3-Methylquinoxaline-2-carboxylic Acid
(Synonyms: 3-甲基-喹啉-2-甲酸,MQCA) 目录号 : GC41619
A major metabolite of olaquindox
Cas No.:74003-63-7
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-Methylquinoxaline-2-carboxylic acid (MQCA) is a major metabolite of olaquindox, an antibiotic and swine growth regulator. It induces cell cycle arrest at the S phase and is toxic to Chang liver cells in a concentration- and time-dependent manner. MQCA has been used as a marker of olaquindox use in livestock applications.
| Cas No. | 74003-63-7 | SDF | |
| 别名 | 3-甲基-喹啉-2-甲酸,MQCA | ||
| Canonical SMILES | CC1=NC2=CC=CC=C2N=C1C(O)=O | ||
| 分子式 | C10H8N2O2 | 分子量 | 188.2 |
| 溶解度 | DMF: 25 mg/mL,DMSO: 30 mg/mL,DMSO:PBS (pH 7.2) (1:10): 0.1 mg/mL,Ethanol: 25 mg/mL | 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。 |
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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 | 5.3135 mL | 26.5675 mL | 53.135 mL |
| 5 mM | 1.0627 mL | 5.3135 mL | 10.627 mL |
| 10 mM | 0.5313 mL | 2.6567 mL | 5.3135 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。
Synthesis of deuterium-labeled 2-quinoxalinecarboxylic acid and 3-Methylquinoxaline-2-carboxylic Acid from deuterium aniline
J Labelled Comp Radiopharm 2018 Dec;61(14):1043-1047.PMID:30132955DOI:10.1002/jlcr.3679.
An efficient and simple synthetic route of deuterium-labeled 2-quinoxalinecarboxylic acid-d4 (QCA-d4 ) and 3-methylquinoxaline-2-carboxylic acid-d4 (MQCA-d4 ) is presented with 99.9% and 99.6% isotopic enrichment using aniline-d5 as labeled starting material. Their chemical structures were confirmed by 1 H NMR, and their isotopic abundance was determined by mass spectrometry analysis.
[Determination of 3-methyl-quinoxaline-2-carboxylic acid residue in pork by high performance liquid chromatography-tandem mass spectrometry]
Se Pu 2019 Oct 8;37(10):1059-1063.PMID:31642284DOI:10.3724/SP.J.1123.2019.04050.
A method was developed for the simultaneous quantitative and confirmatory determination of 3-Methylquinoxaline-2-carboxylic Acid (MQCA) residues in pork by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). The sample was hydrolyzed with 0.3 mol/L hydrochloric acid solution, and MQCA was extracted by water bath oscillation. MQCA was first extracted with acetonitrile and ethyl acetate and then re-extracted from the extraction solution with 0.1 mol/L sodium hydroxide solution. Then MQCA was purified by an anion exchange solid phase extraction column. The chromatographic separation was performed using an Agilent Eclipse Plus C18 column (50 mm×3.0 mm, 1.8 μm). The quantitative analysis was performed by the matrix matching addition method. The correlation coefficient of MQCA in the range of 1.0-50 μg/L was greater than 0.99. The recovery was 90.5%-119.6% at the spiked levels of 0.5, 1.0 and 5.0 μg/kg, and the relative standard deviation was 3.14%-4.22%. The method can be used for the rapid quantitative determination of 3-Methylquinoxaline-2-carboxylic Acid residues in pork.
[Determination of 3-Methylquinoxaline-2-carboxylic Acid of olaquindox marker residue in chicken muscles by liquid chromatography-tandem mass spectrometry]
Se Pu 2018 May 8;36(5):446-451.PMID:30136485DOI:10.3724/SP.J.1123.2017.12023.
A simple, sensitive, scientific and reproducible liquid chromatography-tandem mass spectrometric method was developed to determine 3-Methylquinoxaline-2-carboxylic Acid (MQCA) of olaquindox marker residue in chicken muscle tissues. The chickens were administered orally with olaquindox and used as positive samples. The approaches, enzyme, acid, and base hydrolysis, were adopted to digest MQCA in the medicated chicken muscles. The amounts of MQCA in the medicated chicken were determined and compared using different hydrolysis approaches. It was shown that the highest amount of MQCA was obtained for the base hydrolysis approach. Here, the sample was hydrolyzed with 1.0 mol/L NaOH solution, defatted with n-hexane, and purified with a mixed anion-exchange solid-phase extraction cartridge. The chromatographic separation was performed on a reversed-phase C18 column and detected using mass spectrometry in selected reaction monitoring mode. The analyte showed good linearity in the range 1.0-100 μg/L. The correlation coefficient (r2) was greater than 0.99. The limit of detection of the proposed method was 0.4 μg/kg. At the three spiked levels of 1.0, 5.0 and 50.0 μg/kg, the average recoveries of MQCA were in range 71.7%-82.4% obtained using external standard calibration, and in range 96.3%-103.7% for internal standard calibration, with relative standard deviations below 6.0%. The proposed method is suitable for routinely monitoring of MQCA residues in animal-derived foods.
Cytotoxicity and genotoxicity of 1,4-bisdesoxyquinocetone, 3-Methylquinoxaline-2-carboxylic Acid (MQCA) in human hepatocytes
Res Vet Sci 2012 Dec;93(3):1393-401.PMID:22840332DOI:10.1016/j.rvsc.2012.06.012.
Quinoxaline-1,4-dioxides, widely used as medicinal feed additives as antibacterial growth promoters, have been shown to exert diverse toxicities. Their toxicities are hypothesized to be closely related to the formation of N-oxide reductive metabolites. 1,4-Bisdesoxyquinocetone and MQCA are important N-oxide reductive metabolites of quinocetone or olaquindox. In this study, we evaluated the cytotoxicity and genotoxicity of the metabolites, 1,4-bisdesoxyquinocetone and MQCA, as well as their parental drugs (quinocetone and olaquindox) in two human hepatocyte cell lines, L-02 and Chang liver cells. All these compounds inhibited the growth of cells in a dose-dependent and time-dependent manner by the MTT assay. Hormesis effects were found in L-02 cells treated with quinocetone at low doses. In the comet assay, although the two metabolites induced dose-related DNA damage in both cell lines, the levels of damage were less than that demonstrated for the parent drugs. The flow cytometric analysis showed that only the two metabolites induced cell cycle arrest at the S phase, and a decrease in the G0/G1, G2/M phase of Chang liver cells, which was not found for the L-02 cells treated with any compounds. The results indicate that 1,4-bisdesoxyquinocetone and MQCA are toxic to L-02 and Chang liver cells, and provide important new information towards understanding the olaquindox and quinocetone toxic mechanisms.
In vivo studies to highlight possible illegal treatments of rabbits with carbadox and olaquindox
Food Addit Contam Part A Chem Anal Control Expo Risk Assess 2015;32(12):1976-91.PMID:26400201DOI:10.1080/19440049.2015.1086822.
For the treatment of rabbit dysentery and bacterial enteritis, veterinary practitioners often adopt veterinary medicinal products authorised for other food-producing species, but in some cases non-authorised drugs frequently used in the past, such as carbadox and olaquindox, might be illegally adopted. To verify the carbadox and olaquindox distribution and persistence in rabbit tissues, two independent in vivo studies were carried out. In the first study, 24 healthy rabbits received water medicated with carbadox at 100 mg l(-1) over a period 28 days, whereas in the second one, 24 healthy rabbits were administered water containing olaquindox at 100 mg l(-1). In each study rabbits were randomly assigned to four groups to be sacrificed respectively at 0, 5, 10 and 20 days from treatment withdrawal, for depletion studies. A control group of six animals was adopted for control and as a reservoir of blank tissues. Muscle and liver samples collected from each treated animal were stored at -20°C pending the analysis. Sensitive and robust liquid chromatography-tandem mass spectrometry analytical methods were set up for the parent compounds and their main metabolites quinoxaline-2-carboxylic acid, desoxycarbadox and 3-Methylquinoxaline-2-carboxylic Acid to verify their residual. Data collected demonstrate that the combination of liver as target matrix, quinoxaline-2-carboxylic acid and 3-Methylquinoxaline-2-carboxylic Acid as marker residue and enzymatic digestion is strategic to evidence carbadox and/or olaquindox illegal treatments in rabbits, even 20 days after treatment withdrawal at concentration levels higher than 0.5 µg kg(-1). This findings suggests that liver should be proposed as target matrix for official control in national monitoring plan.