4 chloromercuribenzenesulfonate


Summary: A cytotoxic sulfhydryl reagent that inhibits several subcellular metabolic systems and is used as a tool in cellular physiology.

Top Publications

  1. Stanton J, Rashid M, Mensa Wilmot K. Cysteine-less glycosylphosphatidylinositol-specific phospholipase C is inhibited competitively by a thiol reagent: evidence for glyco-mimicry by p-chloromercuriphenylsulphonate. Biochem J. 2002;366:281-8 pubmed
    ..These data suggest that pCMPS is a glyco-mimetic that occupies the glycan binding site of PI-PLC, from where, depending on the substrate, it inhibits catalysis allosterically or competitively. ..
  2. Zhou A, Wozniak A, Meyer Lipp K, Nietschke M, Jung H, Fendler K. Charge translocation during cosubstrate binding in the Na+/proline transporter of E.coli. J Mol Biol. 2004;343:931-42 pubmed
    ..4) Proline binding proceeds in a two-step process: low affinity (approximately 1mM) electroneutral substrate binding followed by a nearly irreversible electrogenic conformational transition. ..
  3. Boot J. Hepatotoxic effects of SH-reagents in human and rat hepatocyte cultures and in situ perfused rat livers. Cell Struct Funct. 1996;21:221-9 pubmed
    ..Of all tested reagents, organic mercury compounds arose as the most toxic reagents. ..
  4. Silva P, Epstein F, Solomon R. The effect of mercury on chloride secretion in the shark (Squalus acanthias) rectal gland. Comp Biochem Physiol C. 1992;103:569-75 pubmed
  5. Mueckler M, Makepeace C. Transmembrane segment 12 of the Glut1 glucose transporter is an outer helix and is not directly involved in the transport mechanism. J Biol Chem. 2006;281:36993-8 pubmed
    ..Additionally, the pCMBS data indicate that the predicted exoplasmic end of helix 12 is completely exposed to the external solvent when the transporter is in its exofacial configuration. ..
  6. Mueckler M, Makepeace C. Analysis of transmembrane segment 10 of the Glut1 glucose transporter by cysteine-scanning mutagenesis and substituted cysteine accessibility. J Biol Chem. 2002;277:3498-503 pubmed
    ..Two-dimensional models for the conformation of the 12 transmembrane helices and the exofacial glucose-binding site of Glut1 are proposed that are consistent with existing experimental data. ..
  7. Jeremic A, Jeftinija K, Stevanovic J, Glavaski A, Jeftinija S. ATP stimulates calcium-dependent glutamate release from cultured astrocytes. J Neurochem. 2001;77:664-75 pubmed
    ..These results suggest that ATP stimulates excitatory amino acid release from astrocytes via a calcium-dependent anion-transport sensitive mechanism. ..
  8. Berridge M, Tan A. Cell-surface NAD(P)H-oxidase: relationship to trans-plasma membrane NADH-oxidoreductase and a potential source of circulating NADH-oxidase. Antioxid Redox Signal. 2000;2:277-88 pubmed
    ..These results do not support the view the surface NAD(P)H-oxidase is a terminal oxidase for trans-plasma membrane NADH-oxidoreductase. ..
  9. Smith S, Huang W, Chancy C, Ganapathy V. Regulation of the reduced-folate transporter by nitric oxide in cultured human retinal pigment epithelial cells. Biochem Biophys Res Commun. 1999;257:279-83 pubmed
    ..These studies suggest that NO produced during retinal disease may affect the function of RFT in adjacent RPE cells. ..

More Information


  1. Xu M, Akabas M. Identification of channel-lining residues in the M2 membrane-spanning segment of the GABA(A) receptor alpha1 subunit. J Gen Physiol. 1996;107:195-205 pubmed
    ..The ability of the positively charged reagent methanethiosulfonate ethylammonium to reach the level of alpha1 Thr261 suggests that the charge-selectivity filter is at least as cytoplasmic as this residue. ..
  2. Widmer J, Gaillard J, Bovier P, Tissot R. Involvement of sulfhydryl groups in the transport of L-tyrosine and L-tryptophan across the human red cell membrane in vitro. Neuropsychobiology. 1989;21:53-8 pubmed
    ..We concluded that a relationship might exist between these neutral amino acids and D-glucose transport. ..
  3. Fuhrmann G, Fehlau R, Schneider H, Knauf P. The effect of ferricyanide with iodoacetate in calcium-free solution on passive cation permeability in human red blood cells: comparison with the Gardos-effect and with the influence of PCMBS on passive cation permeability. Biochim Biophys Acta. 1989;983:179-85 pubmed
    ..The ferricyanide effect described here does not involve formation of nonspecific channels. The change in Na+ permeability separately from K+ permeability under certain circumstances suggests a more specific effect. ..
  4. Beavis A. The mitochondrial inner-membrane anion channel possesses two mercurial-reactive regulatory sites. Eur J Biochem. 1989;185:511-9 pubmed
    ..It is suggested that these sites may contain thiol groups and that physiological regulators may exist which can effect changes in activity of the inner membrane anion uniporter similar to those exerted by mercurials. ..
  5. Sen S, Bhuyan N, Lakshman K, Roy A, Chakraborty B, Bera T. Membrane bound pyrophosphatase and P-type adenosine triphosphatase of Leishmania donovani as possible chemotherapeutic targets: similarities and differences in inhibitor sensitivities. Biochemistry (Mosc). 2009;74:1382-7 pubmed
    ..We conclude that there are significant differences within promastigote, amastigote, and mammalian host in cytosolic pH homeostasis to merit the inclusion of PPase transporter as a putative target for rational drug design. ..
  6. Nouri Sorkhabi M, Chapman B, O Loughlin E, Li Z, Kuchel P, Gaskin K. NMR measurements of the diffusional permeability of water in cultured colonic epithelial cancer cells. Cell Biol Int. 2005;29:441-8 pubmed
    ..It is concluded that in T84 cells water diffuses through the membrane lipid bilayer and via channels that are inhibited by PCMBS, including the channels that are known to be inhibited by glibenclamide. ..
  7. Tanaka K, Zhou F, Kuze K, You G. Cysteine residues in the organic anion transporter mOAT1. Biochem J. 2004;380:283-7 pubmed
  8. Mazurkiewicz P, Poelarends G, Driessen A, Konings W. Facilitated drug influx by an energy-uncoupled secondary multidrug transporter. J Biol Chem. 2004;279:103-8 pubmed
    ..e. the design and use of modulators of secondary multidrug resistance transporters that uncouple drug efflux from proton influx, thereby allowing transmembrane electrical potential-driven influx of cationic drugs. ..
  9. Ding P. An investigation of cysteine mutants on the cytoplasmic loop X/XI in the melibiose transporter of Escherichia coli by using thiol reagents: implication of structural conservation of charged residues. Biochem Biophys Res Commun. 2003;307:864-9 pubmed
  10. Tosco M, Orsenigo M, Gastaldi G, Faelli A. An endogenous monocarboxylate transport in Xenopus laevis oocytes. Am J Physiol Regul Integr Comp Physiol. 2000;278:R1190-5 pubmed
  11. Swenson T, Brocia R, Tall A. Plasma cholesteryl ester transfer protein has binding sites for neutral lipids and phospholipids. J Biol Chem. 1988;263:5150-7 pubmed
    ..The results indicate that the CETP has binding sites for CE, triglyceride, and PC which readily equilibrate with lipoprotein lipids and suggest that CETP can act as a carrier of lipid between lipoproteins. ..
  12. Harris W, Rayford A. LCAT inhibitors interfere with the enzymatic determination of cholesterol and triglycerides. Lipids. 1990;25:341-3 pubmed
    ..Thus, these inhibitors should be avoided when plasma samples are to be enzymatically analyzed for cholesterol or triglycerides. ..
  13. Mikulski R, Tu C, Swenson E, Silverman D. Reactions of nitrite in erythrocyte suspensions measured by membrane inlet mass spectrometry. Free Radic Biol Med. 2010;48:325-31 pubmed publisher
    ..Inhibition of red cell membrane anion exchangers and aquaporins did not affect these processes. ..
  14. Chiang W, Knowles A. Inhibition of human NTPDase 2 by modification of an intramembrane cysteine by p-chloromercuriphenylsulfonate and oxidative cross-linking of the transmembrane domains. Biochemistry. 2008;47:8775-85 pubmed publisher
    ..These results indicate that the mobility of the transmembrane helices is necessary for maximal catalysis. ..
  15. Ritchie R, Fieuw Makaroff S, Patrick J. Sugar retrieval by coats of developing seeds of Phaseolus vulgaris L. and Vicia faba L. Plant Cell Physiol. 2003;44:163-72 pubmed
    ..These responses are consistent with sugar/H(+) symport acting to retrieve photoassimilates leaked to the apoplasm during post-sieve element transport within seed coats. ..
  16. Kleinzeller A, Booz G, Mills J, Ziyadeh F. pCMBS-induced swelling of dogfish (Squalus acanthias) rectal gland cells: role of the Na+,K(+)-ATPase and the cytoskeleton. Biochim Biophys Acta. 1990;1025:21-31 pubmed
  17. Ding P, Wilson T. Cysteine mutagenesis of the amino acid residues of transmembrane helix I in the melibiose carrier of Escherichia coli. Biochemistry. 2001;40:5506-10 pubmed
    ..Second site revertants were isolated from K18C and Y31C. The revertants were found to have mutations in helices I, IV, and VII. ..
  18. Sakr S, Lemoine R, Gaillard C, Delrot S. Effect of cutting on solute uptake by plasma membrane vesicles from sugar beet (Beta vulgaris L.) leaves. Plant Physiol. 1993;103:49-58 pubmed
  19. Akao T, Kobashi K. Characterization of NADP+: 3 beta-hydroxysteroid dehydrogenase from microsomes of rat liver. Biochim Biophys Acta. 1990;1046:271-6 pubmed
    ..The molecular weight of the enzyme was estimated to be about 43,000 by Sephadex G-200 column chromatography. From these results, it is concluded that the enzyme is a new type of microsomal NADP+:3 beta-hydroxysteroid dehydrogenase. ..
  20. Lahav J, Gofer Dadosh N, Luboshitz J, Hess O, Shaklai M. Protein disulfide isomerase mediates integrin-dependent adhesion. FEBS Lett. 2000;475:89-92 pubmed
    ..These data indicate that: (a) ecto-sulfhydryls are necessary for integrin-mediated platelet adhesion; (b) disulfide exchange takes place during this process; (c) surface PDI is involved in integrin-mediated adhesion. ..
  21. Frolenkov G, Belyantseva I, Kurc M, Mastroianni M, Kachar B. Cochlear outer hair cell electromotility can provide force for both low and high intensity distortion product otoacoustic emissions. Hear Res. 1998;126:67-74 pubmed
    ..Our results suggest that the OHC electromotility might provide the force for DPOAE generation not only at low, but also at high stimulus intensities. ..
  22. Vargas M, Deves R. System y+L-like activities account for high and low amino-acid transport phenotypes in chicken erythrocytes. J Membr Biol. 2001;183:183-93 pubmed
    ..These findings explain previous results obtained in selective breeding experiments of chicken with high and low amino-acid transport activity. ..
  23. Jitsuyama Y, Suzuki T, Harada T, Fujikawa S. Loading process of sugars into cabbage petiole and asparagus shoot apex cells by incubation with hypertonic sugar solutions. Protoplasma. 2001;217:205-16 pubmed
  24. Salminen A, Parfenyev A, Salli K, Efimova I, Magretova N, Goldman A, et al. Modulation of dimer stability in yeast pyrophosphatase by mutations at the subunit interface and ligand binding to the active site. J Biol Chem. 2002;277:15465-71 pubmed
    ..Both effects appear to be mediated by a conformational change involving the C-terminal segment that generally shields the Cys(83) residue in the dimer. ..
  25. Fonteriz R, Villalobos C, Garcia Sancho J. An extracellular sulfhydryl group modulates background Na(+) conductance and cytosolic Ca(2+) in pituitary cells. Am J Physiol Cell Physiol. 2002;282:C864-72 pubmed
    ..The BNC studied here could play a physiological role, regulating excitability and spontaneous activity, and explains satisfactorily the [Ca(2+)](i)-increasing actions of the mercurials reported previously in several excitable tissues. ..
  26. Weber G, Mehr A, Sirota J, Aller S, Decker S, Dawson D, et al. Mercury and zinc differentially inhibit shark and human CFTR orthologues: involvement of shark cysteine 102. Am J Physiol Cell Physiol. 2006;290:C793-801 pubmed
    ..These experiments demonstrate a profound difference in the sensitivity of shark vs. human CFTR to inhibition by three thiol-reactive substances, an effect that involves C102 in the shark orthologue. ..
  27. Schüttert J, Fiedler G, Grupp C, Blaschke S, Grunewald R. Sorbitol transport in rat renal inner medullary interstitial cells. Kidney Int. 2002;61:1407-15 pubmed
  28. Benga G, Chapman B, Cox G, Kuchel P. Comparative NMR studies of diffusional water permeability of red blood cells from different species: XIV. Little Penguin, Eudyptula minor. Cell Biol Int. 2003;27:921-8 pubmed
    ..The discontinuity at approximately 20 degrees C in the Arrhenius plot is an interesting finding, not seen before in other species, and we suggest that it reflects a phase transition in the membrane lipids. ..
  29. Bali M, Akabas M. Defining the propofol binding site location on the GABAA receptor. Mol Pharmacol. 2004;65:68-76 pubmed
    ..Propofol did not protect the cysteine substituted for the aligned alpha1 subunit position or the 15' M2 segment Cys mutants in either subunit. We infer that propofol may bind near the extracellular end of the betasubunit M3 segment. ..
  30. Ohnishi S, Saito H, Fukada A, Inui K. Distinct transport activity of tetraethylammonium from L-carnitine in rat renal brush-border membranes. Biochim Biophys Acta. 2003;1609:218-24 pubmed
  31. Trefzger J, Ronai A, Wassmer B, von Deimling O. Genetically defined lysosomal acetylesterase EC in the cauda epididymidis of mouse, rat, and man. Histochemistry. 1992;98:373-9 pubmed
    ..1.1.6). Control experiments involving isoelectric focusing revealed that this acetylesterase was identical with the genetically defined homologues ES-17, ES-6, and ES-A4 in mouse, rat, and man, respectively. ..
  32. Horigome T, Ogata F, Golding T, Korach K. Estradiol-stimulated proteolytic cleavage of the estrogen receptor in mouse uterus. Endocrinology. 1988;123:2540-8 pubmed
    ..A possible function of the 54 K ER under physiological conditions is discussed since the 54 K ER was also found in nuclear samples. This form of the ER still retains the ability to bind estradiol and DNA...
  33. Musch M, Chauncey B, Schmid E, Kinne R, Goldstein L. Mechanisms of mercurial and arsenical inhibition of tyrosine absorption in intestine of the winter flounder Pseudopleuronectus americanus. Toxicol Appl Pharmacol. 1990;104:59-66 pubmed
    ..Direct effects on Na-tyrosine cotransport may play a role in the inhibition observed with HgCl2, but not for PCMBS or OPA. ..
  34. Knop C, Stadler R, Sauer N, Lohaus G. AmSUT1, a sucrose transporter in collection and transport phloem of the putative symplastic phloem loader Alonsoa meridionalis. Plant Physiol. 2004;134:204-14 pubmed
    ..The data presented indicate that phloem loading of Suc and retrieval of Suc in A. meridionalis are at least partly mediated by the activity of AmSUT1 in addition to symplastic phloem loading. ..
  35. Gordon S, Ralston G. Solubilization and denaturation of monomeric actin from erythrocyte membranes by p-mercuribenzenesulfonate. Biochim Biophys Acta. 1990;1025:43-8 pubmed
    ..Subsequent inactivation also appears to be dependent on the reaction of further multiple sulfhydryl groups, possibly in buried regions of the actin molecule. ..
  36. Rodela T, Gilmour K, Walsh P, McDonald M. Cortisol-sensitive urea transport across the gill basolateral membrane of the gulf toadfish (Opsanus beta). Am J Physiol Regul Integr Comp Physiol. 2009;297:R313-22 pubmed publisher
  37. Mueckler M, Makepeace C. Transmembrane segment 5 of the Glut1 glucose transporter is an amphipathic helix that forms part of the sugar permeation pathway. J Biol Chem. 1999;274:10923-6 pubmed
  38. Delétage Grandon C, Chollet J, Faucher M, Rocher F, Komor E, Bonnemain J. Carrier-mediated uptake and phloem systemy of a 350-Dalton chlorinated xenobiotic with an alpha-amino acid function. Plant Physiol. 2001;125:1620-32 pubmed
    ..Our results show that it is possible to design synthesis of large-size xenobiotics (approximately 350 D) with a lipophilic pole, exhibiting high mobility within the vascular system. ..
  39. Jiang P, Yu T, Perng W, Hwang L. Pore-to-pore hopping model for the interpretation of the pulsed gradient spin echo attenuation of water diffusion in cell suspension systems. Biophys J. 2001;80:2493-504 pubmed
    ..It predicts that the alignment of erythrocytes will become normal to the magnetic field direction after the addition of p-CMBS, and inspection using a light microscope confirms that result. ..
  40. Bragg P, Hou C. The presence of an aqueous cavity in the proton-pumping pathway of the pyridine nucleotide transhydrogenase of Escherichia coli is suggested by the reaction of the enzyme with sulfhydryl inhibitors. Arch Biochem Biophys. 2000;380:141-50 pubmed
    ..A further series of mutants of betaGlu124 on helix 10 confirms the proposal (P. D. Bragg and C. Hou, Arch. Biochem. Biophys. 363, 182-190, 1999) that this residue is involved in passive permeation of protons across domain II. ..
  41. Thelwall P, Grant S, Stanisz G, Blackband S. Human erythrocyte ghosts: exploring the origins of multiexponential water diffusion in a model biological tissue with magnetic resonance. Magn Reson Med. 2002;48:649-57 pubmed
    ..We anticipate that this model system could be used to investigate compartmental diffusion effects to simulate a range of pathologies, especially ischemic stroke. ..
  42. Lebendiker M, Schuldiner S. Identification of residues in the translocation pathway of EmrE, a multidrug antiporter from Escherichia coli. J Biol Chem. 1996;271:21193-9 pubmed
    ..The results demonstrate the existence of a domain accessible only to substrates and provide a unique tool for studying the substrate permeation pathway of an ion-coupled transporter. ..
  43. Tenno M, Toba S, Kézdy F, Elhammer A, Kurosaka A. Identification of two cysteine residues involved in the binding of UDP-GalNAc to UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferase 1 (GalNAc-T1). Eur J Biochem. 2002;269:4308-16 pubmed
    ..Our results indicate that Cys212 and Cys214 are sites of PCMPS modification, and that these cysteine residues are involved in the interaction with the UDP moiety of UDP-GalNAc. ..
  44. McAlear S, Bevensee M. A cysteine-scanning mutagenesis study of transmembrane domain 8 of the electrogenic sodium/bicarbonate cotransporter NBCe1. J Biol Chem. 2006;281:32417-27 pubmed
    ..In summary, TMD8 residues of NBCe1, particularly L750, are involved in ion translocation, and accessibility is influenced by the state of transporter activity. ..
  45. Takasawa K, Suzuki H, Sugiyama Y. Transport properties of 3'-azido-3'-deoxythymidine and 2',3'-dideoxyinosine in the rat choroid plexus. Biopharm Drug Dispos. 1997;18:611-22 pubmed
    ..These results suggest that DDI is transported, at least in part, by the transport system for organic anions located on the rat choroid plexus, whereas AZT is recognized, but not transported by this system. ..
  46. Asaka J, Terada T, Tsuda M, Katsura T, Inui K. Identification of essential histidine and cysteine residues of the H+/organic cation antiporter multidrug and toxin extrusion (MATE). Mol Pharmacol. 2007;71:1487-93 pubmed
    ..In the case of DEPC, no such protective effects were observed. These results suggest that histidine and cysteine residues are required for MATE1 to function and that cysteine residues may serve as substrate-recognition sites. ..
  47. Hosoi R, Matsuyama Y, Hirose S, Koyama Y, Matsuda T, Gee A, et al. Characterization of (14)C-acetate uptake in cultured rat astrocytes. Brain Res. 2009;1253:69-73 pubmed publisher
    ..These results suggest that glutamate stimulation and changes in Ca(2+) and Na(+) concentrations might have important roles in regulation of (14)C-acetate uptake in cultured rat astrocytes. ..
  48. Slugoski M, Ng A, Yao S, Lin C, Mulinta R, Cass C, et al. Substituted cysteine accessibility method analysis of human concentrative nucleoside transporter hCNT3 reveals a novel discontinuous region of functional importance within the CNT family motif (G/A)XKX3NEFVA(Y/M/F). J Biol Chem. 2009;284:17281-92 pubmed publisher
  49. Rocher F, Chollet J, Legros S, Jousse C, Lemoine R, Faucher M, et al. Salicylic acid transport in Ricinus communis involves a pH-dependent carrier system in addition to diffusion. Plant Physiol. 2009;150:2081-91 pubmed publisher
    ..e. the step preceding the symplastic transport to veins) insensitive to pCMBS occurs via the ion-trap mechanism, whereas apoplastic vein loading involves a carrier-mediated mechanism (which is targeted by pCMBS) in addition to diffusion. ..
  50. Mengual R, El Abida K, Mouaffak N, Rieu M, Beaudry M. Pyruvate shuttle in muscle cells: high-affinity pyruvate transport sites insensitive to trans-lactate efflux. Am J Physiol Endocrinol Metab. 2003;285:E1196-204 pubmed
    ..The high-affinity type II sites act as a specific pyruvate shuttle and constitute an essential relay for the intracellular lactate shuttle. ..
  51. Fann M, Busch A, Maloney P. Functional characterization of cysteine residues in GlpT, the glycerol 3-phosphate transporter of Escherichia coli. J Bacteriol. 2003;185:3863-70 pubmed
  52. Hall J, Maloney P. Transmembrane segment 11 of UhpT, the sugar phosphate carrier of Escherichia coli, is an alpha-helix that carries determinants of substrate selectivity. J Biol Chem. 2001;276:25107-13 pubmed
    ..We suggest that this feature is a general property of carrier proteins in the major facilitator superfamily and that for this reason residues in TM11 will serve to carry determinants of substrate selectivity. ..
  53. Chiles T, Dudeck Collart K, Kilberg M. Inactivation of amino acid transport in rat hepatocytes and hepatoma cells by PCMBS. Am J Physiol. 1988;255:C340-5 pubmed
    ..These results illustrate the significant differences that exist between normal and transformed liver cells in respect to amino acid transport inactivation by sulfhydryl reagents. ..