N-Nitroso-N-methylurea
(Synonyms: 1-甲基-1-亚硝基脲,NMU; MNU; NMH) 目录号 : GC39498
N-Nitroso-N-methylurea(NMU; MNU; NMH)是一种有效的致癌剂,诱变剂和致畸剂。
Cas No.:684-93-5
Sample solution is provided at 25 µL, 10mM.
N-Nitroso-N-methylurea (NMU; MNU; NMH) is a potent carcinogen, mutagen and teratogen[1]. N-Nitroso-N-methylurea is a direct-acting alkylating agent that interacts with DNA[2]. N-Nitroso-N-methylurea targets multiple animal organs to cause various cancers and/or degenerative diseases[3]. N-Nitroso-N-methylurea is also a precursor in the synthesis of diazomethane[4].
In vitro, treatment of SCC-13 cells with N-Nitroso-N-methylurea (5µM) for 60 min significantly increased intracellular NF-κB activity by 38% compared to the control group and also increased the amount of I-κBα phosphorylation[5].
In vivo, oral administration of N-Nitroso-N-methylurea (100mg/kg) to male albino Wistar rats for 16 weeks significantly induced a decrease in body weight, water intake, and food intake, increased serum gastrin and gastric tissue lipid peroxidation levels, and decreased reduced glutathione levels [6].
References:
[1] Lawley P D. N-nitroso compounds[M]//Chemical carcinogenesis and mutagenesis I. Berlin, Heidelberg: Springer Berlin Heidelberg, 1990: 409-469.
[2] Likhachev A J, Ivanov M N, Brésil H, et al. Carcinogenicity of single doses of N-nitroso-N-methylurea and N-nitroso-N-ethylurea in Syrian golden hamsters and the persistence of alkylated purines in the DNA of various tissues[J]. Cancer Research, 1983, 43(2): 829-833.
[3] Tsubura A, Lai Y C, Miki H, et al. Animal models of N-methyl-N-nitrosourea-induced mammary cancer and retinal degeneration with special emphasis on therapeutic trials[J]. In Vivo, 2011, 25(1): 11-22.
[4] Hecht S M, Kozarich J W. Mechanism of the base-induced decomposition of N-nitroso-N-methylurea[J]. The Journal of Organic Chemistry, 1973, 38(10): 1821-1824.
[5] Moon K Y. N-nitroso-N-methylurea and N-nitroso-N-ethylurea induce upregulation of cellular NF-κ B activity through protein kinase C-dependent pathway in human malignant keratinocytes[J]. Archives of pharmacal research, 2010, 33(1): 133-139.
[6] Mansingh D P, Pradhan S, Biswas D, et al. Palliative role of aqueous ginger extract on N-nitroso-N-methylurea-induced gastric cancer[J]. Nutrition and cancer, 2020, 72(1): 157-169.
N-Nitroso-N-methylurea(NMU; MNU; NMH)是一种有效的致癌剂,诱变剂和致畸剂[1]。N-Nitroso-N-methylurea是一种直接作用的烷基化剂,与DNA相互作用[2]。N-Nitroso-N-methylurea靶向多种动物器官,以引起各种癌症和/或变性疾病[3]。N-Nitroso-N-methylurea也是一种重氮甲烷合成中的前体物质[4]。
在体外,N-Nitroso-N-methylurea(5µM)处理SCC-13细胞60min,显著升高了细胞内NF-κB活性,与对照组相比高出38%,还增加了I-κBα磷酸化的量[5]。
在体内,N-Nitroso-N-methylurea(100mg/kg)通过口服灌胃处理雄性白化病 Wistar大鼠16周,显著诱导了大鼠体重、饮水量和食物摄入量减少,升高了血清胃泌素和胃组织脂质过氧化水平,降低了还原型谷胱甘肽水平[6]。
Cell experiment [1]: | |
Cell lines | SCC-13 cells |
Preparation Method | The transfectant human SCC-13 cells (2×104) cells were seeded in 96-well plates. When appropriate, the cells were washed with PBS and stimulated with medium containing 2 and 5µM of N-Nitroso-N-methylurea for 60min. At this time, the cells were treated with 4% fixing buffer (100µL) and quenching buffer (100µL), respectively and incubated for 20min at room temperature. Buffers were removed and the cells were washed twice with washing buffer(200µL). |
Reaction Conditions | 5µM; 60min |
Applications | Treatment of transfected keratinocytes with N-Nitroso-N-methylurea resulted in upregulation of NF-κB activity in cells, which was 38% higher than that in the control group. |
Animal experiment [2]: | |
Animal models | Male albino Wistar rats |
Preparation Method | Male albino Wistar rats were equally randomized in to 2 groups of twelve animals each: Normal control rats (Group I) were fed with 1ml of citrate buffer(pH – 4.5) orally and normal saline (1ml/rat) thrice a week throughout the experiment (8 and 16wks. Cancercontrol rats (Group II) were administrated with N-Nitroso-N-methylurea(100mg/kg b.w.) in citrate buffer, pH – 4.5 and normal saline thrice in a week via intragastric route. Initially, N-Nitroso-N-methylurea was administered(n¼ 6) for a period of 8wk and then continued till 16wk(n¼ 6) to check the extent of carcinogenicity. |
Dosage form | 100mg/kg; p.o. |
Applications | N-Nitroso-N-methylurea-induced rats had significantly decreased body weight, water intake and food intake, increased serum gastrin levels, increased lipid peroxidation levels in gastric tissue, and decreased reduced glutathione levels. |
References: [1]Moon K Y. N-nitroso-N-methylurea and N-nitroso-N-ethylurea induce upregulation of cellular NF-κ B activity through protein kinase C-dependent pathway in human malignant keratinocytes[J]. Archives of pharmacal research, 2010, 33(1): 133-139. [2]Mansingh D P, Pradhan S, Biswas D, et al. Palliative role of aqueous ginger extract on N-nitroso-N-methylurea-induced gastric cancer[J]. Nutrition and cancer, 2020, 72(1): 157-169. |
Cas No. | 684-93-5 | SDF | |
别名 | 1-甲基-1-亚硝基脲,NMU; MNU; NMH | ||
Canonical SMILES | O=C(N)N(C)N=O | ||
分子式 | C2H5N3O2 | 分子量 | 103.08 |
溶解度 | DMSO: 125 mg/mL (1212.65 mM) | 储存条件 | 4°C, protect from light, stored under nitrogen |
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1 mg | 5 mg | 10 mg |
1 mM | 9.7012 mL | 48.506 mL | 97.012 mL |
5 mM | 1.9402 mL | 9.7012 mL | 19.4024 mL |
10 mM | 0.9701 mL | 4.8506 mL | 9.7012 mL |
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