Sphingolipid synthesis inhibitors Antifungal agents like lipoxamycin produced by Actino-mycetes sp., sphingofungins produced by A. fumigatus and viridiofungins by Trichoderma viride are known inhi- bitors of serine palmitoyltransferase (Mandala et al. Synthesis, activity, and docking studies of eugenol‐based glucosides as new agents against Comparison and analysis of the structures and binding modes of antifungal SE and CYP51 inhibitors. 5-Nitrofuranes and 5-nitrothiophenes with anti-Trypanosoma cruzi activity and ability to accumulate squalene. Highest squalene levels (over 1000 μg squalene per 10(9) cells) were induced by specific point mutations in ERG1 gene that reduced activity of squalene epoxidase and caused hypersensitivity to terbinafine. This accumulation of squalene in erg1 mutants did not significantly disturb their growth. Terbinafine SF 86-327 is one of the allylamines, which were developed as synthetic antifungal drugs ( 22 ). http://pubs.acs.org/page/copyright/permissions.html, https://doi.org/10.1021/acsmedchemlett.0c00017, https://doi.org/10.1021/acs.chemrestox.9b00006, https://doi.org/10.1021/acs.chemrev.5b00630, https://doi.org/10.1016/j.jddst.2020.102280, https://doi.org/10.1038/s41598-020-58187-0, https://doi.org/10.1016/j.ejmech.2020.112645, https://doi.org/10.1016/j.ejmech.2020.112991, https://doi.org/10.1016/j.plipres.2020.101033, https://doi.org/10.1016/j.bioorg.2020.103749, https://doi.org/10.1016/j.algal.2020.101902, https://doi.org/10.2174/1573406415666190603103012, https://doi.org/10.1080/00498254.2019.1581959, https://doi.org/10.1016/j.fgb.2019.103266, https://doi.org/10.1016/j.mycmed.2019.100903, https://doi.org/10.3390/molecules24193576, https://doi.org/10.1080/17425247.2019.1593962, https://doi.org/10.1016/j.imu.2019.100177, https://doi.org/10.1016/j.canlet.2018.03.034, https://doi.org/10.1126/scitranslmed.aap9840, https://doi.org/10.1016/j.fct.2017.11.027, https://doi.org/10.1007/s00044-017-1948-0, https://doi.org/10.1016/j.jmgm.2017.07.031, https://doi.org/10.1016/S1674-6384(17)60077-7, https://doi.org/10.1016/j.ces.2016.06.004, https://doi.org/10.1016/j.ces.2016.06.014, https://doi.org/10.1007/s12088-015-0524-x, https://doi.org/10.1016/j.cvex.2015.01.008, https://doi.org/10.1371/journal.pone.0120446, https://doi.org/10.1007/978-3-319-11912-0_9, https://doi.org/10.1053/j.jepm.2013.11.006, https://doi.org/10.1016/j.ejmech.2013.07.043, https://doi.org/10.1371/journal.pone.0049004, https://doi.org/10.1053/j.jepm.2012.02.007. Matthias A. Fügi, Marcel Kaiser, Marcel Tanner, Roger Schneiter, Pascal Mäser, Xue Li Guan. Google has not performed a legal analysis and makes no representation as to the … Antifungal Activity of Aspidin BB from Dryopteris fragrans against Trichophyton rubrum Involved Inhibition of Ergosterol Biosynthesis. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. In eukaryotes, squalene is oxidized by squalene epoxidase and then enzymatically cyclized in the first step of steroid biosynthesis. Proteins: Structure, Function, and Bioinformatics. To whom correspondence should be addressed. Squalene-Tetrahymanol Cyclase Expression Enables Sterol-Independent Growth of Find more information about Crossref citation counts. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. In the energetically most likely orientation of terbinafine its interaction energy with the protein is ca. Ligand-Binding Affinity Estimates Supported by Quantum-Mechanical Methods. Yue Dong, Xinyong Liu, Yunfei An, Min Liu, Jun Han, Bin Sun. Cu-Catalyzed tertiary alkylation of α-(trifluoromethyl)styrenes with tertiary alkylmagnesium reagents. Bin Sun, Yue Dong, Yunfei An, Min Liu, Jun Han, Liyu Zhao, Xinyong Liu. Sanne J. Wiersma, Christiaan Mooiman, Martin Giera, Jack T. Pronk, . For permission to reproduce, republish and In constrast, inhibition of rat liver squalene epoxidase only occurs at higher drug concentrations (K i =77 μ m), and is competitive with squalene. CYP2C19 and 3A4 Dominate Metabolic Clearance and Bioactivation of Terbinafine Based on Computational and Experimental Approaches. Mary A. Davis, Dustyn A. Barnette, Noah R. Flynn, Anirudh S. Pidugu, S. Joshua Swamidass, Gunnar Boysen. Approximately 75 % of oral terbinafine is absorbed. system. Design and development of terbinafine hydrochloride ethosomal gel for enhancement of transdermal delivery: In vitro, in vivo, molecular docking, and stability study. You have to login with your ACS ID befor you can login with your Mendeley account. from the ACS website, either in whole or in part, in either machine-readable form or any other form & Account Managers, For Such a position results in the SE conformational changes and prevents the natural substrate from being able to bind to the enzyme’s active site. Squalene monooxygenase: a journey to the heart of cholesterol synthesis. sp.. Gabriella Cirmena, Paola Franceschelli, Edoardo Isnaldi, Lorenzo Ferrando, Marilena De Mariano, Alberto Ballestrero, Gabriele Zoppoli. Guido J. Noguera, Lucas E. Fabian, Elisa Lombardo, Liliana M. Finkielsztein. For each of these agents, the MIC after 14 days of contact was 0.009 g/ml. Rapid detection of terbinafine resistance in Trichophyton species by Amplified refractory mutation system-polymerase chain reaction. Terbinafine is available as both a topical preparation and an oral tablet. It has now been found that, surprisingly, a combination of the squalene epoxidase inhibitor terbinafine (Lamisil®) and an azole 14α-methyldemethylase inhibitor such as fluconazole and/or itraconazole is active against azole-resistant fungal strains. Squalene peroxidase is responsible for catalyzing the first step in ergosterol biosynthesis; inhibition of this enzyme results in disruption of ergosterol synthesis. Studies of 4-arylthiazolylhydrazones derived from 1-indanones as Understanding the antifungal activity of terbinafine analogues using quantitative structure–activity relationship (qsar) models. Design, Synthesis, and Molecular Docking of 1-(1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine as Potent Nonazole Anticandidal Agent. Squalene monooxygenase – a target for hypercholesterolemic therapy. Dissecting cholesterol and phytosterol biosynthesis via mutants and inhibitors. Construction of antifungal dual-target (SE, CYP51) pharmacophore models and the discovery of novel antifungal inhibitors. Journal of Chemical Information and Computer Sciences. Chemical Compositions of Propolis from China and the United States and their Antimicrobial Activities Against Penicillium notatum. Masakazu Umezawa, Masayuki Nakamura, Ashraf A. El-Ghoneimy, Atsuto Onoda, Hazem M. Shaheen, Hiroshi Hori, Yusuke Shinkai, Yasser S. El-Sayed, Ali H. El-Far, Ken Takeda. 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Understanding the Antitumor Activity of Novel Hydroxysemicarbazide Derivatives as Ribonucleotide Reductase Inhibitors Using CoMFA and CoMSIA. Specific inhibitors of squalene epoxidase such as terbinafine have been reported. In: Periti P, Grassi GG (eds) Current chemotherapy and immunotherapy. Georgopapadakou NH(1), Bertasso A. Design, synthesis, antifungal activity, and ADME prediction of functional analogues of terbinafine. Docking studies followed by molecular dynamics simulations and quantum interaction energy calculations [MP2/6-31G(d)] resulted in the identification of the terbinafine−squalene epoxidase mode of interaction. Inhibitors of squalene epoxidase have found application mainly as antifungal drugs: This material is available free of charge via the Internet at http://pubs.acs.org. 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