A 4-(o-methoxyphenyl)-2-aminothiazole: an anti-quorum sensing compound
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The 4-(o-methoxyphenyl)-2 aminothiazole was synthesized by reacting o-methoxyacetophenone, iodine, and thiourea; and characterized by spectral UV–Visible, Infra-Red (IR), H1 nuclear magnetic resonance, C13NMR, gas chromatography-mass spectroscopy, and thermal analyses. From the thermo gravimetric-differential thermal analysis curve, various kinetic parameters like order of reaction (n), energy of activation (E), pre-exponential factor (Z), entropy of activation (ΔS), and free energy change (G) have been calculated using Coats–Redfern, MacCallum–Tanner, and Horowitz–Metzger methods. The compound was evaluated for antibacterial activity against Bacillus subtilis 2063 and Escherichia coli 2931, and its mechanism of action was studied by fluorescence microscopy and scanning electron microscopy. A novel functional application of MPAT, a quorum sensing mediated inhibition of biofilm was studied in Pseudomonas aeruginosa, which is hitherto un-attempted.
KeywordsAminothiazole Thermal analysis Quorum sensing Antibacterial SEM
Authors are thankful to the authorities of Solapur University, University of Pune and Vidya Pratishthan’s, A.S.C.College Baramati, for providing research facilities.
- Dash B, Raut MK (1955) Sulphonamide derivatives of thiazoles Indian. J Chem Soc 32:663Google Scholar
- Donlan RM, Costerton JW (2002) Biofilms: survival mechanisms of clinically relevant microorganisms. Clin. Microbiol Rev 15:167–193Google Scholar
- Hentzer M, Wu H, Andersen JB, Rasmussen RK, TB BN, Kumar N, Schembri MA, Song Z, Kristoffersen P, Manefield M, Costerton JW, Molin S, Eberl L, Steinberg P, Kjelleberg S, Høiby N, Givskov M (2005) Attenuation of Pseudomonas aeruginosa virulence by quorum sensing inhibitors. EMBO J 22:3803–3815CrossRefGoogle Scholar
- Ishida T, Ikeda T, Takiguchi NA, Kuroda AH, Ohtake H, J Kato (2007) Inhibition of quorum sensing in Pseudomonas aeruginosa by N-acyl cyclopentylamides. Appl Environ Microbiol 73:3183–3188Google Scholar
- Manefield M, de Nys R, Kumar N, Read R, Givskov M, Steinberg P, Kjelleberg S (1999) Evidence that halogenated furanones from Deliseapulchra inhibit acylatedhomoserine lactone (AHL)-mediated gene expression by displacing the AHL signal from its receptor protein. Microbiology 145:283–291PubMedCrossRefGoogle Scholar
- Pappenberger G, Schulz-Gasch T, Kusznir EF, Muller F, Hennig M (2007) Structure-assisted discovery of an aminothiazole derivative as a lead molecule for inhibition of bacterial fatty-acid synthesis Acta Cryst D 63:1208–1216Google Scholar
- Silvestein RM, Bassler GC, Morill TC (1991) Spectroscopic identification of organic compound, 4 edn. Wiley, New YorkGoogle Scholar
- Skindersoe ME, Ettinger-Epstein P, Rasmussen TB, Bjarnsholt T, de Nys R, Givskov M (2008) Quorum sensing antagonism from marine organisms. Mar. Biotechnol 10:56–63Google Scholar
- Tripathi KD (2003) Essential of medical pharmacology, 5th edn. Jaypee Publishers, New Delhi, pp 627–686Google Scholar
- Ulusoy N, Kiraz M, Kucukbasmaci O (2002) New 6-(4-bromophenyl) imidazo [2,1-b] thiazole derivatives: synthesis and antimicrobial activity. Monatsh Chem 133:1305–1315Google Scholar