2,4,6-Triiodophenol
(Synonyms: 2,4,6-三碘酚) 目录号 : GC684522,4,6-Triiodophenol 是一种具有口服活性的、强效的 leukotriene B4 (LTB4) 合成抑制剂。2,4,6-Triiodophenol 可诱导小鼠囊胚凋亡。
Cas No.:609-23-4
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
2,4,6-Triiodophenol is an orally active and potent leukotriene B4 (LTB4) synthesis inhibitor. 2,4,6-Triiodophenol can induce mouse blastocysts apoptosis[1][2].
2,4,6-Triiodophenol (5-50 μM; 0-100 h) impairs the quality of pre-implantation mouse embryos in a dose-dependent manner, inducing decline of both total and trophectoderm cell numbers[2].
2,4,6-Triiodophenol (5 μM; 85 h) shows increasement of apoptotic cells in mouse pre-implantation embryos[2].
2,4,6-Triiodophenol (5-50 μM; 100 h) induces oxidative stress in mouse pre-implantation embryos[2].
Apoptosis Analysis[2]
| Cell Line: | Mouse blastocyst cells |
| Concentration: | 5 μM |
| Incubation Time: | 85 hours |
| Result: | Showed signals of activated Caspase-3/7. |
Immunofluorescence[2]
| Cell Line: | Mouse blastocyst cells |
| Concentration: | 5-50 μM |
| Incubation Time: | 100 hours |
| Result: | Resulted in marked increase of oxygen species (ROS) treated with high dose of 2,4,6-Triiodophenol. |
[1]. Liu S, et al. 2,4,6-triiodophenol exhibits embryotoxicity to pre-implantation mouse embryos in an in vitro exposure model. Ecotoxicol Environ Saf. 2022 Aug;241:113745.
[2]. TrocÓniz IF, et al. Dealing with time-dependent pharmacokinetics during the early clinical development of a new leukotriene B4 synthesis inhibitor. Pharm Res. 2006 Jul;23(7):1533-42.
| Cas No. | 609-23-4 | SDF | Download SDF |
| 别名 | 2,4,6-三碘酚 | ||
| 分子式 | C6H3I3O | 分子量 | 471.8 |
| 溶解度 | DMSO : 250 mg/mL (529.89 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light, stored under nitrogen |
| 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 | 2.1195 mL | 10.5977 mL | 21.1954 mL |
| 5 mM | 0.4239 mL | 2.1195 mL | 4.2391 mL |
| 10 mM | 0.212 mL | 1.0598 mL | 2.1195 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。
2,4,6-Triiodophenol exhibits embryotoxicity to pre-implantation mouse embryos in an in vitro exposure model
Ecotoxicol Environ Saf 2022 Aug;241:113745.PMID:35691197DOI:10.1016/j.ecoenv.2022.113745.
2,4,6-Triiodophenol (TIP), a novel type of halophenolic disinfection byproducts, has been widely detected in water bodies, even in drinking water. Recently, TIP has drawn increasing concerns on account of considerable developmental toxicity towards lower organisms and cytotoxicity for mammalian cells. However, it remains unknown about its toxicity on mammalian pre-implantation embryos. Here, by exposing mouse zygotes derived in vitro fertilization to TIP, which ranged from 5 to 50 μM, we found that TIP impaired the quality of pre-implantation mouse embryos in a dose-dependent manner, inducing decline of both total and trophectoderm cell numbers, enhancing caspase 3/7 activity and reactive oxygen species generation, though it did not decrease blastocyst formation efficiency. For the sake that only high qualified embryos are able to implant in endometrium and generate health body finally, we applied a previously modified in vitro culture system to assess TIP-exposed blastocysts' further developmental potency beyond pre-implantation stage. Surprisingly, although the exposed dose was only 5 μM and TIP was removed as soon as the zygotes reached blastocyst stage, these blastocysts still nearly lost their implantation and egg cylinder formation ability, exhibiting abnormal embryonic lineage differentiation pattern as well. Therefore, our study not only entirely shows TIP embryonic toxicity on mouse pre-implantation embryos, but also proposes a model to evaluate embryotoxicity from the zygote to egg cylinder stage.
Reductive deiodination of 2,4,6-Triiodophenol by Vallitalea sp. strain TIP-1 isolated from the marine sponge
J Biosci Bioeng 2021 Aug;132(2):154-160.PMID:34024749DOI:10.1016/j.jbiosc.2021.04.011.
An anaerobic microbial consortium capable of reductively dehalogenating 2,4,6-Triiodophenol (2,4,6-TIP) was enriched from the marine sponge Hymeniacidon sinapium. The enrichment reductively deiodinated 100 μM of 2,4,6-TIP to 4-iodophenol (4-IP) and 2-iodophenol (2-IP) in the presence of sterile sponge tissue as the sole carbon source and electron donor. PCR-denaturing gradient gel electrophoresis and 16S rRNA gene sequence analysis revealed that bacteria closely related with Vallitalea guaymasensis and Oceanirhabdus sediminicola, both of which are members of the order Clostridiales, were predominant in the enrichment. When glucose was added to the enrichment as alternative carbon source, one of these bacteria grew predominantly, which was subsequently isolated as a pure culture. The strain, designated as TIP-1, showed 99.7% 16S rRNA gene sequence similarity with V. guaymasensis. In the presence of glucose, strain TIP-1 reductively deiodinated 2,4,6-TIP to 2-IP and 4-IP at a molar ratio of 3:1, during which 2,4-diiodophenol (2,4-DIP) and 2,6-diiodophenol (2,6-DIP) were observed as deiodinated intermediates. Glucose was required for 2,4,6-TIP deiodination, but 2,4,6-TIP was not essential for growth of strain TIP-1. The strain also deiodinated 2,4-DIP to 2-IP and 4-IP at a molar ratio of 1:1, and 2,6-DIP to 2-IP, but further deiodination of the monoiodophenols was not observed. These results suggest that strain TIP-1 removed both ortho- and para-substituted iodines equally. Such deiodinating bacteria could be applied to the mineralization or dehalogenation of triiodobenzene derivatives, which are widely used as X-ray contrast media.
Enrichment of a microbial consortium capable of reductive deiodination of 2,4,6-Triiodophenol
J Biosci Bioeng 2014 Mar;117(3):310-7.PMID:24041542DOI:10.1016/j.jbiosc.2013.08.011.
An anaerobic microbial consortium capable of reductively dehalogenating 2,4,6-Triiodophenol (2,4,6-TIP) to 4-iodophenol was enriched from sediments collected from an iodine-producing industry, Chiba, Japan. In the presence of lactate, the enrichment reductively deiodinated 2,4,6-TIP, 2,4-diiodophenol and 2-iodophenol, suggesting preferential removal of ortho-substituted iodines. PCR-denaturing gradient gel electrophoresis and 16S rRNA gene sequence analysis showed that at least 4 bacteria, including Pseudomonas stutzeri, Clostridium sp., Sedimentibacter sp., and unidentified Chloroflexi bacterium, were predominant in the enrichment. Interestingly, the DGGE band corresponding to the Chloroflexi bacterium disappeared when the enrichment was grown in the absence of 2,4,6-Triiodophenol. In addition, the DGGE band with a nearly identical gene sequence was detected in another enrichment that consumed 3-amino-2,4,6-triiodobenzoic acid (ATBA). Phylogenetic analysis of 1416 bp of 16S rRNA gene sequence for this putative deiodinating bacterium revealed that it was closely related (93% sequence similarity) with an anaerobic bacterium MO-CFX2 belonging to the class Anaerolineae, which was recently isolated from subseafloor sediments. The sequence similarities with other known reductive dehalogenating bacteria such as Dehalococcoides mccartyi and Dehalobium chlorocoercia were relatively low (78%-80%). Quantitative PCR analysis targeting specific 16S rRNA gene region of the putative deiodinating bacterium showed that the enrichments consuming 2,4,6-TIP or ATBA contained 18 to 1070 times much higher amounts of 16S rRNA gene copies than those in the enrichments that do not consume these iodoaromatic compounds. These results suggest that a novel anaerobic bacterium in the class Anaerolineae is capable of reductively deiodinating 2,4,6-iodobenzene derivatives.
Polymer nanoparticles containing 2,4,6-Triiodophenol: a potential contrast medium for medical imaging
Acta Chim Slov 2014;61(2):414-9.PMID:25125126doi
Contrast agents have been utilized for x-ray imaging to visualize blood vessels. Triiodobenzene derivatives are known contrast agents yet have not been formulated in a nanoparticle form for the purpose of enhancing the contrast of cancer tissues. In this study, experiments to encapsulate 2,4,6-Triiodophenol in a polymer matrix were designed. Spherical NPs made of PLA, PLGA, PLA-TPGS, PLGA-TPGS and TPGS-FOL, were synthesized and characterized. Using the oil-in-water single-emulsion technique, the effect of several experimental parameters such as sonication power, ratio of 2,4,6-Triiodophenol/polymer, type and concentration of emulsifier, and polymer type has been studied. A good morphology of polymer NPs with entrapped 2,4,6-Triiodophenol was successfully obtained however the encapsulated iodine was in the range of 5 to 26%.
Comparative assessment of embryotoxicity of 2,4,6-Triiodophenol to mouse blastoid and pre-implantation embryo models
Ecotoxicol Environ Saf 2023 Mar 1;252:114608.PMID:36738612DOI:10.1016/j.ecoenv.2023.114608.
Embryonic developmental effects of disinfection by-products, which are generated during drinking water treatment and widely detected in environment, have gained more and more attention nowadays, calling for construction of in vitro research models which can mimic early embryonic development to evaluate the embryotoxicity. The embryonic stem cell test offers a promising assay to predict embryotoxicity of environmental pollutions. However, it is not appropriate for the toxicological study of preimplantation embryos. Here, we used mouse extended stem cells (mEPS) to reconstruct embryo-like structures (blastoid), furtherly attempting to evaluate the reliability of this model for the prediction of possible developmental toxicity of 2,4,6-Triiodophenol (TIP, 5-50 μM), a novel halogenated disinfection byproduct widely detected in water and even drinking water, to mammalian preimplantation embryo. To verify this, we treated mouse embryo derived from in vitro fertilization (IVF-embryo) as reference. The results showed that mEPS-blastoid was like natural blastocyst in morphology, cell composition, and could recapitulate key developmental events happened during mouse preimplantation stage. When blastoid and IVF-embryo models were separately exposed to TIP, their final blastocyst formation rates were not impaired, according to morphological features, meanwhile that TIP exposure caused slight cell apoptosis. Besides, TIP induced an ICM cell bias in cell fate decision, resulting in cell proportion change, which implied abnormal developmental potential. Though we could not evaluate TIP's embryotoxicity before 8-cell stage using blastoid model, its viability as a novel and high-throughput assessment platform for increasing environmental pollutants was still recognized.