Dimercaprol
(Synonyms: 二巯基丙醇; 2,3-Dimercapto-1-propanol; Dithioglycerol) 目录号 : GC38662Dimercaprol (Bal, 2,3-Dimercapto-1-propanol, Dithioglycerol) is an acrolein scavenger that inhibits HIV-1 tat activity, viral production, and infectivity in vitro.
Cas No.:59-52-9
Sample solution is provided at 25 µL, 10mM.
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Dimercaprol (Bal, 2,3-Dimercapto-1-propanol, Dithioglycerol) is an acrolein scavenger that inhibits HIV-1 tat activity, viral production, and infectivity in vitro.
Dimercaprol exerts its acrolein scavenging capability, significantly protects PC-12 cells from acrolein-mediated cell death in a dose dependent manner.[3]
Dimercaprol could significantly reduce acrolein contents in spinal cord tissue following a spinal cord contusion injury in rats.[3]
[1] Ran Tian, Riyi Shi. J Neurochem. 2017 Jun;141(5):708-720. [2] S Kubota, et al. AIDS Res Hum Retroviruses. 1990 Jul;6(7):919-27. [3] Tian R, et al. J Neurochem. 2017 Jun;141(5):708-720.
Cas No. | 59-52-9 | SDF | |
别名 | 二巯基丙醇; 2,3-Dimercapto-1-propanol; Dithioglycerol | ||
Canonical SMILES | OCC(S)CS | ||
分子式 | C3H8OS2 | 分子量 | 124.23 |
溶解度 | Water: 41.67 mg/mL (335.43 mM) | 储存条件 | Store at -20°C, stored under nitrogen |
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1 mg | 5 mg | 10 mg | |
1 mM | 8.0496 mL | 40.2479 mL | 80.4959 mL |
5 mM | 1.6099 mL | 8.0496 mL | 16.0992 mL |
10 mM | 0.805 mL | 4.0248 mL | 8.0496 mL |
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Are we ready to replace Dimercaprol (BAL) as an arsenic antidote?
Hum Exp Toxicol 1997 Aug;16(8):460-5.PMID:9292286DOI:10.1177/096032719701600807.
1 Dimercaprol (BAL), 2,3-dimercaptopropanesulphonate sodium (DMPS) and meso-2,3-dimercaptosuccinic acid (DMSA) are effective arsenic antidotes, but the question which one is preferable for optimal therapy of arsenic poisoning is still open to discussion. Major drawbacks of BAL include (a) its low therapeutic index, (b) its tendency to redistribute arsenic to brain and testes, for example, (c) the need for (painful) intramuscular injection and (d) its unpleasant odour. 2 The newer antidotes DMPS and DMSA feature low toxicity and high therapeutic index. They can be given orally or intravenously due to their high water solubility. While these advantages make it likely that DMPS and DMSA will replace BAL for the treatment of chronic arsenic poisoning, acute intoxication-especially with lipophilic organoarsenicals-may pose a problem for the hydrophilic antidotes, because their ionic nature can adversely affect intracellular availability. 3 This article focuses on aspects dealing with the power of BAL, DMPS, and DMSA to mobilize tissue-bound arsenic in various experimental models, such as monolayers of MDCK (= Madin-Darby canine kidney) cells from dog kidney, isolated perfused liver from guinea-pigs, and perfused jejunal segments from rat small intestine. 4 The results show that hydrophilic DMPS and DMSA may fail to rapidly and completely remove arsenic that has escaped from the extracellular space across tight epithelial barriers. However, owing to their low toxicity, which allows larger doses to be applied, and the potential modification of their pharmacokinetics by means of inert oral anion-exchange resins, DMPS and DMSA may advantageously replace BAL whenever intervention time is not critical. With severe intoxication by organic arsenicals, when the point-of-no-return is a limiting factor, BAL may still have a place as an arsenic antidote.
Dimercaprol is an acrolein scavenger that mitigates acrolein-mediated PC-12 cells toxicity and reduces acrolein in rat following spinal cord injury
J Neurochem 2017 Jun;141(5):708-720.PMID:28301040DOI:10.1111/jnc.14025.
Acrolein is one of the most toxic byproducts of lipid peroxidation, and it has been shown to be associated with multiple pathological processes in trauma and diseases, including spinal cord injury, multiple sclerosis, and Alzheimer's disease. Therefore, suppressing acrolein using acrolein scavengers has been suggested as a novel strategy of neuroprotection. In an effort to identify effective acrolein scavengers, we have confirmed that Dimercaprol, which possesses thiol functional groups, could bind and trap acrolein. We demonstrated the reaction between acrolein and Dimercaprol in an abiotic condition by nuclear magnetic resonance spectroscopy. Specifically, Dimercaprol is able to bind to both the carbon double bond and aldehyde group of acrolein. Its acrolein scavenging capability was further demonstrated by in vitro results that showed that Dimercaprol could significantly protect PC-12 cells from acrolein-mediated cell death in a dose-dependent manner. Furthermore, Dimercaprol, when applied systemically through intraperitoneal injection, could significantly reduce acrolein contents in spinal cord tissue following a spinal cord contusion injury in rats, a condition known to have elevated acrolein concentration. Taken together, Dimercaprol may be an effective acrolein scavenger and a viable candidate for acrolein detoxification.
British anti-Lewisite (Dimercaprol): an amazing history
Ann Emerg Med 2003 Mar;41(3):378-83.PMID:12605205DOI:10.1067/mem.2003.72.
Emergency physicians are familiar with British anti-Lewisite (BAL) because it is a heavy metal-chelating agent that is recommended in some cases of metal poisoning, especially arsenic. Although there are more modern chelating agents, the fact that BAL is still recommended and stocked by hospital pharmacies more than 60 years after its initial synthesis is itself remarkable. During World War II, BAL minimized the risk to the Allied infantry of injury or death from Lewisite, a very potent arsenic-based chemical warfare agent. Once developed, BAL revolutionized the treatment of heavy metal poisonings, both accidental and iatrogenic (eg, toxicity from treatment of arthritis with gold salts). In 1951, BAL was used to treat Wilson's disease with striking success. Today, BAL might again become prominent should terrorists or governments use Lewisite against civilians or military forces.
Study on the interaction between 2-mercaptoethanol, Dimercaprol and CdSe quantum dots
Luminescence 2008 Sep-Oct;23(5):321-6.PMID:18500695DOI:10.1002/bio.1038.
The interactions between 2-mercaptoethanol, Dimercaprol and CdSe quantum dots (QDs) in organic media have been investigated by spectral methods. The results showed that the fluorescence (FL) emission of CdSe QDs gradually decreased, with a slight red-shift, after adding thiols to CdSe QDs solutions. With the increase of the concentrations of thiols, the resonance light scattering (RLS) signal of CdSe QDs had been strongly enhanced in the wavelength range 300-500 nm, which was confirmed by the formation of larger CdSe QDs particles. The effect of thiols on the FL emission of CdSe QDs could be described by a Stern-Volmer-type equation with the concentration ranges 1.0 x 10(-6)-7.5 x 10(-4) mol/L for 2-mercaptoethanol and 1.0 x 10(-7)-2.5 x 10(-5) mol/L for Dimercaprol. The possible mechanism of the interaction was proposed according to the results of UV-vis absorption and micro-Raman spectroscopy. The results indicated that FL quenching was mainly attributable to the exchange of the QDs surface molecules.
Reduction of polysaccharide production in Pseudomonas aeruginosa biofilms by bismuth Dimercaprol (BisBAL) treatment
J Antimicrob Chemother 1999 Nov;44(5):601-5.PMID:10552975DOI:10.1093/jac/44.5.601.
Microorganisms in biofilms, cells attached to a surface and embedded in secreted insoluble extracellular polymers, are recalcitrant to chemical biocides and antibiotics. When Pseudomonas aeruginosa ERC1 biofilms were treated continuously with 1 x MIC of bismuth Dimercaprol (BisBAL), biofilm density determined by both total cell counts and viable cell counts increased during the first 30 h period then decreased thereafter. After 120 h of treatment there was an approximate 3-log reduction in viable cell areal density compared with the untreated control. Per-cell total polysaccharide production was significantly reduced in biofilms exposed to 12.5 microM BisBAL compared with the untreated control. In biofilm cultures, 1 x MIC of BisBAL did not initially kill attached cells but was enough to reduce polysaccharide production. As treatment proceeded, the normalized polysaccharide content was reduced and those cells attached became susceptible to 1 x MIC of BisBAL.