Propyl (E)-3-(furan-2-yl) Acrylate
a synthetic antifungal potential with a regulatory effect on the biosynthesis of ergosterol in Candida Albicans
DOI:
https://doi.org/10.1590/s2175-97902023e22045Keywords:
Antimicrobial, Candida, New drugs, ErgosterolAbstract
The genus Candida represents the main cause of infections of fungal origin. Some species stand out as disease promoters in humans, such as C. albicans, C. glabrata, C. parapsilosis, and C. tropicalis. This study evaluated the antifungal effects of propyl (E)-3-(furan-2-yl) acrylate. The minimum inhibitory concentration of the synthetic compound, amphotericin B and fluconazole alone against four species of Candida ranged from 64 to 512 μg/mL, 1 to 2 μg/mL, and 32 to 256 μg/mL, respectively. The synergistic effect of the test substance was observed when associated with fluconazole against C. glabrata, there was no antagonism between the substances against any of the tested strains. The potential drug promoted morphological changes in C. albicans, decreasing the amount of resistance, virulence, and reproduction structures, such as the formation of pseudohyphae, blastoconidia, and chlamydospores, ensuring the antifungal potential of this substance. It was also possible to identify the fungicidal profile of the test substance through the study of the growth kinetics of C. albicans. Finally, it was observed that the test compound inhibited the ergosterol biosynthesis by yeast.
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Andrews JM. Determination of minimum inhibitory concentrations. J Antimicrob Chemother. 2001;49:1049-1049. https://academic.oup.com/jac/article/48/ suppl_1/5/2473513?login=true
» https://academic.oup.com/jac/article/48/ suppl_1/5/2473513?login=true
Arthington-Skaggs BA, Warnock DW, Morrison CJ. Quantitation of Candida albicans ergosterol content improves the correlation between in vitro antifungal susceptibility test results and in vivo outcome after fluconazole treatment in a murine model of invasive Candidiasis. Antimicrob Agents Chemother. 2000;44(8):2081-2085.
Aslani N, Janbabaei G, Abastabar M, Meis JF, Babaeian M, Khodavaisy S, et al. Identification of uncommon oral yeasts from cancer patients by MALDI-TOF mass spectrometry. BMC Infect Dis. 2018;18(1):24-34.
Cabral ME, Figueroa LIC, Fariña JI. Synergistic antifungal activity of statin-azole associations as witnessed by Saccharomyces cerevisiae- and Candida utilis-bioassays and ergosterol quantification. Rev Iberoam Micol. 2013;30(1):31-38.
Calugi C, Trabocchi A, Guarna A. Novel small molecules for the treatment of infections caused by Candida albicans: a patent review (2002 - 2010). Expert Opin Ther Pat. 2011;21(3):381-397.
Campitelli M, Zeineddine N, Samaha G, Maslak S. Combination antifungal therapy: A review of current data. J Clin Med Res. 2017;9(6):451-456.
Capoci IRG, Sakita KM, Faria DR, Vendramini FAVR, Arita GS, Oliveira AG, et al. Two new 1,3,4-oxadiazoles with effective antifungal activity against Candida albicans. Front Microbiol. 2019;10:2130-2141.
Chiocchio VM, Matković L. Determination of ergosterol in cellular fungi by HPLC. A modified technique. J Arg Chem Soc. 2011;98:10-15.
Clinical Laboratory Standards Institute. “Reference method for broth dilution antifungal susceptibility testing of yeasts; approved standard.” Third edition. 2008;28.
Correa-Royero J, Tangarife V, Durán C, Stashenko E, Mesa-Arango A. In vitro antifungal activity and cytotoxic effect of essential oils and extracts of medicinal and aromatic plants against Candida krusei and Aspergillus fumigatus. Rev Bras Farmacogn. 2010;20(5):734-741.
Cuenca-Estrella M. Combinations of antifungal agents in therapy-what value are they? J Antimicrob Chemother . 2004;54(5):854-869.
Denning DW, Bromley MJ. How to bolster the antifungal pipeline. Science. 2015;347(6229):1414-1416.
Doern CD. When does 2 plus 2 equal 5? a review of antimicrobial synergy testing. J Clin Microbiol. 2014;52(12):4124-4128.
Hussain MA, Ahmed D, Anwar A, Perveen S, Anis I, Shah MR, et al. Combination therapy of clinically approved antifungal drugs is enhanced by conjugation with silver nanoparticles. Int Microbiol. 2019;22(2):239-246.
Jacobsen ID, Wilson D, Wächtler B, Brunke S, Naglik JR, Hube B. Candida albicans dimorphism as a therapeutic target. Expert Rev Anti Infect Ther. 2012;10(1):85-93.
Keighley C, Chen SCA, Marriott D, Pope A, Chapman B, Kennedy K, et al. Candidaemia and a risk predictive model for overall mortality: a prospective multicentre study. BMC Infect Dis . 2019;19(1):445-455.
Klepser ME, Ernst EJ, Lewis RE, Ernst ME, Pfaller MA. Influence of Test Conditions on antifungal time-kill curve results: Proposal for standardized methods. Antimicrob Agents Chemother . 1998;42(5):1207-1212.
Kibbler CC. The Pro-debate: How can we improve the outcome of invasive fungal infection? The case for combination therapy. Infectio. 2012;16(Suppl 3):3-10.
Lignell A, Johansson A, Löwdin E, Cars O, Sjölin J. A new in-vitro kinetic model to study the pharmacodynamics of antifungal agents: inhibition of the fungicidal activity of amphotericin B against Candida albicans by voriconazole. Clin Microbiol Infect. 2007;13(6):613-619.
Lin Y-L, Tsai Y-L, Kuo Y-H, Liu Y-H, Shiao M-S. Phenolic Compounds from Tournefortia sarmentosa. J Nat Prod. 1999;62(11):1500-1503.
Liu R-H, Shang Z-C, Li T-X, Yang M-H, Kong L-Y. In Vitro antibiofilm activity of Eucarobustol E against Candida albicans. Antimicrob Agents Chemother . 2017;61(8):2707-2716.
Loğoğlu E, Yilmaz M, Katircioğlu H, Yakut M, Mercan S. Synthesis and biological activity studies of furan derivatives. Med Chem Res. 2010;19(5):490-497.
Lu M, Li T, Wan J, Li X, Yuan L, Sun S. Antifungal effects of phytocompounds on Candida species alone and in combination with fluconazole. Int J Antimicrob Agents. 2017;49(2):125-136.
Manoharan RK, Lee J-H, Kim Y-G, Kim S-I, Lee J. Inhibitory effects of the essential oils α-longipinene and linalool on biofilm formation and hyphal growth of Candida albicans. Biofouling. 2017;33(2):143-155.
Masubuchi M, Ebiike H, Kawasaki K, Sogabe S, Morikami K, Shiratori Y, et al. Synthesis and biological activities of benzofuran antifungal agents targeting fungal N-myristoyltransferase. Bioorg Med Chem. 2003;11(20):4463-4478.
Minnebruggen GV, François IEJA, Cammue BPA, Vroome V, Borgers M, Shroot B. A general overview on past, present and future antimycotics. Open Mycol J. 2010;4(1):22-32.
Mutasa T, Mangoyi R, Mukanganyama S. The Effects of combretum zeyheri leaf extract on ergosterol synthesis in Candida albicans. J Herbs Spices Med Plants. 2015;21(2):211-217.
Pagniez F, Lebouvier N, Na YM, Garnier IO, Picot C, Le Borgne M, et al. Biological exploration of a novel 1,2,4-triazole-indole hybrid molecule as antifungal agent. J Enzyme Inhib Med Chem. 2020;35(1):398-403.
Prasad R, Shah AH, Rawal, MK. Antifungals: mechanism of action and drug resistance. In: Yeast Membrane Transport. Springer. 2016;892:327-349.
Rehan M, Nallagonda R, Das BG, Meena T, Ghorai P. Synthesis of functionalized benzo[b]furans via oxidative cyclization of o-cinnamyl phenols. J Org Chem.2017;82(7):3411-3424.
Schneider K, Keller S, Wolter FE, Röglin L, Beil W, Seitz O, et al. Proximicins A, B, and C-Antitumor Furan Analogues of Netropsin from the Marine ActinomyceteVerrucosispora Induce Upregulation of p53 and the Cyclin Kinase Inhibitor p21. Angew Chemie Int Ed. 2008;47(17):3258-3261.
Scorneaux B, Angulo D, Borroto-Esoda K, Ghannoum M, Peel M, Wring S. SCY-078 Is fungicidal against candida species in time-kill studies. Antimicrob Agents Chemother . 2017;61(3):1961-1971.
Sharafutdinov IS, Ozhegov GD, Sabirova AE, Novikova VV, Lsovskaya SA, Khabibrakhmanova AM, et al. Increasing susceptibility of drug-resistant candida albicans to fluconazole and terbinafine by 2 (5h)-furanone derivative. Molecules. 2010;25(3):642-660.
Shareck J, Belhumeur P. Modulation of morphogenesis in candida albicans by various small molecules. Eukaryot Cell. 2011;10(8):1004-1012.
Silverstein RM, Webster FX, Kiemle DJ, Bryce DL. Identification Of Organic Compounds. 7th New York: College of Environmental Science and Forestry, 2005.
Su H, Han L, Ding N, Guan P, Hu C, Huang X. Bafilomycin C1 exert antifungal effect through disturbing sterol biosynthesis in Candida albicans. J Antibiot. 2018;71(4):467-476.
Vila T, Romo JA, Pierce CG, McHardy SF, Saville SP, Lopez-Ribot JL. Targeting Candida albicans filamentation for antifungal drug development. Virulence. 2017;8(2):150-158.
Walsh TJ, Hayden RT, Larone DH. Larones’s Medically Importante Fungi: A Guide To Identification, 6th Washington: American Society of Microbiology (ASM press), 2018.
Wiederhold NP. Antifungal Susceptibility Testing: A Primer for Clinicians. Open Forum Infect Dis. 2021;8(11):1-13.
Wu X, Pang XJ, Xu LL, Zhao T, Long XY, Zhang QY, et al. Two new alkylated furan derivatives with antifungal and antibacterial activities from the plant endophytic fungus Emericella sp. XL029. Nat Prod Res. 2018;32(22):2625-2631.
Zhao S, Huang J-J, Sun X, Huang X, Fu S, Yang L, et al. (1-aryloxy-2-hydroxypropyl)-phenylpiperazine derivatives suppress Candida albicans virulence by interfering with morphological transition. Microb Biotechnol. 2018;11(6):1080-1089.
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