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Chemical Compound Review

divinylsulfone     1-ethenylsulfonylethene

Synonyms: vinyl sulphone, V3700_ALDRICH, VINYL SULFONE, CHEMBL349205, CCRIS 4349, ...
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Disease relevance of Divinyl sulfone


High impact information on Divinyl sulfone

  • Proteasome inhibitor studies with carboxybenzyl-leucyl-leucyl-leucine vinyl sulfone suggest an HCMV-associated enhancement of Jak1 protein degradation [6].
  • Resistant parasites grown in the absence of the vinyl sulfone for 12 weeks showed partial reversion, with increased inhibitor sensitivity and apparent decreases in copy numbers of falcipain-2 and falcipain-3 [7].
  • To identify deneddylases, proteases with specificity for hydrolysis of Nedd8 derivatives, a facile method was developed for the synthesis of Nedd8 amidomethylcoumarin (a substrate) and Nedd8 vinyl sulfone (an inhibitor) [8].
  • The deubiquitinating enzyme UCH-L3 is labeled by both ubiquitin vinyl sulfone and Nedd8 vinyl sulfone [8].
  • The change in binding properties was monitored by fluorescence resonance energy transfer between Lucifer Yellow vinyl sulfone covalently bound to one alpha subunit and trinitrophenyl-ATP (TNP-ATP) tightly bound to nucleotide binding site 1 [9].

Biological context of Divinyl sulfone

  • Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5 [10].
  • Peptidomimetic vinyl sulfone and epoxide inhibitors designed to interact with the S2, S1 and S' subsites of the active site cleft revealed differences between rhodesain and the related trypanosome protease cruzain [11].
  • Compared to ethylvinyl sulfone, divinyl sulfone was more than 8 times more potent in causing either ATP depletion or cell death [12].

Anatomical context of Divinyl sulfone


Associations of Divinyl sulfone with other chemical compounds


Gene context of Divinyl sulfone


Analytical, diagnostic and therapeutic context of Divinyl sulfone

  • Expression, purification, crystallization and preliminary X-ray diffraction studies of human cathepsin F complexed with an irreversible vinyl sulfone inhibitor [19].
  • An HPLC method is described for the electrochemiluminescence (ECL) detection of amino acids, following cycloaddition reaction of their amino groups with divinyl sulfone (DVS), using electrogenerated tris(bipyridine)ruthenium(III) [20].
  • Structural and oxygen-binding properties of divinyl-sulfone-reacted bovine hemoglobin as a function of protein ligation state and reactant concentration [21].
  • Hyaluronan (HA) gels (hylans) crosslinked with divinyl sulfone (DVS) are highly biocompatible and can be structurally modified to obtain desired mechanical properties that are attractive for their use as tissue-engineering scaffolds [22].


  1. Specific and covalent targeting of conjugating and deconjugating enzymes of ubiquitin-like proteins. Hemelaar, J., Borodovsky, A., Kessler, B.M., Reverter, D., Cook, J., Kolli, N., Gan-Erdene, T., Wilkinson, K.D., Gill, G., Lima, C.D., Ploegh, H.L., Ovaa, H. Mol. Cell. Biol. (2004) [Pubmed]
  2. Active site-directed inhibitors of Rhodococcus 20 S proteasome. Kinetics and mechanism. Mc Cormack, T., Baumeister, W., Grenier, L., Moomaw, C., Plamondon, L., Pramanik, B., Slaughter, C., Soucy, F., Stein, R., Zühl, F., Dick, L. J. Biol. Chem. (1997) [Pubmed]
  3. Crystal structure of HslUV complexed with a vinyl sulfone inhibitor: corroboration of a proposed mechanism of allosteric activation of HslV by HslU. Sousa, M.C., Kessler, B.M., Overkleeft, H.S., McKay, D.B. J. Mol. Biol. (2002) [Pubmed]
  4. The 20S proteasome of Streptomyces coelicolor. Nagy, I., Tamura, T., Vanderleyden, J., Baumeister, W., De Mot, R. J. Bacteriol. (1998) [Pubmed]
  5. Relationship between sulfhydryl reactivity and toxicity of vinyl sulfone molluscicidal agents. La Rocca, P.T., Carlson, G.P., Fuller, G.C. Toxicol. Appl. Pharmacol. (1975) [Pubmed]
  6. Human cytomegalovirus inhibits major histocompatibility complex class II expression by disruption of the Jak/Stat pathway. Miller, D.M., Rahill, B.M., Boss, J.M., Lairmore, M.D., Durbin, J.E., Waldman, J.W., Sedmak, D.D. J. Exp. Med. (1998) [Pubmed]
  7. Selection of cysteine protease inhibitor-resistant malaria parasites is accompanied by amplification of falcipain genes and alteration in inhibitor transport. Singh, A., Rosenthal, P.J. J. Biol. Chem. (2004) [Pubmed]
  8. Identification and characterization of DEN1, a deneddylase of the ULP family. Gan-Erdene, T., Nagamalleswari, K., Yin, L., Wu, K., Pan, Z.Q., Wilkinson, K.D. J. Biol. Chem. (2003) [Pubmed]
  9. Substrate binding-induced alteration of nucleotide binding site properties of chloroplast coupling factor 1. Shapiro, A.B., McCarty, R.E. J. Biol. Chem. (1990) [Pubmed]
  10. Regioselective reduction of 3-sulfonyl glutarimides to 3,4-dihydro-5-sulfonylpyridin-2-ones. Formal synthesis of the indolizidine 8a-epi-dendroprimine. Hsu, R.T., Cheng, L.M., Chang, N.C., Tai, H.M. J. Org. Chem. (2002) [Pubmed]
  11. Active site mapping, biochemical properties and subcellular localization of rhodesain, the major cysteine protease of Trypanosoma brucei rhodesiense. Caffrey, C.R., Hansell, E., Lucas, K.D., Brinen, L.S., Alvarez Hernandez, A., Cheng, J., Gwaltney, S.L., Roush, W.R., Stierhof, Y.D., Bogyo, M., Steverding, D., McKerrow, J.H. Mol. Biochem. Parasitol. (2001) [Pubmed]
  12. Glyceraldehyde-3-phosphate dehydrogenase as a biochemical marker of cytotoxicity by vinyl sulfones in cultured murine spleen lymphocytes. Choi, D.S., Kim, Y.B., Lee, Y.H., Cha, S.H., Sok, D.E. Cell Biol. Toxicol. (1995) [Pubmed]
  13. Population growth impairment of sulfur-containing compounds to Tetrahymena pyriformis. Schultz, T.W., Sinks, G.D., Miller, L.A. Environ. Toxicol. (2001) [Pubmed]
  14. Crystal structure of human cathepsin V. Somoza, J.R., Zhan, H., Bowman, K.K., Yu, L., Mortara, K.D., Palmer, J.T., Clark, J.M., McGrath, M.E. Biochemistry (2000) [Pubmed]
  15. Localization of rat cathepsin K in osteoclasts and resorption pits: inhibition of bone resorption and cathepsin K-activity by peptidyl vinyl sulfones. Xia, L., Kilb, J., Wex, H., Li, Z., Lipyansky, A., Breuil, V., Stein, L., Palmer, J.T., Dempster, D.W., Brömme, D. Biol. Chem. (1999) [Pubmed]
  16. The crystal structure of human cathepsin F and its implications for the development of novel immunomodulators. Somoza, J.R., Palmer, J.T., Ho, J.D. J. Mol. Biol. (2002) [Pubmed]
  17. Influences of energization and nucleotide binding on the reaction of Lucifer Yellow vinyl sulfone with the alpha subunits of the chloroplast ATP synthase. Cunningham, K.M., McCarty, R.E. Biochemistry (2000) [Pubmed]
  18. Inhibitors of the eukaryotic 20S proteasome core particle: a structural approach. Groll, M., Huber, R. Biochim. Biophys. Acta (2004) [Pubmed]
  19. Expression, purification, crystallization and preliminary X-ray diffraction studies of human cathepsin F complexed with an irreversible vinyl sulfone inhibitor. Ho, J.D., Meltser, Y., Buggy, J.J., Palmer, J.T., Elrod, K.C., Chan, H., Mortara, K.D., Somoza, J.R. Acta Crystallogr. D Biol. Crystallogr. (2002) [Pubmed]
  20. Determination of aromatic and branched-chain amino acids in plasma by HPLC with electrogenerated Ru(bpy)3(3+) chemiluminescence detection. Uchikura, K. Chem. Pharm. Bull. (2003) [Pubmed]
  21. Structural and oxygen-binding properties of divinyl-sulfone-reacted bovine hemoglobin as a function of protein ligation state and reactant concentration. Ilan, E. Artificial cells, blood substitutes, and immobilization biotechnology. (1994) [Pubmed]
  22. Ultraviolet light-induced modification of crosslinked hyaluronan gels. Ramamurthi, A., Vesely, I. Journal of biomedical materials research. Part A. (2003) [Pubmed]
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