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Research Articles

Azoles containing naphthalene with activity against Gram-positive bacteria: in vitro studies and in silico predictions for flavohemoglobin inhibition

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Pages 10220-10229 | Received 27 Mar 2021, Accepted 03 Jun 2021, Published online: 17 Jun 2021

References

  • Acar, M.F., Sari, S., & Dalkara, S. (2019). Synthesis, in vivo anticonvulsant testing, and molecular modeling studies of new nafimidone derivatives. Drug Development Research, 80, 606–616. https://doi.org/10.1002/ddr.21538
  • Azevedo, M.M., Teixeira-Santos, R., Silva, A.P., Cruz, L., Ricardo, E., Pina-Vaz, C., & Rodrigues, A.G. (2015). The effect of antibacterial and non-antibacterial compounds alone or associated with antifugals upon fungi. Frontiers in Microbiology, 6, 669. https://doi.org/10.3389/fmicb.2015.00669
  • Baell, J., & Walters, M.A. (2014). Chemistry: Chemical con artists foil drug discovery. Nature, 513, 481–483. https://doi.org/10.1038/513481a
  • Boyen, F., Verstappen, K.M., De Bock, M., Duim, B., Weese, J.S., Schwarz, S., Haesebrouck, F., & Wagenaar, J.A. (2012). In vitro antimicrobial activity of miconazole and polymyxin B against canine meticillin-resistant Staphylococcus aureus and meticillin-resistant Staphylococcus pseudintermedius isolates. Veterinary Dermatology, 23, 381–385, e70. https://doi.org/10.1111/j.1365-3164.2012.01040.x
  • Bozbey, İ., Sari, S., Salva, E., Kart, D., & Karakurt, A. (2020). p-Trifluoroacetophenone oxime ester derivatives: Synthesis, antimicrobial and cytotoxic evaluation, and molecular modeling studies. Letters in Drug Design & Discovery, 17, 169–183. https://doi.org/10.2174/1570180816666181128112249
  • Clinical and Laboratory Standards Institute (CLSI) (2009). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically (Vol 29, 2nd ed.; Approved standard. M07-A8). Wayne, PA: CLSI. https://pdfs.semanticscholar.org/e835/8b37d8b98cef3a4c575e7be30944f9f0c93d.pdf
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports 7, 42717. https://doi.org/10.1038/srep42717
  • Dixon, S.L., Smondyrev, A.M., Knoll, E.H., Rao, S.N., Shaw, D.E., & Friesner, R.A. (2006). PHASE: A new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. Journal of Computer-Aided Molecular Design, 20, 647–671. https://doi.org/10.1007/s10822-006-9087-6
  • Dogan, I.S., Sarac, S., Sari, S., Kart, D., Essiz Gokhan, S., Vural, I., & Dalkara, S. (2017). New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies. European Journal of Medicinal Chemistry, 130, 124–138. https://doi.org/10.1016/j.ejmech.2017.02.035
  • Dukic, V.M., Lauderdale, D.S., Wilder, J., Daum, R.S., & David, M.Z. (2013). Epidemics of community-associated methicillin-resistant Staphylococcus aureus in the United States: A meta-analysis. PLoS One, 8, e52722. https://doi.org/10.1371/journal.pone.0052722
  • El Hammi, E., Warkentin, E., Demmer, U., Limam, F., Marzouki, N.M., Ermler, U., & Baciou, L. (2011). Structure of Ralstonia eutropha flavohemoglobin in complex with three antibiotic azole compounds. Biochemistry, 50, 1255–1264. https://doi.org/10.1021/bi101650q
  • El Hammi, E., Warkentin, E., Demmer, U., Marzouki, N.M., Ermler, U., & Baciou, L. (2012). Active site analysis of yeast flavohemoglobin based on its structure with a small ligand or econazole. The FEBS Journal, 279, 4565–4575. https://doi.org/10.1111/febs.12043
  • Freeman-Cook, K.D., Hoffman, R.L., & Johnson, T.W. (2013). Lipophilic efficiency: The most important efficiency metric in medicinal chemistry. Future Medicinal Chemistry, 5, 113–115 https://doi.org/10.4155/fmc.12.208
  • Frey, A.D., Farres, J., Bollinger, C.J., & Kallio, P.T. (2002). Bacterial hemoglobins and flavohemoglobins for alleviation of nitrosative stress in Escherichia coli. Applied and Environmental Microbiology, 68, 4835–4840. https://doi.org/10.1128/aem.68.10.4835-4840.2002
  • Friesner, R.A., Banks, J.L., Murphy, R.B., Halgren, T.A., Klicic, J.J., Mainz, D.T., Repasky, M.P., Knoll, E.H., Shelley, M., Perry, J.K., Shaw, D.E., Francis, P., & Shenkin, P.S. (2004). Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. Journal of Medicinal Chemistry, 47, 1739–1749. https://doi.org/10.1021/jm0306430
  • Friesner, R.A., Murphy, R.B., Repasky, M.P., Frye, L.L., Greenwood, J.R., Halgren, T.A., Sanschagrin, P.C., & Mainz, D.T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. Journal of Medicinal Chemistry, 49, 6177–6196. https://doi.org/10.1021/jm051256o
  • Halgren, T.A., Murphy, R.B., Friesner, R.A., Beard, H.S., Frye, L.L., Pollard, W.T., & Banks, J.L. (2004). Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. Journal of Medicinal Chemistry, 47, 1750–1759. https://doi.org/10.1021/jm030644s
  • Harder, E., Damm, W., Maple, J., Wu, C., Reboul, M., Xiang, J.Y., Wang, L., Lupyan, D., Dahlgren, M.K., Knight, J.L., Kaus, J.W., Cerutti, D.S., Krilov, G., Jorgensen, W.L., Abel, R., & Friesner, R.A. (2016). OPLS3: A force field providing broad coverage of drug-like small molecules and proteins. Journal of Chemical Theory and Computation, 12, 281–296. https://doi.org/10.1021/acs.jctc.5b00864
  • Helmick, R.A., Fletcher, A.E., Gardner, A.M., Gessner, C.R., Hvitved, A.N., Gustin, M.C., & Gardner, P.R. (2005). Imidazole antibiotics inhibit the nitric oxide dioxygenase function of microbial flavohemoglobin. Antimicrobial Agents and Chemotherapy 49, 1837–1843 https://doi.org/10.1128/AAC.49.5.1837-1843.2005
  • Ioakimidis, L., Thoukydidis, L., Mirza, A., Naeem, S., & Reynisson, J. (2008). Benchmarking the reliability of QikProp. Correlation between experimental and predicted values. QSAR & Combinatorial Science, 27, 445–456. https://doi.org/10.1002/qsar.200730051
  • Karakurt, A., Alagoz, M.A., Sayoglu, B., Calis, U., & Dalkara, S. (2012). Synthesis of some novel 1-(2-naphthyl)-2-(imidazol-1-yl)ethanone oxime ester derivatives and evaluation of their anticonvulsant activity. European Journal of Medicinal Chemistry, 57, 275–282. https://doi.org/10.1016/j.ejmech.2012.08.037
  • Karakurt, A., Dalkara, S., Ozalp, M., Ozbey, S., Kendi, E., & Stables, J.P. (2001). Synthesis of some 1-(2-naphthyl)-2-(imidazole-1-yl)ethanone oxime and oxime ether derivatives and their anticonvulsant and antimicrobial activities. European Journal of Medicinal Chemistry, 36, 421–433. https://doi.org/10.1016/S0223-5234(01)01223-5
  • Keniya, M.V., Sabherwal, M., Wilson, R.K., Woods, M.A, Sagatova, A.A., Tyndall, J.D.A., Monk, B.C. (2018). Crystal structures of full-length lanosterol 14alpha-demethylases of prominent fungal pathogens Candida albicans and Candida glabrata provide tools for antifungal discovery. Antimicrobial Agents and Chemotherapy, 62(11), e01134–18. https://doi.org/10.1128/AAC.01134-18
  • Khabnadideh, S., Rezaei, Z., Younes, G., & Montazeri-Najafabady, N. (2012). Antibacterial activity of some new azole compounds. Anti-Infective Agents, 10, 26–33. https://doi.org/10.2174/2211362611201010026
  • Lipinski, C.A., Lombardo, F., Dominy, B.W., & Feeney, P.J. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 46, 3–26. https://doi.org/10.1016/S0169-409X(00)00129-0
  • McGann, M. (2012). FRED and HYBRID docking performance on standardized datasets. Journal of Computer-Aided Molecular Design, 26, 897–906. https://doi.org/10.1007/s10822-012-9584-8
  • Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., & Olson, A.J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30, 2785–2791. https://doi.org/10.1002/jcc.21256
  • Mourad, A., & Perfect, J.R. (2018). Tolerability profile of the current antifungal armoury. Journal of Antimicrobial Chemotherapy, 73, i26–i32. https://doi.org/10.1093/jac/dkx446
  • Nenoff, P., Koch, D., Kruger, C., Drechsel, C., & Mayser, P. (2017). New insights on the antibacterial efficacy of miconazole in vitro. Mycoses 60, 552–557. https://doi.org/10.1111/myc.12620
  • Ohguro, N., Fukuda, M., Sasabe, T., & Tano, Y. (1999). Concentration dependent effects of hydrogen peroxide on lens epithelial cells. British Journal of Ophthalmology, 83, 1064–1068. https://doi.org/10.1136/bjo.83.9.1064
  • Ozdemir, Z., Sari, S., Karakurt, A., & Dalkara, S. (2019). Synthesis, anticonvulsant screening, and molecular modeling studies of new arylalkylimidazole oxime ether derivatives Drug Development Research 80, 269–280. https://doi.org/10.1002/ddr.21491
  • Raucy, J.L., Carpenter, S.J., & Trzaskos, J.M. (1991). Identification of lanosterol 14 alpha-methyl demethylase in human tissues Biochemical and Biophysical Research Communications 177, 497–503. https://doi.org/10.1016/0006-291X(91)92011-8
  • Sari, S., Karakurt, A., Uslu, H., Kaynak, F.B., Calis, U., & Dalkara, S. (2016). New (arylalkyl)azole derivatives showing anticonvulsant effects could have VGSC and/or GABAAR affinity according to molecular modeling studies. European Journal of Medicinal Chemistry, 124, 407–416 https://doi.org/10.1016/j.ejmech.2016.08.032
  • Sari, S., Koçak, E., Kart, D., Özdemir, Z., Acar, M.F., Sayoğlu, B., Karakurt, A., & Daklara, S. (2021). Azole derivatives with naphthalene showing potent antifungal effects against planktonic and biofilm forms of Candida spp.: An in vitro and in silico study. International Microbiology, 24, 93–102. https://doi.org/10.1007/s10123-020-00144-y
  • Sastry, G.M., Adzhigirey, M., Day, T., Annabhimoju, R., & Sherman, W. (2013). Protein and ligand preparation: Parameters, protocols, and influence on virtual screening enrichments. Journal of Computer-Aided Molecular Design 27, 221–234. https://doi.org/10.1007/s10822-013-9644-8
  • Sud, I.J., & Feingold, D.S. (1982). Action of antifungal imidazoles on Staphylococcus aureus. Antimicrobial Agents and Chemotherapy 22, 470–474. https://doi.org/10.1128/AAC.22.3.470
  • Veber, D.F., Johnson, S.R., Cheng, H.Y., Smith, B.R., Ward, K.W., & Kopple, K.D. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry 45, 2615–2623 https://doi.org/10.1021/jm020017n
  • Wang, J. (2009). Comprehensive assessment of ADMET risks in drug discovery. Current Pharmaceutical Design 15, 2195–2219. https://doi.org/10.2174/138161209788682514

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