMZ to enhance the anti-tumour effect in glioblastoma cells.  JOURNAL OF MICROENCAPSULATION,      [PMID:38989705] [10.1080/02652048.2024.2376114]

31. Junqing Lin, Zhenhu Lin, Leilei Liu, Wenjin Lin, Xiaodong Xie, Xiujuan Zhang.  (2024)  Enhancing glioma-specific drug delivery through self-assembly of macrophage membrane and targeted polymer assisted by low-frequency ultrasound irradiation.  Materials Today Bio,      [PMID:38706730] [10.1016/j.mtbio.2024.101067]

32. Xiangxiang Zhang, Chao Li, Shubin Li, Xuefeng Tang, Jingjing Zhao, Weili Xu, Xiaojun Han.  (2025)  High-Throughput Programmable Tumor Spheroid Generation Using the Magneto-Archimedes Effect.  ACS Applied Materials & Interfaces,      [PMID:40022287] [10.1021/acsami.4c21198]

33. Wei Cheng, Zhiran Duan, Han Chen, Yanjun Wang, Chao Wang, Yuqing Pan, Jie Wu, Ning Wang, Haijing Qu, Xiangdong Xue.  (2025)  Macrophage membrane-camouflaged pure-drug nanomedicine for synergistic chemo- and interstitial photodynamic therapy against glioblastoma.  Acta Biomaterialia,      [PMID:39800099] [10.1016/j.actbio.2025.01.016]

34. Zhao Wenpeng, Zhou Liwei, Zhao Wentao, Yang Huiying, Lu Zhenwei, Zhang Liang, Zhang Yaya, Xie Yuanyuan, Lu Hanwen, Han Wanhong, He Jiawei, Qiu Xiansheng, Jia Fang, Zhao Wujie, Zhang Bingchang, Wang Zhanxiang.  (2024)  The combination of temozolomide and perifosine synergistically inhibit glioblastoma by impeding DNA repair and inducing apoptosis.  Cell Death Discovery,  10  (1): (1-11).  [PMID:38977680] [10.1038/s41420-024-02085-1]

35. Fangfei Li, Zhaoxin Zhang, Qinyan Shi, Rubing Wang, Ming Ji, Xiaoguang Chen, Yong Li, Yunbao Liu, Shishan Yu.  (2025)  Thermal proteome profiling (TPP) reveals NAMPT as the anti-glioma target of phenanthroindolizidine alkaloid PF403.  Acta Pharmaceutica Sinica B,      [PMID:40486861] [10.1016/j.apsb.2025.02.027]

36. Shuai Wu, Ya Wang, Yunfan Li, Minyao Qiu, Yuan Zhong, Maolan Zhang, Haifeng Yang, Jianshu Li, Wei Wu.  (2025)  Microglial Membrane Camouflaged Nano-AUTAC to Promote Autophagy-Mediated β-Catenin Degradation for Reducing TMZ Resistance in Glioblastoma.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202528010]

37. Lin Xu, Baoju Wang, Zhenbo Gang, Zhibin Han, Aowen Wang, Qi Liu, Hongyang Liu, Shilong Wei, Zhiguo Lin, Chuncheng Xie, Li Hu.  (2025)  Ubiquitin-conjugating enzyme E2S decreases the sensitivity of glioblastoma cells to temozolomide by upregulating PGAM1 via the interaction with OTUB2.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:39904430] [10.1016/j.ijbiomac.2025.140583]

38. Fu Qiang, Chen Peipei, Wang Zening, Liu Bo, Zhou Qingjiu, Anwar Ilhamjan, Wang Yongxin.  (2025)  The function of TRIML2 on the temozolomide resistance in glioblastoma.  Annals of Medicine and Surgery,      [PMID:40110305] [10.1097/MS9.0000000000002888]

39. Mingyu Xia, Songsong Zhao, Zhiwei Sun, Yan Shi, Wenhai Lin, Zhiyuan Zhong, Fenghua Meng.  (2025)  Brain-targeted polymersomes mediating RNAi of STAT3 sensitize glioblastoma to temozolomide and immunotherapy.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:40339287] [10.1016/j.jcis.2025.137751]

40. Jianping Wen, Dongxu Wu, Yi Le, Zonghua Yin, Minglong Chen, Yulong Shen, Xia Wu, Kebo Liu, Kun Luo, Zhicheng Shu, Qingxia Shu, Dongsheng Ouyang.  (2025)  Engineered nanovesicles targeting SERPINE1 overcome temozolomide resistance in glioblastoma.  CELLULAR SIGNALLING,      [PMID:40139622] [10.1016/j.cellsig.2025.111763]

41. Ying Qu, Jingjing Zhao, Long Ma, Xue Wang, Feifei Sun, Yizhe Li, Yihua Wu, Guozhi Zhao, Shijia Liu, Wenqing Ma, Tao Li, Zhongxi Zhao.  (2025)  Intranasal delivery of temozolomide and disulfiram in situ gel combined with copper for enhanced glioblastoma therapy.  COLLOIDS AND SURFACES B-BIOINTERFACES,      [PMID:40592114] [10.1016/j.colsurfb.2025.114898]

42. Ling Chen, Xiao-Qin Ma, Hai-Li Wu, Shun Zhang, Jie-Feng Chen, Ning Lin, Qing Chen.  (2025)  Resveratrol–Temozolomide Cocrystal Induced Antiglioblastoma Effects via Enhanced Dissolution Behavior and Mitochondrial Apoptosis.  CRYSTAL GROWTH & DESIGN,      [PMID:] [10.1021/acs.cgd.5c01202]

43. Cao Xuejun, Li Yishen, Guo Bin, Liu Yan, Wang Baoshuai, Wang Hao, Lu Jingbo, Wei Libin, Gao Yuan, Guo Yongjian, Wu Tao.  (2026)  Targeting VCP with V8 suppresses glioblastoma development via formation of aggregates and disruption of mitophagy flux.  CELLULAR ONCOLOGY,  49  (1): (21).  [PMID:41505038] [10.1007/s13402-025-01149-3]