Advertisement

Medicinal Chemistry Research

, Volume 22, Issue 9, pp 4183–4191 | Cite as

A 4-(o-methoxyphenyl)-2-aminothiazole: an anti-quorum sensing compound

  • P. G. MoreEmail author
  • N. N. Karale
  • A. S. Lawand
  • S. V. Rajmane
  • S. V. Pawar
  • R. H. Patil
Original Research

Abstract

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.

Keywords

Aminothiazole Thermal analysis Quorum sensing Antibacterial SEM 

Notes

Acknowledgments

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.

References

  1. Al-Saddi MS, Faidallah HM, Rostom SAF (2008) Synthesis and biological evaluation of some 2,4,5-trisubstituted thiazole derivatives as potential antimicrobial and anticancer agents. Archived der pharmazie 341:424–434CrossRefGoogle Scholar
  2. Baselt T, Rehse K (2008) New 2-amino-thiazole-4-acetamides with antiplatelet activity. Archived der pharmazie 341:645–654CrossRefGoogle Scholar
  3. Bjarnsholt T, Givskov M (2008) Quorum sensing inhibitory drugs as next generation antimicrobials: worth the effort? Curr Infect Dis Rep 10:22–28PubMedCrossRefGoogle Scholar
  4. Coats AW, Reddfern JP (1964) Kinetic parameters from thermogravimetric data. Nature 201:68–69CrossRefGoogle Scholar
  5. Convover LH, Tarbell DS (1950) Thiazole analogs of pyridoxine. J Am Chem Soc 72:5221–5225CrossRefGoogle Scholar
  6. Costerton JW, Stewart PS, Greenberg EP (1999) Bacterial biofilms: a common cause of persistent infections. Science 284:1318–1322PubMedCrossRefGoogle Scholar
  7. Cvitkovitch DG, Li YH, Ellen RP (2003) Quorum sensing and biofilm formation in Streptococcal infections. J Clin Invest 112:1626–1632PubMedGoogle Scholar
  8. Dash B, Raut MK (1955) Sulphonamide derivatives of thiazoles Indian. J Chem Soc 32:663Google Scholar
  9. Davies J (1994) Inactivation of antibiotics and the dissemination of resistance genes. Science 264:375–382PubMedCrossRefGoogle Scholar
  10. Davies D (2003) Understanding biofilm resistance to antibacterial agents. Nat Rev Drug Discov 2:114–122PubMedCrossRefGoogle Scholar
  11. Davies J (2006) Where have all the antibiotics gone? Can J Infect Dis Med Microbiol 17:287–290PubMedGoogle Scholar
  12. Dickschat JS (2010) Quorum sensing and bacterial biofilms. Nat Prod Rep 27:343–369PubMedCrossRefGoogle Scholar
  13. Donlan RM, Costerton JW (2002) Biofilms: survival mechanisms of clinically relevant microorganisms. Clin. Microbiol Rev 15:167–193Google Scholar
  14. Dwyer DJ, Kohanski MA, Collins JJ (2009) Role of reactive oxygen species in antibiotic action and resistance. Curr Opin Microbiol 12:482–489PubMedCrossRefGoogle Scholar
  15. Geske GD, Wezeman RJ, Siegel AP, Blackwell HE (2005) Small molecule inhibitors of bacterial quorum sensing and biofilm formation. J Am Chem Soc 127:12762–12763PubMedCrossRefGoogle Scholar
  16. Givskov M, De NysR, Manefield M, Gram L, Maximilien R, Eberl L, Molin S, Steinberg PD, Kjelleberg S (1996) Eukaryotic interference with homoserine lactone-mediated prokaryotic signaling. J Bacteriol 178:6618–6622PubMedGoogle Scholar
  17. Gonzalez JE, Keshavan ND (2006) Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 70:859–875PubMedCrossRefGoogle Scholar
  18. Gram L, de Nys R, Maximilien R, Givskov M, Steinberg P, Kjelleberg S (1996) Inhibitory effects of secondary metabolites from the red alga Deliseapulchraon swarming motility of Proteus mirabilis. Appl Environ Microbiol 62:4284–4287PubMedGoogle Scholar
  19. Hammer BK, Bassler BL (2003) Quorum sensing controls biofilm formation in Vibrio cholerae. Mol Microbiol 50:101–104PubMedCrossRefGoogle Scholar
  20. 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
  21. Horowitz HH, Metzger G (1963) A new analysis of thermogravimetric traces. Anal Chem 35:1464–1468CrossRefGoogle Scholar
  22. Imlay JA (2003) Pathways of oxidative damage. Annu Rev Microbiol 57:395–418PubMedCrossRefGoogle Scholar
  23. Ines Albesa M, Becerra C, Battan PC, Paez PL (2004) Oxidative stress involved in the antibacterial action of different antibiotics. Biochem Biophys Res Commun 317:605–609PubMedCrossRefGoogle Scholar
  24. 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
  25. Kaplancikli ZA, Zitouni GT, Revial G, Guven K (2004) Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl)sulfanyl] acetylamino] thiazoles. Arch Pharm Res 27:1081–1085PubMedCrossRefGoogle Scholar
  26. Karade HN, Acharya BN, Manisha S, Kaushik MP (2008) Design, synthesis, and antimalarial evaluation of thiazole-derived amino acids. Med Chem Res 17:19–29CrossRefGoogle Scholar
  27. Karpov KA, Nazarenko AV, Pekarevskii BV, Potekhin VM (2001) Biocidal and anticorrosive effect of aminothiazole derivatives used as additives to jet fuels. Russ J Appl Chem 74:998–1001CrossRefGoogle Scholar
  28. Kovacic JE (1967) The CN stretching frequency in the infrared spectra of Schiff’s base complexes-I. Copper complexes of salicylidene anilines. Spectochim Acta 23A:183–187CrossRefGoogle Scholar
  29. Leone S, CesareMutti AK, Mattia Sturlese SM, Cattaneo E, DoroteaRigamontib AC (2008) SAR and QSAR study on 2-aminothiazole derivatives, modulators of transcriptional repression in Huntington’s disease. Bioorg Med Chem 16:5695–5703PubMedCrossRefGoogle Scholar
  30. MacCallum JR, Tanner J (1970) A comparative study of some methods of assessing kinetic parameters from thermogravimetric analysis. Euro Poly J 6:907–917CrossRefGoogle Scholar
  31. 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
  32. Mathews RA, Gregory JT (1952) Reactions of 3-thiocyano-2-butanone. II.1 The preparation of 2-arylamino- and 2-alkylamino-4,5-dimethylthiazoles. J Am Chem Soc 74:3867–3868CrossRefGoogle Scholar
  33. McDougaldD RiceSA, Kjelleberg S (2007) Bacterial quorum sensing and interference by naturally occurring biomimics. Anal Bioanal Chem 387:445–453CrossRefGoogle Scholar
  34. Miller MB, Bassler BL (2001) Quorum sensing in bacteria. Annu Rev Microbiol 55:165–199PubMedCrossRefGoogle Scholar
  35. Moreau-Marquis S, Stanton BA, O’Toole GA (2008) Pseudomonas aeruginosa biofilm formation in the cystic fibrosis airway. Pulm Pharmacol Ther 21:595–599PubMedCrossRefGoogle Scholar
  36. Muh U, Schuster M, Heim R, Singh A, Olson ER, Greenberg EP (2006) Novel Pseudomonas aeruginosa quorum-sensing inhibitors identified in an ultra-high-throughput screen. Antimicrob Agents Chemother 50:3674–3679PubMedCrossRefGoogle Scholar
  37. Musk DJ, Hergenrother PJ (2006) Chemical countermeasures for the control of bacterial biofilms: effective compounds and promising targets. Curr Med Chem 13:2163–2177PubMedCrossRefGoogle Scholar
  38. 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
  39. Rasmussen TB, Givskov M (2006) Quorum-sensing inhibitors as anti-pathogenic drugs. Int J Med Microbiol 296:149–161PubMedCrossRefGoogle Scholar
  40. Rossolini GM, Mantengoli E (2005) Treatment and control of severe infections caused by multiresistant Pseudomonas aeruginosa. Clin Microbiol Infect 11:17–32PubMedCrossRefGoogle Scholar
  41. Saydam S, Yilmaz E (2005) Synthesis, characterization, and thermal behavior of 4-chloromethyl-2-(2-hydroxynaphthylidenehydrazino) thiazole and its Complexes with Cr(III), Co(II), Ni(II), and Cu(II). Synth React Inorg Met-Org Chem and Nano-Met Chem 35:767–771CrossRefGoogle Scholar
  42. Silvestein RM, Bassler GC, Morill TC (1991) Spectroscopic identification of organic compound, 4 edn. Wiley, New YorkGoogle Scholar
  43. Skindersoe ME, Alhede M, Phipps R, Yang L, Jensen PO, Rasmussen TB, Bjarnsholt T, Tolker-Nielsen T, Hoiby N, Givskov M (2008a) Effects of antibiotics on quorum sensing in Pseudomonas aeruginosa. Antimicrob Agents Chemother 52:3648–3663PubMedCrossRefGoogle Scholar
  44. 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
  45. Smith KM, Bu YG, Suga H (2003) Library screening for synthetic agonists and antagonists of a Pseudomonas aeruginosa autoinducer. Chem Biol 10:81–89PubMedCrossRefGoogle Scholar
  46. Tripathi KD (2003) Essential of medical pharmacology, 5th edn. Jaypee Publishers, New Delhi, pp 627–686Google Scholar
  47. 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
  48. Van Delden C, Iglewski BH (1998) Cell-to-cell signaling and Pseudomonas aeruginosa infections. Emerg Infect Dis 4:551–560PubMedCrossRefGoogle Scholar
  49. Waters CM, Bassler BL (2005) Quorum sensing: cell-to-cell communication in bacteria. Annu Rev Cell Dev Biol 21:319–346PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • P. G. More
    • 1
    Email author
  • N. N. Karale
    • 2
  • A. S. Lawand
    • 1
  • S. V. Rajmane
    • 1
  • S. V. Pawar
    • 3
  • R. H. Patil
    • 4
  1. 1.School of Chemical SciencesSolapur UniversitySolapurIndia
  2. 2.Vidya Pratishthan’s ArtSciences and Commerce College BaramatiPuneIndia
  3. 3.Institute of Bioinformatics and BiotechnologyUniversity of PunePuneIndia
  4. 4.Department of BiotechnologyUniversity of PunePuneIndia

Personalised recommendations