3,5,6-Trichloro-2-pyridinol
(Synonyms: 3,5,6-三氯吡啶-2-醇,TCPy) 目录号 : GC60495
3,5,6-Trichloro-2-pyridinol(TCPy)是除草剂Triclopyr和杀虫剂Chlorpyrifos和Chlorpyrifos-methyl的主要降解产物。
Cas No.:6515-38-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,5,6-Trichloro-2-pyridinol (TCPy) is the main degradation product of the herbicide Triclopyr and the insecticides Chlorpyrifos and Chlorpyrifos-methyl[1].
[1]. Jingquan Li, et al. Novel gene clusters and metabolic pathway involved in 3,5,6-trichloro-2-pyridinol degradation by Ralstonia sp. strain T6. Appl Environ Microbiol. 2013 Dec;79(23):7445-53.
| Cas No. | 6515-38-4 | SDF | |
| 别名 | 3,5,6-三氯吡啶-2-醇,TCPy | ||
| Canonical SMILES | O=C1C(Cl)=CC(Cl)=C(Cl)N1 | ||
| 分子式 | C5H2Cl3NO | 分子量 | 198.43 |
| 溶解度 | DMSO : 32.5 mg/mL (163.79 mM; Need ultrasonic) | 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 | 5.0396 mL | 25.1978 mL | 50.3956 mL |
| 5 mM | 1.0079 mL | 5.0396 mL | 10.0791 mL |
| 10 mM | 0.504 mL | 2.5198 mL | 5.0396 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。
The Role of CYP2B6*6 Gene Polymorphisms in 3,5,6-Trichloro-2-pyridinol Levels as a Biomarker of Chlorpyrifos Toxicity Among Indonesian Farmers
J Prev Med Public Health 2022 May;55(3):280-288.PMID:35678002DOI:10.3961/jpmph.21.641.
Objectives: One of the most widely used pesticides today is chlorpyrifos (CPF). Cytochrome P450 (CYP)2B6, the most prominent catalyst in CPF bioactivation, is highly polymorphic. The objective of our study was to evaluate the role of CYP2B6*6, which contains both 516G>T and 785A>G polymorphisms, in CPF toxicity, as represented by the concentration of 3,5,6-Trichloro-2-pyridinol (TCPy), among vegetable farmers in Central Java, Indonesia, where CPF has been commonly used. Methods: A cross-sectional study was conducted among 132 vegetable farmers. Individual socio-demographic and occupational characteristics, as determinants of TCPy levels, were obtained using a structured interviewer-administered questionnaire and subsequently used to estimate the cumulative exposure level (CEL). TCPy levels were detected with liquid chromatography-mass spectrometry. CYP2B6*6 gene polymorphisms were analyzed using a TaqMan® SNP Genotyping Assay and Sanger sequencing. Linear regression analysis was performed to analyze the association between TCPy, as a biomarker of CPF exposure, and its determinants. Results: The prevalence of CYP2B6*6 polymorphisms was 31% for *1/*1, 51% for *1/*6, and 18% for *6/*6. TCPy concentrations were higher among participants with CYP2B6*1/*1 than among those with *1/*6 or *6/*6 genotypes. CYP2B6*6 gene polymorphisms, smoking, CEL, body mass index, and spraying time were retained in the final linear regression model as determinants of TCPy. Conclusions: The results suggest that CYP2B6*6 gene polymorphisms may play an important role in influencing susceptibility to CPF exposure. CYP2B6*6 gene polymorphisms together with CEL, smoking habits, body mass index, and spraying time were the determinants of urinary TCPy concentrations, as a biomarker of CPF toxicity.
3,5,6-Trichloro-2-pyridinol intensifies the effect of chlorpyrifos on the paracrine function of Sertoli cells by preventing binding of testosterone and the androgen receptor
Toxicology 2021 Aug;460:152883.PMID:34352351DOI:10.1016/j.tox.2021.152883.
3,5,6-Trichloro-2-pyridinol (TCP) is an important biomarker and one of the final metabolites of chlorpyrifos (CPF). TCP inhibits secretion of sex hormones. Similar to CPF, TCP can bind to sex steroid hormone receptors and decrease the secretion of sex hormones. However, little attention has been paid to the ability of TCP and CPF to interfere with androgen receptor (AR) in Sertoli cells. This study aimed to explain how TCP promotes the inhibitory effect of CPF on the paracrine function of Sertoli cells. Western blotting indicated that after 20 weeks of exposure, expression of AR in testes was significantly reduced by CPF. An in vitro assay measured the cytotoxicity of CPF, TCP and diethylphosphate (DEP) on viability of Sertoli cells by Cell Counting Kit-8. CPF cytotoxicity was greater than that of TCP, and TCP cytotoxicity was greater than that of DEP at concentrations of 1000 μmol/L. Western blotting indicated that TCP and CPF both decreased expression of AR and cAMP-response element binding protein phosphorylation, while DEP had no effect in Sertoli cells, which are important in regulating paracrine function of Sertoli cells. The fluorescence measurements and docking studies revealed that testosterone, CPF and TCP showed four types of intermolecular interactions with AR, highlighting alkyl bonds with some of the same amino acids. Compared with testosterone, CPF and TCP also showed significant synergistic interaction with AR. CPF interacted with more amino acids and interaction energy than TCP did. This research elucidates TCP in the antiandrogenic effect of CPF on the paracrine function and suggests that TCP or chemicals with a trichloropyridine structure must be considered during reproductive toxicity assessment of potential environmental pollutants.
Quantifying dynamic desorption of 3,5,6-Trichloro-2-pyridinol in loamy farmland soils
Environ Sci Pollut Res Int 2019 Oct;26(30):30782-30793.PMID:31444723DOI:10.1007/s11356-019-06233-4.
Reliable estimate of the release of adsorbed pesticide from soil particles is crucial to evaluating the pesticide fate, mobility, efficacy, and remediation. In this study, the dynamics of TCP (3,5,6-Trichloro-2-pyridinol) desorption, the main degradation product of chlorpyrifos and triclopyr, is explored quantitatively by the breakthrough curve (BTC) experiment with the tracer of Br- in the loamy farmland purple soil sampled from Sichuan Basin of southwestern China. TCP in the outflow originates from two sources: dissolved TCP in pore water and desorbed TCP from soil particles by infiltrating water. The dissolved TCP is considered proportional to the amount of Br- because both TCP and Br- are dissolved in water uniformly. According to the mass balance equation, the desorbed TCP are estimated and the typical patterns of dynamic TCP desorption are revealed. Characteristics of TCP desorption are compared between packed and undisturbed soil columns as well as between different planting types. The dynamics of the proportion of desorbed TCP during the breakthrough process are characterized. In particular, the high heterogeneity of the undisturbed soil may be responsible for the observed fluctuation of desorbed TCP in the outflow. Additionally, the obtained increase-decrease pattern of the desorbed rate of TCP released from the soil shows that most models proposed to simulate the desorption processes are not appropriate, because these models display a monotone decreasing trend, such as the Noyes-Whitney Rule and other release kinetic models (zero order, first order, Higuchi and Korsmeyer-Peppas model, etc.). After a comparison among linear model, Gamma distribution and Weibull distribution, the CDF of gamma distribution is identified as a better method to describe the proportion of desorbed TCP in outflow. Therefore, this study provides an alternative method to measure the dynamic desorption process of TCP in different environment of the purple soil, and their affecting factors are also identified. These results are useful in quantifying the leaching of the TCP in the field, in support of the prevention of agricultural non-point pollution of pesticides.
Degradation of 3,5,6-Trichloro-2-pyridinol by a microbial consortium in dryland soil with anaerobic incubation
Biodegradation 2019 Jun;30(2-3):161-171.PMID:30929106DOI:10.1007/s10532-019-09873-y.
Biodegradation of 3,5,6-Trichloro-2-pyridinol (TCP) in drylands is an important biological process of detoxification. Flooding in drylands can result in the formation of anaerobic habitats. However, little is known about the microbial metabolism of TCP in dryland soil under anaerobic conditions. Here, chlorpyrifos-contaminated dryland soil was incubated to enrich the TCP-degrading microbial consortium under anaerobic conditions. Chloridion and CO2 were released with TCP degradation, and the enrichment cultures of dryland soil could metabolize 97% of TCP (100 mg/L) within 20 h. Both reductive and hydrolysis dechlorination mechanisms were involved in TCP biodegradation under anaerobic conditions. Bacterial taxonomic analysis revealed that the aerobic TCP-degrading bacteria Ochrobactrum and dechlorination bacteria Delftia were the dominant genera. Anaerobic and facultative bacteria; i.e., Bacteroides, Bacillus, and Cupriavidus had lower relative abundances, but they were significantly enriched following treatment with TCP. These results indicate that the enrichment cultures of dryland soil dominated by aerobic bacteria could dechlorinate and degrade TCP under anaerobic conditions.
Acute toxicity of chlorpyrifos and its metabolite 3,5,6-Trichloro-2-pyridinol alone and in combination using a battery of bioassays
Environ Sci Pollut Res Int 2020 Sep;27(26):32770-32778.PMID:32519098DOI:10.1007/s11356-020-09392-x.
Acute toxicity of chlorpyrifos (CP) and its principal metabolite 3,5,6-Trichloro-2-pyridinol (TCP) alone and in combination have been evaluated using a test battery comprising aquatic organisms from different trophic levels: luminescent marine bacteria Aliivibrio fischeri, freshwater unicellular alga Pseudokirchneriella subcapitata, and cladoceran Daphnia magna. As expected, D. magna was the more sensitive organism to the compounds tested, being CP more toxic than its metabolite. On the contrary, TCP was found to be more toxic than its parental compound to A. fischeri and P. subcapitata. In all cases, the mixture of CP and its metabolite was more toxic than the compounds tested separately, multiplying between 5 and 200 times CP toxicity level and up to 15 times TCP toxicity level. These results indicate that the co-existence of parent chemical and its degradation product in the environment can result in a synergic interaction involving high risk to the aquatic ecosystems. Graphical abstract.