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Research Paper

Design, synthesis, and biological evaluation of benzoheterocyclic sulfoxide derivatives as quorum sensing inhibitors in Pseudomonas aeruginosa

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Article: 2175820 | Received 25 Oct 2022, Accepted 30 Jan 2023, Published online: 07 Feb 2023

References

  • Kalia VC, Rani A, Lal S, Cheema S, Raut CP. Combing databases reveals potential antibiotic producers. Expert Opin Drug Discov. 2007;2(2):211–224.
  • Kalia VC. Quorum sensing inhibitors: an overview. Biotechnol Adv. 2013;31(2):224–245.
  • Lewis K. Persister cells, dormancy and infectious disease. Nat Rev Microbiol. 2007;5(1):48–56.
  • de Kievit TR. Quorum sensing in Pseudomonas aeruginosa biofilms. Environ Microbiol. 2009;11(2):279–288.
  • Costerton JW, Stewart PS, Greenberg EP. Bacterial biofilms: a common cause of persistent infections. Science. 1999;284 (5418):1318–1322.
  • Hentzer M, Givskov M. Pharmacological inhibition of quorum sensing for the treatment of chronic bacterial infections. J Clin Invest. 2003;112 (9):1300–1307.
  • Persson T, Givskov M, Nielsen J. Quorum sensing inhibition: targeting chemical communication in gram-negative bacteria. Curr Med Chem. 2005;12(26):3103–3115.
  • Brackman G, Cos P, Maes L, Nelis HJ, Coenye T. Quorum sensing inhibitors increase the susceptibility of bacterial biofilms to antibiotics in vitro and in vivo. Antimicrob Agents Chemother. 2011;55(6):2655–2661.
  • LaSarre B, Federle MJ. Exploiting quorum sensing to confuse bacterial pathogens. Microbiol Mol Biol Rev. 2013;77(1):73–111.
  • Lee J, Zhang L. The hierarchy quorum sensing network in Pseudomonas aeruginosa. Protein Cell. 2015;6(1):26–41.
  • Soukarieh F, Williams P, Stocks MJ, Camara M. Pseudomonas aeruginosa quorum sensing systems as drug discovery targets: current position and future perspectives. J Med Chem. 2018;61(23):10385–10402.
  • Papaioannou E, Utari PD, Quax WJ. Choosing an appropriate infection model to study quorum sensing inhibition in Pseudomonas Infections. Int J Mol Sci. 2013;14(9):19309–19340.
  • Haussler S, Becker T. The Pseudomonas quinolone signal (PQS) balances life and death in Pseudomonas aeruginosa populations. PLoS Pathog. 2008;4(9):e1000166.
  • Schuster M, Lostroh CP, Ogi T, Greenberg EP. Identification, timing, and signal specificity of Pseudomonas aeruginosa quorum-controlled genes: a transcriptome analysis. J Bacteriol. 2003;185(7):2066–2079.
  • Zou Y, Nair SK. Molecular basis for the recognition of structurally distinct autoinducer mimics by the Pseudomonas aeruginosa LasR quorum-sensing signaling receptor. Chem Biol. 2009;16(9):961–970.
  • Ochsner UA, Reiser J. Autoinducer-mediated regulation of rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa. Proc Natl Acad Sci USA. 1995;92(14):6424–6428.
  • Ilangovan A, Fletcher M, Rampioni G, Pustelny C, Rumbaugh K, Heeb S, Camara M, Truman A, Chhabra SR, Emsley J, et al. Structural basis for native agonist and synthetic inhibitor recognition by the Pseudomonas aeruginosa quorum sensing regulator PqsR (MvfR). PLoS Pathog. 2013;9(7):e1003508.
  • Chugani SA, Whiteley M, Lee KM, D’Argenio D, Manoil C, Greenberg EP. QscR, a modulator of quorum-sensing signal synthesis and virulence in Pseudomonas aeruginosa. Proc Natl Acad Sci USA. 2001;98(5):2752–2757.
  • Preston MJ, Seed PC, Toder DS, Iglewski BH, Ohman DE, Gustin JK, Goldberg JB, Pier GB. Contribution of proteases and LasR to the virulence of Pseudomonas aeruginosa during corneal infections. Infect Immun. 1997;65(8):3086–3090.
  • Kalia VC, Purohit HJ. Quenching the quorum sensing system: potential antibacterial drug targets. Crit Rev Microbiol. 2011;37(2):121–140.
  • Bjarnsholt T, van Gennip M, Jakobsen TH, Christensen LD, Jensen PØ, Givskov M. In vitro screens for quorum sensing inhibitors and in vivo confirmation of their effect. Nat Protoc. 2010;5(2):282–293.
  • Jakobsen TH, van Gennip M, Phipps RK, Shanmugham MS, Christensen LD, Alhede M, Skindersoe ME, Rasmussen TB, Friedrich K, Uthe F, et al. Ajoene, a sulfur-rich molecule from garlic, inhibits genes controlled by quorum sensing. Antimicrob Agents Chemother. 2012;56(5):2314–2325.
  • Fong J, Yuan M, Jakobsen TH, Mortensen KT, Delos Santos MMS, Chua SL, Yang L, Tan CH, Nielsen TE, Givskov M. Disulfide bond-containing ajoene analogues as novel quorum sensing inhibitors of Pseudomonas aeruginosa. J Med Chem. 2017;60(1):215–227.
  • Gong Z, Peng Y, Qiu J, Cao A, Wang G, Peng Z. Synthesis, in vitro α-Glucosidase inhibitory activity and molecular docking studies of novel benzothiazole-triazole derivatives. Molecules. 2017;22(9):1555.
  • He M, Fan M, Liu W, Li Y, Wang G. Design, synthesis, molecular modeling, and biological evaluation of novel kojic acid derivatives containing bioactive heterocycle moiety as inhibitors of tyrosinase and antibrowning agents. Food Chem. 2021;362:130241.
  • Ye X, Moeljadi AMP, Chin KF, Hirao H, Zong L, Tan CH. Enantioselective sulfoxidation catalyzed by a bisguanidinium diphosphatobisperoxotungstate ion pair. Angew Chem Int Ed Engl. 2016;55(25):7101–7105.
  • Zhu JX, Lu Y, Chen J, Chen JW, Zhang H, Bao X, Ye X, Wang H. Total synthesis of quinolactacin-H from marine-derived Penicillium sp. ENP701 and biologic activities. RSC Adv. 2020;10(41):24251–24254.
  • Frei R, Breitbach AS, Blackwell HE. 2-Aminobenzimidazole derivatives strongly inhibit and disperse Pseudomonas aeruginosa biofilms. Angew Chem Int Ed Engl. 2012;51(21):5226–5229.
  • Rasmussen TB, Bjarnsholt T, Skindersoe ME, Hentzer M, Kristoffersen P, Köte M, Nielsen J, Eberl L, Givskov M. Screening for quorum-sensing inhibitors (QSI) by use of a novel genetic system, the QSI selector. J Bacteriol. 2005;187(5):1799–1814.
  • Hentzer M, Riede K, Rasmussen TB, Heydorn A, Andersen JB, Parsek MR, Rice SA, Eber L, Molin S, Høiby N, et al. Inhibition of quorum sensing in Pseudomonas aeruginosa biofilm bacteria by a halogenated furanone compound. Microbiol. 2002;148(Pt 1):87–102.
  • Yang L, Rybtke MT, Jakobsen TH, Hentzer M, Bjarnsholt T, Givskov M, Tolker-Nielsen T. Computer-aided identification of recognized drugs as Pseudomonas aeruginosa quorum-sensing inhibitors. Antimicrob Agents Chemother. 2009;53(6):2432–2443.
  • Passador L, Cook JM, Gambello MJ, Rust L, Iglewski BH. Expression of Pseudomonas aeruginosa virulence genes requires cell-to-cell communication. Science. 1993;260(5111):1127–1130.
  • Williams P, Camara M, Hardman A, Swift S, Milton D, Hope VJ, Winzer K, Middleton B, Pritchard DI, Bycroft BW. Quorum sensing and the population-dependent control of virulence. Phil. Trans R Soc Lond B. 2000;355(1397):667–680.
  • Gallagher LA, McKnight SL, Kuznetsova MS, Pesci EC, Manoil C. Functions required for extracellular quinolone signaling by Pseudomonas aeruginosa. J Bacteriol. 2002;184(23):6472–6480.
  • Christensen GD, Simpson WA, Younger JJ, Baddour LM, Barrett FF, Melton DM, Beachey EH. Adherence of coagulase-negative staphylococci to plastic tissue culture plates: a quantitative model for the adherence of staphylococci to medical devices. J Clin Microbiol. 1985;22(6):996–1006.
  • Tan SYY, Chua SL, Chen Y, Rice SA, Kjelleberg S, Nielsen TE, Yang L, Givskov M. Identification of five structurally unrelated quorum-sensing inhibitors of Pseudomonas aeruginosa from a natural-derivative database. Antimicrob Agents Chemother. 2013;57(11):5629–5641.
  • Hamood AN, Griswold J, Colmer J. Characterization of elastase-deficient clinical isolates of Pseudomonas aeruginosa. Infect Immun. 1996;64(8):3154–3160.
  • Smith K, Rajendran R, Kerr S, Lappin DF, Mackay WG, Williams C, Ramage G. Aspergillus fumigatus enhances elastase production in Pseudomonas aeruginosa co-cultures. Med Mycol. 2015;53(7):645–655.
  • Essar DW, Eberly L, Hadero A, Crawford IP. Identification and characterization of genes for a second anthranilate synthase in Pseudomonas aeruginosa: interchangeability of the two anthranilate synthases and evolutionary implications. J Bacteriol. 1990;172(2):884–900.
  • Koch AK, Kappeli O, Fiechter A, Reiser J. Hydrocarbon assimilation and biosurfactant production in Pseudomonas aeruginosa mutants. J Bacteriol. 1991;173(13):4212–4219.
  • Bottomley MJ, Muraglia E, Bazzo R, Carfi A. Molecular insights into quorum sensing in the human pathogen Pseudomonas aeruginosa from the structure of the virulence regulator LasR bound to its autoinducer. J Biol Chem. 2007;282(18):13592–13600.