The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Mesylate     methanesulfonic acid

Synonyms: Sulfomethane, PubChem2058, PubChem11149, AGN-PC-0CMCAX, NSC-3718, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of methanesulfonic acid


High impact information on methanesulfonic acid

  • These studies indicate that mitochondrial or nuclear targeting of MGMT protects hematopoietic cells against cell killing by BCNU, TMZ, and MMS, which is consistent with the possibility that mitochondrial DNA damage and nuclear DNA damage contribute equally to alkylating agent-induced cell killing during chemotherapy [6].
  • The formation of S-3-sulfopropylcysteine in proteins and the subsequent hydrolysis of the proteins with methanesulfonic acid are particularly useful for complete amino acid analysis at the picomole level using a single sample [7].
  • The key intermediate for these syntheses, 12-methoxy-DB[a,l]P, was successfully obtained by cyclization of 6-(3-methoxybenzyl)benzanthrone with methanesulfonic acid, which in turn was prepared by 1,4 conjugate addition of 3-methoxybenzyl magnesium bromide to benzanthrone [8].
  • Esterification of taxol using N,N-dialkylated amino acids gave 2'-amino acid esters of taxol, 2'-(N,N-dimethylglycyl)taxol (4) and 2'-[3-(N,N-diethylamino)propionyl]taxol as its methanesulfonic acid salt (5b), in good yield [9].
  • 8-Amino-3-deazaguanine, as its methanesulfonic acid (mesylate 7), exhibited an inhibition constant (IC50) of 9.9 microM against isolated mammalian PNP [10].

Chemical compound and disease context of methanesulfonic acid


Biological context of methanesulfonic acid

  • Twelve mutants with increased sensitivity to MMS and one mutant with increased sensitivity to histidine showed Mendelian segregation of the mutant phenotypes [14].
  • The close association of these putative transport genes to the MSAMO structural genes msmABCD suggested a role for these genes in transport of methanesulfonic acid (MSA) into M. methylovora. msmEFGH and msmABCD constituted two operons for the coordinated expression of MSAMO and the MSA transporter systems [15].
  • For MMS and ENU we followed cultures for several days, and found that WI-L2-NS cells underwent delayed apoptosis 3 to 5 days after treatment, in parallel with published observations with ionizing radiation [16].
  • The results of this in vivo study showed that TA had no suppressing effect on chromosome loss occurring spontaneously or after induction by MMS in mature spermatozoa [17].
  • The observed difference between MMS and MNU when combined with GEN would not have been predicted on the basis of a simplistic interpretation of DNA methylation as the mode of action and may be due to differences in the profile of DNA methylations and/or epigenetic effects [18].

Anatomical context of methanesulfonic acid

  • The data indicate that MMS and MNNG-induced cell death in mouse fibroblasts is triggered by the activation of the mitochondrial damage pathway and that apaf-1 is required for eliciting this response [19].
  • The SS breaks induced by MMS and 4NQO were largely repaired by HeLa cells during a 5-h post-treatment incubation [20].

Associations of methanesulfonic acid with other chemical compounds


Gene context of methanesulfonic acid

  • Sensitivity of dap1 strains to MMS is not due to loss of damage checkpoints [25].
  • The N-terminal region of Sgs1, which interacts with Top3, is required for complementation of MMS sensitivity and suppression of hyper-recombination in sgs1 disruptants [26].
  • Cleavage does not occur during necrosis or following exposure to H(2)O(2) or methanesulfonic acid methyl ester. p140 is unlikely to be able to functionally replace p261 in vivo, since it does not bind to PCNA or the other pol epsilon subunits [27].
  • Marinosulfonomonas methylotropha strain TR3 is a marine methylotroph that uses methanesulfonic acid (MSA) as a sole carbon and energy source [28].
  • Colony forming efficiency was measured for APC, MMS and ENU, and was greater in the p53 mutant cells [16].

Analytical, diagnostic and therapeutic context of methanesulfonic acid


  1. Isolation and characterization of proteins cross-linked to DNA by the antitumor agent methylene dimethanesulfonate and its hydrolytic product formaldehyde. O'Connor, P.M., Fox, B.W. J. Biol. Chem. (1989) [Pubmed]
  2. The importance of hydrophobicity in the mutagenicity of methanesulfonic acid esters with Salmonella typhimurium TA100. Debnath, A.K., Hansch, C. Chem. Res. Toxicol. (1993) [Pubmed]
  3. Different repair of O6-methylguanine occurring in DNA modified by MMS in vivo or in vitro. Sledziewska-Gójska, E., Torzewska, D. Mutat. Res. (1997) [Pubmed]
  4. Rat hepatocytes with elevated metallothionein expression are resistant to N-methyl-N'-nitro-N-nitrosoguanidine cytotoxicity. Moffatt, P., Plaa, G.L., Denizeau, F. Toxicol. Appl. Pharmacol. (1996) [Pubmed]
  5. Primary mouse fibroblasts deficient for c-Fos, p53 or for both proteins are hypersensitive to UV light and alkylating agent-induced chromosomal breakage and apoptosis. Lackinger, D., Kaina, B. Mutat. Res. (2000) [Pubmed]
  6. Mitochondrial targeting of human O6-methylguanine DNA methyltransferase protects against cell killing by chemotherapeutic alkylating agents. Cai, S., Xu, Y., Cooper, R.J., Ferkowicz, M.J., Hartwell, J.R., Pollok, K.E., Kelley, M.R. Cancer Res. (2005) [Pubmed]
  7. Derivatization of cysteine and cystine for fluorescence amino acid analysis with the o-phthaldialdehyde/2-mercaptoethanol reagent. Lee, K.S., Drescher, D.G. J. Biol. Chem. (1979) [Pubmed]
  8. Synthesis and tumor-initiating activity in mouse skin of dibenzo[a,l]pyrene syn- and anti-fjord-region diolepoxides. Gill, H.S., Kole, P.L., Wiley, J.C., Li, K.M., Higginbotham, S., Rogan, E.G., Cavalieri, E.L. Carcinogenesis (1994) [Pubmed]
  9. Synthesis and evaluation of some water-soluble prodrugs and derivatives of taxol with antitumor activity. Mathew, A.E., Mejillano, M.R., Nath, J.P., Himes, R.H., Stella, V.J. J. Med. Chem. (1992) [Pubmed]
  10. Synthesis of 8-amino-3-deazaguanine via imidazole precursors. Antitumor activity and inhibition of purine nucleoside phosphorylase. Berry, D.A., Gilbertsen, R.B., Cook, P.D. J. Med. Chem. (1986) [Pubmed]
  11. Antithrombotic effects of DMP 728, a platelet GPIIb/IIIa receptor antagonist, in a canine model of arterial thrombosis. Rote, W.E., Davis, J.H., Mousa, S.A., Reilly, T.M., Lucchesi, B.R. J. Cardiovasc. Pharmacol. (1994) [Pubmed]
  12. The effect of an Na+/H+ exchange inhibitor, SM-20550, on ischemia/reperfusion-induced endothelial dysfunction in isolated perfused rat hearts. Yamamoto, S., Matsui, K., Itoh, N., Ohashi, N. International journal of tissue reactions. (2001) [Pubmed]
  13. Chemotherapeutic management of bronchogenic carcinoma: trials with NSC-140117, a new methanesulfonic acid ester of aminoglycol. Gad-el-Mawia, N., Mahmoud, M., Osman, A., El-Morsi, B., El-Merzabani, M.M., Aboul-Enein, M., Sakurai, Y. Cancer chemotherapy reports. Part 1. (1975) [Pubmed]
  14. The isolation of mms- and histidine-sensitive mutants in Neurospora crassa. Delange, A.M., Mishra, N.C. Genetics (1981) [Pubmed]
  15. Identification, mutagenesis, and transcriptional analysis of the methanesulfonate transport operon of Methylosulfonomonas methylovora. Jamshad, M., De Marco, P., Pacheco, C.C., Hanczar, T., Murrell, J.C. Appl. Environ. Microbiol. (2006) [Pubmed]
  16. Fewer chromosome aberrations and earlier apoptosis induced by DNA synthesis inhibitors, a topoisomerase II inhibitor or alkylating agents in human cells with normal compared with mutant p53. Greenwood, S.K., Armstrong, M.J., Hill, R.B., Bradt, C.I., Johnson, T.E., Hilliard, C.A., Galloway, S.M. Mutat. Res. (1998) [Pubmed]
  17. Co-mutagenic effect of tannic acid on ring-X chromosome loss induced by mitomycin C in sperm cells of Drosophila melanogaster. Cunha, K.S., Reguly, M.L., Gimmler-Luz, M.C., Santos, J.H., Lehmann, M., de Andrade, H.H. Mutat. Res. (1994) [Pubmed]
  18. Different types of combination effects for the induction of micronuclei in mouse lymphoma cells by binary mixtures of the genotoxic agents MMS, MNU, and genistein. Lutz, W.K., Tiedge, O., Lutz, R.W., Stopper, H. Toxicol. Sci. (2005) [Pubmed]
  19. Apaf-1 deficient mouse fibroblasts are resistant to MNNG and MMS-induced apoptotic death without attenuation of Bcl-2 decline. Tomicic, M.T., Christmann, M., Fabian, K., Kaina, B. Toxicol. Appl. Pharmacol. (2005) [Pubmed]
  20. The formation and repair of single-strand breaks in DNA of cultured mammalian cells treated with UV-light, methylating agents or 4-nitroquinoline-1-oxide. Walker, I.G., Sridhar, R. Chem. Biol. Interact. (1976) [Pubmed]
  21. Isotope dilution gas chromatography/mass spectrometry method for the determination of methionine sulfoxide in protein. Sochaski, M.A., Jenkins, A.J., Lyons, T.J., Thorpe, S.R., Baynes, J.W. Anal. Chem. (2001) [Pubmed]
  22. Tryptophan in bovine rhodopsin: its content, spectral properties and environment. Rafferty, C.N., Muellenberg, C.G., Shichi, H. Biochemistry (1980) [Pubmed]
  23. Mechanism of increased susceptibility to 4-nitroquinoline-1-oxide in cultured skin fibroblasts from patients with familial polyposis coli. Akamatsu, N., Miyaki, M., Suzuki, K., Ono, T., Sasaki, M.S. Mutat. Res. (1983) [Pubmed]
  24. Misincorporation in DNA synthesis after modification of template or polymerase by MNNG, MMS and UV radiation. Miyaki, M., Suzuki, K., Aihara, M., Ono, T. Mutat. Res. (1983) [Pubmed]
  25. Saccharomyces cerevisiae Dap1p, a novel DNA damage response protein related to the mammalian membrane-associated progesterone receptor. Hand, R.A., Jia, N., Bard, M., Craven, R.J. Eukaryotic Cell (2003) [Pubmed]
  26. The N-terminal region of Sgs1, which interacts with Top3, is required for complementation of MMS sensitivity and suppression of hyper-recombination in sgs1 disruptants. Ui, A., Satoh, Y., Onoda, F., Miyajima, A., Seki, M., Enomoto, T. Mol. Genet. Genomics (2001) [Pubmed]
  27. Proteolysis of the human DNA polymerase epsilon catalytic subunit by caspase-3 and calpain specifically during apoptosis. Liu, W., Linn, S. Nucleic Acids Res. (2000) [Pubmed]
  28. Duplicate copies of genes encoding methanesulfonate monooxygenase in Marinosulfonomonas methylotropha strain TR3 and detection of methanesulfonate utilizers in the environment. Baxter, N.J., Scanlan, J., De Marco, P., Wood, A.P., Murrell, J.C. Appl. Environ. Microbiol. (2002) [Pubmed]
  29. Dehydration behavior of eprosartan mesylate dihydrate. Sheng, J., Venkatesh, G.M., Duddu, S.P., Grant, D.J. Journal of pharmaceutical sciences. (1999) [Pubmed]
  30. Amino acid analysis by high-performance liquid chromatography with methanesulfonic acid hydrolysis and 9-fluorenylmethylchloroformate derivatization. Malmer, M.F., Schroeder, L.A. J. Chromatogr. (1990) [Pubmed]
  31. Isotachophoretic separation of alkylsulfonates and determination of methanesulfonic acid as main component and as trace component in pharmaceutical drug substances. Meissner, T., Niess, M. Journal of chromatography. A. (2004) [Pubmed]
  32. HPLC analysis of fatty acyl-glycine in the aqueous methanesulfonic acid hydrolysates of N-terminally fatty acylated peptides. Okimura, K., Ohki, K., Nagai, S., Sakura, N. Biol. Pharm. Bull. (2003) [Pubmed]
  33. Effect of an Na+/H+ exchange inhibitor, SM-20550, on ischemic preconditioning in rabbits. Yamada, K., Matsui, K., Yamamoto, S., Kitano, M., Ohashi, N. International journal of tissue reactions. (2002) [Pubmed]
WikiGenes - Universities