197
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Elucidation of furanone as ergosterol pathway inhibitor in Cryptococcus neoformans

, , ORCID Icon, ORCID Icon &
Pages 6013-6026 | Received 31 Mar 2023, Accepted 21 Jun 2023, Published online: 05 Jul 2023

References

  • Ademe, M. (2020). Immunomodulation for the treatment of fungal infections: Opportunities and challenges. Frontiers in Cellular and Infection Microbiology, 10, 469. https://doi.org/10.3389/fcimb.2020.00469
  • Arastehfar, A., Gabaldón, T., Garcia-Rubio, R., Jenks, J. D., Hoenigl, M., Salzer, H. J., Ilkit, M., Lass-Flörl, C., & Perlin, D. S. (2020). Drug-resistant fungi: An emerging challenge threatening our limited antifungal armamentarium. Antibiotics, 9(12), 877. https://doi.org/10.3390/antibiotics9120877
  • Arthington-Skaggs, B. A., Jradi, H., Desai, T., & Morrison, C. J. (1999). Quantitation of ergosterol content: Novel method for determination of fluconazole susceptibility of candida albicans. Journal of Clinical Microbiology, 37(10), 3332–3337. https://doi.org/10.1128/jcm.37.10.3332-3337.1999
  • Azam, F., Khan, M. A., Khan, A., Ahmad, S., Zofair, S. F. F., & Younus, H. (2022). In silico and in vitro studies on the inhibition of laccase activity by ellagic acid: Implications in drug designing for the treatment of cryptococcal infections. International Journal of Biological Macromolecules, 209(Pt A), 642–654. https://doi.org/10.1016/j.ijbiomac.2022.04.060
  • Badavath, V. N., Nayan Sinha, B., & Jayaprakash, V. (2015). Design, in-silico docking and predictive adme properties of novel pyrazoline derivatives with selective human MAO inhibitory activity. International Journal of Pharmacy and Pharmaceutical Sciences, 7(12), 277–282.
  • Beg, M. A., Shivangi Thakur, S. C., & Meena, L. S. (2018). Structural prediction and mutational analysis of Rv3906c gene of mycobacterium tuberculosis H37Rv to determine its essentiality in survival. Advances in Bioinformatics, 2018, 6152014. https://doi.org/10.1155/2018/6152014
  • Bellamine, A., Lepesheva, G. I., & Waterman, M. R. (2004). Fluconazole binding and sterol demethylation in three CYP51 isoforms indicate differences in active site topology. Journal of Lipid Research, 45(11), 2000–2007. https://doi.org/10.1194/jlr.M400239-JLR200
  • Benitez, L. L., & Carver, P. L. (2019). Adverse effects associated with long-term administration of azole antifungal agents. Drugs, 79(8), 833–853. https://doi.org/10.1007/s40265-019-01127-8
  • Binkowski, T. A., Naghibzadeh, S., & Liang, J. (2003). CASTp: Computed atlas of surface topography of proteins. Nucleic Acids Research, 31(13), 3352–3355. https://doi.org/10.1093/nar/gkg512
  • Bowers, K. J., Chow, E., Xu, H., Dror, R. O., Eastwood, M. P., Gregersen, B. A., & Klepeis, J. L. (2006). Scalable algorithms for molecular dynamics simulations on commodity clusters [Paper presentation]. https://doi.org/10.1145/1188455.1188544
  • Chen, Y., Shi, Z. W., Strickland, A. B., & Shi, M. (2022). Cryptococcus neoformans infection in the central nervous system: The battle between host and pathogen. Journal of Fungi,8(10), 1069. https://doi.org/10.3390/jof8101069
  • Dallakyan, S., & Olson, A. J. (2014). Small-molecule library screening by docking with PyRx. Methods in Molecular Biology, 1263, 243–250. https://doi.org/10.1007/978-1-4939-2269-7
  • Dyląg, M., Colon-Reyes, R. J., & Kozubowski, L. (2020). Titan cell formation is unique to cryptococcus species complex ABSTRACT. Virulence, 11(1), 719–729. https://doi.org/10.1080/21505594.2020.1772657
  • Firacative, C. (2020). Invasive fungal disease in humans: Are we aware of the real impact. Memórias do Instituto Oswaldo Cruz, 115, 1–9. https://doi.org/10.1590/0074-02760200430
  • Gahlawat, A., Kumar, N., Kumar, R., & Sandhu, H. (2020). Structure-based virtual screening to discover potential lead molecules for the SARS-CoV-2 main protease. Journal of Chemical Information and Modeling, 60, 5781–5793. https://doi.org/10.1021/acs.jcim.0c00546
  • Hosseini, M., Chen, W., Xiao, D., & Wang, C. (2021). Computational molecular docking and virtual screening revealed promising SARS-CoV-2 drugs. Precision Clinical Medicine, 4(1), 1–16. (November 2020): https://doi.org/10.1093/pcmedi/pbab001
  • Houšť, J., Spížek, J., & Havlíček, V. (2020). Antifungal drugs. Metabolites, 10(3), 106. https://doi.org/10.3390/metabo10030106
  • Husain, A., Alam, S., Iram, F., Iqbal, A., & Asif, M. (2019). European journal of medicinal chemistry insights into the chemistry and therapeutic potential of furanones: A versatile pharmacophore. European Journal of Medicinal Chemistry, 171, 66–92. https://doi.org/10.1016/j.ejmech.2019.03.021
  • Kalem, M. C., Subbiah, H., Leipheimer, J., Glazier, V. E., & Panepinto, J. C. (2021). Puf4 mediates post-transcriptional regulation of cell wall biosynthesis and caspofungin resistance in cryptococcus neoformans. MBio, 12(1), 1–20. https://doi.org/10.1128/mBio.03225-20
  • Laniado-Laborín, R., & Cabrales-Vargas, M. N. (2009). Amphotericin B: Side effects and toxicity. Revista Iberoamericana de Micologia, 26(4), 223–227. https://doi.org/10.1016/j.riam.2009.06.003
  • Lilienfeld-Toal, M., Von Wagener, J., Einsele, H., Cornely, O. A., & Kurzai, O. (2019). New treatments to meet new challenges. https://doi.org/10.3238/arztebl.2019.0271
  • Lin, Y. Y., Shiau, S., & Fang, C. T. (2015). Risk factors for invasive cryptococcus neoformans diseases: A case-control study (pp. 1–13). https://doi.org/10.1371/journal.pone.0119090
  • Lockhart, S. R., Toda, M., Benedict, K., & Caceres, D. H. (2021). Endemic and other dimorphic mycoses in the Americas (pp. 1–14).
  • Majik, M. S., Gawas, U. B., & Mandrekar, V. K. (2020). Bioorganic & medicinal chemistry next generation quorum sensing inhibitors: Accounts on structure activity relationship studies and biological activities. Bioorganic & Medicinal Chemistry, 28(21), 115728. https://doi.org/10.1016/j.bmc.2020.115728
  • Matkovic, L. (2014). Determination of ergosterol in cellular fungi by HPLC. A Modified Technique DETERMINATION OF ERGOSTEROL IN CELLULAR FUNGI BY HPLC. A MODIFIED TECHNIQUE.,” no. January 2011.
  • Maziarz, E. K., & Perfect, J. R. (2016). Cryptococcosis. Infectious Disease Clinics of North America, 30(1), 179–206. https://doi.org/10.1016/j.idc.2015.10.006
  • McCarthy, M. W., Kontoyiannis, D. P., Cornely, O. A., Perfect, J. R., & Walsh, T. J. (2017). Novel agents and drug targets to meet the challenges of resistant fungi. The Journal of Infectious Diseases, 216(3), S474–S483. https://doi.org/10.1093/infdis/jix130
  • Mohankumar, T., Chandramohan, V., Lalithamba, H. S., Jayaraj, R. L., Kumaradhas, P., Sivanandam, M., Hunday, G., Vijayakumar, R., Balakrishnan, R., Manimaran, D., & Elangovan, N. (2020). Design and molecular dynamic investigations of as potential neuroprotective agents against alpha-synuclein. Scientific Reports, 10(1), 599. https://doi.org/10.1038/s41598-020-57417-9
  • Nucci, M., & Marr, K. A. (2005). Emerging fungal diseases. Clinical Infectious Diseases, 41(4), 521–526. https://doi.org/10.1086/432060
  • Oliveira, H. C., & De Rodrigues, M. L. (2022). Antifungal development and the urgency of minimizing the impact of fungal diseases on public health. ACS Biochemistry, Medicinal Chemistry, Chemical Biology, Molecular Pharmacology, Pharmaceutics, Molecular Biology , 3, 137–146. https://doi.org/10.1021/acsbiomedchemau.2c00055
  • Park, Y. D., Sun, W., Salas, A., Antia, A., Carvajal, C., Wang, A., Xu, X., Meng, Z., Zhou, M., Tawa, G. J., Dehdashti, J., Zheng, W., Henderson, C. M., Zelazny, A. M., & Williamson, P. R. (2016). Identification of multiple cryptococcal fungicidal drug targets by combined gene dosing and drug affinity responsive target stability screening. MBio, 7(4), e01073-16. https://doi.org/10.1128/mBio.01073-16
  • Pasquier, E., Kunda, J., De Beaudrap, P., Loyse, A., Temfack, E., Molloy, S. F., Harrison, T. S., & Lortholary, O. (2018). Long-term mortality and disability in cryptococcal meningitis: A systematic literature review. Clinical Infectious Diseases 66, 1122–1132. https://doi.org/10.1093/cid/cix870
  • Pudipeddi, A., Vasudevan, S., Shanmugam, K., Mohan S, S., Vairaprakash, P., Neelakantan, P., Balraj, A. S., & Solomon, A. P. (2022). Design, dynamic docking, synthesis, and in vitro validation of a novel DNA gyrase B inhibitor. Journal of Biomolecular Structure and Dynamics, 1–14. https://doi.org/10.1080/07391102.2022.2107073
  • Rathore, S. S., Isravel, M., Vellaisamy, S., Chellappan, D. R., Cheepurupalli, L., Raman, T., & Ramakrishnan, J. (2017). Exploration of antifungal and immunomodulatory potentials of a furanone derivative to rescue disseminated cryptococosis in mice. Scientific Reports, 7(1), 1–14. https://doi.org/10.1038/s41598-017-15500-8
  • Revie, N. M., Iyer, K. R., Robbins, N., & Cowen, L. E. (2018). Sciencedirect antifungal drug resistance: Evolution, mechanisms and impact. Current Opinion in Microbiology, 45, 70–76. https://doi.org/10.1016/j.mib.2018.02.005
  • Rico, M. I., Lebedenko, C. G., Mitchell, S. M., & Banerjee, I. A. (2022). Molecular dynamics simulations, docking and MMGBSA studies of newly designed peptide-conjugated glucosyloxy stilbene derivatives with tumor cell receptors. Molecular Diversity, 26(5), 2717–2743. https://doi.org/10.1007/s11030-021-10354-9
  • Rodriguez-Morelos, V. H., Calonne-Salmon, M., Bremhorst, V., Mónica, G-r., & Stéphane, D. (2021). Fungicides with contrasting mode of action differentially affect hyphal healing mechanism in Gigaspora Sp. and Rhizophagus Irregularis. Frontiers in Plant Science, 12, 1–11. https://doi.org/10.3389/fpls.2021.642094
  • Schrodinger. (2012). Schrödinger press prime user manual prime 3.1 user manual prime user manual. Schrodinger.
  • Schrödinger LLC. (2015). QikProp, Version 4.4 (pp. 1–45). Schrodinger Press. http://gohom.win/ManualHom/Schrodinger/Schrodinger_2015-2_docs/qikprop/qikprop_user_manual.pdf.
  • Setianingrum, F., Rautemaa-Richardson, R., & Denning, D. W. (2019). Review article pulmonary cryptococcosis : A review of pathobiology and clinical aspects (pp. 133–50). October 2018. https://doi.org/10.1093/mmy/myy086
  • Sheng, C., Miao, Z., Ji, H., Yao, J., Wang, W., Che, X., Dong, G., Lü, J., Guo, W., & Zhang, W. (2009). Three-dimensional model of lanosterol 14α-demethylase from cryptococcus neoformans: Active-site characterization and insights into azole binding. Antimicrobial Agents and Chemotherapy, 53(8), 3487–3495. https://doi.org/10.1128/AAC.01630-08
  • Singh, N. (2001). Trends in the epidemiology of opportunistic fungal infections: Predisposing factors and the impact of antimicrobial use practices. Clinical Infectious Diseases, 33(10), 1692–1696. https://doi.org/10.1086/323895
  • Spadari, C. D. C., Wirth, F., Lopes, L. B., & Ishida, K. (2020). New approaches for cryptococcosis treatment. Microorganisms, 8(4), 613. https://doi.org/10.3390/microorganisms8040613
  • Tian, W., Chen, C., Lei, X., Zhao, J., & Liang, J. (2018). CASTp 3.0: Computed atlas of surface topography of proteins. Nucleic Acids Research, 46(W1), W363–W367. https://doi.org/10.1093/nar/gky473
  • Vella, F. M., & Laratta, B. (2017). UV-based evaluation of ergosterol for monitoring the fungal exposure in Italian buffalo farms. FEMS Microbiology Letters, 364(22), 1–6. https://doi.org/10.1093/femsle/fnx224
  • Vinoth, P., Vivekanand, T., Suryavanshi, P. A., Menendez, J. C., Sasai, H., & Sridharan, V. (2015). Palladium (II) -catalyzed intramolecular carboxypalladation-olefin insertion cascade : Direct access to indeno [1, 2-b] furan-2-ones. Organic and Biomolecular Chemistry, 13(18), 5175–5181.
  • Vittorio, S., Gitto, R., Adornato, I., Russo, E., & De Luca, L. (2021). In silico strategy for targeting the MTOR kinase at rapamycin binding site by small molecules. Molecules, 26(4), 1103. https://doi.org/10.3390/molecules26041103
  • Waterhouse, A., Bertoni, M., Bienert, S., Studer, G., Tauriello, G., Gumienny, R., & Heer, F. T. (2018). SWISS-MODEL : Homology modelling of protein structures and complexes. Nucleic Acids Research, 46, 296–303. https://doi.org/10.1093/nar/gky427
  • World Health Organization. (2022). WHO fungal priority pathogens list to guide research, development and public health action. Licence: CC BY-NC-SA 3.0 IGO (Vol. 1). World Health Organization.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.