Genomes and Genes
Summary: Organic compounds that have the general formula R-SO-R. They are obtained by oxidation of mercaptans (analogous to the ketones). (From Hackh's Chemical Dictionary, 4th ed)
- Swinney D, Xu Y, Scarafia L, Lee I, Mak A, Gan Q, et al. A small molecule ubiquitination inhibitor blocks NF-kappa B-dependent cytokine expression in cells and rats. J Biol Chem. 2002;277:23573-81 pubmed..We propose that Ro106-9920 selectively inhibits an uncharacterized but essential ubiquitination activity associated with LPS- and TNFalpha-induced IkappaB(alpha) degradation and NF-kappaB activation. ..
- Honda E, Gin D. C2-hydroxyglycosylation with glycal donors. Probing the mechanism of sulfonium-mediated oxygen transfer to glycal enol ethers. J Am Chem Soc. 2002;124:7343-52 pubmed..These findings are consistent with the initial formation of a C2-sulfonium[bond]C1-oxosulfonium pyranosyl species upon activation of the glycal donor with Aryl(2)SO x Tf(2)O. ..
- Periclou A, Goldwater R, Lee S, Park D, Kim D, Cho K, et al. A comparative pharmacodynamic study of IY-81149 versus omeprazole in patients with gastroesophageal reflux disease. Clin Pharmacol Ther. 2000;68:304-11 pubmed..Administration of 10 and 20 mg IY-81149 produced a statistically significantly greater and prolonged suppression of gastric pH than 20 mg omeprazole. ..
- Myung S, Min H, Jin C, Kim M, Lee S, Chung G, et al. Identification of IY81149 and its metabolites in the rat plasma using the on-line HPLC/ESI mass spectrometry. Arch Pharm Res. 1999;22:189-93 pubmed..The CID technique allowed the sensitive identification of sulfonyl-IY81149 and hydroxy-IY81149 from the rat plasma. ..
- Tsuge K, Kataoka M, Seto Y. Determination of S-methyl-, S-propyl-, and S-propenyl-L-cysteine sulfoxides by gas chromatography-mass spectrometry after tert-butyldimethylsilylation. J Agric Food Chem. 2002;50:4445-51 pubmed..The contents of 1, 2, and 3 in commercial onion were estimated to be 0.3, 3.1, and 3.0 mg, respectively, per gram of fresh weight. ..
- Robinson M, Lawson J, Trudgett A, Hoey E, Fairweather I. The comparative metabolism of triclabendazole sulphoxide by triclabendazole-susceptible and triclabendazole-resistant Fasciola hepatica. Parasitol Res. 2004;92:205-10 pubmed..29% greater in the resistant flukes compared with the susceptible flukes. The results are discussed with regard to the mechanism of triclabendazole resistance in F. hepatica. ..
- He Y, Ma C, Yang Z, Zhou M, Xing Z, Ma J, et al. Highly enantioselective oxidation of phenyl methyl sulfide and its derivatives into optically pure (S)-sulfoxides with Rhodococcus sp. CCZU10-1 in an n-octane-water biphasic system. Appl Microbiol Biotechnol. 2013;97:10329-37 pubmed publisherEnantiopure sulfoxides can be prepared via the asymmetric oxidation of sulfides using sulfide monooxygenases...
- Fuessl S, Trapp O. Integration of on-column catalysis and EKC analysis: investigation of enantioselective sulfoxidations. Electrophoresis. 2012;33:1060-7 pubmed publisher..to perform high-throughput kinetic measurements of substrate libraries, rapid screening and investigation of stereolabile compounds, that is, chiral sulfoxides, and screening of reactions using only minute amounts of reagents.
- Darabi K. Proton-pump-inhibitor-induced hepatitis. South Med J. 2005;98:844-5 pubmed
- Bai J, Zambroń B, Vogel P. Amides in one pot from carboxylic acids and amines via sulfinylamides. Org Lett. 2014;16:604-7 pubmed publisher..It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their ?-epimerization. ..
- Moreno Escobosa M, Amat López J, Cruz Granados S, Moya Quesada M. Pancreatitis due to codeine. Allergol Immunopathol (Madr). 2005;33:175-7 pubmed..Allergy departments should be aware of possible non-immunological adverse. ..
- Matsuzawa T, Uchida K, Yoshida S, Hosoya T. Synthesis of Diverse o-Arylthio-Substituted Diaryl Ethers by Direct Oxythiolation of Arynes with Diaryl Sulfoxides Involving Migratory O-Arylation. Org Lett. 2017;19:5521-5524 pubmed publisherA diverse range of o-arylthio-substituted diaryl ethers has been synthesized by direct oxythiolation of arynes with diaryl sulfoxides that involves the formation of the C-O and C-S bonds followed by migratory O-arylation.
- Dean W, Šiaučiulis M, Storr T, Lewis W, Stockman R. Versatile C(sp(2) )-C(sp(3) ) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes. Angew Chem Int Ed Engl. 2016;55:10013-6 pubmed publisherThe reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98?% yield and greater than 99.5?% enantiomeric excess...
- Lee J, Harnly J. Free amino acid and cysteine sulfoxide composition of 11 garlic (Allium sativum L.) cultivars by gas chromatography with flame ionization and mass selective detection. J Agric Food Chem. 2005;53:9100-4 pubmed..The solid-phase extraction, alkylchloroformate derivatization, GC-FID, and GC-MS methods used in this study were simple and rapid, allowing 18 free amino acids in garlic to be separated within 10 min. ..
- Dunn D, Hostetler G, Iqbal M, Marcy V, Lin Y, Jones B, et al. Wake promoting agents: search for next generation modafinil, lessons learned: part III. Bioorg Med Chem Lett. 2012;22:3751-3 pubmed publisher..Extensive pharmacokinetic studies of a potent member of the series (compound 15) revealed that the wake promotion activity of the analog was likely due to an active metabolite (compound 3). ..
- Aschmann S, Tuazon E, Long W, Atkinson R. Kinetics and products of the gas-phase reactions of divinyl sulfoxide with OH and NO3 radicals and O3. J Phys Chem A. 2008;112:8723-30 pubmed publisher..5%. The data obtained here for DVSO are compared with literature data for the corresponding reactions of dimethyl sulfoxide. ..
- Ochiai M, Naito M, Miyamoto K, Hayashi S, Nakanishi W. Imination of sulfides and sulfoxides with sulfonylimino-lambda3-bromane under mild, metal-free conditions. Chemistry. 2010;16:8713-8 pubmed publisherExposure of sulfides and sulfoxides to trifluoromethanesulfonylimino(aryl)-lambda(3)-bromane in dichloromethane at 0 degrees C results in a facile transfer of the sulfonylimino group to sulfur atoms and affords N-triflylsulfilimines and -..
- Tsegay S, Williams R, Williams S. Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates. Carbohydr Res. 2012;357:16-22 pubmed publisherGlycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide...
- Lee E, Yoo K, Jifon J, Patil B. Characterization of shortday onion cultivars of 3 pungency levels with flavor precursor, free amino acid, sulfur, and sugar contents. J Food Sci. 2009;74:C475-80 pubmed publisher..This study indicates that onion pungency is primarily determined by the content of flavor precursor compounds and not by total S, total sugars, or individual/total free amino acids in shortday bulbs. ..
- Johnson C. Stability of pantoprazole in 0.9% sodium chloride injection in polypropylene syringes. Am J Health Syst Pharm. 2005;62:2410-2 pubmed
- Plowright A, Nilsson K, Antonsson M, Amin K, Broddefalk J, Jensen J, et al. Discovery of agonists of cannabinoid receptor 1 with restricted central nervous system penetration aimed for treatment of gastroesophageal reflux disease. J Med Chem. 2013;56:220-40 pubmed publisher..A range of compounds demonstrated a dose-dependent inhibition of transient lower esophageal sphincter relaxations in a dog model. ..
- Keiser J, Manneck T, Kirchhofer C, Braissant O. Isothermal microcalorimetry to study the activity of triclabendazole and its metabolites on juvenile and adult Fasciola hepatica. Exp Parasitol. 2013;133:265-8 pubmed publisher..05)h. In conclusion, IMC is useful to document drug effects on juvenile F. hepatica and since rapid technological developments in this field are occurring IMC might also hold promise to study adult F. hepatica in the near future. ..
- Aurisicchio C, Baciocchi E, Gerini M, Lanzalunga O. Thermal and photochemical racemization of chiral aromatic sulfoxides via the intermediacy of sulfoxide radical cations. Org Lett. 2007;9:1939-42 pubmedEfficient racemization of enantiomerically pure methyl aryl sulfoxides was obtained by N-methylquinolinium tetrafluoborate (NMQ+) sensitized photolysis and by one-electron oxidation catalyzed by tris(2,2'-bipyridyl)ruthenium(III) ..
- Uhlig S, Stanic A, Hofgaard I, Kluger B, Schuhmacher R, Miles C. Glutathione-Conjugates of Deoxynivalenol in Naturally Contaminated Grain Are Primarily Linked via the Epoxide Group. Toxins (Basel). 2016;8: pubmed..The identities of the conjugates were confirmed by LC-HRMS comparison with authentic standards, oxidation to the sulfoxides with hydrogen peroxide, and examination of product-ion spectra from LC-HRMS/MS analysis...
- Ramadan A, Mandil H. Spectrophotometric determination of carbinoxamine maleate in pharmaceutical formulations by ternary complex formation with Cu(II) and eosin. Anal Biochem. 2006;353:133-7 pubmed..87-1.55%). The method was again successfully applied, with high accuracy and good precision, for the determination of carbinoxamine maleate in various pharmaceutical formulations (syrup, drops, and tablets). ..
- Cao H, Wang M, Sun L, Ikejima T, Hu Z, Zhao W. Pharmacodynamic comparison of pantoprazole enantiomers: inhibition of acid-related lesions and acid secretion in rats and guinea-pigs. J Pharm Pharmacol. 2005;57:923-7 pubmed..Na had an inhibitory rate of only 24.7% at the same dose. The above results indicate that (-)-PAN.Na is more potent than (+)-PAN.Na at inhibiting acid-related lesions owing to its stronger inhibition of acid secretion. ..
- Barrett M, Khan G, Davies P, Grainger R. Alkynyl sulfoxides as Î±-sulfinyl carbene equivalents: gold-catalysed oxidative cyclopropanation. Chem Commun (Camb). 2017;53:5733-5736 pubmed publisherAlkynyl sulfoxides are shown to act as Î±-sulfinyl metallocarbene synthons under oxidative gold catalysis, enabling reactions that are not available from diazo-precursors...
- Antczak M, Cai F, Ready J. Asymmetric synthesis of tertiary benzylic alcohols. Org Lett. 2011;13:184-7 pubmed publisher..Tertiary alcohols are generated in diastereomerically and enantiomerically pure form. Reductive lithiation converts the sulfoxide into a variety of useful functional groups. ..
- Wang X, Kim H, Szuchman Sapir A, McMahon A, Dennis J, Witting P. Neutrophils recruited to the myocardium after acute experimental myocardial infarct generate hypochlorous acid that oxidizes cardiac myoglobin. Arch Biochem Biophys. 2016;612:103-114 pubmed publisher..Peptide mass mapping revealed oxidation of Met9 and Met132 to the corresponding sulfoxides yet Cys67 remained unmodified...
- Meisner P, Gebicki J. Determination of hydroperoxides in aqueous solutions containing surfactants by the ferrous oxidation-xylenol orange method. Acta Biochim Pol. 2009;56:523-7 pubmed..From our preliminary studies we conclude that the method can be applied for determination of hydroperoxides in systems containing non-ionic or anionic surfactants provided careful calibration is performed for each surfactant. ..
- Kaeothip S, Demchenko A. Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation. Carbohydr Res. 2011;346:1371-88 pubmed publisher..Surveyed in this article, are representative examples wherein these excellent innovations have been applied to the synthesis of various oligosaccharide sequences. ..
- Ruano J, Fraile A, Martín M, Gonzalez G, Fajardo C, Martín Castro A. Asymmetric synthesis of pyrrolo[2,1-a]isoquinoline derivatives by 1,3-dipolar cycloadditions of stabilized isoquinolinium N-ylides with sulfinyl dipolarophiles. J Org Chem. 2011;76:3296-305 pubmed publisher..Complete endo selectivity is observed with cyclic dipolarophiles and substituted acrylonitriles, but it is low with butenoate. The sulfinyl group also exerts a positive influence on the dipolarophilic reactivity toward these ylides. ..
- Wetli H, Brenneisen R, Tschudi I, Langos M, Bigler P, Sprang T, et al. A gamma-glutamyl peptide isolated from onion (Allium cepa L.) by bioassay-guided fractionation inhibits resorption activity of osteoclasts. J Agric Food Chem. 2005;53:3408-14 pubmed..As no other peak displayed inhibitory activity, it likely is responsible for the effect of onion on bone resorption. ..
- Thiehoff C, Holland M, Daniliuc C, Houk K, Gilmour R. Can acyclic conformational control be achieved via a sulfur-fluorine gauche effect?. Chem Sci. 2015;6:3565-3571 pubmed publisher..Conformational analyses of Î²-fluorosulfides, -sulfoxides and -sulfones are disclosed here, thus extending the scope of the fluorine gauche effect to the 3rd ..
- Mariz R, Poater A, Gatti M, Drinkel E, Bürgi J, Luan X, et al. C2-symmetric chiral disulfoxide ligands in rhodium-catalyzed 1,4-addition: from ligand synthesis to the enantioselection pathway. Chemistry. 2010;16:14335-47 pubmed publisher..Density functional theory calculations on the step of the catalytic cycle that determines the enantioselectivity are presented and reinforce the first hypothetical explanations for the high levels of asymmetric induction observed. ..
- Baker D. Intravenous proton pump inhibitors. Rev Gastroenterol Disord. 2006;6:22-34 pubmed
- Fukuzawa K, Shibata A, Okamura C, Fujiwara Y, Akai K, Tsuchiya K, et al. Measurement of lipid hydroperoxides by the ferric-xylenol orange method (1) characteristics of the ferric-xylenol orange/membrane phosphatidylcholine complex. J Nutr Sci Vitaminol (Tokyo). 2009;55:9-14 pubmed..Our observations are consistent with binding of one XO/Fe3+ complex to about 3 molecules of the egg yolk phosphatidylcholine carrying a zero net charge. ..
- Zhao Q, Rong X, Chen L, Ma H, Tao G. Layer-by-layer self-assembly xylenol orange functionalized CdSe/CdS quantum dots as a turn-on fluorescence lead ion sensor. Talanta. 2013;114:110-6 pubmed publisher..05 to 6 ?mol L(-1). A detection limit of 0.02 ?mol L(-1) was achieved. This method was successfully applied to the determination of lead in real samples with satisfactory results. ..
- Wang L, Zhou L, Hu H, Lin S, Xia J. Ilaprazole for the treatment of duodenal ulcer: a randomized, double-blind and controlled phase III trial. Curr Med Res Opin. 2012;28:101-9 pubmed publisher..5% vs. 11.5%). Ilaprazole (10?mg/d) is as effective as omeprazole (20?mg/d) in the treatment of DU with similar side effects. The efficacy of ilaprazole is not affected by CYP2C19 polymorphisms. ..
- Costa B, Rodrigues V, Oliveira V, Ottoboni L, Marsaioli A. Enzymatic potential of heterotrophic bacteria from a neutral copper mine drainage. Braz J Microbiol. 2016;47:846-852 pubmed publisher..SO5-9) efficiently oxidized three different organic sulfides to their corresponding sulfoxides. In conclusion, this study revealed that neutral copper mine drainages are a promising source of biocatalysts ..
- Belaz K, Coimbra M, Barreiro J, Montanari C, Cass Q. Multimilligram enantioresolution of sulfoxide proton pump inhibitors by liquid chromatography on polysaccharide-based chiral stationary phase. J Pharm Biomed Anal. 2008;47:81-7 pubmed publisher..The higher enantiomeric purity obtained for the isolated enantiomers suggests that the methods here described should be considered as a simple and rapid way to obtain enantiomeric pure standards for analytical purpose. ..
- Lücking U. Sulfoximines: a neglected opportunity in medicinal chemistry. Angew Chem Int Ed Engl. 2013;52:9399-408 pubmed publisher..This Minireview provides an overview of a widely neglected opportunity in medicinal chemistry--the sulfoximine group. ..
- Kaspari S, Kupcinskas L, Heinze H, Berghöfer P. Pantoprazole 20 mg on demand is effective in the long-term management of patients with mild gastro-oesophageal reflux disease. Eur J Gastroenterol Hepatol. 2005;17:935-41 pubmed..Hence, on-demand treatment with pantoprazole 20 mg is safe and effective in maintaining control of the symptoms heartburn, acid regurgitation and pain on swallowing symptoms in patients with GORD grade 0/I with superiority to placebo. ..
- Pérez Pérez E, Rodriguez Malaver A, Padilla N, Medina Ramírez G, Dávila J. Antioxidant capacity of crude extracts from clones of banana and plane species. J Med Food. 2006;9:517-23 pubmed..When antioxidant activity was calculated, a value was found that was equivalent to a concentration of uric acid between 0.20 and 0.30 mM at the highest concentration of extract used, with uric acid being a potent antioxidant at 1 mM. ..
- McConville M, Brennan G, McCoy M, Castillo R, Hernandez Campos A, Ibarra F, et al. Adult triclabendazole-resistant Fasciola hepatica: surface and subsurface tegumental responses to in vitro treatment with the sulphoxide metabolite of the experimental fasciolicide compound alpha. Parasitology. 2006;133:195-208 pubmed..The EM results confirm that compound alpha is a fasciolicide capable of disrupting the tegument of mature TCBZ-resistant F. hepatica; however, this was not accompanied by any change in tubulin immunoreactivity. ..
- Moussous O, Medjadj T, Benguerba M. FBX aqueous chemical dosimeter for measurement of dosimetric parameters. Appl Radiat Isot. 2011;69:399-402 pubmed publisher..We thus believe that the tissue equivalent FBX dosimetry system can measure the dosimetric parameters for (60)Co with reasonable accuracy...
- Chen B, Chen Y, Tu J, Li Y, Zhang W, Li Q, et al. Clopidogrel inhibits CYP2C19-dependent hydroxylation of omeprazole related to CYP2C19 genetic polymorphisms. J Clin Pharmacol. 2009;49:574-81 pubmed publisher..832) in CYP2C19*1/*1. No significant alteration is observed in CYP2C19*2/*2 or *3. Clopidogrel inhibits CYP2C19-dependent hydroxylation of omeprazole in CYP2C19*1/*1 and has no impact on CYP3A4-catalyzed sulfoxidation of omeprazole. ..
- Zhou G, Tan Z, Zhang W, Ou Yang D, Chen Y, Guo D, et al. An improved LC-MS/MS method for quantitative determination of ilaprazole and its metabolites in human plasma and its application to a pharmacokinetic study. Acta Pharmacol Sin. 2009;30:1330-6 pubmed publisher..This method was successfully applied for the evaluation of the pharmacokinetics of ilaprazole and its two metabolites after single oral doses of 5 mg ilaprazole to 12 healthy Chinese volunteers. ..
- Batista J, Schlechtingen G, Friedrichson T, Braxmeier T, Bajorath J. Lipid-like sulfoxides and amine oxides as inhibitors of mast cell activation. Eur J Med Chem. 2011;46:2147-51 pubmed publisher..Sulfoxide and amine oxide derivatives were found to be only slightly less active than miltefosine. ..