Arsenobetaine
(Synonyms: 砷甜菜碱) 目录号 : GC49292An organoarsenical and a compatible solute
Cas No.:64436-13-1
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
Arsenobetaine is an organoarsenical and a compatible solute that has been found in various marine animals, such as lobsters and crabs, as well as terrestrial organisms, including earthworms and lichens.1,2 It is protective against B. subtilis cell death induced by high osmolarity or extreme temperatures when used at a concentration of 1 mM.2 Arsenobetaine is non-toxic to mice (LD50 = 10 g/kg).1,2
1.Popowich, A., Zhang, Q., and Le, X.Arsenobetaine: The ongoing mysteryNatl. Sci. Rev.3(4)451-458(2016) 2.Hoffmann, T., Warmbold, B., Smits, S.H.J., et al.Arsenobetaine: An ecophysiologically important organoarsenical confers cytoprotection against osmotic stress and growth temperature extremesEnviron. Microbiol.20(1)305-323(2018)
| Cas No. | 64436-13-1 | SDF | |
| 别名 | 砷甜菜碱 | ||
| Canonical SMILES | O=C(C[As+](C)(C)C)[O-] | ||
| 分子式 | C5H11AsO2 | 分子量 | 178.1 |
| 溶解度 | Water: soluble | 储存条件 | -20°C; protect from light |
| 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 | 5.6148 mL | 28.0741 mL | 56.1482 mL |
| 5 mM | 1.123 mL | 5.6148 mL | 11.2296 mL |
| 10 mM | 0.5615 mL | 2.8074 mL | 5.6148 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。
Arsenobetaine formation in plankton: a review of studies at the base of the aquatic food chain
J Environ Monit 2012 Nov;14(11):2841-53.PMID:23014956DOI:10.1039/c2em30572k.
Arsenobetaine is one of the major organoarsenic compounds found in aquatic organisms, including seafood and fish meant for human consumption. It has been widely studied over the last 50 years because of its non-toxic properties, and its origin is postulated to be at bottom of the aquatic food chains. The present review focuses on Arsenobetaine formation in marine and freshwater plankton, comparing the arsenic compounds found in the different plankton organisms, and the methods used to assess arsenic speciation. The main findings indicate that in the marine environment, phytoplankton and micro-algae contain arsenosugars, with the first traces of Arsenobetaine appearing in herbivorous zooplankton, and becoming a major arsenic compound in carnivorous zooplankton. Freshwater plankton contains less Arsenobetaine than their marine relatives, with arsenosugars dominating. The possible role and formation pathways of Arsenobetaine in plankton organisms are reviewed and the literature suggests that Arsenobetaine in zooplankton comes from the degradation of ingested arsenosugars, and is selectively accumulated by the organism to serve as osmolyte. Several arsenic compounds such as arsenocholine, dimethylarsinoylacetate or dimethylarsinoylethanol that are intermediates of this pathway have been detected in plankton. The gaps in research on Arsenobetaine in aquatic environments are also addressed: primarily most of the conclusions are drawn on culture-based experiments, and few data are present from the natural environment, especially for freshwater ecosystems. Moreover, more data on arsenic in different zooplankton species would be helpful to confirm the trends observed between herbivorous and carnivorous organisms.
Key genes for Arsenobetaine synthesis in marine medaka (Oryzias melastigma) by transcriptomics
Aquat Toxicol 2022 Dec;253:106349.PMID:36395554DOI:10.1016/j.aquatox.2022.106349.
Marine fish undergo detoxification to overcome As stress, forming non-toxic metabolites Arsenobetaine (AsB). Genes associated with AsB synthesis remain unknown. Therefore, in this study, we explored the key genes involved in the synthesis of AsB by transcriptomic analysis in marine medaka (Oryzias melastigma), and then screened candidate genes related to AsB synthesis. In the liver, 40 genes were up-regulated and 23 genes were down-regulated, whereas in muscle, 83 genes were up-regulated and 331 genes were down-regulated. We revealed that bhmt, mat2aa, and gstt1a can play a significant role in the glutathione and methionine metabolic pathway. These three genes can affect the conversion of arsenocholine (AsC) to AsB by the vitro gene transformation experiments of E. coli BL21(DE3). E. coli BL21-bhmt overexpressing bhmt resulted in more oxidation of precursor AsC to AsB. Furthermore, the AsB concentration was decreased after E. coli BL21 overexpressing mat2aa and gstt1a, which were down-regulated in marine medaka. Therefore, we concluded that bhmt, mat2aa, and gstt1a are involved in AsB synthesis. Overall, this is the first report on transcriptome screening and identification of key genes for AsB synthesis in marine medaka. We provided important insights to reveal the mystery of AsB synthesis in marine fish.
Accumulation or production of Arsenobetaine in humans?
J Environ Monit 2010 Apr;12(4):832-7.PMID:20383363DOI:10.1039/b921588c.
Arsenobetaine has always been referred to as a non-toxic but readily bioavailable compound and the available data would suggest that it is neither metabolised by nor accumulated in humans. Here this study investigates the urine of five volunteers on an Arsenobetaine exclusive diet for twelve days and shows that Arsenobetaine was consistently excreted by three of the five volunteers. From the expected elimination pattern of Arsenobetaine in rodents, no significant amount of Arsenobetaine should have been detectable after 5 days of the trial period. The Arsenobetaine concentration found in the urine was constant after 5 days and varied between 0.2 and 12.2 microg As per L for three of the volunteers. Contrary to the established belief that Arsenobetaine is neither accumulated nor generated by humans, the presented results would suggest that either accumulated Arsenobetaine in the tissues is slowly released over time or that Arsenobetaine is a human metabolite of dimethylarsinic acid or inorganic arsenic from the trial food, or both. Either possibility is intriguing and raises fundamental questions about human arsenic metabolism and the toxicological and environmental inertness of Arsenobetaine.
Biodegradation of Arsenobetaine to inorganic arsenic regulated by specific microorganisms and metabolites in mice
Toxicology 2022 Jun 15;475:153238.PMID:35718002DOI:10.1016/j.tox.2022.153238.
Arsenobetaine (AsB) is a primary arsenic (As) compound found in marine organisms. However, in mammals, the metabolic mechanism of AsB remains indistinct. Therefore, in this study, we investigated the biotransformation and regulatory mechanism of AsB, particularly the biodegradation process, in a mouse model to assess the underlying health hazards of AsB. We studied the biotransformation process of AsB in mice through the food chain [AsB feed-marine fish (Epinephelus fuscoguttatus)-mice (Mus musculus)]. Our results showed the significant bioaccumulation of total As, AsB, and, in particular, arsenate [As(V)] through biodegradation in mice tissues. As the abundance of Staphylococcus and Blautia (phylum, Firmicutes) increased, the expression of aqp7 (absorption) and methyltransferase (as3mt) (methylation) was upregulated. In contrast, the expression of S-adenosyl methionine (sam) (methylation) was downregulated. These findings suggest that demethylation and methylation occurred simultaneously in the intestines, with demethylation capacity being greater than that of methylation. Furthermore, Firmicutes such as Staphylococcus and Blautia showed a significant inverse relationship with arachidonic acid, choline, and sphingosine. Gene, microbiome, and metabolomics analyses indicated that Staphylococcus and Blautia and arachidonic acid, choline, and sphingosine participated in the degradation of AsB to As(V) in mouse intestines. Therefore, long-term AsB ingestion through marine fish consumption could cause potential health hazards in humans.
Arsenobetaine: an ecophysiologically important organoarsenical confers cytoprotection against osmotic stress and growth temperature extremes
Environ Microbiol 2018 Jan;20(1):305-323.PMID:29159878DOI:10.1111/1462-2920.13999.
Arsenic, a highly cytotoxic and cancerogenic metalloid, is brought into the biosphere through geochemical sources and anthropogenic activities. A global biogeochemical arsenic biotransformation cycle exists in which inorganic arsenic species are transformed into organoarsenicals, which are subsequently mineralized again into inorganic arsenic compounds. Microorganisms contribute to this biotransformation process greatly and one of the organoarsenicals synthesized and degraded in this cycle is Arsenobetaine. Its nitrogen-containing homologue glycine betaine is probably the most frequently used compatible solute on Earth. Arsenobetaine is found in marine and terrestrial habitats and even in deep-sea hydrothermal vent ecosystems. Despite its ubiquitous occurrence, the biological function of Arsenobetaine has not been comprehensively addressed. Using Bacillus subtilis as a well-understood platform for the study of microbial osmostress adjustment systems, we ascribe here to Arsenobetaine both a protective function against high osmolarity and a cytoprotective role against extremes in low and high growth temperatures. We define a biosynthetic route for Arsenobetaine from the precursor arsenocholine that relies on enzymes and genetic regulatory circuits for glycine betaine formation from choline, identify the uptake systems for Arsenobetaine and arsenocholine, and describe crystal structures of ligand-binding proteins from the OpuA and OpuB ABC transporters complexed with either Arsenobetaine or arsenocholine.