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Chemical Compound Review

DMPS     2,3-bis-sulfanylpropane-1- sulfonic acid

Synonyms: CHEBI:888, AG-G-96772, CHEMBL1624767, CTK5E0154, AR-1D2786, ...
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Disease relevance of DMPS


High impact information on DMPS

  • To determine the influence of dental amalgams on the mercury body burden of humans, we have given volunteers, with and without amalgams in their mouth, the sodium salt of 2,3-dimercaptopropane-1-sulfonic acid (DMPS), a chelating agent safely used in the Soviet Union and West Germany for a number of years [6].
  • At 0.5 M LiCl, the crystalline DMPS exhibits a bilayer gel leads to liquid crystal transition at 89 degrees C accompanied by a high enthalpy change, delta H = 16.0 kcal/mol [7].
  • Light microscopy demonstrated that erythrocytes incubated with an equimolar mixture of DMPC-d54/DMPS or DMPC/DMPS-d54 remained mostly discocytic whereas cells incubated with either DMPC-d54 or DMPS-d54 alone became echinocytic or stomatocytic, respectively [8].
  • The conformation of phosphatidylserine (DMPS) diluted in perdeuterated dodecylphosphocholine micelles (DPC) has been investigated by 1D and 2D proton NMR spectroscopy [9].
  • Whereas incorporation of the anesthetic into DOPS bilayers does not affect significantly the structural and dynamic properties of the disordered acyl chains in the liquid-crystalline phase, it orders the DMPS acyl chains in the gel phase [10].

Chemical compound and disease context of DMPS


Biological context of DMPS


Anatomical context of DMPS


Associations of DMPS with other chemical compounds

  • Fourier transform infrared (IR) spectroscopic studies of phosphatidylserine/cholesterol/Ca2+ complexes are reported using the synthetic phosphatidylserines (PS) 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (DOPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS), and 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine (DMPS) [21].
  • The model membrane systems studied were multilamellar aqueous dispersions of 1,2-dimyristoyl-sn-glycero-3-phospho-L-serine (DMPS) and 1,2-dioleoyl-sn-glycero-3-phospho-L-serine (DOPS) in the absence and the presence of tetracaine at pH 5.5 and 9 [10].
  • With increasing MgCl2 concentration, progressive conversion to a phase exhibiting a high melting (98 degrees C), high enthalpy (delta H congruent to 11.0 kcal/mol of DMPS) transition is observed [22].
  • The in vitro evidence suggests that two molecules of DMPS are required to prevent the effects of one molecule of sodium arsenite [13].
  • DMPS was released from the isolated DMPS-albumin complex after treatment with dithiothreitol, indicating that it was bound via a disulfide linkage [23].

Gene context of DMPS

  • Protonated DPC, DMPC and DMPS were incorporated in deuterated micelles containing the PMP1 fragment for studying lipid-peptide interactions [24].
  • The mercury excreted for 6 hr before and 6 hr after DMPS treatment was 113 micrograms +/- 26 and 5037 micrograms +/- 682 S.E.M. for the skin lotion makers; 16.2 micrograms +/- 3.4 and 1410 micrograms +/- 346 S.E.M. for the skin lotions users; and 0.49 micrograms +/- 0.11 and 18.4 micrograms +/- 7.1 S.E.M. for the controls, respectively [25].
  • Treatment with DMPS also prevented mercury-induced IgG1 anti-nucleolar antibody synthesis and the development of mesangial IgG1 immune complex deposits in SJL mice [26].
  • This Ca2+ response was prevented by the thiol reducing agents, 2-mercaptoethanol, N-acetyl-L-cysteine, dithiothreitol, 2,3-dimercaptopropane-1-sulfonic acid (DMPS) and tris-(2-carboxyethyl)phosphine (TCEP), but slightly reduced by the antioxidant, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox) [27].
  • The present study evaluated the influence of BAL (2,3-dimercapto-1-propanol) and DMPS (sodium 2,3-dimercapto-1-propanesulfonic acid), a water-soluble analogue of BAL, on arsenic-induced embryotoxic and teratogenic effects in the mouse [28].

Analytical, diagnostic and therapeutic context of DMPS


  1. The use of 212Pb-labeled monoclonal antibody in the treatment of murine erythroleukemia. Ruble, G., Wu, C., Squire, R.A., Ganswo, O.A., Strand, M. Int. J. Radiat. Oncol. Biol. Phys. (1996) [Pubmed]
  2. Sodium 2,3-dimercapto-1-propanesulfonate (DMPS) treatment does not redistribute lead or mercury to the brain of rat. Aposhian, M.M., Maiorino, R.M., Xu, Z., Aposhian, H.V. Toxicology (1996) [Pubmed]
  3. Arsenic excretion after treatment of arsenic poisoning with DMSA or DMPS in mice. Maehashi, H., Murata, Y. Jpn. J. Pharmacol. (1986) [Pubmed]
  4. Evaluation of the developmental toxicity of 2,3-dimercapto-1-propanesulfonate (DMPS) in mice. Effect on mineral metabolism. Bosque, M.A., Domingo, J.L., Paternain, J.L., Llobet, J.M., Corbella, J. Toxicology (1990) [Pubmed]
  5. Mercury vapor inhalation from Chinese red (Cinnabar). Ho, B.S., Lin, J.L., Huang, C.C., Tsai, Y.H., Lin, M.C. J. Toxicol. Clin. Toxicol. (2003) [Pubmed]
  6. Urinary mercury after administration of 2,3-dimercaptopropane-1-sulfonic acid: correlation with dental amalgam score. Aposhian, H.V., Bruce, D.C., Alter, W., Dart, R.C., Hurlbut, K.M., Aposhian, M.M. FASEB J. (1992) [Pubmed]
  7. Crystallization of phosphatidylserine bilayers induced by lithium. Hauser, H., Shipley, G.G. J. Biol. Chem. (1981) [Pubmed]
  8. Conformational order of specific phospholipids in human erythrocytes: correlations with changes in cell shape. Moore, D.J., Sills, R.H., Mendelsohn, R. Biochemistry (1997) [Pubmed]
  9. 2D 1H-NMR conformational study of phosphatidylserine diluted in perdeuterated dodecylphosphocholine micelles. Evidence for a pH-induced conformational transition. Sanson, A., Monck, M.A., Neumann, J.M. Biochemistry (1995) [Pubmed]
  10. High-pressure infrared study of phosphatidylserine bilayers and their interactions with the local anesthetic tetracaine. Auger, M., Smith, I.C., Mantsch, H.H., Wong, P.T. Biochemistry (1990) [Pubmed]
  11. Relative effectiveness of dithiol and dithiocarbamate chelating agents in reducing retention of polonium-210 in rats. Rencová, J., Volf, V., Jones, M.M., Singh, P.K. Int. J. Radiat. Biol. (1993) [Pubmed]
  12. Prevention by chelating agents of metal-induced developmental toxicity. Domingo, J.L. Reprod. Toxicol. (1995) [Pubmed]
  13. Optical isomers of 2,3-dimercapto-1-propanesulfonate: antidotal activity, in vitro and in vivo, against sodium arsenite. Hsu, C.A., Aposhian, H.V., Heydolph, S., Parr, W. J. Pharmacol. Exp. Ther. (1983) [Pubmed]
  14. Novel biotinylated phenylarsonous acids as bifunctional reagents for spatially close thiols: studies on reduced antibodies and the agonist binding site of reduced Torpedo nicotinic receptors. Moaddel, R., Sharma, A., Huseni, T., Jones, G.S., Hanson, R.N., Loring, R.H. Bioconjug. Chem. (1999) [Pubmed]
  15. Recovery from severe arsenic-induced peripheral neuropathy with 2,3-dimercapto-1-propanesulphonic acid. Wax, P.M., Thornton, C.A. J. Toxicol. Clin. Toxicol. (2000) [Pubmed]
  16. Effect of DMPS and various adsorbents on the arsenic excretion in guinea-pigs after injection with As2O3. Reichl, F.X., Hunder, G., Liebl, B., Fichtl, B., Forth, W. Arch. Toxicol. (1995) [Pubmed]
  17. Evaluation of the developmental effects on mice after prenatal, or pre- and postnatal exposure to 2,3-dimercaptopropane-1-sulfonic acid (DMPS). Domingo, J.L., Ortega, A., Bosque, M.A., Corbella, J. Life Sci. (1990) [Pubmed]
  18. Reversal of gallium arsenide-induced suppression of the antibody response by a mixed disulfide metabolite of meso-2,3-dimercaptosuccinic acid. Burns, L.A., Butterworth, L.F., Munson, A.E. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  19. BAL modulates glutamate transport in synaptosomes and synaptic vesicles from rat brain. Nogueira, C.W., Rotta, L.L., Tavares, R.G., Souza, D.O., Rocha, J.B. Neuroreport (2001) [Pubmed]
  20. Silicone: a critical review. Duffy, D.M. Advances in dermatology. (1990) [Pubmed]
  21. Infrared spectroscopic studies on the phosphatidylserine bilayer interacting with calcium ion: effect of cholesterol. Choi, S., Ware, W., Lauterbach, S.R., Phillips, W.M. Biochemistry (1991) [Pubmed]
  22. Interactions of divalent cations with phosphatidylserine bilayer membranes. Hauser, H., Shipley, G.G. Biochemistry (1984) [Pubmed]
  23. Determination and metabolism of dithiol chelating agents. XVII. In humans, sodium 2,3-dimercapto-1-propanesulfonate is bound to plasma albumin via mixed disulfide formation and is found in the urine as cyclic polymeric disulfides. Maiorino, R.M., Xu, Z.F., Aposhian, H.V. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  24. 1H- and 2H-NMR studies of a fragment of PMP1, a regulatory subunit associated with the yeast plasma membrane H(+)-ATPase. Conformational properties and lipid-peptide interactions. Beswick, V., Roux, M., Navarre, C., Coïc, Y.M., Huynh-Dinh, T., Goffeau, A., Sanson, A., Neumann, J.M. Biochimie (1998) [Pubmed]
  25. Sodium 2,3-dimercaptopropane-1-sulfonate challenge test for mercury in humans. III. Urinary mercury after exposure to mercurous chloride. Maiorino, R.M., Gonzalez-Ramirez, D., Zuniga-Charles, M., Xu, Z., Hurlbut, K.M., Aposhian, M.M., Dart, R.C., Woods, J.S., Ostrosky-Wegman, P., Gonsebatt, M.E., Aposhian, H.V. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  26. Thiol compounds inhibit mercury-induced immunological and immunopathological alterations in susceptible mice. Hu, H., Möller, G., Abedi-Valugerdi, M. Clin. Exp. Immunol. (1997) [Pubmed]
  27. GEA3162, a nitric oxide-releasing agent, activates non-store-operated Ca2+ entry and inhibits store-operated Ca2+ entry pathways in neutrophils through thiol oxidation. Hsu, M.F., Chen, Y.S., Huang, L.J., Tsao, L.T., Kuo, S.C., Wang, J.P. Eur. J. Pharmacol. (2006) [Pubmed]
  28. Amelioration by BAL (2,3-dimercapto-1-propanol) and DMPS (sodium 2,3-dimercapto-1-propanesulfonic acid) of arsenite developmental toxicity in mice. Domingo, J.L., Bosque, M.A., Llobet, J.M., Corbella, J. Ecotoxicol. Environ. Saf. (1992) [Pubmed]
  29. Lipid lateral heterogeneity in phosphatidylcholine/phosphatidylserine/diacylglycerol vesicles and its influence on protein kinase C activation. Dibble, A.R., Hinderliter, A.K., Sando, J.J., Biltonen, R.L. Biophys. J. (1996) [Pubmed]
  30. Fluorometric determination of 2,3-dimercaptopropane-1-sulfonic acid and other dithiols by precolumn derivatization with bromobimane and column liquid chromatography. Maiorino, R.M., Weber, G.L., Aposhian, H.V. J. Chromatogr. (1986) [Pubmed]
  31. Heavy metals and fertility. Gerhard, I., Monga, B., Waldbrenner, A., Runnebaum, B. J. Toxicol. Environ. Health Part A (1998) [Pubmed]
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