sulfuric acid esters


Summary: Organic esters of sulfuric acid.

Top Publications

  1. Bergé Lefranc D, Chaspoul F, Calaf R, Charpiot P, Brunet P, Gallice P. Binding of p-cresylsulfate and p-cresol to human serum albumin studied by microcalorimetry. J Phys Chem B. 2010;114:1661-5 pubmed publisher
    ..The low fraction of bound toxin (13-20%) appears to be insufficient to link strong binding to poor removal of this toxin by hemodialysis. ..
  2. Flanigan A, Gardner J. Interaction of the Gifsy-1 Xis protein with the Gifsy-1 attP sequence. J Bacteriol. 2007;189:6303-11 pubmed
    ..Our studies suggest that, while the Gifsy-1 Xis does not require additional factors for specific and high-affinity binding, it may form a microfilament on DNA similar to that described for the phage lambda Xis protein...
  3. Meyer T, Hostetter T. Uremic solutes from colon microbes. Kidney Int. 2012;81:949-954 pubmed publisher
    ..To the extent that they are toxic, suppressing their production could improve the health of renal failure patients without the need for more intensive or prolonged dialysis. ..
  4. Schepers E, Meert N, Glorieux G, Goeman J, Van der Eycken J, Vanholder R. P-cresylsulphate, the main in vivo metabolite of p-cresol, activates leucocyte free radical production. Nephrol Dial Transplant. 2007;22:592-6 pubmed
    ..This effect could contribute to the propensity to vascular disease in the uraemic population. ..
  5. Vishchuk O, Ermakova S, Zvyagintseva T. Sulfated polysaccharides from brown seaweeds Saccharina japonica and Undaria pinnatifida: isolation, structural characteristics, and antitumor activity. Carbohydr Res. 2011;346:2769-76 pubmed publisher
    ..These results indicated that the use of sulfated polysaccharides from brown seaweeds S. japonica and U. pinnatifida might be a potential approach for cancer treatment. ..
  6. Raff A, Meyer T, Hostetter T. New insights into uremic toxicity. Curr Opin Nephrol Hypertens. 2008;17:560-5 pubmed publisher
    ..It is hoped that as knowledge emerges on the causes and consequences of uremia, we are embarking on an era not only of new insights but also new and effective treatments for patients with the ill effects of uremia. ..
  7. Wikoff W, Nagle M, Kouznetsova V, Tsigelny I, Nigam S. Untargeted metabolomics identifies enterobiome metabolites and putative uremic toxins as substrates of organic anion transporter 1 (Oat1). J Proteome Res. 2011;10:2842-51 pubmed publisher
    ..The possibility that some of the compounds identified may be part of a larger remote sensing and signaling pathway is also discussed. ..
  8. Cordero P, Kladwang W, Vanlang C, Das R. Quantitative dimethyl sulfate mapping for automated RNA secondary structure inference. Biochemistry. 2012;51:7037-9 pubmed
    ..These results establish DMS mapping, an already routine technique, as a quantitative tool for unbiased RNA secondary structure modeling. ..
  9. Wu I, Hsu K, Lee C, Sun C, Hsu H, Tsai C, et al. p-Cresyl sulphate and indoxyl sulphate predict progression of chronic kidney disease. Nephrol Dial Transplant. 2011;26:938-47 pubmed publisher
    ..In addition to traditional and uraemia-related risk factors such as renal function, serum IS and PCS levels may help in predicting the risk of renal progression in patients having different stages of CKD. ..

More Information


  1. Liabeuf S, Barreto D, Barreto F, Meert N, Glorieux G, Schepers E, et al. Free p-cresylsulphate is a predictor of mortality in patients at different stages of chronic kidney disease. Nephrol Dial Transplant. 2010;25:1183-91 pubmed publisher
    ..Serum levels of free and total p-cresylsulphate (the main in vivo circulating metabolites of p-cresol) were elevated in later CKD stages. However, only free p-cresylsulphate seems to be a predictor of survival in CKD. ..
  2. Surratt J, Kroll J, Kleindienst T, Edney E, Claeys M, Sorooshian A, et al. Evidence for organosulfates in secondary organic aerosol. Environ Sci Technol. 2007;41:517-27 pubmed
    ..S. It is likely that this pathway is important for other biogenic terpenes, and may be important in the formation of humic-like substances (HULIS) in ambient aerosol. ..
  3. Alekseyenko T, Zhanayeva S, Venediktova A, Zvyagintseva T, Kuznetsova T, Besednova N, et al. Antitumor and antimetastatic activity of fucoidan, a sulfated polysaccharide isolated from the Okhotsk Sea Fucus evanescens brown alga. Bull Exp Biol Med. 2007;143:730-2 pubmed
    ..Fucoidan in a dose of 25 mg/kg potentiated the toxic effect of cyclophosphamide...
  4. Surratt J, Gómez González Y, Chan A, Vermeylen R, Shahgholi M, Kleindienst T, et al. Organosulfate formation in biogenic secondary organic aerosol. J Phys Chem A. 2008;112:8345-78 pubmed publisher
    ..S., can be as high as 30%. ..
  5. Darer A, Cole Filipiak N, O Connor A, Elrod M. Formation and stability of atmospherically relevant isoprene-derived organosulfates and organonitrates. Environ Sci Technol. 2011;45:1895-902 pubmed publisher
    ..This finding provides a potential explanation for the fact that organosulfates are more commonly detected in ambient SOA than are organonitrates. ..
  6. Meijers B, de Loor H, Bammens B, Verbeke K, Vanrenterghem Y, Evenepoel P. p-Cresyl sulfate and indoxyl sulfate in hemodialysis patients. Clin J Am Soc Nephrol. 2009;4:1932-8 pubmed publisher
    ..Indoxyl sulfate and p-cresyl sulfate are both valid markers to monitor behavior of protein-bound solutes during dialysis. Finally, they are competitive binding inhibitors for the same albumin binding site. ..
  7. Hatch L, Creamean J, Ault A, Surratt J, Chan M, Seinfeld J, et al. Measurements of isoprene-derived organosulfates in ambient aerosols by aerosol time-of-flight mass spectrometry-part 2: temporal variability and formation mechanisms. Environ Sci Technol. 2011;45:8648-55 pubmed publisher
    ..This work highlights the potential for additional SOA formation pathways in biogenically influenced urban regions to enhance the organic aerosol burden. ..
  8. Rocha H, Moraes F, Trindade E, Franco C, Torquato R, Veiga S, et al. Structural and hemostatic activities of a sulfated galactofucan from the brown alga Spatoglossum schroederi. An ideal antithrombotic agent?. J Biol Chem. 2005;280:41278-88 pubmed
    ..In this case the highly sulfated heparan sulfate produced by the endothelial cells is in fact the antithrombotic agent. Our results suggested that this sulfated galactofucan may have a potential application as an antithrombotic drug. ..
  9. de Loor H, Bammens B, Evenepoel P, De Preter V, Verbeke K. Gas chromatographic-mass spectrometric analysis for measurement of p-cresol and its conjugated metabolites in uremic and normal serum. Clin Chem. 2005;51:1535-8 pubmed
  10. Yim J, Son E, Pyo S, Lee H. Novel sulfated polysaccharide derived from red-tide microalga Gyrodinium impudicum strain KG03 with immunostimulating activity in vivo. Mar Biotechnol (NY). 2005;7:331-8 pubmed
    ..The p-KG03 polysaccharide may be useful for the development of biotechnological and pharmaceutical products that incorporate bioactive marine exopolysaccharides. ..
  11. Bates S, Zhou N, Federico L, Xia L, O Connor T. Repair of cyclobutane pyrimidine dimers or dimethylsulfate damage in DNA is identical in normal or telomerase-immortalized human skin fibroblasts. Nucleic Acids Res. 2005;33:2475-85 pubmed
    ..Thus, telomerase expression and consequent immortalization of skin fibroblasts do not alter nucleotide or base excision repair in human cells. ..
  12. Saha T, Usdin K. Tetraplex formation by the progressive myoclonus epilepsy type-1 repeat: implications for instability in the repeat expansion diseases. FEBS Lett. 2001;491:184-7 pubmed
    ..However, EPM1 is unique in that tetraplexes are the only structures likely to form in long unpaired repeat tracts under physiological conditions. ..
  13. Chevolot L, Foucault A, Chaubet F, Kervarec N, Sinquin C, Fisher A, et al. Further data on the structure of brown seaweed fucans: relationships with anticoagulant activity. Carbohydr Res. 1999;319:154-65 pubmed
    ..Anticoagulant activity is apparently related not only to MW and sulfation content, as previously determined, but also (and more precisely) to 2-O-sulfation and 2,3-O-disulfation levels. ..
  14. Martinez A, Recht N, Hostetter T, Meyer T. Removal of P-cresol sulfate by hemodialysis. J Am Soc Nephrol. 2005;16:3430-6 pubmed
    ..PCS is poorly removed by hemodialysis because its clearance is limited by protein binding and the ratio of its volume of distribution to its clearance is high. ..
  15. Yang S, Chan T, Pomponi S, Chen G, Loebenberg D, Wright A, et al. Structure elucidation of a new antifungal sterol sulfate, Sch 575867, from a deep-water marine sponge (Family: Astroscleridae). J Antibiot (Tokyo). 2003;56:186-9 pubmed
  16. Pereira M, Vilela Silva A, Valente A, Mourao P. A 2-sulfated, 3-linked alpha-L-galactan is an anticoagulant polysaccharide. Carbohydr Res. 2002;337:2231-8 pubmed
  17. Pomin V, Pereira M, Valente A, Tollefsen D, Pavão M, Mourao P. Selective cleavage and anticoagulant activity of a sulfated fucan: stereospecific removal of a 2-sulfate ester from the polysaccharide by mild acid hydrolysis, preparation of oligosaccharides, and heparin cofactor II-dependent anticoagulant activity. Glycobiology. 2005;15:369-81 pubmed
    ..We speculate that the template mechanism may predominate over the allosteric effect in the case of the linear sulfated fucan inactivation of thrombin in the presence of heparin cofactor II...
  18. Vincent S, Reed J, Bergman A, Elmore C, Zhu B, Xu S, et al. Metabolism and excretion of the dipeptidyl peptidase 4 inhibitor [14C]sitagliptin in humans. Drug Metab Dispos. 2007;35:533-8 pubmed
    ..CYP3A4 was the major cytochrome P450 isozyme responsible for the limited oxidative metabolism of sitagliptin, with some minor contribution from CYP2C8. ..
  19. Grillo M, Hua F. Enantioselective formation of ibuprofen-S-acyl-glutathione in vitro in incubations of ibuprofen with rat hepatocytes. Chem Res Toxicol. 2008;21:1749-59 pubmed publisher
    ..Results from these studies demonstrate that the reactive I-CoA derivative, and not the I-1-O-G metabolite, plays a central role in the transacylation of GSH in incubations with rat hepatocytes. ..
  20. Cassolato J, Noseda M, Pujol C, Pellizzari F, Damonte E, Duarte M. Chemical structure and antiviral activity of the sulfated heterorhamnan isolated from the green seaweed Gayralia oxysperma. Carbohydr Res. 2008;343:3085-95 pubmed publisher
    ..The 3- and 2-linked rhamnosyl units are unsulfated (20%), disulfated (16%), and mostly monosulfated at C-2 (27%) and C-4 (37%). The branched and sulfated heterorhamnan had high and specific activity against herpes simplex virus. ..
  21. Kisby G, Olivas A, Park T, Churchwell M, Doerge D, Samson L, et al. DNA repair modulates the vulnerability of the developing brain to alkylating agents. DNA Repair (Amst). 2009;8:400-12 pubmed publisher
  22. Meyer T. The removal of protein-bound solutes by dialysis. J Ren Nutr. 2012;22:203-6 pubmed publisher
    ..A trial testing whether reducing bound solute levels clinically benefits dialysis patients is required to determine whether these measures should be adopted in routine clinical practice. ..
  23. Tong Z, Chandrasekaran A, Li H, Rotshteyn Y, Erve J, DeMaio W, et al. In vitro metabolism and identification of human enzymes involved in the metabolism of methylnaltrexone. Drug Metab Dispos. 2010;38:801-7 pubmed publisher
    ..AKR1C4 appeared to play a major role in the carbonyl reduction of MNTX, although multiple enzymes in the AKR1C subfamily may be involved. Human SULT2A1 and SULT1E1 were involved in MNTX sulfation. ..
  24. Zander W, Irschik H, Augustiniak H, Herrmann M, Jansen R, Steinmetz H, et al. Sulfangolids, macrolide sulfate esters from Sorangium cellulosum. Chemistry. 2012;18:6264-71 pubmed publisher
    ..The relative configuration of sulfangolid C (3) was assigned by extensive 1D and 2D NMR analysis and molecular modelling. In addition, the biosynthesis of 3 was studied by feeding experiments. ..
  25. Matsumori N, Hiradate Y, Shibata H, Oishi T, Shimma S, Toyoda M, et al. A novel sperm-activating and attracting factor from the ascidian Ascidia sydneiensis. Org Lett. 2013;15:294-7 pubmed publisher
    ..This study not only provides insight into the chemical tactics in sperm chemotaxis but demonstrates that the innovative techniques allow structure determination of natural products in trace amounts. ..
  26. Shu C, Chen X, Xia T, Zhang F, Gao S, Chen W. LC-MS/MS method for simultaneous determination of serum p-cresyl sulfate and indoxyl sulfate in patients undergoing peritoneal dialysis. Biomed Chromatogr. 2016;30:1782-1788 pubmed publisher
    ..The results showed that pCS and IS levels were partially correlated with renal function in CKD patients, and IS was directly related to serum creatinine and estimated glomerular filtration rate. ..
  27. Tsai T, Kao C, Wang J. Remediation of TCE-contaminated groundwater using acid/BOF slag enhanced chemical oxidation. Chemosphere. 2011;83:687-92 pubmed publisher
    ..Results also indicate that the pH value had a linear correlation with the observed first-order decay constant of TCE, and thus, lower pH caused a higher TCE oxidation rate. ..
  28. Cuoghi A, Caiazzo M, Bellei E, Monari E, Bergamini S, Palladino G, et al. Quantification of p-cresol sulphate in human plasma by selected reaction monitoring. Anal Bioanal Chem. 2012;404:2097-104 pubmed publisher
    ..The percentage recoveries indicate an optimal selectivity of the analytical method. The MRM assay to quantify pCS in a small amount of human plasma is rapid, highly sensitive, selective and with a good repeatability. ..
  29. Qiang Z, Ye Z, Hauck C, Murphy P, McCoy J, Widrlechner M, et al. Permeability of rosmarinic acid in Prunella vulgaris and ursolic acid in Salvia officinalis extracts across Caco-2 cell monolayers. J Ethnopharmacol. 2011;137:1107-12 pubmed publisher
  30. Moreira L, Pilo Veloso D, de Mello R, Coelho P, Nelson D. A study of the activity of 2-(alkylamino)-1-phenyl-1-ethanethiosulfuric acids against infection by Schistosoma mansoni in a murine model. Trans R Soc Trop Med Hyg. 2007;101:385-90 pubmed
    ..9% (male worms) and 84.8% (female worms) for 1c and 50.4% (male worms) and 94.2% (female worms) for 1f. ..
  31. Botnick I, Xue W, Bar E, Ibdah M, Schwartz A, Joel D, et al. Distribution of primary and specialized metabolites in Nigella sativa seeds, a spice with vast traditional and historical uses. Molecules. 2012;17:10159-77 pubmed publisher
    ..Chemical analyses shed light to the ample traditional and historical uses of this plant...
  32. Rajkumar K, Muthukumar M. Optimization of electro-oxidation process for the treatment of Reactive Orange 107 using response surface methodology. Environ Sci Pollut Res Int. 2012;19:148-60 pubmed publisher
    ..4, NaCl concentration of 0.08 M, and electrolysis time of 16.0 min show maximum color and COD removal of 98%, and 90%, respectively. UV-visible spectrum confirms the decoloration and FTIR spectra show the formation of intermediates. ..
  33. Mamidi R, Mannens G, Annaert P, Hendrickx J, Goris I, Bockx M, et al. Metabolism and excretion of RWJ-333369 [1,2-ethanediol, 1-(2-chlorophenyl)-, 2-carbamate, (S)-] in mice, rats, rabbits, and dogs. Drug Metab Dispos. 2007;35:566-75 pubmed
    ..Unchanged drug was the major plasma circulating drug-related substance in the preclinical species and humans. ..
  34. Bruzzoniti M, De Carlo R, Sarzanini C. Determination of sulfonic acids and alkylsulfates by ion chromatography in water. Talanta. 2008;75:734-9 pubmed publisher
    ..This is the first application of an ion-exchange chromatographic method to a seawater sample for this kind of analytes. ..
  35. Grinberg N, Albu F, Fandrick K, Iorgulescu E, Medvedovici A. Assay at low ppm level of dimethyl sulfate in starting materials for API synthesis using derivatization in ionic liquid media and LC-MS. J Pharm Biomed Anal. 2013;75:1-6 pubmed publisher
    ..05 ?g/ml DMS was achievable, with a linearity range up to 10 ?g/ml. Both analytical alternatives were applied to assay DMS in 4-(2-methoxyethyl)phenol, which is used as a starting material in the synthesis of metoprolol. ..
  36. Vogt C, Gödeke S, Treutler H, Weiss H, Schirmer M, Richnow H. Benzene oxidation under sulfate-reducing conditions in columns simulating in situ conditions. Biodegradation. 2007;18:625-36 pubmed
  37. Zhang H, Cui D, Wang B, Han Y, Balimane P, Yang Z, et al. Pharmacokinetic drug interactions involving 17alpha-ethinylestradiol: a new look at an old drug. Clin Pharmacokinet. 2007;46:133-57 pubmed
    ..An effort is made to relate this information to known clinical drug-drug interactions. The inhibition and induction of drug-metabolising enzymes by EE is also reviewed. ..
  38. Kelly A, Mozayani A. An overview of alcohol testing and interpretation in the 21st century. J Pharm Pract. 2012;25:30-6 pubmed publisher
    ..Finally, an explanation will be given on how to interpret alcohol levels as well as the extrapolation and calculation of blood alcohol levels at times prior to sample collection. ..
  39. de Britto D, de Assis O. Synthesis and mechanical properties of quaternary salts of chitosan-based films for food application. Int J Biol Macromol. 2007;41:198-203 pubmed
    ..Conversely the quaternization reaction increased the hardness of the parent sample, viz. for quaternary salt of dodecyl chitosan: maximum strain=2.6%; tensile strength=38.3 MPa and Young's modulus=1792 MPa. ..
  40. Tyburski J, Patterson A, Krausz K, Slavík J, Fornace A, Gonzalez F, et al. Radiation metabolomics. 1. Identification of minimally invasive urine biomarkers for gamma-radiation exposure in mice. Radiat Res. 2008;170:1-14 pubmed publisher
    ..This approach is useful for identifying mice exposed to gamma radiation and for developing metabolomic strategies for noninvasive radiation biodosimetry in humans. ..
  41. Sachsenmaier N, Handl S, Debeljak F, Waldsich C. Mapping RNA structure in vitro using nucleobase-specific probes. Methods Mol Biol. 2014;1086:79-94 pubmed publisher
    ..With this fast and inexpensive method local changes in RNA secondary and tertiary structure, as well as the formation of contacts between RNA and its ligands can be detected independent of the RNA's length. ..
  42. Mencherini T, Picerno P, Russo P, Meloni M, Aquino R. Composition of the fresh leaves and stems of Melissa officinalis and evaluation of skin irritation in a reconstituted human epidermis model. J Nat Prod. 2009;72:1512-5 pubmed publisher
  43. Yasumoto K, Nishigami A, Aoi H, Tsuchihashi C, Kasai F, Kusumi T, et al. Isolation and absolute configuration determination of aliphatic sulfates as the Daphnia kairomones inducing morphological defense of a phytoplankton-part 2. Chem Pharm Bull (Tokyo). 2008;56:129-32 pubmed
    ..heterospina (NIES-802). The absolute configuration at C4 of 1 was determined by Ohrui's method applied to alcohol 3. The absolute stereochemistry at C3 of 2 was determined by (1)H-NMR analysis of the (R)-1NMA ester of alcohol 11. ..
  44. Hernández Redondo A, Schroeck A, Kneubuehl B, Weinmann W. Determination of ethyl glucuronide and ethyl sulfate from dried blood spots. Int J Legal Med. 2013;127:769-75 pubmed publisher
    ..In addition, the Bland-Altman analysis and Mountain plot confirmed that the concentration differences that were measured in DBS specimens were not relevant. ..
  45. Tillotson G. Anti-Infectives Partnering and Deal-Making - fourth GTCbio summit. IDrugs. 2007;10:249-52 pubmed
  46. Lin C, Pan C, Liu H, Chuang C, Jayakumar T, Wang T, et al. The role of protein-bound uremic toxins on peripheral artery disease and vascular access failure in patients on hemodialysis. Atherosclerosis. 2012;225:173-9 pubmed publisher
    ..02). This study shows that the serum levels of PCS and IS were associated with PAD and total PCS could be a valuable determinant of access viability other than traditional or nontraditional risk factors in HD patients. ..
  47. Morini L, Politi L, Zucchella A, Polettini A. Ethyl glucuronide and ethyl sulphate determination in serum by liquid chromatography-electrospray tandem mass spectrometry. Clin Chim Acta. 2007;376:213-9 pubmed
    ..To our knowledge, this is the first fully validated method for the simultaneous determination of the two alcohol metabolites in serum. ..
  48. Jourde Chiche N, Dou L, Cerini C, Dignat George F, Brunet P. Vascular incompetence in dialysis patients--protein-bound uremic toxins and endothelial dysfunction. Semin Dial. 2011;24:327-37 pubmed publisher
  49. Lin C, Chen H, Pan C, Chuang C, Wang T, Sun F, et al. p-Cresylsulfate and indoxyl sulfate level at different stages of chronic kidney disease. J Clin Lab Anal. 2011;25:191-7 pubmed publisher
    ..01). Indoxyl sulfate and p-cresylsulfate level increased gradually while renal function declined and reached the peak at the stage of HD. Serum indoxyl sulfate level was closely associated with p-cresylsulfate level in CKD patients. ..
  50. Pérez Recalde M, Noseda M, Pujol C, Carlucci M, Matulewicz M. Sulfated mannans from the red seaweed Nemalion helminthoides of the South Atlantic. Phytochemistry. 2009;70:1062-8 pubmed publisher
    ..0 M NaCl (yield 0.5%) which contained single stubs of beta-D-xylose. A xylan, soluble in cetrimide solution, containing (1-->3, 1-->4)-linked beta-D-xylose residues, was also isolated in minor amount. ..
  51. Hayama T, Yada K, Onimaru S, Yoshida H, Todoroki K, Nohta H, et al. Simplified method for determination of polycarbamate fungicide in water samples by liquid chromatography with tandem mass spectrometry following derivatization with dimethyl sulfate. J Chromatogr A. 2007;1141:251-8 pubmed
    ..0, and 5.0 microg/L in the tap water and river water samples, and accuracy was achieved in the range of 94-109%. The proposed method can be applied to the determination of trace amounts of polycarbamate in environmental water samples. ..
  52. Wildauer M, Zemora G, Liebeg A, Heisig V, Waldsich C. Chemical probing of RNA in living cells. Methods Mol Biol. 2014;1086:159-76 pubmed publisher
    ..Importantly, in vivo chemical probing can be easily adapted to study RNAs in different cell types. ..
  53. Fiorucci S, Distrutti E, Bifulco G, D Auria M, Zampella A. Marine sponge steroids as nuclear receptor ligands. Trends Pharmacol Sci. 2012;33:591-601 pubmed publisher
    ..These findings pave the way to the development of novel FXR and PXR agonists and antagonists to target human diseases...