Endosulfan sulfate
(Synonyms: 硫丹硫酸酯) 目录号 : GC47290
A major metabolite of the insecticide endosulfan
Cas No.:1031-07-8
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
Endosulfan sulfate is a major metabolite of endosulfan, a broad-spectrum organochlorine insecticide.1 Endosulfan sulfate is formed through oxidation of endosulfan by bacteria and fungi in the environment, where it is considered a persistent organic pollutant (POP). It accumulates in the liver and gonads of wild silverside fish (O. bonariensis) and is found in higher amounts in mature fish than pre-spawning fish.2 Levels of endosulfan sulfate in the gills of mature O. bonariensis correlate with increased levels of lipid peroxidation. It is toxic to freshwater fish, including G. affinis, H. formosa, P. latipinna, and P. promelas, with LC50 values ranging from 2.1 to 3.5 µg/L after a 96-hour exposure.3 Endosulfan sulfate is the main metabolite found in the liver of mice following endosulfan administration at doses of 0.3 and 3 mg/kg.4 It decreases the levels of glutathione (GSH) and malondialdehyde (MDA), a product of lipid peroxidation, in the liver, but increases MDA in the kidney when administered at a dose of 3 mg/kg.
1.Kataoka, R., and Takagi, K.Biodegradability and biodegradation pathways of endosulfan and endosulfan sulfateAppl. Microbiol. Biotechnol.97(8)3285-3292(2013) 2.Barni, M.F.Assessment of persistent organic pollutants accumulation and lipid peroxidation in two reproductive stages of wild silverside (Odontesthes bonariensis)Ecotoxicol. Environ. Saf.9945-53(2014) 3.Carriger, J.F., Hoang, T.C., Rand, G.M., et al.Acute toxicity and effects analysis of endosulfan sulfate to freshwater fish speciesArch. Environ. Contam. Toxicol.60(2)281-289(2011) 4.Yan, J., Wang, D., Miao, J., et al.Discrepant effects of α-endosulfan, β-endosulfan, and endosulfan sulfate on oxidative stress and energy metabolism in the livers and kidneys of miceChemosphere205223-233(2018)
| Cas No. | 1031-07-8 | SDF | |
| 别名 | 硫丹硫酸酯 | ||
| Canonical SMILES | ClC1(C2(Cl)Cl)C(COS(OC3)(=O)=O)C3C2(Cl)C(Cl)=C1Cl | ||
| 分子式 | C9H6Cl6O4S | 分子量 | 422.9 |
| 溶解度 | DMSO: Slightly Soluble,Methanol: Slightly Soluble | 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 | 2.3646 mL | 11.8231 mL | 23.6463 mL |
| 5 mM | 0.4729 mL | 2.3646 mL | 4.7293 mL |
| 10 mM | 0.2365 mL | 1.1823 mL | 2.3646 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。
Biodegradability and biodegradation pathways of endosulfan and Endosulfan sulfate
Appl Microbiol Biotechnol 2013 Apr;97(8):3285-92.PMID:23463248DOI:10.1007/s00253-013-4774-4.
Endosulfan and Endosulfan sulfate are persistent organic pollutants that cause serious environmental problems. Although these compounds are already prohibited in many countries, residues can be detected in soils with a history of endosulfan application. Endosulfan is transformed in the environment into Endosulfan sulfate, which is a toxic and persistent metabolite. However, some microorganisms can degrade endosulfan without producing Endosulfan sulfate, and some can degrade Endosulfan sulfate. Therefore, biodegradation has the potential to clean up soil contaminated with endosulfan. In this review, we provide an overview of aerobic endosulfan degradation by bacteria and fungi, and a summary of recent advances and prospects in this research field.
Different effects of α-endosulfan, β-endosulfan, and Endosulfan sulfate on sex hormone levels, metabolic profile and oxidative stress in adult mice testes
Environ Res 2019 Feb;169:315-325.PMID:30502743DOI:10.1016/j.envres.2018.11.028.
In the environment, endosulfan persists in forms of two isomers (α and β) and a toxic metabolite, Endosulfan sulfate. The toxicity of endosulfan on various mammalian tissues has been investigated, but whether the different isomers and metabolites of endosulfans affect mammalian reproductive function remains unclear. This study is aimed to elucidate the different toxicological effects of α-endosulfan, β-endosulfan, and Endosulfan sulfate on adult mice testes. We found that the three endosulfans (α endosulfan, β endosulfan and Endosulfan sulfate) altered serum sex steroid hormone levels, and changed expression of steroidogenesis genes. By comparing results of 1H-NMR and LC-MS/MS metabolomics between samples treated with different endosulfans, we found that endosulfans changed levels of metabolites involved in energy metabolism and oxidative stress, and these were associated with the imbalance of sex sterol hormone synthesis. Moreover, endosulfan isomers and sulfate metabolite treatment disrupted the mice testicular antioxidant systems and caused an increase in lipid peroxidation. Interestingly, the three endosulfans tested in this study each yielded different effects on serum sex hormone levels and testicular metabolic profiles in the adult mice. Beta-endosulfan exposure caused the strongest disturbance in the testes compared to the other endosulfans, with significantly higher testosterone levels and more pronounced changes to endogenous metabolites. Taken together, we identified the different effects of endosulfans on the testis by exposing mice to α endosulfan, β endosulfan and Endosulfan sulfate, and we found that changes in sex sterol hormone levels induced by treatment with endosulfans were correlated to changes in endogenous metabolites. These findings provide new insight into mechanism of endosulfan-induced testicular toxicity.
Endosulfan I and Endosulfan sulfate disrupts zebrafish embryonic development
Aquat Toxicol 2009 Dec 13;95(4):355-61.PMID:19883949DOI:10.1016/j.aquatox.2009.10.008.
Fish in agricultural and remote areas may be exposed to endosulfan and its degradation products as a result of direct runoff, atmospheric transport and deposition. The following study used the zebrafish developmental model to investigate the responses to endosulfan I and Endosulfan sulfate, the major degradation product of endosulfan I and II. Embryos were dechorionated and waterborne exposed to the endosulfan I or Endosulfan sulfate from 6 to 120h post-fertilization (hpf). Endosulfan I exposure concentrations ranged from 0.01 to 10microg/L and Endosulfan sulfate from 1 to 100microg/L. Water solutions were renewed every 24h and fish were scored for overt developmental and behavioral abnormalities. Chemical analysis was performed on water, whole embryo, and larvae samples to determine waterborne exposure concentrations and tissue concentrations throughout the 5-day period. The most sensitive toxicity endpoint for both endosulfan I and Endosulfan sulfate was an abnormal response of the embryo/larvae to touch, suggesting that endosulfan I and sulfate are developmentally neurotoxic. The waterborne exposure EC(50)s for inhibition of touch response for endosulfan I and Endosulfan sulfate were 2.2microg/L and 23microg/L, respectively. The endosulfans were highly concentrated by the organisms, and the inhibition of touch response tissue EC(50), determined from the measured tissue concentrations, was 367ng/g for endosulfan I and 4552ng/g for Endosulfan sulfate.
Endosulfan isomers and sulfate metabolite induced reproductive toxicity in Caenorhabditis elegans involves genotoxic response genes
Environ Sci Technol 2015 Feb 17;49(4):2460-8.PMID:25612189DOI:10.1021/es504837z.
Endosulfan is enlisted as one of the persistent organic pollutants (POPs) and exists in the form of its α and β isomers in the environment as well as in the form of Endosulfan sulfate, a toxic metabolite. General endosulfan toxicity has been investigated in various organisms, but the effect of the isomers and sulfate metabolites on reproductive function is unclear. This study was aimed at studying the reproductive dysfunction induced by endosulfan isomers and its sulfate metabolite in Caenorhabditis elegans (C. elegans). We also determined a role for the DNA-damage-checkpoint gene hus-1. Compared to β-endosulfan and its sulfate metabolite, α-endosulfan caused a dramatically higher level of germ cell apoptosis, which was regulated by DNA damage signal pathway. Both endosulfan isomers and the sulfate metabolite induced germ cell cycle arrest. Loss-of-function studies using hus-1, egl-1, and cep-1 mutants revealed that hus-1 specifically influenced the fecundity, hatchability, and sexual ratio after endosulfan exposure. Our data provide clear evidence that the DNA-checkpoint gene hus-1 has an essential role in endosulfan-induced reproductive dysfunction and that α-endosulfan exhibited the highest reproductive toxicity among the different forms of endosulfan.
Identification of enzyme(s) capable of degrading endosulfan and Endosulfan sulfate using in silico techniques
Enzyme Microb Technol 2019 May;124:32-40.PMID:30797477DOI:10.1016/j.enzmictec.2019.01.003.
Endosulfan is one of the most widely used organochlorine cyclodiene insecticides. Microbial oxidation of endosulfan forms Endosulfan sulfate, which is more or less toxic and persistent as endosulfan. Due to lack of specificity and efficiency of microbial bioremediation technique in the field conditions, enzymatic bioremediation is receiving huge attention to clean-up the environment. In the present study, X-ray crystal structures of enzymes from Brookhaven Protein Data Bank were screened for their potential to degrade endosulfan and Endosulfan sulfate using molecular docking and molecular dynamics simulation techniques. A phenol hydroxylase, 1PN0 from Trichosporon cutaneum was found to have the potential to degrade both α-endosulfan and Endosulfan sulfate while a bacterial CotA laccase, 3ZDW from Bacillus subtilis has the potential to degrade α-endosulfan. The in silico result correlate with in vitro degradation study using two different strains of Trichosporon cutaneum. In vitro degradation study found that the fungal strain was capable of degrading 60.36% α-endosulfan, 70.73% β-endosulfan, and 52.08% Endosulfan sulfate. The presence of phenol hydroxylase inhibitor in the sulfur-free medium with endosulfan and Endosulfan sulfate as sole sulfur source inhibits the growth of both the fungal strains. Such in silico techniques can provide an easy and reliable way to speed up the development of bioremediation processes through rapid identification of potential enzymes and microbes to counter the ever-increasing number of toxic compounds in the environment.