Identification of the potential biological target of N-benzenesulfonyl-1,2,3,4-tetrahydroquinoline compounds active against gram-positive and gram-negative bacteria

References

• Alavi, S., Mosslemin, M. H., Mohebat, R., & Massah, A. R. (2017). Green synthesis of novel quinoxaline sulfonamides with antibacterial activity. Research on Chemical Intermediates, 43(8), 4549–4559. doi: 10.1007/s11164-017-2895-6
   Web of Science ®Google Scholar
• Bacellar, I. O. L., Pavani, C., Sales, E. M., Itri, R., Wainwright, M., & Baptista, M. S. (2014). Membrane damage efficiency of phenothiazinium photosensitizers. Photochemistry and Photobiology, 90(4), 801–813. doi: 10.1111/php.12264
   PubMed Web of Science ®Google Scholar
• Bajusz, D., Rácz, A., & Héberger, K. (2015). Why is Tanimoto index an appropriate choice for fingerprint-based similarity calculations?. Journal of Cheminformatics, 7(1), 20. doi: 10.1186/s13321-015-0069-3
   PubMedGoogle Scholar
• Boucher, H. W., Talbot, G. H., Bradley, J. S., Edwards, J. E., Gilbert, D., Rice, L. B., … Bartlett, J. (2009). Bad bugs, no drugs: No ESKAPE! An update from the Infectious Diseases Society of America. Clinical Infectious Diseases, 48(1), 1–12. doi: 10.1086/595011
   PubMed Web of Science ®Google Scholar
• Brown, K., Pompeo, F., Dixon, S., Mengin‐Lecreulx, D., Cambillau, C., & Bourne, Y. (1999). Crystal structure of the bifunctional N‐acetylglucosamine 1‐phosphate uridyltransferase from Escherichia coli a paradigm for the related pyrophosphorylase superfamily. The EMBO Journal, 18(15), 4096–4107. doi: 10.1093/emboj/18.15.4096
   PubMed Web of Science ®Google Scholar
• Butler, M. S., Blaskovich, M. A., & Cooper, M. A. (2013). Antibiotics in the clinical pipeline in 2013. The Journal of Antibiotics, 66(10), 571. doi: 10.1038/ja.2013.86
   PubMed Web of Science ®Google Scholar
• Case, D. A., Berryman, J. T., Betz, R. M., Cerutti, D. S., Cheatham, I. T. E., Darden, T. A., … Luchko, T. P. A. (2016). AMBER16. San Francisco: University of California.
   Google Scholar
• Charrier, C., Salisbury, A.-M., Savage, V. J., Duffy, T., Moyo, E., Chaffer-Malam, N., … Stokes, N. R. (2017). Novel bacterial topoisomerase inhibitors with potent broad-spectrum activity against drug-resistant bacteria. Antimicrobial Agents and Chemotherapy, 61(5). doi: 10.1128/AAC.02100-16
   PubMed Web of Science ®Google Scholar
• Cox, J. A. G., & Worthington, T. (2017). The ‘antibiotic apocalypse’ – Scaremongering or scientific reporting?. Trends in Microbiology, 25(3), 167–169. doi: 10.1016/j.tim.2016.11.016
   PubMed Web of Science ®Google Scholar
• Davies, M., Nowotka, M., Papadatos, G., Dedman, N., Gaulton, A., Atkinson, F., … Overington, J. P. (2015). ChEMBL web services: Streamlining access to drug discovery data and utilities. Nucleic Acids Research, 43(W1), W612–W620. doi: 10.1093/nar/gkv352
   PubMed Web of Science ®Google Scholar
• Delgado, D. A., Doherty, K., Cheng, Q., Kim, H., Xu, D., Dong, H., … Qiang, W. (2016). Distinct membrane disruption pathways are induced by 40-residue β-amyloid peptides. Journal of Biological Chemistry, 291(23), 12233–12244. doi: 10.1074/jbc.M116.720656
   PubMed Web of Science ®Google Scholar
• Ding, J., Wang, K., Liu, W., She, Y., Sun, Q., Shi, J., … Shao, F. (2016). Pore-forming activity and structural autoinhibition of the gasdermin family. Nature, 535(7610), 111. doi: 10.1038/nature18590
   PubMed Web of Science ®Google Scholar
• Epand, R. F., Savage, P. B., & Epand, R. M. (2007). Bacterial lipid composition and the antimicrobial efficacy of cationic steroid compounds (Ceragenins). Biochimica et Biophysica Acta (BBA) - Biomembranes, 1768(10), 2500–2509. doi: 10.1016/j.bbamem.2007.05.023
   PubMed Web of Science ®Google Scholar
• Firsov, A. M., Kotova, E. A., & Antonenko, Y. N. (2018). Calcein leakage as a robust assay for cytochrome c/H2O2–mediated liposome permeabilization. Analytical Biochemistry, 552, 19–23. doi: 10.1016/j.ab.2017.03.014
   PubMed Web of Science ®Google Scholar
• Fred.3.0.0. (n.d.). Fred.3.0.0. OpenEye.Sientific.Software, Santa Fe, NM, http://www.eyesopen.com.
   Google Scholar
• Gaulton, A., Hersey, A., Nowotka, M., Bento, A. P., Chambers, J., Mendez, D., … Leach, A. R. (2017). The ChEMBL database in 2017. Nucleic Acids Research, 45(D1), D945–D954. doi: 10.1093/nar/gkw1074
   PubMed Web of Science ®Google Scholar
• Geiger, O., & Sohlenkamp, C. (2015). Bacterial membrane lipids: Diversity in structures and pathways. FEMS Microbiology Reviews, 40(1), 133–159. doi: 10.1093/femsre/fuv008
   PubMed Web of Science ®Google Scholar
• Gerits, E., Blommaert, E., Lippell, A., O’Neill, A. J., Weytjens, B., De Maeyer, D., … Michiels, J. (2016). Elucidation of the mode of action of a new antibacterial compound active against Staphylococcus aureus and Pseudomonas aeruginosa. PLos One, 11(5), e0155139. doi: 10.1371/journal.pone.0155139
   PubMed Web of Science ®Google Scholar
• Green, O. M., McKenzie, A. R., Shapiro, A. B., Otterbein, L., Ni, H., Patten, A., … Breed, J. (2012). Inhibitors of acetyltransferase domain of N-acetylglucosamine-1-phosphate-uridyltransferase/glucosamine-1-phosphate-acetyltransferase (GlmU). Part 1: Hit to lead evaluation of a novel arylsulfonamide series. Bioorganic & Medicinal Chemistry Letters, 22(4), 1510–1519. doi: 10.1016/j.bmcl.2012.01.016
   PubMed Web of Science ®Google Scholar
• Hay, S. I., Rao, P. C., Dolecek, C., Day, N. P. J., Stergachis, A., Lopez, A. D., & Murray, C. J. L. (2018). Measuring and mapping the global burden of antimicrobial resistance. BMC Medicine, 16(1), 78. doi: 10.1186/s12916-018-1073-z
   PubMedGoogle Scholar
• Humljan, J., Kotnik, M., Contreras-Martel, C., Blanot, D., Urleb, U., Dessen, A., … Gobec, S. (2008). Novel naphthalene-N-sulfonyl-d-glutamic acid derivatives as inhibitors of MurD, a key peptidoglycan biosynthesis enzyme. Journal of Medicinal Chemistry, 51(23), 7486–7494. doi: 10.1021/jm800762u
   PubMed Web of Science ®Google Scholar
• Humphrey, W., Dalke, A., & Schulten, K. (1996). VMD: Visual molecular dynamics. Journal of Molecular Graphics, 14(1), 33–38. doi: 10.1016/0263-7855(96)00018-5
   PubMedGoogle Scholar
• Instant JChem. (2016). Instant JChem was used for structure database management, search and prediction, Instant JChem 16.5.30.0, ChemAxon (http://www.chemaxon.com).
   Google Scholar
• Kollman, P. A., Massova, I., Reyes, C., Kuhn, B., Huo, S., Chong, L., …., Cheatham, III., T. E. (2000). Calculating structures and free energies of complex molecules: Combining molecular mechanics and continuum models. Accounts of Chemical Research, 33(12) doi: 10.1021/ar000033j
   PubMed Web of Science ®Google Scholar
• Kotnik, M., Humljan, J., Contreras-Martel, C., Oblak, M., Kristan, K., Hervé, M., … Solmajer, T. (2007). Structural and functional characterization of enantiomeric glutamic acid derivatives as potential transition state analogue inhibitors of MurD ligase. Journal of Molecular Biology, 370(1), 107–115. doi: 10.1016/j.jmb.2007.04.048
   PubMed Web of Science ®Google Scholar
• Laskowski, R. A., & Swindells, M. B. (2011). LigPlot+: Multiple ligand–protein interaction diagrams for drug discovery. Journal of Chemical Information and Modeling, 51(10), 2778–2786. doi: 10.1021/ci200227u
   PubMed Web of Science ®Google Scholar
• Leelananda, S. P., & Lindert, S. (2016). Computational methods in drug discovery. Beilstein Journal of Organic Chemistry, 12, 2694–2718. doi: 10.3762/bjoc.12.267
   PubMed Web of Science ®Google Scholar
• Maier, J. A., Martinez, C., Kasavajhala, K., Wickstrom, L., Hauser, K. E., & Simmerling, C. (2015). ff14SB: Improving the accuracy of protein side chain and backbone parameters from ff99SB. Journal of Chemical Theory and Computation, 11(8), 3696–3713. doi: 10.1021/acs.jctc.5b00255
   PubMed Web of Science ®Google Scholar
• Martínez, S. R., Miana, G. E., Albesa, I., Mazzieri, M. R., & Becerra, M. C. (2016). Evaluation of antibacterial activity and reactive species generation of n-benzenesulfonyl derivatives of heterocycles. Chemical & Pharmaceutical Bulletin, 64(2), 135–141. doi: 10.1248/cpb.c15-00682
   PubMed Web of Science ®Google Scholar
• Mbaveng, A. T., Ignat, A. G., Ngameni, B., Zaharia, V., Ngadjui, B. T., & Kuete, V. (2016). In vitro antibacterial activities of p-toluenesulfonyl-hydrazinothiazoles and hydrazinoselenazoles against multi-drug resistant Gram-negative phenotypes. BMC Pharmacology and Toxicology, 17(1), 3.
   PubMedGoogle Scholar
• Mengin-Lecreulx, D., & van Heijenoort, J. (1994). Copurification of glucosamine-1-phosphate acetyltransferase and N-acetylglucosamine-1-phosphate uridyltransferase activities of Escherichia coli: Characterization of the glmU gene product as a bifunctional enzyme catalyzing two subsequent steps in the pathway for UDP-N-acetylglucosamine synthesis. Journal of Bacteriology, 176(18), 5788–5795. doi: 10.1128/jb.176.18.5788-5795.1994
   PubMed Web of Science ®Google Scholar
• Miana, G. E., Ribone, S. R., Vera, D. A., Sánchez-Moreno, M., Mazzieri, M. R., & Quevedo, M. A. (2019). Design, synthesis and molecular docking studies of novel N-arylsulfonyl-benzimidazoles with anti Trypanosoma cruzi activity. European Journal of Medicinal Chemistry, 165, 1. doi: 10.1016/j.ejmech.2019.01.013
   PubMed Web of Science ®Google Scholar
• Miller, B. R., McGee, T. D., Swails, J. M., Homeyer, N., Gohlke, H., & Roitberg, A. E. (2012). MMPBSA.py: An efficient program for end-state free energy calculations. Journal of Chemical Theory and Computation, 8(9), 3314–3321. doi: 10.1021/ct300418h
   PubMed Web of Science ®Google Scholar
• Mojsoska, B., Carretero, G., Larsen, S., Mateiu, R. V., & Jenssen, H. (2017). Peptoids successfully inhibit the growth of gram negative E. coli causing substantial membrane damage. Scientific Reports, 7, 42332. doi: 10.1038/srep42332
   PubMed Web of Science ®Google Scholar
• O’Boyle, N. M., Banck, M., James, C. A., Morley, C., Vandermeersch, T., & Hutchison, G. R. (2011). Open Babel: An open chemical toolbox. Journal of Cheminformatics, 3(1), 33. doi: 10.1186/1758-2946-3-33
   PubMed Web of Science ®Google Scholar
• Omega.2.4.3. (n.d.). Omega.2.4.3. OpenEye.Sientific.Software, Santa Fe, NM, http://www.eyesopen.com.
   Google Scholar
• Pagliero, R. J., Kaiser, M., Brun, R., Nieto, M. J., & Mazzieri, M. R. (2017). Lead selection of antiparasitic compounds from a focused library of benzenesulfonyl derivatives of heterocycles. Bioorganic and Medicinal Chemistry Letters, 27(17), 3945–3949. doi: 10.1016/j.bmcl.2017.07.081
   PubMed Web of Science ®Google Scholar
• Pagliero, R. J., Lusvarghi, S., Pierini, A. B., Brun, R., & Mazzieri, M. R. (2010). Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1, 2, 3, 4-tetrahydroquinolines. Bioorganic & Medicinal Chemistry, 18(1), 142–150. doi: 10.1016/j.bmc.2009.11.010
   PubMed Web of Science ®Google Scholar
• Pagliero, R. J., Mercado, R., McCracken, V., Mazzieri, M. R., & Nieto M. J. (2011). Rapid and facile synthesis of n-benzenesulfonyl derivatives of heterocycles and their antimicrobial properties. Letters in Drug Design & Discovery, doi: 10.2174/157018011797200803
   Web of Science ®Google Scholar
• Pompeo, F., van Heijenoort, J., & Mengin-Lecreulx, D. (1998). Probing the role of cysteine residues in glucosamine-1-phosphate acetyltransferase activity of the bifunctional GlmU protein from Escherichia coli: Site-directed mutagenesis and characterization of the mutant enzymes. Journal of Bacteriology, 180(18), 4799–4803. Retrieved from http://www.ncbi.nlm.nih.gov/pmc/articles/PMC107502/
   PubMed Web of Science ®Google Scholar
• Randall, C. P., Mariner, K. R., Chopra, I., & O'Neill, A. J. (2013). The target of daptomycin is absent from Escherichia coli and other gram-negative pathogens. Antimicrobial Agents and Chemotherapy, 57(1), 637–639. doi: 10.1128/AAC.02005-12
   PubMed Web of Science ®Google Scholar
• Rice, L. B. (2008). Federal funding for the study of antimicrobial resistance in nosocomial pathogens: No ESKAPE. The Journal of Infectious Diseases, 197(8), 1079–1081. Retrieved from doi: 10.1086/533452
   PubMed Web of Science ®Google Scholar
• Rogers, D. J., & Tanimoto, T. T. (1960). A computer program for classifying plants. Science (New York, N.Y.), 132(3434), 1115–1118. Retrieved from http://science.sciencemag.org/content/132/3434/1115.abstract doi: 10.1126/science.132.3434.1115
   PubMed Web of Science ®Google Scholar
• Sadashiva, R., Naral, D., Kudva, J., Shivalingegowda, N., Lokanath, N. K., & Pampa, K. J. (2017). Synthesis, spectral, biological activity, and crystal structure evaluation of novel pyrazoline derivatives having sulfonamide moiety. Medicinal Chemistry Research, 26(6), 1213–1227. doi: 10.1007/s00044-017-1838-5
   Web of Science ®Google Scholar
• Sławiński, J., Żołnowska, B., Pirska, D., Kędzia, A., & Kwapisz, E. (2013). Synthesis and antibacterial activity of novel 4-chloro-2-mercaptobenzenesulfonamide derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry, 28(1), 41–51. doi: 10.3109/14756366.2011.625024
   PubMed Web of Science ®Google Scholar
• Smith, C. A. (2006). Structure, function and dynamics in the mur family of bacterial cell wall ligases. Journal of Molecular Biology, 362(4), 640–655. doi: 10.1016/j.jmb.2006.07.066
   PubMed Web of Science ®Google Scholar
• Sosič, I., Barreteau, H., Simčič, M., Šink, R., Cesar, J., Zega, A., … Gobec, S. (2011). Second-generation sulfonamide inhibitors of d-glutamic acid-adding enzyme: Activity optimisation with conformationally rigid analogues of d-glutamic acid. European Journal of Medicinal Chemistry, 46(7), 2880–2894. doi: 10.1016/j.ejmech.2011.04.011
   PubMed Web of Science ®Google Scholar
• Sridharan, V., Suryavanshi, P. A., & Menéndez, J. C. (2011). Advances in the chemistry of tetrahydroquinolines. Chemical Reviews, doi: 10.1021/cr100307m
   PubMedGoogle Scholar
• Tacconelli, E., Carrara, E., Savoldi, A., Harbarth, S., Mendelson, M., Monnet, D. L., … Zorzet, A. (2018). Discovery, research, and development of new antibiotics: The WHO priority list of antibiotic-resistant bacteria and tuberculosis. The Lancet Infectious Diseases, 18(3), 318–327. doi: 10.1016/S1473-3099(17)30753-3
   PubMed Web of Science ®Google Scholar
• Talevi, A. (2018). Computer-aided drug design: An overview. In Gore, M. and Jagtap, U. (Eds.), Computational drug discovery and design (pp. 1–19). Clifton, NJ: Springer.
   Google Scholar
• Todeschini, R., Consonni, V., Xiang, H., Holliday, J., Buscema, M., & Willett, P. (2012). Similarity coefficients for binary chemoinformatics data: Overview and extended comparison using simulated and real data sets. Journal of Chemical Information and Modeling, 52(11), 2884–2901. doi: 10.1021/ci300261r
   PubMed Web of Science ®Google Scholar
• Wang, J., Wolf, R. M., Caldwell, J. W., Kollman, P. A., & Case, D. A. (2004). Development and testing of a general amber force field. Journal of Computational Chemistry, 25(9), 1157–1174. doi: 10.1002/jcc.20035
   PubMed Web of Science ®Google Scholar
• World Health Organization. (2014). Antimicrobial resistance: global report on surveillance. Geneva, Switzerland: World Health Organization Press.
   Google Scholar