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Chemical Compound Review

Xanthate     ethoxymethanedithioic acid

Synonyms: ETHYLXANTHATE, Ethyl xanthate, AG-G-34851, HSDB 5652, AC1L1RRS, ...
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Disease relevance of ethoxymethanedithioic acid


High impact information on ethoxymethanedithioic acid


Biological context of ethoxymethanedithioic acid

  • At 100 mM, ethylxanthate produced a slight stimulation in the rate of MC alkylation of NBP [6].
  • Here we examined the relationship between the site of ceramide deposition and inhibition of protein translation and induction of apoptosis by the antitumor/antiviral xanthate, D609 [11].
  • [reaction: see text] A short synthesis of the tricyclic skeleton of pleuromutilin is reported, featuring an unusually efficient 8-endo-trig radical cyclization of a xanthate precursor [12].
  • Dose-response kinetics revealed a synergistic interaction between the xanthate and the monocarbonic acid [13].
  • In vivo protection by the xanthate tricyclodecan-9-yl-xanthogenate against amyloid beta-peptide (1-42)-induced oxidative stress [14].

Anatomical context of ethoxymethanedithioic acid

  • The specific inhibitors of collagen biosynthesis 8,9-dihydroxy-7-methyl-benzo[b]quinolizinium bromide and tricyclodecane-9-yl xanthate arrested sea urchin embryo development at early blastula, prevented the invagination of the archenteron, and reverted the expression of type IV collagen-degrading activity to non-detectable levels [15].
  • Antitumoral activity of a xanthate compound. I. Cytotoxicity studies with neoplastic cell lines in vitro [16].
  • Both ethylxanthate and diethyldithiocarbamate can form highly lipophilic complexes with nickel and a facilitated penetration of these complexes through the cellular membranes of the tissues probably explains the increased uptake of the metal [17].
  • Xanthate derivatives were shown previously to display antitumor activity against transformed fibroblasts and lymphoma cells in combination with monocarboxylic acids [1] [16].

Associations of ethoxymethanedithioic acid with other chemical compounds

  • Without the cyano group, acid 26 and xanthate 27 were found to be more selective over Cdc25A (IC(50) = 5.1 microM and 1.1 microM, respectively) than toward CD45 (IC(50) > 100 microM, in each case), a receptor protein tyrosine phosphatase [18].
  • Gamma-carbonyl vinyl boronates can be prepared by a visible light induced radical chain addition of an S-acyl dithiocarbonate (xanthate) to the pinacol ester of vinyl boronic acid, followed by treatment with base [19].
  • Synthesis of tetrakis(cyclopropylmethyl)methane, a new symmetric product has been described using the radical mediated gem-diallylation of cyclopropylmethyl xanthate as a key step and its single crystal X-ray analysis established its C2-symmetry [20].
  • [reaction: see text] Cyano(ethoxycarbonothioylthio)methyl benzoate 3 has been prepared and shown to be an excellent one-carbon radical equivalent that can be applied for the introduction of an acyl unit via xanthate transfer radical addition to olefins [21].
  • The two xanthate complexes are characterized by (1)H NMR, IR, mass spectrometry, elemental analysis, and UV-vis techniques [22].

Gene context of ethoxymethanedithioic acid

  • Thus, these results provide evidence that the xanthate inhibits a TPA-induced phospholipase C activity in the intact cell [23].
  • The inactivation was mechanism-based and the loss in enzymatic activity was due to covalent binding of a reactive xanthate intermediate to the P450 2B1 apoprotein [24].
  • Further, upon disulfide formation, dixanthogens are reduced by glutathione reductase to a redox active xanthate [25].
  • With the exception of the C14 xanthate, virtually no loss of absorbance at 418 or 450 nm in the reduced-CO complex was observed [24].
  • Interpretation of colloidal dyeing of polyester fabrics pretreated with ethyl xanthogenate in terms of zeta potential and surface free energy balance [26].

Analytical, diagnostic and therapeutic context of ethoxymethanedithioic acid


  1. DNA and RNA virus species are inhibited by xanthates, a class of antiviral compounds with unique properties. Sauer, G., Amtmann, E., Melber, K., Knapp, A., Müller, K., Hummel, K., Scherm, A. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  2. The therapeutic efficacy of a xanthate compound on herpes simplex virus in skin lesions of mice and guinea-pigs. Amtmann, E., Hummel, K., Sauer, G. J. Gen. Virol. (1985) [Pubmed]
  3. Antiviral effects of xanthate D609 on the human respiratory syncytial virus growth cycle. Villanueva, N., Navarro, J., Cubero, E. Virology (1991) [Pubmed]
  4. Antiviral xanthate causes conformational changes in simian virus 40 DNA and chromatin. Waldeck, W. Oncology (1990) [Pubmed]
  5. Inhibition of the phosphorylation of the regulatory non-structural protein of vesicular stomatitis virus by an antiviral xanthate compound. Müller-Decker, K., Amtmann, E., Sauer, G. J. Gen. Virol. (1987) [Pubmed]
  6. Effects of glutathione and ethylxanthate on mitomycin C activation by isolated rat hepatic or EMT6 mouse mammary tumor nuclei. Kennedy, K.A., Mimnaugh, E.G., Trush, M.A., Sinha, B.K. Cancer Res. (1985) [Pubmed]
  7. The lysosomal transport of prosaposin requires the conditional interaction of its highly conserved d domain with sphingomyelin. Lefrancois, S., May, T., Knight, C., Bourbeau, D., Morales, C.R. J. Biol. Chem. (2002) [Pubmed]
  8. Casein kinase 2-mediated phosphorylation of respiratory syncytial virus phosphoprotein P is essential for the transcription elongation activity of the viral polymerase; phosphorylation by casein kinase 1 occurs mainly at Ser(215) and is without effect. Dupuy, L.C., Dobson, S., Bitko, V., Barik, S. J. Virol. (1999) [Pubmed]
  9. Interruption of growth signal transduction by an antiviral and antitumoral xanthate compound. Müller-Decker, K., Doppler, C., Amtmann, E., Sauer, G. Exp. Cell Res. (1988) [Pubmed]
  10. Synthesis and structure-activity relationship of novel antitumoral platinum xanthate complexes. Friebolin, W., Schilling, G., Zöller, M., Amtmann, E. J. Med. Chem. (2004) [Pubmed]
  11. The role of de novo ceramide synthesis in the mechanism of action of the tricyclic xanthate D609. Perry, R.J., Ridgway, N.D. J. Lipid Res. (2004) [Pubmed]
  12. A concise synthesis of the tricyclic skeleton of pleuromutilin and a new approach to cycloheptenes. Bacqué, E., Pautrat, F., Zard, S.Z. Org. Lett. (2003) [Pubmed]
  13. Synergistic antiviral effect of xanthates and ionic detergents. Amtmann, E., Müller-Decker, K., Hoss, A., Schalasta, G., Doppler, C., Sauer, G. Biochem. Pharmacol. (1987) [Pubmed]
  14. In vivo protection by the xanthate tricyclodecan-9-yl-xanthogenate against amyloid beta-peptide (1-42)-induced oxidative stress. Perluigi, M., Joshi, G., Sultana, R., Calabrese, V., De Marco, C., Coccia, R., Butterfield, D.A. Neuroscience (2006) [Pubmed]
  15. Expression of type IV collagen-degrading activity during early embryonal development in the sea urchin and the arresting effects of collagen synthesis inhibitors on embryogenesis. Karakiulakis, G., Papakonstantinou, E., Maragoudakis, M.E., Misevic, G.N. J. Cell. Biochem. (1993) [Pubmed]
  16. Antitumoral activity of a xanthate compound. I. Cytotoxicity studies with neoplastic cell lines in vitro. Schick, H.D., Amtmann, E., Berdel, W.E., Danhauser-Riedl, S., Reichert, A., Steinhauser, G., Rastetter, J., Sauer, G. Cancer Lett. (1989) [Pubmed]
  17. Mobilization of nickel by potassium ethylxanthate in mice: comparison with sodium diethyldithiocarbamate and effect of intravenous versus oral administration. Jasim, S., Tjälve, H. Toxicol. Lett. (1986) [Pubmed]
  18. Syntheses and biological activities of a novel group of steroidal derived inhibitors for human Cdc25A protein phosphatase. Peng, H., Xie, W., Otterness, D.M., Cogswell, J.P., McConnell, R.T., Carter, H.L., Powis, G., Abraham, R.T., Zalkow, L.H. J. Med. Chem. (2001) [Pubmed]
  19. A convergent approach to gamma-carbonyl vinyl boronates. Heinrich, M.R., Sharp, L.A., Zard, S.Z. Chem. Commun. (Camb.) (2005) [Pubmed]
  20. An expedient synthesis of tetrakis(cyclopropylmethyl)methane. Ramana, C.V., Baquer, S.M., Gonnade, R.G., Gurjar, M.K. Chem. Commun. (Camb.) (2002) [Pubmed]
  21. Cyano(ethoxycarbonothioylthio)methyl benzoate: a novel one-carbon radical equivalent. Bagal, S.K., de Greef, M., Zard, S.Z. Org. Lett. (2006) [Pubmed]
  22. Synthesis, characterization, and luminescent properties of dinuclear gold(I) xanthate complexes: X-ray structure of [Au2(nBu-xanthate)2]. Mohamed, A.A., Kani, I., Ramirez, A.O., Fackler, J.P. Inorganic chemistry. (2004) [Pubmed]
  23. Interruption of TPA-induced signals by an antiviral and antitumoral xanthate compound: inhibition of a phospholipase C-type reaction. Müller-Decker, K. Biochem. Biophys. Res. Commun. (1989) [Pubmed]
  24. Mechanistic studies of cytochrome P450 2B1 inactivation by xanthates. Yanev, S.G., Kent, U.M., Roberts, E.S., Ballou, D.P., Hollenberg, P.F. Arch. Biochem. Biophys. (2000) [Pubmed]
  25. Derivatives of xanthic acid are novel antioxidants: application to synaptosomes. Lauderback, C.M., Drake, J., Zhou, D., Hackett, J.M., Castegna, A., Kanski, J., Tsoras, M., Varadarajan, S., Butterfield, D.A. Free Radic. Res. (2003) [Pubmed]
  26. Interpretation of colloidal dyeing of polyester fabrics pretreated with ethyl xanthogenate in terms of zeta potential and surface free energy balance. Espinosa-Jiménez, M., Padilla-Weigand, R., Ontiveros-Ortega, A., Ramos-Tejada, M.M., Perea-Carpio, R. Journal of colloid and interface science. (2003) [Pubmed]
  27. Systemic treatment of a human epidermoid non-small cell lung carcinoma xenograft with a xanthate compound causes extensive intratumoral necrosis. Sauer, G., Amtmann, E., Hofmann, W. Cancer Lett. (1990) [Pubmed]
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