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Design, synthesis, evaluation of antimicrobial activity and docking studies of thiazole-based chalcones.

Author(s):

Christophe Tratrat, Michelyne Haroun, Iakovos Xenikakis, Konstantinos Liaras, Evangelia Tsolaki, Phaedra Eleftheriou, Anthi Petrou, Bandar Aldhubiab, Mahesh Attimarad, Katharigatta N. Venugopala, Sree Harsha, Heba S. Elsewedy, Athina Geronikaki* and Marina Soković  

Abstract:


Background: Thiazole derivates as well as chalcones, are very important scaffold for medicinal chemistry. Literature survey revealed that they possess wide spectrum of biological activities among which are anti-inflammatory and antimicrobial.

Objectives: The current studies describe the synthesis and evaluation of antimicrobial activity of twenty eight novel thiazole-based chalcones.

Methods: The designed compounds were synthesized using classical methods of organic synthesis. The in vivo evaluation of antimicrobial activity was performed by microdilution method.

Results: All compounds have shown antibacterial properties better than that of ampicillin and in many cases better than streptomycin. As far as the antifungal activity is concerned, all compounds possess much higher activity than reference drugs bifonazole and ketoconazole. The most sensitive bacterial species was B. cereus (MIC 6.5-28.4 μmol × 10-2/mL and MBC 14.2-105.0 μmol × 10-2/mL) while the most resistant ones were L. monocytogenes (MIC 21.4-113.6 μmol × 10-2/mL) and E. coli (MIC 10.7-113.6 μmol × 10-2/mL) and MBC at 42.7-358.6 μmol × 10-2/mL and 21.4-247.2 μmol × 10-2/mL, respectively. All the compounds exhibited antibacterial activity against the three resistant strains, MRSA, P. aeruginosa and E.coli. with MIC and MBC in the range of 0.65-11.00 μmol/mL × 10-2 and 1.30-16.50 μmol/mL × 10-2. Docking studies were performed.

Conclusions: Twenty eight novel thiazole-based chalcones were designed, synthesized and evaluated for antimicrobial activity. The results showed that these derivatives could be lead compounds in search for new potent antimicrobial agents. Docking studies indicated that DNA gyrase, GyrB and MurA inhibition may explain antibacterial activity.

Keywords:

Thiazole, chalcone, antimicrobial, antifungal, microdilution, docking, GyrB(1KZN), MurA, CYP51, dihydrofolate reductase .

Affiliation:

Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, School of Health, Faculty of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, School of Health, Faculty of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, School of Health, Faculty of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Department of Medical Laboratory Studies, School of Health and Medical Care, Alexander Technological Educational Institute of Thessaloniki, 54700, Sindos, Thessaloniki , School of Health, Faculty of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, School of Health, Faculty of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Department of Biotechnology and Food Technology, Faculty of Applied Sciences, Durban University of Technology, Durban 4001



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