{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,1]],"date-time":"2025-10-01T18:06:26Z","timestamp":1759341986280,"version":"3.37.3"},"reference-count":27,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2015,1,14]],"date-time":"2015-01-14T00:00:00Z","timestamp":1421193600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004281","name":"National Science Centre Poland","doi-asserted-by":"crossref","award":["UMO-2011\/03\/D\/NZ7\/06198"],"award-info":[{"award-number":["UMO-2011\/03\/D\/NZ7\/06198"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2015,2]]},"abstract":"<jats:sec><jats:label\/><jats:p>The influence of halogenated methyl sulfones, i.e. bromodichloromethyl\u20104\u2010chloro\u20103\u2010nitrophenyl sulfone (named halogenated methyl sulfone <jats:bold>1<\/jats:bold>), dichloromethyl\u20104\u2010chloro\u20103\u2010nitrophenyl sulfone (halogenated methyl sulfone <jats:bold>2<\/jats:bold>), and chlorodibromomethyl\u20104\u2010hydrazino\u20103\u2010nitrophenyl sulfone (halogenated methyl sulfone <jats:bold>3<\/jats:bold>), on cell growth inhibition, aspartic protease gene (<jats:italic>SAP4\u20136<\/jats:italic>) expression, adhesion to epithelium, and filamentation was investigated. Antifungal susceptibility of the halogenated methyl sulfones was determined with the M27\u2010A3 protocol in the range of 16\u20130.0313\u2009\u00b5g\/mL. Adherence to Caco\u20102 cells was performed in 24\u2010well plates; relative quantification was normalized against ACT1 in cells after 18\u2009h of growth in YEPD and on Caco\u20102 cells. <jats:italic>SAP4\u20136<\/jats:italic> expression was analyzed using RT\u2010PCR. Structure\u2013activity relationship studies suggested that halogenated methyl sulfone <jats:bold>1<\/jats:bold> containing bromodichloromethyl or dichloromethyl function at C\u20104 (halogenated methyl sulfone <jats:bold>2<\/jats:bold>) of the phenyl ring showed the best activity (100% cell inhibition at 0.5\u2009\u00b5g\/mL), while hydrazine at C\u20101 (halogenated methyl sulfone <jats:bold>3<\/jats:bold>) reduced the sulfone potential (100%\u2009=\u20094\u2009\u00b5g\/mL). <jats:italic>SAP4\u20136<\/jats:italic> were up\u2010 or down\u2010regulated depending on the strains\u2019 genetic background and the substitutions on the phenyl ring. Halogenated methyl sulfone <jats:bold>2<\/jats:bold> repressed germination and affected adherence to epithelium (<jats:italic>P<\/jats:italic>\u2009\u2264\u20090.05). The tested halogenated methyl sulfones interfered with the adhesion of <jats:italic>Candida albicans<\/jats:italic> cells to the epithelial tissues, without affecting their viability after 90\u2009min of incubation. The mode of action of the halogenated methyl sulfones was attributed to the reduced virulence of <jats:italic>C. albicans<\/jats:italic>. <jats:italic>SAP5<\/jats:italic> and <jats:italic>SAP6<\/jats:italic> contribute to halogenated methyl sulfones resistance. Thus, halogenated methyl sulfones can inhibit biofilm formation due to their interference with adherence and with the yeast\u2010to\u2010hyphae transition.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ardp.201400360","type":"journal-article","created":{"date-parts":[[2015,1,14]],"date-time":"2015-01-14T20:14:02Z","timestamp":1421266442000},"page":"132-143","source":"Crossref","is-referenced-by-count":5,"title":["Susceptibility of <i>Candida albicans<\/i> to New Synthetic Sulfone Derivatives"],"prefix":"10.1002","volume":"348","author":[{"given":"Monika","family":"Staniszewska","sequence":"first","affiliation":[{"name":"National Institute of Public Health \u2013 National Institute of Hygiene Warsaw Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ma\u0142gorzata","family":"Bondaryk","sequence":"additional","affiliation":[{"name":"National Institute of Public Health \u2013 National Institute of Hygiene Warsaw Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zbigniew","family":"Ochal","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry Warsaw University of Technology Warsaw Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,1,14]]},"reference":[{"doi-asserted-by":"publisher","key":"e_1_2_7_2_1","DOI":"10.1099\/mic.0.2008\/022293-0"},{"doi-asserted-by":"publisher","key":"e_1_2_7_3_1","DOI":"10.2478\/s11535-014-0311-4"},{"doi-asserted-by":"publisher","key":"e_1_2_7_4_1","DOI":"10.1016\/j.ijantimicag.2009.03.008"},{"doi-asserted-by":"publisher","key":"e_1_2_7_5_1","DOI":"10.1099\/jmm.0.045054-0"},{"doi-asserted-by":"publisher","key":"e_1_2_7_6_1","DOI":"10.2174\/092986711795843182"},{"doi-asserted-by":"publisher","key":"e_1_2_7_7_1","DOI":"10.4331\/wjbc.v1.i2.21"},{"doi-asserted-by":"publisher","key":"e_1_2_7_8_1","DOI":"10.1038\/ja.2014.25"},{"doi-asserted-by":"publisher","key":"e_1_2_7_9_1","DOI":"10.1111\/j.1462-5822.2009.01394.x"},{"doi-asserted-by":"publisher","key":"e_1_2_7_10_1","DOI":"10.1016\/j.biomed.2012.12.004"},{"unstructured":"I.Hiromichi T.Masakazu U.Ten 1994 S. K Preparation of disulfonylthiadiazoles and their use as agrochemical microbiocides Tokyo Japan.","key":"e_1_2_7_11_1"},{"doi-asserted-by":"publisher","key":"e_1_2_7_12_1","DOI":"10.1016\/j.tetlet.2012.09.121"},{"doi-asserted-by":"publisher","key":"e_1_2_7_13_1","DOI":"10.1016\/j.ejmech.2010.08.003"},{"doi-asserted-by":"publisher","key":"e_1_2_7_14_1","DOI":"10.1016\/j.tetlet.2013.12.012"},{"doi-asserted-by":"publisher","key":"e_1_2_7_15_1","DOI":"10.1016\/j.micpath.2009.12.003"},{"doi-asserted-by":"publisher","key":"e_1_2_7_16_1","DOI":"10.1016\/j.fgb.2009.08.002"},{"key":"e_1_2_7_17_1","first-page":"517529","author":"Brand A.","year":"2012","journal-title":"Int. J. Microbiol."},{"doi-asserted-by":"publisher","key":"e_1_2_7_18_1","DOI":"10.1590\/S0074-02762009000300018"},{"doi-asserted-by":"publisher","key":"e_1_2_7_19_1","DOI":"10.1128\/mBio.00117-12"},{"doi-asserted-by":"publisher","key":"e_1_2_7_20_1","DOI":"10.1016\/j.cell.2011.10.048"},{"doi-asserted-by":"publisher","key":"e_1_2_7_21_1","DOI":"10.1007\/BF00328721"},{"doi-asserted-by":"publisher","key":"e_1_2_7_22_1","DOI":"10.1099\/mic.0.2008\/022525-0"},{"issue":"1","key":"e_1_2_7_23_1","doi-asserted-by":"crossref","first-page":"15","DOI":"10.33073\/pjm-2014-002","volume":"63","author":"Staniszewska M.","year":"2014","journal-title":"Pol. J. Microbiol."},{"unstructured":"Method M27\u2013A2 CLSI 2002.","key":"e_1_2_7_24_1"},{"doi-asserted-by":"publisher","key":"e_1_2_7_25_1","DOI":"10.1007\/s11274-014-1676-2"},{"doi-asserted-by":"publisher","key":"e_1_2_7_26_1","DOI":"10.1016\/j.tiv.2012.01.008"},{"key":"e_1_2_7_27_1","first-page":"127","volume-title":"Methods in Yeast Genetics","author":"Amberg D.","year":"2005"},{"doi-asserted-by":"publisher","key":"e_1_2_7_28_1","DOI":"10.1006\/meth.2001.1262"}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fardp.201400360","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.201400360","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,6]],"date-time":"2023-10-06T13:31:26Z","timestamp":1696599086000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.201400360"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,1,14]]},"references-count":27,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2015,2]]}},"alternative-id":["10.1002\/ardp.201400360"],"URL":"https:\/\/doi.org\/10.1002\/ardp.201400360","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"type":"print","value":"0365-6233"},{"type":"electronic","value":"1521-4184"}],"subject":[],"published":{"date-parts":[[2015,1,14]]}}}