2,2',3,3',5,5'-六氯联苯 | 35694-04-3

• 物质功能分类: 分析化学 - 食品安全 - 二噁英，多氯联苯，呋喃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2',3,3',5,5'-六氯联苯
• 中文别名: 2,2’,3,3’,5,5’-六氯联苯
• 英文名称: 2,2',3,3',5,5'-hexachlorobiphenyl
• 英文别名: PCB 133；1,2,5-trichloro-3-(2,3,5-trichlorophenyl)benzene
• CAS: 35694-04-3
• 化学式: C₁₂H₄Cl₆
• 分子量: 360.882
• InChiKey: AJKLKINFZLWHQE-UHFFFAOYSA-N

物化性质

• 熔点：
  129°C
• 沸点：
  446.99°C (rough estimate)
• 密度：
  1.5940 (rough estimate)
• 保留指数：
  2206

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

多氯联苯（PCBs）通过吸入、口服和皮肤接触途径被吸收。它们通过血液传输，通常与白蛋白结合。由于其亲脂性，它们倾向于在富含脂质的组织中积累，如肝脏、脂肪组织和皮肤。多氯联苯的代谢非常缓慢，并且根据氯化的程度和位置而有所不同。多氯联苯通过微粒体单加氧酶系统进行代谢，该系统由细胞色素P-450酶催化，转化为极性代谢物，这些代谢物可以与谷胱甘肽和葡萄糖醛酸结合。主要代谢物是羟基化产物，通过胆汁和粪便排出。多氯联苯的缓慢代谢意味着它们倾向于在身体组织中积累。

PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are trasported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

PCB的作用机制因具体类型而异。类似于二噁烷的PCB会与芳基烃受体结合，通过改变基因的转录来扰乱细胞功能，主要是通过诱导肝脏第一阶段和第二阶段酶的表达，特别是细胞色素P450家族。人们认为PCB的大部分毒性效应是Ah受体结合的结果。其他PCB被认为会干扰钙通道和/或改变大脑中的多巴胺水平。PCB还可能通过改变甲状腺激素的生成和与雌激素受体结合来引起内分泌紊乱，这可能会刺激某些癌细胞的生长并产生其他类雌激素效应，如生殖功能障碍。它们会通过结合如uteroglobin等受体蛋白进行生物积累。(A3, A4, A30, A66)

The mechanism of action varies with the specific PCB. Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family. Most of the toxic effects of PCBs are believed to be results of Ah receptor binding. Other PBCs are believed to interfere with calcium channels and/or change brain dopamine levels. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. They will bioaccumulate by binding to receptor proteins such as uteroglobin. (A3, A4, A30, A66)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

1, 对人类致癌。

1, carcinogenic to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

PCBs最常见的健康影响是皮肤状况，如氯痤疮和皮疹。长期暴露于PCBs还可能导致肝脏、胃和肾脏损害、黄疸、水肿、贫血、免疫系统变化、行为改变以及生殖能力受损。

The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L4级）；吸入（L4级）；皮肤给药（L4级）

Oral (L4) ; inhalation (L4) ; dermal (L4)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

慢性 PCB 暴露会导致如下症状：腹痛、恶心、呕吐、腹泻、头痛、眩晕、抑郁、神经紧张、皮肤和眼睛损伤、疲劳、月经周期不规律以及免疫力下降。

Chronic PCB exposure results in symptoms such as abdominal pain, nausea, vomiting, diarrhea, headache, dizziness, depression, nervousness, dermal and ocular lesions, fatigue, irregular menstrual cycles and a lowered immune response. (A3)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  9
• 海关编码：
  2903999090
• 包装等级：
  II
• 危险品运输编号：
  UN 2315

反应信息

• 作为反应物：
  描述：

  2,2',3,3',5,5'-六氯联苯 生成 2,4,6,8-Tetrachlorodibenzothiophene
  参考文献：
  名称：

  BUSER, HANS-RUDOLF;RAPPE, CHRISTOFFER, ANAL. CHEM., 63,(1991) N3, C. 1210-1217

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2',5,5'-四氯二苯胺 在 氯 作用下， 以 二氯甲烷 为溶剂， 生成 2,2',3,3',5,5'-六氯联苯
  参考文献：
  名称：

  多氯联苯的质谱

  摘要：

  几种二氯和四氯联苯的质谱表明，在裂解之前，氯在分子离子中的两个苯环上均是随机化的。2,2'-和2,6-二氯-，2,2'，4,4'-，2,2'，5,5'-，2,3,5,6-和2除外2'，6,6'-四氯联苯都含有两个或多个与Ph-Ph键邻位的氯原子，它们的亚稳离子强度由M → M – Cl 2引起反应明显不同于其他异构体。大多数异构化合物的主离子光谱相似，分子离子连续损失Cl·。此过程通常伴随着从较低氯同系物（2）-（5）排出HCl，但只有将Cl·排出的反应才伴随有亚稳离子。二氯和四氯异构体的离子动能谱证实了建议的裂解途径。

  DOI：

  10.1039/p19720000686

文献信息

• Instruments for detecting low-molecular weight substance
  申请人：Mizukami Haruki

  公开号：US20050148097A1

  公开（公告）日：2005-07-07

  To provide the following instruments 1 and 2 as a low-molecular-weight substance detection instrument employing immunochromatography capable of detecting conveniently and sensitively detecting a low-molecular weight substance such as an environmental pollutant (e.g., a dioxin), as a target substance contained in a test sample: 1. an instrument, which comprises 1) a test sample application section with which a test sample is brought into contact; 2) a label product reaction section containing a label product containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, the label product being not bound to the reaction section; 3) an unbound label product capturing section containing an element capable of capturing the label product which is not bound to the target substance, the element being bound to the capturing section; and 4) a detection section containing a detection element which, when coming into contact with the target substance bound to the label product, causes a visually observable change, and 2. an instrument wherein a test sample is reacted with a labeled antibody containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, and the resultant reaction product is employed for detecting the target substance contained in the test sample.

  提供以下仪器1和2作为低分子量物质检测仪器，采用免疫层析技术，能够方便敏感地检测低分子量物质，例如环境污染物（例如二恶英），作为测试样品中包含的目标物质：1. 仪器，包括1）测试样品应用部分，用于将测试样品接触；2）标签产物反应部分，包含一种标签产物，其中包含一种能够结合到测试样品中的目标物质的抗体，标签产物未结合到反应部分；3）未结合标签产物捕获部分，包含一种能够捕获未结合到目标物质的标签产物的元素，该元素与捕获部分结合；以及4）检测部分，包含一种检测元素，当与结合到标签产物的目标物质接触时，会引起可视的变化；2. 仪器，其中测试样品与标记抗体反应，其中一部分包含能够结合到测试样品中的目标物质的抗体，产生的反应产物用于检测测试样品中包含的目标物质。
• Liver cell clones for artifical liver and extracorporeal liver assist device
  申请人：JMS Co., Ltd.

  公开号：EP1063289A1

  公开（公告）日：2000-12-27

  Disclosed is a blood perfusion device or apparatus that is used for bioartificial liver support. Human hepatocyte lines established from normal regenerating liver tissue and modulated in toxin-challenging conditions are provided. These functional hepatocytes exhibit extraordinarily enhanced detoxification functions, which are characterised by the elevated glutathione content and glutathione S-transferase activity. A bioreactor is constructed with the functional hepatocytes for bioartificial liver support system, which includes perfusion inlets and perfusion outlets, a containment vessel, a centrifugal pump and macroporous microcarriers where the functional hepatocytes are grown.

  所公开的是一种用于生物人工肝支持的血液灌流装置或设备。提供了从正常再生肝组织中建立并在毒素挑战条件下调节的人类肝细胞系。这些功能性肝细胞的解毒功能异常增强，其特点是谷胱甘肽含量和谷胱甘肽 S 转移酶活性升高。该系统包括灌注入口和灌注出口、密闭容器、离心泵和生长功能肝细胞的大孔微载体。
• INSTRUMENTS FOR DETECTING LOW-MOLECULAR WEIGHT SUBSTANCE
  申请人：Enbiotec Laboratories Co., Ltd.

  公开号：EP1489420A1

  公开（公告）日：2004-12-22

  To provide the following instruments 1 and 2 as a low-molecular-weight substance detection instrument employing immunochromatography capable of detecting conveniently and sensitively detecting a low-molecular weight substance such as an environmental pollutant (e.g., a dioxin), as a target substance contained in a test sample: 1. an instrument, which comprises 1) a test sample application section with which a test sample is brought into contact; 2) a label product reaction section containing a label product containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, the label product being not bound to the reaction section; 3) an unbound label product capturing section containing an element capable of capturing the label product which is not bound to the target substance, the element being bound to the capturing section; and 4) a detection section containing a detection element which, when coming into contact with the target substance bound to the label product, causes a visually observable change, and 2. an instrument wherein a test sample is reacted with a labeled antibody containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, and the resultant reaction product is employed for detecting the target substance contained in the test sample.

  提供以下仪器 1 和 2，作为一种采用免疫层析技术的低分子量物质检测仪器，能够方便、灵敏地检测作为检测样品中目标物质的低分子量物质，如环境污染物（如二恶英）： 1.仪器，包括：1）测试样品应用部分，测试样品与之接触；2）标签产品反应部分，包含标签产品，作为其一部分，该标签产品含有能够与测试样品中所含目标物质结合的抗体，标签产品未与反应部分结合；3) 非结合标签产品捕获部分，包含能够捕获未与目标物质结合的标签产品的元件，该元件与捕获部分结合；以及 4) 检测部分，包含检测元件，该元件与结合在标签产品上的目标物质接触时，会引起视觉上可观察到的变化，以及 2. 2. 一种仪器，其中测试样品与标记抗体反应，标记抗体的一部分能够与测试样品中的目标物质结合，反应产物用于检测测试样品中的目标物质。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Physical, spectral and chromatographic properties of all 209 individual PCB congeners
  作者：Michael Bolgar、James Cunningham、Russell Cooper、Richard Kozloski、Jack Hubball、Don P. Miller、Terry Crone、Harry Kimball、Anita Janooby、Barry Miller、Billy Fairless

  DOI：10.1016/0045-6535(95)00140-4

  日期：1995.7

  Physical, spectral and chromatographic data for all 209 individual PCB congeners is presented. The individual congeners were synthesized and then isolated and purified. Recent emphasis on the source of the toxicity of commercial PCB formulations has increased the need for a complete set of the PCB congeners. Through the use of two capillary GC columns: 40% octadecyl/ 15% phenyl methyl siloxane and 50% phenyl methyl siloxane, it was possible to separate 201 PCB congeners with only four unresolved pairs. The data compiled in this study for all 209 congeners will aid in the identification of selected individual components of these environmental pollutants. The use of this data also presents the opportunity for the improved quantification of the commercial PCB formulations.

表征谱图