REPOZYTORIUM UNIWERSYTETU
W BIAŁYMSTOKU
UwB

Proszę używać tego identyfikatora do cytowań lub wstaw link do tej pozycji: http://hdl.handle.net/11320/18172
Pełny rekord metadanych
Pole DCWartośćJęzyk
dc.contributor.authorJastrzębska, Izabella-
dc.contributor.authorMellea, Stefano-
dc.contributor.authorSalerno, Valerio-
dc.contributor.authorGrześ, Paweł Adam-
dc.contributor.authorSiergiejczyk, Leszek-
dc.contributor.authorNiemirowicz-Laskowska, Katarzyna-
dc.contributor.authorBucki, Robert-
dc.contributor.authorMonti, Bonifacio-
dc.contributor.authorSanti, Claudio-
dc.date.accessioned2025-04-08T07:38:41Z-
dc.date.available2025-04-08T07:38:41Z-
dc.date.issued2019-
dc.identifier.citationInternational Journal of Molecular Sciences, 2019, Volume 20, Issue 9, 2121pl
dc.identifier.issn1422-0067-
dc.identifier.urihttp://hdl.handle.net/11320/18172-
dc.descriptionThe authors would like to thank Erasmus + Program (SM and VS). The project was performed under the umbrella of “SeS Redox & Catalyst Network”. Part of the study was conducted with the use of equipment purchased by Medical University of Białystok as part of the RPOWP 2007-2013 funding, Priority I, Axis 1.1, contract No. UDA-RPPD.01.01.00-20-001/15-00 dated 26.06.2015. CS also thanks the inter-universities consortium C.I.N.M.P.I.S.pl
dc.description.abstractWe 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 a ording 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.pl
dc.description.sponsorshipThis research was funded by National Science Center, Poland, grant number UMO-2015/17/B/ST5/02892.pl
dc.language.isoenpl
dc.publisherMDPIpl
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectsteroidspl
dc.subjectseleniumpl
dc.subjectantibacterialpl
dc.subjectantibiofilmpl
dc.titlePhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activitypl
dc.typeArticlepl
dc.rights.holder© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).pl
dc.identifier.doi10.3390/ijms20092121-
dc.description.EmailIzabella Jastrzębska: i.jastrzebska@uwb.edu.plpl
dc.description.EmailStefano Mellea: stefano.mellea@gmail.compl
dc.description.EmailValerio Salerno: vale_1192@hotmail.itpl
dc.description.EmailPaweł Adam Grześ: felolix@gmail.compl
dc.description.EmailLeszek Siergiejczyk: nmrbial@uwb.edu.plpl
dc.description.EmailKatarzyna Niemirowicz-Laskowska: katia146@wp.plpl
dc.description.EmailRobert Bucki: buckirobert@gmail.compl
dc.description.EmailBonifacio Monti: bonifaciomonti@gmail.compl
dc.description.EmailClaudio Santi: claudio.santi@unipg.itpl
dc.description.AffiliationIzabella Jastrzębska - Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Polandpl
dc.description.AffiliationStefano Mellea - Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Polandpl
dc.description.AffiliationValerio Salerno - Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Polandpl
dc.description.AffiliationPaweł Adam Grześ - Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Polandpl
dc.description.AffiliationLeszek Siergiejczyk - Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Polandpl
dc.description.AffiliationKatarzyna Niemirowicz-Laskowska - Department of Microbiological and Nanobiomedical Engineering, Medical University of Białystok, ul. Mickiewicza 2C, 15-222 Bialystok, Polandpl
dc.description.AffiliationRobert Bucki - Department of Microbiological and Nanobiomedical Engineering, Medical University of Białystok, ul. Mickiewicza 2C, 15-222 Bialystok, Polandpl
dc.description.AffiliationBonifacio Monti - Group of Catalysis and Organic Green Chemistry–Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italypl
dc.description.AffiliationClaudio Santi - Group of Catalysis and Organic Green Chemistry–Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06132 Perugia, Italypl
dc.description.referencesSk, U.H.; Sharma, A.K.; Ghosh, S.; Bhattacharya, S. Synthesis and biological evaluation of novel spiro 6-methoxytetralin-1,30-pyrrolidine based organoselenocyanates against cadmium-induced oxidative and hepatic damage in mice. Eur. J. Med. Chem. 2010, 45, 3265–3273.pl
dc.description.referencesde Souza, D.; Mariano, D.O.C.; Nedel, F.; Schultze, E.; Campos, V.F.; Seixas, F.; da Silva, R.S.; Munchen, T.S.; Ilha, V.; Dornelles, L.; et al. New Organochalcogen Multitarget Drug: Synthesis and Antioxidant and Antitumoral Activities of Chalcogenozidovudine Derivatives. J. Med. Chem. 2015, 58, 3329–3339.pl
dc.description.referencesBarcellos, A.M.; Abenante, L.; Sarro, M.T.; Leo, I.D.; Lenardao, E.J.; Perin, G.; Santi, C. New Prospective for Redox Modulation Mediated by Organo selenium and Organotellurium Compounds. Curr. Org. Chem. 2017, 21, 2044–2061.pl
dc.description.referencesBrigelius-Flohé, R.; Maiorino, M. Glutathione peroxidases. Biochim. Biophys. Acta Gen. Subj. 2013, 1830, 3289–3303.pl
dc.description.referencesSancineto, L.; Piccioni, M.; De Marco, S.; Pagiotti, R.; Nascimento, V.; Braga, A.L.; Santi, C.; Pietrella, D. Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection. BMC Microbiol. 2016, 16, 220.pl
dc.description.referencesRossato, L.; Loreto, E.S.; Venturini, T.P.; de Azevedo, M.I.; Al-Hatmi, A.M.S.; Santurio, J.M.; Alves, S.H. In vitro combination between antifungals and diphenyl diselenide against Cryptococcus species. Mycoses 2019.pl
dc.description.referencesSancineto, L.; Mariotti, A.; Bagnoli, L.; Marini, F.; Desantis, J.; Iraci, N.; Santi, C.; Pannecouque, C.; Tabarrini, O. Design and Synthesis of DiselenoBisBenzamides (DISeBAs) as Nucleocapsid Protein 7 (NCp7) Inhibitors with anti-HIV Activity. J. Med. Chem. 2015, 58, 9601–9614.pl
dc.description.referencesBartolini, D.; Commodi, J.; Piroddi, M.; Incipini, L.; Sancineto, L.; Santi, C.; Galli, F. Glutathione S-transferase pi expression regulates the Nrf2-dependent response to hormetic diselenides. Free Radic. Biol. Med. 2015, 88, 466–480.pl
dc.description.referencesBartolini, D.; Piroddi, M.; Tidei, C.; Giovagnoli, S.; Pietrella, D.; Manevich, Y.; Tew, K.D.; Giustarini, D.; Rossi, R.; Townsend, D.M.; et al. Reaction kinetics and targeting to cellular glutathione S-transferase of the glutathione peroxidase mimetic PhSeZnCl and its d,l-polylactide microparticle formulation. Free Radic. Biol. Med. 2015, 78, 56–65.pl
dc.description.referencesBartolini, D.; Sancineto, L.; Fabro de Bem, A.; Tew, K.D.; Santi, C.; Radi, R.; Toquato, P.; Galli, F. Selenocompounds in Cancer Therapy: An Overview. In Advances in Cancer Research; Elsevier: San Diego, CA, USA, 2017; pp. 259–302. ISBN 978-0-12-812016-3.pl
dc.description.referencesTan, S.M.; Sharma, A.; Stefanovic, N.; de Haan, J.B. Late-intervention study with ebselen in an experimental model of type 1 diabetic nephropathy. Free Radic. Res. 2015, 49, 219–227.pl
dc.description.referencesHe, J.; Li, D.; Xiong, K.; Ge, Y.; Jin, H.; Zhang, G.; Hong, M.; Tian, Y.; Yin, J.; Zeng, H. Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy. Bioorg. Med. Chem. 2012, 20, 3816–3827.pl
dc.description.referencesRomero-Hernandez, L.L.; Merino-Montiel, P.; Montiel-Smith, S.; Meza-Reyes, S.; Vega-Báez, J.L.; Abasolo, I.; Schwartz, S., Jr.; Lopez, O.; Fernandez-Bolanos, J.G. Diosgenin-based thio (seleno) ureas and triazolyl glycoconjugates as hybrid drugs. Antioxidant and antiproliferative profile. Eur. J. Med. Chem. 2015, 99, 67–81.pl
dc.description.referencesFuentes-Aguilar, A.; Romero-Hernández, L.L.; Arenas-González, A.; Merino-Montiel, P.; Montiel-Smith, S.; Meza-Reyes, S.; Fernández-Bolaños, J.G. New selenosteroids as antiproliferative agents. Org. Biomol. Chem. 2017, 15, 5041–5054.pl
dc.description.referencesCui, J.G.; Qi, B.B.; Gan, C.F. Synthesis and in vitro antiproliferative evaluation of some B-norcholesteryl benzimidazole and benzothiazole derivatives. Mar. Drugs 2015, 13, 2488–2504.pl
dc.description.referencesAffeldt, R.F.; Santos, F.P.; da Silva, R.S.; Rodrigues, O.E.D.;Wessjohann, L.A.; Lüdtke, D.S. Stereoselective glycoconjugation of steroids with selenocarbohydrates. RSC Advances 2016, 6, 93905–93914.pl
dc.description.referencesRodrigues, O.E.D.; de Souza, D.; Soares, L.C.; Dornelles, L.; Burrow, R.A.; Appelt, H.R.; Alves, C.F.; Alves, D.; Braga, A.L. Stereoselective synthesis of selenosteroids. Tetrahedron Letters 2010, 51, 2237–2240.pl
dc.description.referencesSanti, C.; Capoccia, L.; Monti, B. Zinc-Selenium reagents in organic synthesis. Phys. Sci. Rev. 2018, 3. Available online: https://www.degruyter.com/view/j/psr.2018.3.issue-12/psr-2017-0129/psr-2017-0129.xml (accessed on 11 August 2018).pl
dc.description.referencesSanti, C.; Santoro, S.; Battistelli, B.; Testaferri, L.; Tiecco, M. Preparation of the First Bench-Stable Phenyl Selenolate: An Interesting “On Water” Nucleophilic Reagent. Eur. J. Org. Chem. 2008, 2008, 5387–5390.pl
dc.description.referencesPerin, G.; Alves, D.; Jacob, R.G.; Barcellos, A.M.; Soares, L.K.; Lenardão, E.J. Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media. ChemistrySelect 2016, 1, 205–258.pl
dc.description.referencesSanti, C.; Battistelli, B.; Testaferri, L.; Tiecco, M. On water preparation of phenylselenoesters. Green Chemistry 2012, 14, 1277.pl
dc.description.referencesBattistelli, B.; Lorenzo, T.; Tiecco, M.; Santi, C. “On-Water” Michael-Type Addition Reactions Promoted by PhSeZnCl. Eur. J. Org. Chem. 2011, 2011, 1848–1851.pl
dc.description.referencesSantoro, S.; Battistelli, B.; Testaferri, L.; Tiecco, M.; Santi, C. Vinylic Substitutions Promoted by PhSeZnCl: Synthetic and Theoretical Investigations. Eur. J. Org. Chem. 2009, 2009, 4921–4925.pl
dc.description.referencesSalman, S.; Schwab, R.; Alberto, E.; Vargas, J.; Dornelles, L.; Rodrigues, O.; Braga, A. E cient Ring Opening of Protected and Unprotected Aziridines Promoted by Stable Zinc Selenolate in Ionic Liquid. Synlett 2011, 2011, 69–72.pl
dc.description.referencesNagasawa, T.; Shimada, N.; Torihata, M.; Kuwahara, S. Enantioselective total synthesis of idesolide via NaHCO₃-promoted dimerization. Tetrahedron 2010, 66, 4965–4969.pl
dc.description.referencesJiang, H.; Pan, X.; Li, N.; Zhang, Z.; Zhu, J.; Zhu, X. Selenide-containing high refractive index polymer material with adjustable refractive index and Abbe’s number. React. Funct. Polym. 2017, 111, 1–6.pl
dc.description.referencesPaillasse, M.R.; Saffon, N.; Gornitzka, H.; Silvente-Poirot, S.; Poirot, M.; de Medina, P. Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. J. Lipid Res. 2012, 53, 718–725.pl
dc.description.referencesJastrzebska, I. Chemistry of Steroidal Sapogenins-New Advances in a Classical Field. Curr. Org. Chem. 2012, 16, 353–372.pl
dc.description.referencesPetrow, V.A. 212. Steroids and related compounds. Part III. The constitution ofWestphalen’s diol. J. Chem. Soc. (Resumed) 1939, 998.pl
dc.description.referencesKasal, A.; Budesinsky, M.; Gri ths, W.J. Spectroscopic Methods of Steroid Analysis. In Steroid Analysis, 2nd ed.; Makin, H.L.J., Gower, D.B., Eds.; Springer: London, UK, 2010; pp. 62–106.pl
dc.description.referencesFürst, A.; Plattner, P.A. 2 , 3 -und 2 , 3 -Oxido-chlolestane; Konfiguration der 2-Oxy-cholestane. Helvetica Chimica Acta 1949, 32, 275–283.pl
dc.description.referencesVeesenmeyer, J.L.; Hauser, A.R.; Lisboa, T.; Rello, J. Pseudomonas aeruginosa virulence and therapy: Evolving translational strategies. Crit. Care Med. 2009, 37, 1777–1786.pl
dc.description.referencesKadurugamuwa, J.L.; Sin, L.; Albert, E.; Yu, J.; Francis, K.; DeBoer, M.; Rubin, M.; Bellinger-Kawahara, C.; Parr, T.R.; Contag, P.R. Direct Continuous Method for Monitoring Biofilm Infection in a Mouse Model. Infect. Immun. 2003, 71, 882–890.pl
dc.description.referencesEpand, R.M.; Epand, R.F.; Savage, P.B. Ceragenins (Cationic Steroid Compounds), a novel class of antimicrobial agents. Drug News Perspect. 2008, 21, 307.pl
dc.description.referencesMori, K.; Nakayama, T.; Sakuma, M. Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach. Bioorganic Med. Chem. 1996, 4, 401–408.pl
dc.description.referencesShawakfeh, K.Q.; Al-Said, N.H. Synthesis of new symmetrical bis-steroidal pyrazine analogues from diosgenin. Steroids 2011, 76, 232–237.pl
dc.description.referencesWeissenberg, M.; Lavie, D.; Glotter, E. Studies on epoxides—VI. Tetrahedron 1973, 29, 353–358.pl
dc.description.referencesWeissenberg, M.; Glotter, E. Steric course of reduction with sodium borohydride of steroidal αβ-epoxy-ketones. J. Chem. Soc. Perkin Trans. 1978, 1, 568–571.pl
dc.description.referencesNiemirowicz, K.; Piktel, E.; Wilczewska, A.; Markiewicz, K.; Durnaś, B.; Wątek, M.; Puszkarz, I.; Wróblewska, M.; Niklińska, W.; Savage, P.; et al. Core-shell magnetic nanoparticles display synergistic antibacterial effects against Pseudomonas aeruginosa and Staphylococcus aureus when combined with cathelicidin LL-37 or selected ceragenins. Int. J. Nanomed. 2016, 11, 5443–5455.pl
dc.description.volume20pl
dc.description.issue9pl
dc.identifier.citation2International Journal of Molecular Sciencespl
dc.identifier.orcidbrakorcid-
dc.identifier.orcidbrakorcid-
dc.identifier.orcidbrakorcid-
dc.identifier.orcidbrakorcid-
dc.identifier.orcidbrakorcid-
dc.identifier.orcidbrakorcid-
dc.identifier.orcid0000-0001-7664-9226-
dc.identifier.orcidbrakorcid-
dc.identifier.orcid0000-0002-7698-8970-
Występuje w kolekcji(ach):Artykuły naukowe (WChem)

Pliki w tej pozycji:
Plik Opis RozmiarFormat 
I_Jastrzebska_S_Mellea_V_Salerno_at_al_PhSeZnCl_in_the_Synthesis_of_Steroidal.pdf4,62 MBAdobe PDFOtwórz
Pokaż uproszczony widok rekordu Zobacz statystyki


Pozycja ta dostępna jest na podstawie licencji Licencja Creative Commons CCL Creative Commons