{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,5]],"date-time":"2025-11-05T14:26:44Z","timestamp":1762352804417,"version":"build-2065373602"},"reference-count":39,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2019,4,29]],"date-time":"2019-04-29T00:00:00Z","timestamp":1556496000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their antibacterial properties against multidrug-resistant bacteria, such as Pseudomonas aeruginosa Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation.<\/jats:p>","DOI":"10.3390\/ijms20092121","type":"journal-article","created":{"date-parts":[[2019,4,29]],"date-time":"2019-04-29T07:01:22Z","timestamp":1556521282000},"page":"2121","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["PhSeZnCl in the Synthesis of Steroidal \u03b2-Hydroxy-Phenylselenides Having Antibacterial Activity"],"prefix":"10.3390","volume":"20","author":[{"given":"Izabella","family":"Jastrzebska","sequence":"first","affiliation":[{"name":"Institute of Chemistry, University of Bia\u0142ystok, ul. 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J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3329","DOI":"10.1021\/jm5015296","article-title":"New Organochalcogen Multitarget Drug: Synthesis and Antioxidant and Antitumoral Activities of Chalcogenozidovudine Derivatives","volume":"58","author":"Mariano","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2044","DOI":"10.2174\/1385272820666161020162113","article-title":"New Prospective for Redox Modulation Mediated by Organo selenium and Organotellurium Compounds","volume":"21","author":"Barcellos","year":"2017","journal-title":"Curr. Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3289","DOI":"10.1016\/j.bbagen.2012.11.020","article-title":"Glutathione peroxidases","volume":"1830","author":"Maiorino","year":"2013","journal-title":"Biochim. Biophys. Acta Gen. Subj."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Sancineto, L., Piccioni, M., De Marco, S., Pagiotti, R., Nascimento, V., Braga, A.L., Santi, C., and Pietrella, D. (2016). Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection. BMC Microbiol., 16.","DOI":"10.1186\/s12866-016-0837-x"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Rossato, L., Loreto, E.S., Venturini, T.P., de Azevedo, M.I., Al-Hatmi, A.M.S., Santurio, J.M., and Alves, S.H. (2019). In vitro combination between antifungals and diphenyl diselenide against Cryptococcus species. Mycoses.","DOI":"10.1111\/myc.12905"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"9601","DOI":"10.1021\/acs.jmedchem.5b01183","article-title":"Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity","volume":"58","author":"Sancineto","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1016\/j.freeradbiomed.2015.06.039","article-title":"Glutathione S-transferase pi expression regulates the Nrf2-dependent response to hormetic diselenides","volume":"88","author":"Bartolini","year":"2015","journal-title":"Free Radic. Biol. Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.freeradbiomed.2014.10.008","article-title":"Reaction kinetics and targeting to cellular glutathione S-transferase of the glutathione peroxidase mimetic PhSeZnCl and its d,l-polylactide microparticle formulation","volume":"78","author":"Bartolini","year":"2015","journal-title":"Free Radic. Biol. Med."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Bartolini, D., Sancineto, L., Fabro de Bem, A., Tew, K.D., Santi, C., Radi, R., Toquato, P., and Galli, F. (2017). Selenocompounds in Cancer Therapy: An Overview. Advances in Cancer Research, Elsevier.","DOI":"10.1016\/bs.acr.2017.07.007"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"219","DOI":"10.3109\/10715762.2014.993628","article-title":"Late-intervention study with ebselen in an experimental model of type 1 diabetic nephropathy","volume":"49","author":"Tan","year":"2015","journal-title":"Free Radic. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3816","DOI":"10.1016\/j.bmc.2012.04.033","article-title":"Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy","volume":"20","author":"He","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.ejmech.2015.05.018","article-title":"Diosgenin-based thio (seleno) ureas and triazolyl glycoconjugates as hybrid drugs. Antioxidant and antiproliferative profile","volume":"99","author":"Abasolo","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5041","DOI":"10.1039\/C7OB00458C","article-title":"New selenosteroids as antiproliferative agents","volume":"15","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2488","DOI":"10.3390\/md13042488","article-title":"Synthesis and in vitro antiproliferative evaluation of some B-norcholesteryl benzimidazole and benzothiazole derivatives","volume":"13","author":"Cui","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"93905","DOI":"10.1039\/C6RA21485A","article-title":"Stereoselective glycoconjugation of steroids with selenocarbohydrates","volume":"6","author":"Affeldt","year":"2016","journal-title":"RSC Advances"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2237","DOI":"10.1016\/j.tetlet.2010.02.090","article-title":"Stereoselective synthesis of selenosteroids","volume":"51","author":"Rodrigues","year":"2010","journal-title":"Tetrahedron Letters"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Santi, C., Capoccia, L., and Monti, B. (2018). Zinc-Selenium reagents in organic synthesis. Phys. Sci. Rev., 3, Available online: https:\/\/www.degruyter.com\/view\/j\/psr.2018.3.issue-12\/psr-2017-0129\/psr-2017-0129.xml.","DOI":"10.1515\/psr-2017-0129"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5387","DOI":"10.1002\/ejoc.200800869","article-title":"Preparation of the First Bench-Stable Phenyl Selenolate: An Interesting \u201cOn Water\u201d Nucleophilic Reagent","volume":"2008","author":"Santi","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1002\/slct.201500031","article-title":"Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media","volume":"1","author":"Perin","year":"2016","journal-title":"ChemistrySelect"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1277","DOI":"10.1039\/c2gc16541d","article-title":"On water preparation of phenylselenoesters","volume":"14","author":"Santi","year":"2012","journal-title":"Green Chemistry"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1848","DOI":"10.1002\/ejoc.201100045","article-title":"\u201cOn-Water\u201d Michael-Type Addition Reactions Promoted by PhSeZnCl","volume":"2011","author":"Battistelli","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4921","DOI":"10.1002\/ejoc.200900800","article-title":"Vinylic Substitutions Promoted by PhSeZnCl: Synthetic and Theoretical Investigations","volume":"2009","author":"Santoro","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1055\/s-0030-1259082","article-title":"Efficient Ring Opening of Protected and Unprotected Aziridines Promoted by Stable Zinc Selenolate in Ionic Liquid","volume":"2011","author":"Salman","year":"2011","journal-title":"Synlett"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4965","DOI":"10.1016\/j.tet.2010.05.034","article-title":"Enantioselective total synthesis of idesolide via NaHCO3-promoted dimerization","volume":"66","author":"Nagasawa","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.reactfunctpolym.2016.12.007","article-title":"Selenide-containing high refractive index polymer material with adjustable refractive index and Abbe\u2019s number","volume":"111","author":"Jiang","year":"2017","journal-title":"React. Funct. Polym."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"718","DOI":"10.1194\/jlr.M023689","article-title":"Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles","volume":"53","author":"Paillasse","year":"2012","journal-title":"J. Lipid Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"353","DOI":"10.2174\/138527212799499895","article-title":"Chemistry of Steroidal Sapogenins-New Advances in a Classical Field","volume":"16","author":"Jastrzebska","year":"2012","journal-title":"Curr. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Petrow, V.A. (1939). 212. Steroids and related compounds. Part III. The constitution of Westphalen\u2019s diol. J. Chem. Soc. (Resumed), 998.","DOI":"10.1039\/jr9390000998"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Makin, H.L.J., and Gower, D.B. (2010). Spectroscopic Methods of Steroid Analysis. Steroid Analysis, Springer. [2nd ed.].","DOI":"10.1007\/978-1-4020-9775-1"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1002\/hlca.19490320139","article-title":"2\u03b1, 3\u03b1-und 2\u03b2, 3\u03b2-Oxido-chlolestane; Konfiguration der 2-Oxy-cholestane","volume":"32","author":"Plattner","year":"1949","journal-title":"Helvetica Chimica Acta"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1777","DOI":"10.1097\/CCM.0b013e31819ff137","article-title":"Pseudomonas aeruginosa virulence and therapy: Evolving translational strategies","volume":"37","author":"Veesenmeyer","year":"2009","journal-title":"Crit. Care Med."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"882","DOI":"10.1128\/IAI.71.2.882-890.2003","article-title":"Direct Continuous Method for Monitoring Biofilm Infection in a Mouse Model","volume":"71","author":"Kadurugamuwa","year":"2003","journal-title":"Infect. Immun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1358\/dnp.2008.21.6.1246829","article-title":"Ceragenins (Cationic Steroid Compounds), a novel class of antimicrobial agents","volume":"21","author":"Epand","year":"2008","journal-title":"Drug News Perspect."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1016\/0968-0896(96)00018-1","article-title":"Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach","volume":"4","author":"Mori","year":"1996","journal-title":"Bioorganic Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/j.steroids.2010.10.002","article-title":"Synthesis of new symmetrical bis-steroidal pyrazine analogues from diosgenin","volume":"76","author":"Shawakfeh","year":"2011","journal-title":"Steroids"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1016\/S0040-4020(01)93301-0","article-title":"Studies on epoxides\u2014VI","volume":"29","author":"Weissenberg","year":"1973","journal-title":"Tetrahedron"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"568","DOI":"10.1039\/P19780000568","article-title":"Steric course of reduction with sodium borohydride of steroidal \u03b1\u03b2-epoxy-ketones","volume":"1","author":"Weissenberg","year":"1978","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"5443","DOI":"10.2147\/IJN.S113706","article-title":"Core-shell magnetic nanoparticles display synergistic antibacterial effects against Pseudomonas aeruginosa and Staphylococcus aureus when combined with cathelicidin LL-37 or selected ceragenins","volume":"11","author":"Niemirowicz","year":"2016","journal-title":"Int. J. 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