Sulfenamide formation – chemical and biochemical reactions and their applications in cell biology

References

• Craine L, Raban M. The chemistry of sulfenamides. Chem Rev. 1989;89:689–712. doi:10.1021/cr00094a001
   Web of Science ®Google Scholar
• Patai S. Chapter 1: the chemistry of sulphenic acids and their derivatives. In: The chemistry of sulphenic acids and their derivatives. Wiley; 2010. p. 1–22. doi:10.1002/9780470772287
   Google Scholar
• Benati L, Montevecchi PC, Spagnolo P. 4′-Nitroarenesulphenanilides: their use in the synthesis of unsymmetrical disulphides. Tetrahedron Lett. 1986;27:1739–1742. doi:10.1016/S0040-4039(00)84361-0
   Web of Science ®Google Scholar
• Heimer NE, Field L. Organic disulfides and related substances. XXIX. Studies in the chemistry of sulfenamides. J Org Chem. 1970;35:3012–3022. doi:10.1021/jo00834a035
   Web of Science ®Google Scholar
• Erol I. Synthesis and characterization of novel sulfonamide functionalized maleimide polymers: conventional kinetic analysis, antimicrobial activity and dielectric properties. J Mol Struct. 2022;1255:132362. doi:10.1016/j.molstruc.2022.132362
   Web of Science ®Google Scholar
• Devendar P, Yang G-F. Sulfur-containing agrochemicals. Cham: Springer; 2019. p. 35–78. doi:10.1007/978-3-030-25598-5_2
   Google Scholar
• Sukul P, Spiteller M. Sulfonamides in the environment as veterinary drugs. Rev Environ Contam Toxicol. 2006;187:67–101.
   PubMed Web of Science ®Google Scholar
• Shelver WL, Shappell NW, Franek M, et al. ELISA for sulfonamides and its application for screening in water contamination. J Agric Food Chem. 2008;56:6609–6615. doi:10.1021/jf800657u
   PubMed Web of Science ®Google Scholar
• Markowicz-Piasecka M, Huttunen KM, Broncel M, et al. Sulfenamide and sulfonamide derivatives of metformin – a new option to improve endothelial function and plasma haemostasis. Sci Rep. 2019;91(9):1–19.
   Google Scholar
• Ovung A, Bhattacharyya J. Sulfonamide drugs: structure, antibacterial property, toxicity, and biophysical interactions. Biophys Rev. 2021;13:259. doi:10.1007/s12551-021-00795-9
   PubMedGoogle Scholar
• Gradwell MHS, Stephenson NR. The action of N-(cyclohexylthio)phthalimide as a prevulcanization inhibitor of 2-bisbenzothiazole-2,2′-disulfide accelerated sulfur vulcanization. Rubber Chem Technol. 2001;74:44–56. doi:10.5254/1.3547638
   Web of Science ®Google Scholar
• Cao Y, Abdolmohammadi S, Ahmadi R, et al. Direct synthesis of sulfenamides, sulfinamides, and sulfonamides from thiols and amines. RSC Adv. 2021;11:32394–32407. doi:10.1039/D1RA04368D
   PubMed Web of Science ®Google Scholar
• Apaydın S, Török M. Sulfonamide derivatives as multi-target agents for complex diseases. Bioorg Med Chem Lett. 2019;29:2042–2050. doi:10.1016/j.bmcl.2019.06.041
   PubMed Web of Science ®Google Scholar
• Nandi GC, Arvidsson PI. Sulfonimidamides: synthesis and applications in preparative organic chemistry. Adv Synth Catal. 2018;360:2976–3001. doi:10.1002/adsc.201800273
   Web of Science ®Google Scholar
• Wojaczyńska E, Wojaczyński J. Modern stereoselective synthesis of chiral sulfinyl compounds. Chem Rev. 2020;120:4578–4611. doi:10.1021/acs.chemrev.0c00002
   PubMed Web of Science ®Google Scholar
• Andresini M, Carret S, Degennaro L, et al. Multistep continuous flow synthesis of isolable NH2-sulfinamidines via nucleophilic addition to transient sulfurdiimide. Chem Eur J. 2022;28:e202202066. doi:10.1002/chem.202202066
   PubMed Web of Science ®Google Scholar
• Andresini M, Spennacchio M, Colella M, et al. Sulfinimidate esters as an electrophilic sulfinimidoyl motif source: synthesis of N-protected sulfilimines from grignard reagents. Org Lett. 2021;23:6850–6854. doi:10.1021/acs.orglett.1c02413
   PubMed Web of Science ®Google Scholar
• Raban M, Hu C, Craine LH. Stereochemistry in trivalent nitrogen compounds. 40. Torsional barriers in N-2,4-dinitrobenzenesulfenylbenzimidazoles. Tetrahedron Lett. 1984;25:1337–1340. doi:10.1016/S0040-4039(01)80151-9
   Web of Science ®Google Scholar
• Raban M, Chang H, Craine L, et al. N-(arylthio)benzimidazoles. Torsional barriers and 1,3 rearrangement. J Org Chem. 1985;50:2205–2210. doi:10.1021/jo00213a001
   Web of Science ®Google Scholar
• Armitage DA, Clark MJ, Kinsey AC. The sulphur(II)–nitrogen bond. Part III. The synthesis of the sulphur-(II)–nitrogen bond from sulphenates. J Chem Soc C Org. 1971:3867–3869. doi:10.1039/J39710003867.
   Google Scholar
• Taniguchi N. Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines. Tetrahedron. 2017;73:2030–2035. doi:10.1016/j.tet.2017.02.047
   Web of Science ®Google Scholar
• Dunbar JE, Rogers JH. Reactions of thiolsulfonates with amines. J Org Chem. 1966;31:2842–2846. doi:10.1021/jo01347a025
   Web of Science ®Google Scholar
• Major RT, Peterson LH. Aliphatic sulfenamides. J Am Chem Soc. 1956;78:6181–6182. doi:10.1021/ja01604a063
   Web of Science ®Google Scholar
• Taniguchi N. Copper-catalyzed formation of sulfur–nitrogen bonds by dehydrocoupling of thiols with amines. European J Org Chem. 2010;2010:2670–2673. doi:10.1002/ejoc.201000167
   Web of Science ®Google Scholar
• Taniguchi N. Copper-catalyzed synthesis of sulfenamides utilizing diaryl disulfides with alkyl amines. Synlett. 2007;2007:1917–1920. doi:10.1055/s-2007-984539
   Google Scholar
• Harpp DN, Back TG. A general synthesis of sulfenamides. Tetrahedron Lett. 1971;12:4953–4956. doi:10.1016/S0040-4039(01)97598-7
   Google Scholar
• Atkinson RS, Awad SB. Reactions of N-nitrenes with allyl aryl sulphides: N-heteroarylsulphenamides. J Chem Soc Perkin Trans. 1977;1:346–351. doi:10.1039/P19770000346.
   Google Scholar
• Torii S, Tanaka H, Ukida M. Electrosynthesis of hetero-hetero atom bonds. 2. An efficient preparation of (2-benzothiazolyl)- and thiocarbamoylsulfenamides by electrolytic cross-coupling reaction Of 2-mercaptobenzothiazole, bis(2-benzothiazolyl) disulfide, and/or bis(dialkylthiocarb) disulfides with various amines. J Org Chem. 1978;43:3223–3227. doi:10.1021/jo00410a025
   Web of Science ®Google Scholar
• Zhang T, Wang R, Ma L, et al. High-efficiency synthesis of sulfenamides and disulfides by electrochemical dehydrogenative coupling. Environ Chem Lett. 2022:1–7. doi:10.1007/S10311-022-01459-0/FIGURES/2.
   PubMed Web of Science ®Google Scholar
• Kanakarajan K, Meier H. Ring expansion of benzothiete to 2,3-dihydrobenz[d]isothiazoles. Angew Chemie Int Ed Eng. 1984;23:244–244. doi:10.1002/anie.198402441
   Web of Science ®Google Scholar
• Torii S, Sayo N, Tanaka H. Reaction of sulfenamides with di-alkyl and trialkyl phosphites.an efficient synthesis of phosphoramidates by unusual substitution at S–N bond in (2-benzothiazolyl)sulfenamides. Chem Lett. 1980;9:695–698. doi:10.1246/cl.1980.695
   Google Scholar
• Blake ES. The reaction of carbon disulfide with amine sulfides. J Am Chem Soc. 1943;65:1267–1269. doi:10.1021/ja01247a004
   Google Scholar
• Zervas L, Borovas D, Gazis E. New methods in peptide synthesis. I. Tritylsulfenyl and o-nitrophenylsulfenyl groups as N-protecting groups. J Am Chem Soc. 1963;85:3660–3666. doi:10.1021/ja00905a029
   Web of Science ®Google Scholar
• Zincke T, Farr F. Über o-nitrophenylschwefelchlorid und umwandlungsprodukte. Justus Liebigs Ann Chem. 1912;391:57–88. doi:10.1002/jlac.19123910106
   Google Scholar
• Datta M, Buglass AJ. Fast and efficient synthesis of sulfinamides by the oxidation of sulfenamides using potassium fluoride and m-chloroperoxybenzoic acid. Synth Commun. 2012;42:1760–1769. doi:10.1080/00397911.2010.543748
   Web of Science ®Google Scholar
• Atkinson RS, Judkins BD. Intermolecular trapping of sulphenylnitrenes by alkenes. Chem Soc Perkin Trans. 1981;1:2615–2619. doi:10.1039/p19810002615
   Google Scholar
• Haas A. The chemistry of the sulfenic acids. Von E. Kühle. Georg Thieme publishers, Stuttgart 1973. 1. Aufl., VIII, 163 S., 123 Abb., geb. DM 59,-. Chemie Ing Tech. 1974;46:170–170. doi:10.1002/cite.330460420
   Google Scholar
• Yang GF, Huang H, Nie X, et al. One-pot tandem oxidative bromination and amination of sulfenamide for the synthesis of sulfinamidines. J Org Chem. 2023;88:4581–4591. doi:10.1021/acs.joc.3c00042
   PubMed Web of Science ®Google Scholar
• Andresini M, Spennacchio M, Romanazzi G, et al. Synthesis of sulfinamidines and sulfinimidate esters by transfer of nitrogen to sulfenamides. Org Lett. 2020;22:7129–7134. doi:10.1021/acs.orglett.0c02471
   PubMed Web of Science ®Google Scholar
• Davis FA, Fretz ER, Horner CJ, et al. Chemistry of the sulfur-nitrogen bond.1,2 V. Evidence for an intermolecular rearrangement in the rearrangement of arenesulfenanilides to o- and p-aminodiphenyl sulfides. J Org Chem. 1973;38:695–699. doi:10.1021/jo00944a017
   Web of Science ®Google Scholar
• Ghose AK, Crippen GM, Revankar GR, et al. Analysis of the in vitro antiviral activity of certain ribonucleosides against parainfluenza virus using a novel computer aided receptor modeling procedure. J Med Chem. 1989;32:746–756. doi:10.1021/jm00124a005
   PubMed Web of Science ®Google Scholar
• Viswanadhan VN, Ghose AK, Hanna NB, et al. Analysis of the in vitro antitumor activity of novel purine-6-sulfenamide, -sulfinamide, and -sulfonamide nucleosides and certain related compounds using a computer-aided receptor modeling procedure. J Med Chem. 1991;34:526–532. doi:10.1021/jm00106a007
   PubMed Web of Science ®Google Scholar
• Revankar GR, Hanna NB, Imamura N, et al. Synthesis and in vivo antitumor activity of 2-amino-9ff-purine-6-sulfenamide, -sulfinamide, and-sulfonamide and related purine ribonucleosides. J Med Chem. 1990;33:121–128. doi:10.1021/jm00163a020
   PubMed Web of Science ®Google Scholar
• Stella VJ, Charman WNA, Naringrekar VH. Prodrugs: do they have advantages in clinical practice? Drugs. 1985;29:455–473. doi:10.2165/00003495-198529050-00002
   PubMed Web of Science ®Google Scholar
• Gillman KW, Starrett JE, Parker MF, et al. Discovery and evaluation of BMS-708163, a potent, selective and orally bioavailable γ-secretase inhibitor. ACS Med Chem Lett. 2010;1:120–124. doi:10.1021/ml1000239
   PubMed Web of Science ®Google Scholar
• Guarino VR, Olson RE, Everlof JG, et al. An amide-based sulfenamide prodrug of gamma secretase inhibitor BMS–708163 delivers parent drug from an oral conventional solid dosage form in male beagle dog. Bioorg Med Chem Lett. 2020;30:126856. doi:10.1016/j.bmcl.2019.126856
   PubMed Web of Science ®Google Scholar
• Role of prodrugs in solubility enhancement of drugs | PharmaTutor. Available from: https://www.pharmatutor.org/articles/role-prodrugs-solubility-enhancement-of-drugs.
   Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 1997;23:3–25. doi:10.1016/S0169-409X(96)00423-1
   Web of Science ®Google Scholar
• Hörter D, Dressman JB. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv Drug Deliv Rev. 2001;46:75–87. doi:10.1016/S0169-409X(00)00130-7
   PubMed Web of Science ®Google Scholar
• Guarino VR, Karunaratne V, Stella VJ. Sulfenamides as prodrugs of NH-acidic compounds: a new prodrug option for the amide bond. Bioorg Med Chem Lett. 2007;17:4910–4913. doi:10.1016/j.bmcl.2007.06.037
   PubMed Web of Science ®Google Scholar
• Hemenway JN, Nti-Addae K, Guarino VR, et al. Preparation, characterization and in vivo conversion of new water-soluble sulfenamide prodrugs of carbamazepine. Bioorg Med Chem Lett. 2007;17:6629–6632. doi:10.1016/j.bmcl.2007.09.045
   PubMed Web of Science ®Google Scholar
• Nti-Addae KW, Guarino VR, Dalwadi G, et al. Determination of the permeability characteristics of Two sulfenamide prodrugs of linezolid across caco-2 cells. J Pharm Sci. 2012;101:3134–3141. doi:10.1002/jps.23084
   PubMed Web of Science ®Google Scholar
• Nti-Addae KW, Stella VJ. In vitro conversion of model sulfenamide prodrugs in the presence of small molecule thiols. J Pharm Sci. 2011;100:1001–1008. doi:10.1002/jps.22347
   PubMed Web of Science ®Google Scholar
• Ktihler TC, Fryklund J, Bergman N, et al. Structure-activity relationship of omeprazole and analogues as helicobacter pylori urease inhibitors. J Med Chem. 1995;38:4906–4916. doi:10.1021/jm00025a008
   PubMed Web of Science ®Google Scholar
• Jana K, Bandyopadhyay T, Ganguly B. Revealing the mechanistic pathway of acid activation of proton pump inhibitors to inhibit the gastric proton pump: a DFT study. J Phys Chem B. 2016;120:13031–13038. doi:10.1021/acs.jpcb.6b09334
   PubMed Web of Science ®Google Scholar
• Figura N, Crabtree JE, Dattilo M. In-vitro activity of lansoprazole against helicobacter pylori. J Antimicrob Chemother. 1997;39:585–590. doi:10.1093/jac/39.5.585
   PubMedGoogle Scholar
• Shin JM, Besancon M, Simon A, et al. The site of action of pantoprazole in the gastric H+/K+-ATPase. Biochim Biophys Acta Biomembr. 1993;1148:223–233. doi:10.1016/0005-2736(93)90133-K
   PubMed Web of Science ®Google Scholar
• Kov L, Bohmerovj E, Butko P. Ionophores and intact cells I. Valinomycin and nigericin act preferentially on mitochondria and not on the plasma membrane of Saccharomyces cerevisiae. Biochim Biophys Acta. 1982;721:341–348. doi:10.1016/0167-4889(82)90088-X
   PubMedGoogle Scholar
• Revell KD, Heldreth B, Long TE, et al. N-thiolated β-lactams: studies on the mode of action and identification of a primary cellular target in staphylococcus aureus. Bioorg Med Chem. 2007;15:2453–2467. doi:10.1016/j.bmc.2006.12.027
   PubMed Web of Science ®Google Scholar
• Wang X, Jia X, Chang T, et al. Attenuation of hypertension development by scavenging methylglyoxal in fructose-treated rats. J Hypertens. 2008;26:765–772. doi:10.1097/HJH.0b013e3282f4a13c
   PubMed Web of Science ®Google Scholar
• Markowicz-Piasecka M, Huttunen KM, Mateusiak L, et al. Is metformin a perfect drug? Updates in pharmacokinetics and pharmacodynamics. Curr Pharm Des. 2016;23:2532–2550.
   Web of Science ®Google Scholar
• Huttunen KM, Mannila A, Laine K, et al. The first bioreversible prodrug of metformin with improved lipophilicity and enhanced intestinal absorption. J Med Chem. 2009;52:4142–4148. doi:10.1021/jm900274q
   PubMed Web of Science ®Google Scholar
• Peura L, Huttunen KM. Sustained release of metformin via red blood cell accumulated sulfenamide prodrug. J Pharm Sci. 2014;103:2207–2210. doi:10.1002/jps.24040
   PubMed Web of Science ®Google Scholar
• Huttunen KM, Leppänen J, Laine K, et al. Convenient microwave-assisted synthesis of lipophilic sulfenamide prodrugs of metformin. Eur J Pharm Sci. 2013;49:624–628. doi:10.1016/j.ejps.2013.05.023
   PubMed Web of Science ®Google Scholar
• Torunoglu ST, Zajda A, Tampio J, et al. Metformin derivatives – researchers’ friends or foes? Biochem Pharmacol. 2023;215:115743. doi:10.1016/j.bcp.2023.115743
   PubMed Web of Science ®Google Scholar
• Trang A, Khandhar PB. Physiology, acetylcholinesterase. StatPearls. Treasure Island (FL): StatPearls Publishing; 2019.
   Google Scholar
• Markowicz-Piasecka M, Sikora J, Mateusiak Ł, et al. Metformin and its sulfenamide prodrugs inhibit human cholinesterase activity. Oxid Med Cell Longev. 2017;2017:1–11. doi:10.1155/2017/7303096
   Web of Science ®Google Scholar
• Shimizu I, Yoshida Y, Suda M, et al. DNA damage response and metabolic disease. Cell Metab. 2014;20:967–977. doi:10.1016/j.cmet.2014.10.008
   PubMed Web of Science ®Google Scholar
• Greig NH, Utsuki T, Ingram DK, et al. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer β-amyloid peptide in rodent. Proc Natl Acad Sci USA. 2005;102:17213–17218. doi:10.1073/pnas.0508575102
   PubMed Web of Science ®Google Scholar
• Sridhar GR, Rao AA, Srinivas K, et al. Butyrylcholinesterase in metabolic syndrome. Med Hypotheses. 2010;75:648–651. doi:10.1016/j.mehy.2010.08.008
   PubMed Web of Science ®Google Scholar
• Markowicz-Piasecka M, Huttunen KM, Mateusiak Ł, et al. Sulfenamide and sulfonamide derivatives of metformin can exert anticoagulant and profibrinolytic properties. Chem Biol Interact. 2018;284:126–136. doi:10.1016/j.cbi.2018.02.012
   PubMed Web of Science ®Google Scholar