3-Amino-1,2,4-triazine
目录号 : GC680813-Amino-1,2,4-triazine 是 NO 合成酶 (NO Synthase) 抑制剂，也能抑制亚硝酸盐的分泌。
Cas No.:1120-99-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-Amino-1,2,4-triazine is an inhibitor of NO Synthase, and also inhibits nitrite secretion[1].
3-Amino-1,2,4-triazine (50 mM; 7 h) inhibits NO synthase activity in cytosolic extracts of activated cells[1].
3-Amino-1,2,4-triazine (5-50 mM; 24 h) inhibits both nitrite secretion and parasite killing by activated macrophages[1].
[1]. BuchmÜller-Rouiller Y, et al. 3-amino-1,2,4-triazole inhibits macrophage NO synthase. Biochem Biophys Res Commun. 1992 Feb 28;183(1):150-5.
| Cas No. | 1120-99-6 | SDF | Download SDF |
| 分子式 | C3H4N4 | 分子量 | 96.09 |
| 溶解度 | 储存条件 | 4°C, protect from light | |
| 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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 10.4069 mL | 52.0346 mL | 104.0691 mL |
| 5 mM | 2.0814 mL | 10.4069 mL | 20.8138 mL |
| 10 mM | 1.0407 mL | 5.2035 mL | 10.4069 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。
3-Amino-1,2,4-triazine
Acta Crystallogr C 2002 Jul;58(Pt 7):o431-2.PMID:12094068DOI:10.1107/s0108270102009733.
In the crystal structure of 3-Amino-1,2,4-triazine, C(3)H(4)N(4), the molecules form hydrogen-bonded chains that are almost parallel to the b axis (3.2 degrees), and which are inclined to the a and c axes by approximately 21 and approximately 69 degrees, respectively. The distortion of the 1,2,4-triazine ring in the crystal is compared with gas-phase ab initio molecular-orbital calculations.
3-amino-1,2,4-triazole inhibits macrophage NO synthase
Biochem Biophys Res Commun 1992 Feb 28;183(1):150-5.PMID:1371917DOI:10.1016/0006-291x(92)91621-v.
Murine macrophages activated by interferon-gamma and lipopolysaccharide become leishmanicidal through a process involving L-arginine-derived nitrogen oxidation products. Both nitrite secretion and parasite killing by activated macrophages were inhibited by 3-amino-1,2,4-triazole as well as the related compound, 3-Amino-1,2,4-triazine. Moreover, NO synthase activity in cytosolic extracts of activated cells was inhibited by both compounds. 4-amino-1,2,4-triazole, an isomer of 3-amino-1,2,4-triazole, was without effect. Our results suggest that besides its known inhibitory effect on catalases and peroxidases, 3-amino-1,2,4-triazole is an inhibitor of NO synthase. The resemblance between the tautomeric form of 3-amino-1,2,4-triazole and the guanidino group of L-arginine, the natural substrate for NO synthase, might be responsible for the observed inhibition.
Crystal structure and Hirshfeld surface analysis of the 1:3 adduct of tetra-aqua-trinitrato-neodymium(III) with 3-Amino-1,2,4-triazine
Acta Crystallogr E Crystallogr Commun 2018 Aug 24;74(Pt 9):1309-1313.PMID:30225123DOI:10.1107/S2056989018011714.
In the title compound, [Nd(NO3)3(H2O)4]·3C3H4N4, neodymium is ten-coordinate with a distorted bicapped square-anti-prismatic geometry formed from six O atoms from three nitrate ions and four O atoms from four coordinated water mol-ecules. The structure also contains neutral 3-Amino-1,2,4-triazine mol-ecules which are not coordinated to the central metal atom. The coordinated water mol-ecules and nitrate ions of adjacent complexes are linked by O-H⋯O hydrogen bonds to form cyclic R22(8) ring motifs, which in turn are further connected via hydrogen bonds to generate a sheet-like structure. The triazine mol-ecules are involved in a number of hydrogen-bonding inter-actions: N-H⋯N and O-H⋯N inter-actions to form R33(9) motifs and N-H⋯N inter-actions to link the organic mol-ecules into chains. Weak C-H⋯O hydrogen bonds also occur between triazine mol-ecules and coordinated nitrate atoms. All these inter-molecular contacts contribute to the stabilization of the three-dimensional supra-molecular framework. Hirshfeld surface analysis shows that N⋯H/H⋯N and H⋯H inter-actions account for 42.9 and 20.6% of the surface, respectively.
Detection of 3-Amino-1,2,4-triazine adulteration in milk using an oxidation product 3-amino-1,2,4-triazin-5(2H)-one
J Chromatogr A 2013 Apr 12;1285:165-7.PMID:23473510DOI:10.1016/j.chroma.2013.02.021.
A rapid liquid chromatography-mass spectrometry method to detect 3-Amino-1,2,4-triazine (ATZ) in milk was developed as part of a programme to set up methods for detecting the economically motivated adulteration of raw milk with nitrogen-containing compounds. When ATZ was added to unpasteurised or pasteurised milk at levels of 10-1000 ppm, the levels declined over a period of a few days and in some cases declined below the limit of detection of the analytical method (1 ppm). ATZ did not degrade in deproteinised milk extracts, in aqueous standards or in aqueous (non-milk) controls, suggesting that degradation was mediated by a pasteurisation-resistant enzymatic or microbial process. An oxidation product of ATZ was detected by mass spectrometry, and a tentative structure for this compound (3-amino-1,2,4-triazin-5-one, ATZO) was determined by fragmentation analysis and high resolution mass spectrometry. The accumulation of this oxidation product correlated with the loss of ATZ in milk samples. It was concluded that the detection of ATZO could be used as a marker for the addition of ATZ and that both compounds should be monitored during surveys looking for the ATZ adulteration of milk.
Discovery of the 3-Amino-1,2,4-triazine-Based Library as Selective PDK1 Inhibitors with Therapeutic Potential in Highly Aggressive Pancreatic Ductal Adenocarcinoma
Int J Mol Sci 2023 Feb 12;24(4):3679.PMID:36835086DOI:10.3390/ijms24043679.
Pyruvate dehydrogenase kinases (PDKs) are serine/threonine kinases, that are directly involved in altered cancer cell metabolism, resulting in cancer aggressiveness and resistance. Dichloroacetic acid (DCA) is the first PDK inhibitor that has entered phase II clinical; however, several side effects associated with weak anticancer activity and excessive drug dose (100 mg/kg) have led to its limitation in clinical application. Building upon a molecular hybridization approach, a small library of 3-Amino-1,2,4-triazine derivatives has been designed, synthesized, and characterized for their PDK inhibitory activity using in silico, in vitro, and in vivo assays. Biochemical screenings showed that all synthesized compounds are potent and subtype-selective inhibitors of PDK. Accordingly, molecular modeling studies revealed that a lot of ligands can be properly placed inside the ATP-binding site of PDK1. Interestingly, 2D and 3D cell studies revealed their ability to induce cancer cell death at low micromolar doses, being extremely effective against human pancreatic KRAS mutated cancer cells. Cellular mechanistic studies confirm their ability to hamper the PDK/PDH axis, thus leading to metabolic/redox cellular impairment, and to ultimately trigger apoptotic cancer cell death. Remarkably, preliminary in vivo studies performed on a highly aggressive and metastatic Kras-mutant solid tumor model confirm the ability of the most representative compound 5i to target the PDH/PDK axis in vivo and highlighted its equal efficacy and better tolerability profile with respect to those elicited by the reference FDA approved drugs, cisplatin and gemcitabine. Collectively, the data highlights the promising anticancer potential of these novel PDK-targeting derivatives toward obtaining clinical candidates for combatting highly aggressive KRAS-mutant pancreatic ductal adenocarcinomas.