o,p'-DDE
(Synonyms: 3-邻氯苯基-2-对氯苯-1,1'-二乙烯) 目录号 : GC44479
A metabolite and degradation product of the pesticide DDT
Cas No.:3424-82-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
o,p'-DDE is a metabolite and degradation product of the organochlorine pesticide DDT. It accumulates in smallmouth buffalo, channel catfish, and largemouth bass as well as sediment in the Huntsville Spring Branch-Indian Creek tributary system surrounding a DDT manufacturing plant where it is considered a persistent organic pollutant (POP). o,p'-DDE inhibits estrogen binding to rainbow trout estrogen receptors (rtERs) with an IC50 value of 3.2 μM. It induces concentration-dependent secretion of estradiol by granulosa and theca cell co-cultures isolated from porcine ovarian follicles. In ovo exposure to o,p'-DDE increases degeneration of ovarian follicles and reduces testicular size in Japanese medaka (O. latipes).
| Cas No. | 3424-82-6 | SDF | |
| 别名 | 3-邻氯苯基-2-对氯苯-1,1'-二乙烯 | ||
| Canonical SMILES | ClC1=CC=C(/C(C2=CC=CC=C2Cl)=C(Cl)\Cl)C=C1 | ||
| 分子式 | C14H8Cl4 | 分子量 | 318 |
| 溶解度 | Chloroform: Heated,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 | 3.1447 mL | 15.7233 mL | 31.4465 mL |
| 5 mM | 0.6289 mL | 3.1447 mL | 6.2893 mL |
| 10 mM | 0.3145 mL | 1.5723 mL | 3.1447 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。
Effects of o,p'-DDE, a Mitotane Metabolite, in an Adrenocortical Carcinoma Cell Line
Pharmaceuticals (Basel) 2022 Nov 29;15(12):1486.PMID:36558937DOI:10.3390/ph15121486.
In South Brazil, the incidence of pediatric adrenocortical carcinoma (ACC) is higher than in other regions and countries worldwide. The ACC treatment includes therapy with mitotane, the only adrenolytic drug approved by the FDA. The mitotane metabolism occurs via two main reactions: the β-hydroxylation, which yields the final product o,p'-DDA, and the α-hydroxylation, which will give the final product o,p'-DDE. It is speculated that o,p'-DDE may be an active metabolite since it has a cytotoxic effect on adrenocortical carcinoma cells (H295R). No further studies have been conducted to confirm this hypothesis; however, it was found that mitotane and its metabolites are present at significantly different concentrations in the plasma of the patients. Our study aimed to assess the in vitro effects of o,p'-DDE and o,p'-DDD in cell death pathways, oxidative parameters, and interaction with adrenal CYP's involved in the steroidogenic process in the H295R cell line. It was found that o,p'-DDE had a different effect than the o,p'-DDD on apoptosis, inhibiting this cell death pathway, but it promotes cell necrosis at higher concentrations. In contrast to o,p'-DDD, the o,p'-DDE did not have effects on the different oxidative parameters evaluated, but exhibited stimulatory interactions with steroidogenic CYP's, at intermediate concentrations. Therefore, we demonstrated important cell effects of o,p'-DDE; its plasma levels during mitotane therapy should be monitored as an important therapeutic parameter.
DDE-induced eggshell thinning in birds: effects of p,p'-DDE on the calcium and prostaglandin metabolism of the eggshell gland
Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 1997 Oct;118(2):113-28.PMID:9490182DOI:10.1016/s0742-8413(97)00105-9.
1. The focus of this review is the effects and mechanism of action of p,p'-DDE on eggshell formation in birds. Inhibition of prostaglandin synthesis in the eggshell gland mucosa is a probable mechanism for p,p'-DDE-induced eggshell thinning. 2. The duck is sensitive to p,p'-DDE-induced eggshell thinning but the domestic fowl is not, and studies comparing the two species in regard to the calcium and prostaglandin metabolism of the eggshell gland have shown that eggshell thinning induced by p,p'-DDE in ducks is accompanied by reduced activity of prostaglandin synthetase, reduced levels of prostaglandin E2, and reduced uptake of 45Ca by the eggshell gland mucosa. The content of calcium, bicarbonate, chloride, sodium, and potassium are also reduced in the eggshell gland lumen in ducks exhibiting eggshell thinning. None of these effects are seen in the domestic fowl. 3. Inhibition of prostaglandin synthesis is a specific effect of p,p'-DDE. The detrimental effects of p,p'-DDE on the eggshell gland seem to be unique when comparing the compound with structurally related substances, i.e., similar treatment regimens with o,p'-DDE, p,p'-DDT, o,p'-DDT, and p,p'-DDD do not cause eggshell thinning in ducks. Neither do they inhibit prostaglandin synthesis in the eggshell gland mucosa. 4. Administration of other compounds that do inhibit prostaglandin synthesis, e.g., indomethacin, does cause the same effects as those seen with p,p'-DDE, i.e., eggshell thinning and the described effects on the calcium and prostaglandin metabolism of the eggshell gland.
Effects of o,p'-DDE, heptachlor, and 17beta-estradiol on vitellogenin gene expression and the growth hormone/insulin-like growth factor-I axis in the tilapia, Oreochromis mossambicus
Comp Biochem Physiol C Toxicol Pharmacol 2009 May;149(4):507-14.PMID:19101654DOI:10.1016/j.cbpc.2008.11.007.
Effects of two endocrine disruptors, o,p'-DDE and heptachlor, and 17beta-estradiol (E(2)) on vitellogenin (Vg) and the growth hormone (GH)/insulin-like growth factor-I (IGF-I) axis were examined in male tilapia. In the first experiment, fish were given 5 weekly injections of either E(2), o,p'-DDE or heptachlor (5 microg/g). E(2) treatment increased plasma Vg and hepatic expression of three Vg genes (Vgs A, B, and C) and estrogen receptor alpha (ERalpha), while reducing plasma levels of IGF-I and suppressing the expression of IGF-I, the GH receptor (GHR2) and the putative somatolactin receptor (GHR1). Neither pesticide greatly affected the other parameters examined, except for a significant reduction in expression of GHR2 and increased plasma IGF-I. In the second experiment, fish were given a single injection of o,p'-DDE or heptachlor (100 microg/g), or E(2) (5 microg/g) and sacrificed 5 days post-injection. Treatment with E(2) stimulated expression of all three Vg genes. Both o,p'-DDE and heptachlor increased expression of VgB, whereas only o,p'-DDE increased VgA expression. There was no effect of o,p'-DDE or heptachlor on VgC expression or plasma Vg levels. Treatment with o,p'-DDE and heptachlor as well as E(2) increased ERalpha and ERbeta transcript levels. Similarly, both pesticides increased GHR1 and IGF-I expression, whereas no significant effect of E(2) was observed on GHR1, GHR2 or IGF-I expression. These results indicate that o,p'-DDE and heptachlor have varying temporal and dose effects on modulation of Vg and the GH/IGF-I axis that are distinct from E(2).
Behaviors and trophodynamics of o,p'-dichlorodiphenyltrichloroethane (o,p'-DDT) in the aquatic food web: Comparison with p,p'-DDT
Sci Total Environ 2022 May 15;821:153447.PMID:35092765DOI:10.1016/j.scitotenv.2022.153447.
The broad-spectrum insecticide p,p'-dichlorodiphenyltrichloroethane (p,p'-DDT) has been banned in most countries since the 1970s on account of its environmental persistence as well as the high biomagnification of its major metabolite 1,1-dichloro-2,2-bis(4-chorophenyl)ethylene (p,p'-DDE). However, the information on the bioaccumulation and behavior of p,p'-DDTs in aquatic organisms is lacking. In this study, all 6 DDT isomers were detected in biota from the food web of the Liaodong Bay, China, and the total concentrations of DDT isomers in Chinese anchovy (Thrissa kammalensis) and Japanese Spanish mackerel (Scomberomrus niphonius) were 223 ± 42 ng/g ww and 242 ± 70 ng/g ww, respectively. In biota, o,p'-DDD dominated among the o,p'-isomers (80.5 ± 17.3%), while p,p'-DDE dominated among the p,p'-isomers (61.8 ± 15.2%). Contrastingly, sediment from the Liaodong Bay contained similar proportions of o,p'-DDT and p,p'-DDTs, suggesting an isomer-specific metabolism of the compounds in biota. A well-controlled laboratory exposure experiment with Japanese medaka (Oryzias latipes) demonstrated that o,p'-DDT was more difficult to metabolize to o,p'-DDE compared with that of p,p'-DDT. Significantly positive regressions were found between trophic levels and lipid equivalent concentrations for both o,p'-DDT and o,p'-DDD, and the trophic magnification factors (TMFs) were estimated as 12.3 and 9.12 (p < 0.05), respectively. The TMFs of o,p'-DDT and o,p'-DDD in the aquatic food web were higher than p,p'-DDT (7.76), p,p'-DDD (4.17), and p,p'-DDE (3.39), which may be explained by the isomer-specific metabolism differences in biota.
Use of GC/MS/SIM for rapid determination of plasma levels of o,p'-DDD, o,p'-DDE and o,p'-DDA
Clin Chim Acta 1987 Dec;170(2-3):305-14.PMID:3436064DOI:10.1016/0009-8981(87)90141-0.
A new method for extraction and quantification of plasma o,p'-DDD (2,2-(2-chlorophenyl,4'-chlorophenyl)1,1-dichloroethane) and its metabolites has been developed. When plasma (0.1 ml) adsorbed to and dried on a filter paper was heated with 5% hydrogen chloride in methanol (1 ml) in a boiling water bath, o,p'-DDD and its metabolites were liberated from the serum protein and were able to be easily extracted with benzene. The recovery rate was raised compared with conventional methods. In addition, this procedure also carried out the simultaneous methylation of o,p'-DDA, one of the metabolites. Mass numbers of 199, 210, 235 and 246 were selected from the mass spectra of o,p'-DDD and its related substances, and they were monitored. Identification was performed on the basis of the retention time and the mass peak intensity ratio. Quantitative determination was performed using the internal standard technique. It was learned that o,p'-DDA is present in the plasma at a concentration about 10 times higher than the levels of o,p'-DDD and o,p'-DDE.