{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T17:51:04Z","timestamp":1785433864107,"version":"3.56.0"},"reference-count":32,"publisher":"FapUNIFESP (SciELO)","license":[{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2023,1,1]],"date-time":"2023-01-01T00:00:00Z","timestamp":1672531200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Braz. J. Biol."],"abstract":"<jats:p>Abstract Onychomycosis is the most common disease affecting the nail unit and accounts for at least 50% of all nail diseases. In addition, Candida albicans is responsible for approximately 70% of onychomycoses caused by yeasts. This study investigated the antifungal effect of (R) and (S)-citronellal enantiomers, as well as its predictive mechanism of action on C. albicans from voriconazole-resistant onychomycoses. For this purpose, in vitro broth microdilution and molecular docking techniques were applied in a predictive and complementary manner to the mechanisms of action. The main results of this study indicate that C. albicans was resistant to voriconazole and sensitive to the enantiomers (R) and (S)-citronellal at a dose of 256 and 32 \u00b5g\/mL respectively. In addition, there was an increase in the minimum inhibitory concentration (MIC) of the enantiomers in the presence of sorbitol and ergosterol, indicating that these molecules possibly affect the integrity of the cell wall and cell membrane of C. albicans. Molecular docking with key biosynthesis proteins and maintenance of the fungal cell wall and plasma membrane demonstrated the possibility of (R) and (S)-citronellal interacting with two important enzymes: 1,3-\u03b2-glucan synthase and lanosterol 14\u03b1-demethylase. Therefore, the findings of this study indicate that the (R) and (S)-citronellal enantiomers are fungicidal on C. albicans from onychomycoses and probably these substances cause damage to the cell wall and cell membrane of these micro-organisms possibly by interacting with enzymes in the biosynthesis of these fungal structures.<\/jats:p>","DOI":"10.1590\/1519-6984.271530","type":"journal-article","created":{"date-parts":[[2023,5,22]],"date-time":"2023-05-22T12:31:59Z","timestamp":1684758719000},"source":"Crossref","is-referenced-by-count":8,"title":["Antifungal effect of (R) and (S)-citronellal enantiomers and their predictive mechanism of action on Candida albicans from voriconazole-resistant onychomycoses"],"prefix":"10.1590","volume":"83","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7648-6794","authenticated-orcid":false,"given":"R. G.","family":"Gouveia","sequence":"first","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6794-1601","authenticated-orcid":false,"given":"N. R.","family":"Oliveira","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0681-8439","authenticated-orcid":false,"given":"F.P.","family":"Andrade-J\u00fanior","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9489-7394","authenticated-orcid":false,"given":"R. C.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7269-891X","authenticated-orcid":false,"given":"G. M. W.","family":"Amorim","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4605-4509","authenticated-orcid":false,"given":"D. K. F.","family":"Silva","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5238-9594","authenticated-orcid":false,"given":"S. S.","family":"Duarte","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6413-8303","authenticated-orcid":false,"given":"C. I. S.","family":"Medeiros","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7466-9933","authenticated-orcid":false,"given":"A. A.","family":"Oliveira-Filho","sequence":"additional","affiliation":[{"name":"Universidade Federal de Campina Grande,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9547-0886","authenticated-orcid":false,"given":"E. O.","family":"Lima","sequence":"additional","affiliation":[{"name":"Universidade Federal da Para\u00edba,  Brasil; Universidade Federal da Para\u00edba,  Brasil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"530","published-online":{"date-parts":[[2023]]},"reference":[{"issue":"2","key":"ref1","doi-asserted-by":"crossref","DOI":"10.1016\/j.mycmed.2020.100949","article-title":"Treatment and management strategies of onychomycosis","volume":"30","author":"AGGARWAL R.","year":"2020","journal-title":"Journal de Mycologie M\u00e9dicale"},{"key":"ref2","doi-asserted-by":"crossref","first-page":"214","DOI":"10.3389\/fmicb.2019.00214","article-title":"The still underestimated problem of fungal diseases worldwide","volume":"10","author":"ALMEIDA F.","year":"2019","journal-title":"Frontiers in Microbiology"},{"key":"ref3","article-title":"In vitro antifungal and antibacterial potentials of organic extracts of Avicennia marina collected from Rabigh Lagoon, Red Sea Coasts in Saudi Arabia","volume":"82","author":"BELHADJ-SALAH K.","year":"2022","journal-title":"Brazilian Journal of Biology = Revista Brasileira de Biologia"},{"issue":"1","key":"ref4","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1186\/s13321-019-0362-7","article-title":"DockRMSD: an open-source tool for atom mapping and RMSD calculation of symmetric molecules through graph isomorphism","volume":"11","author":"BELL E.W.","year":"2019","journal-title":"Journal of Cheminformatics"},{"issue":"4","key":"ref5","doi-asserted-by":"crossref","first-page":"1613","DOI":"10.1007\/s00204-016-1916-3","article-title":"New developments and directions in the clinical application of the echinocandins","volume":"91","author":"CHANG C.C.","year":"2017","journal-title":"Archives of Toxicology"},{"issue":"3","key":"ref6","doi-asserted-by":"crossref","first-page":"87","DOI":"10.3390\/jof4030087","article-title":"Challenges and opportunities in the management of 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