N-Nitrosodibutylamine
(Synonyms: N-亚硝基二丁胺,N-Nitroso-di-n-butylamine) 目录号 : GC39837
An N-nitrosamine
Cas No.:924-16-3
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
N-Nitrosodibutylamine is an N-nitrosamine.1 It induces apoptosis and the production of reactive oxygen species (ROS) in HL-60 leukemia cells when used at concentrations of 10 and 20 mM.2 N-Nitrosodibutylamine (0.05% in the drinking water) induces tumor formation in rats.3 It has been found in various food products, including fresh vegetables and pork, and influent and effluent of wastewater.1,4
1.Park, J.-E., Seo, J.-E., Lee, J.-Y., et al.Distribution of seven N-nitrosamines in foodToxicol. Res.31(3)279-288(2015) 2.García, A., Morales, P., Arranz, N., et al.Induction of apoptosis and reactive oxygen species production by N-nitrosopiperidine and N-nitrosodibutylamine in human leukemia cellsJ. Appl. Toxicol.28(4)455-465(2008) 3.Okajima, E., Hiramatsu, T., Motomiya, Y., et al.Effect of DL-tryptophan on tumorigenesis in the urinary bladder and liver of rats treated with N-nitrosodibutylamineGan.62(3)163-169(1971) 4.Krauss, M., Longrée, P., Dorusch, F., et al.Occurrence and removal of N-nitrosamines in wastewater treatment plantsWater Res.43(17)4381-4391(2009)
| Cas No. | 924-16-3 | SDF | |
| 别名 | N-亚硝基二丁胺,N-Nitroso-di-n-butylamine | ||
| Canonical SMILES | CCCCN(CCCC)N=O | ||
| 分子式 | C8H18N2O | 分子量 | 158.24 |
| 溶解度 | DMSO: 250 mg/mL (1579.88 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 6.3195 mL | 31.5976 mL | 63.1951 mL |
| 5 mM | 1.2639 mL | 6.3195 mL | 12.639 mL |
| 10 mM | 0.632 mL | 3.1598 mL | 6.3195 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Transmission electron microscopy of the liver mitochondria of N-Nitrosodibutylamine-treated mice
Microsc Res Tech 2021 Dec;84(12):2832-2836.PMID:34048103DOI:10.1002/jemt.23842.
N-Nitrosodibutylamine (DBN) has been found in a wide variety of products because of the nitrosation of amines present in these products. An extensive series of synthesis and carcinogenicity studies of various compounds related to DBN and its metabolites have revealed that they have markedly different carcinogenic effects. The role of mitochondria in disease has been found to be expanded beyond the respiratory chain, as defects in additional mitochondrial functions and behaviors have been linked to cancer, metabolic disorders, and many neurodegenerative diseases, such as Alzheimer's, Parkinson's, and Huntington's disease (Nunnari & Suomalainen (2012) Cell, 148, 1145-1159). The sample preparation was performed using the protocol standardized by Sophisticated Analytical Instrumentation Facility (SAIF) laboratory in NEHU. The prepared sample was then mounted and observed under the transmission electron microscope model JEM-100 CC II. The micrographs obtained from transmission electron microscopy (TEM) at various magnifications 2,000, 5,000, and 12,000× from DBN-treated mice showed significant changes. Mitochondria showed variability in number, size, and shape. This significant alteration in the morphology and population of liver mitochondria observed in DBN-treated animals in comparison to that of the age-matched normal control mice provide a unique potential for the use of mitochondria as markers for the early detection for the treatment of liver cancer.
N-Nitrosopiperidine and N-Nitrosodibutylamine induce apoptosis in HepG2 cells via the caspase dependent pathway
Cell Biol Int 2009 Dec;33(12):1280-6.PMID:19748591DOI:10.1016/j.cellbi.2009.08.015.
The human hepatoma cell line (HepG2) exhibited a dose and time-dependent apoptotic response following treatment with N-Nitrosopiperidine (NPIP) and N-Nitrosodibutylamine (NDBA), two recognized human carcinogens. Our results showed a significant apoptotic cell death (95%) after 24h treatment with NDBA (3.5 mM), whereas it was necessary to use high doses of NPIP (45 mM) to obtain a similar percentage of apoptotic cells (86%). In addition, both extrinsic (caspase-8) and intrinsic pathway (caspase-9) could be implicated in the N-Nitrosamines-induced apoptosis. This study also addresses the role of reactive oxygen species (ROS) as intermediates for apoptosis signaling. A significant increase in ROS levels was observed after NPIP treatment, whereas NDBA did not induce ROS. However, N-acetylcysteine (NAC) did not block NPIP-induced apoptosis. All these findings suggest that NPIP and NDBA induce apoptosis in HepG2 cells via a pathway that involves caspases but not ROS.
Urinary metabolites of N-Nitrosodibutylamine in the rat: identification of N-acetyl-S-butyl-L-cysteine derivatives
IARC Sci Publ 1987;(84):153-5.PMID:3679356doi
N-Acetyl-S-(butyl, 3-oxobutyl and 3-hydroxybutyl)-L-cysteines have been isolated and identified (as their methyl esters) from the urine of rats given N-Nitrosodibutylamine (NDBA), N-nitrodibutylamine (NTDBA) and their corresponding alpha-acetoxy derivatives, N-nitroso-N-butyl(1-acetoxybutyl)amine and N-nitro-N-butyl(1-acetoxybutyl)amine, respectively. Greater amounts of these L-cysteine derivatives were detected in urine after administration of NDBA than of NTDBA. This suggests that the markedly different biological activities of NDBA and NTDBA might be due, in part, to a difference in their alkylating abilities in vivo.
Tissue-specificity of N-Nitrosodibutylamine metabolism in Sprague-Dawley rats
Chem Biol Interact 1982 Jan;38(2):231-42.PMID:6276033DOI:10.1016/0009-2797(82)90042-4.
The distribution and metabolism of N-[14C]nitrosodibutylamine were studied in Sprague-Dawley rats. The results indicated that in addition to the liver, metabolism of the substance occurred in the nasal mucosa, the lung and the oesophagus. Metyrapone and diethyldithiocarbamate reduced the production of 14CO2 from N-[14C]nitrosodibutylamine by all these tissues. There was no indication of metabolic capacity in the urinary bladder or the kidney. The results fit with the assumption that tumours of the urinary tract are induced by metabolites reaching these tissues via the urine. Besides the liver, the oesophagus and the lung are target tissues for the carcinogenicity of N-Nitrosodibutylamine in Sprague-Dawley rats and in these tissues the local formation of reactive metabolites may play a role in the pathogenesis of N-nitrosodibutylamine-induced lesions.
Fluoro-substituted N-nitrosamines. 8. N-Nitrosodibutylamine and omega-fluorinated analogues: in vivo metabolism in relation to the induction of urinary bladder cancer in the rat
Carcinogenesis 1985 Nov;6(11):1559-64.PMID:4053275DOI:10.1093/carcin/6.11.1559.
Urinary excretion of N-Nitrosodibutylamine (NDBA) and of two omega-fluorinated analogues [N-nitroso-4,4,4-trifluorobutyl-butylamine, NDBA-F3; N-nitroso-bis(4,4,4-trifluorobutyl)-amine, NDBA-F6] was studied in male Sprague-Dawley (SD) rats. After oral application of equimolar doses (0.44 and 1.32 mmol/kg body wt.) urines were collected (48 h) and analyzed for parent compounds, and for nitrosamine metabolites by gas chromatography/Thermal Energy Analyzer (GC/TEA) and gas chromatography/mass spectrometry (GC/MS). After administration of NDBA the known major metabolites N-nitroso-3- hydroxybutylbutylamine (3-OH-NDBA) and N-nitroso-3-carboxypropylbutylamine (BCPN) were excreted in urine. After application of the omega-fluorinated analogue NDBA-F6, however, urinary and biliary nitrosamine metabolites were detected only in trace amounts. This finding demonstrates a strong inhibitory effect of fluorine substitution on oxidations at omega, (omega-1) and beta-positions. Confirmation of this inhibitory effect of omega-fluorine substitution is given from the excretion profiles of NDBA-F3 which shows metabolic oxidations only at the nonfluorinated chain: N-nitroso-3-hydroxybutyl-4,4,4-trifluorobutylamine (3-OH-NDBA-F3) and N-nitroso-3-carboxypropyl-4,4,4-trifluorobutylamine (BCPN-F3) were excreted as main metabolites. Our results on metabolism together with the available data on carcinogenicity of the compounds in the rat strongly support the hypothesis that omega-oxidation of one butyl-chain is a prerequisite for the induction of urinary bladder tumors with NDBA. For the induction of liver tumors, alpha-C-hydroxylation appears to be the crucial event.