Design and biological evaluation of a novel type of potential multi-targeting antimicrobial sulfanilamide hybrids in combination of pyrimidine and azoles |
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| Institution: | 1. Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China;2. Chongqing Engineering Research Center of Pharmaceutical Sciences, School of Pharmacy, Chongqing Medical and Pharmaceutical College, Chongqing 401331, China;1. Department of Chemistry, Collage of Science, Qassim University, Buraydah, Saudi Arabia;2. Department of Applied Organic Chemistry, National Research Center, Dokki, Egypt;3. Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt;4. Environmental Microbiology Lab., Water Pollution Research Department, National Research Centre, 33 El-Bohouth St., Dokki, Giza 12622, Egypt;5. Hormones Department, National Research Centre, Dokki, Cairo, Egypt;1. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Modern University for Technology and Information MTI, Cairo 11571, Egypt;2. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt;3. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Badr University, Badr City, Cairo 11829, Egypt;4. Medicinal Chemistry Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt;5. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Nahda University, Beni Suef, Egypt;1. Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China;2. School of Chemical Engineering, Chongqing University of Technology, Chongqing, 400054, PR China;1. Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Luminescence Analysis and Molecular Sensing, Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China;2. School of Pharmaceutical Sciences, Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chongqing University, Chongqing, 401331, China;3. College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, Chongqing Key Laboratory of Kinase Modulators As Innovative Medicine, Chongqing University of Arts and Sciences, Chongqing, 402160, China;1. Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Luminescence Analysis and Molecular Sensing, Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China;2. National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, College of Pharmacy, Chongqing University of Arts and Sciences, Chongqing 402160, China;1. Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Luminescence Analysis and Molecular Sensing (Southwest University), Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China;2. School of Chemical Engineering, Chongqing University of Technology, Chongqing 400054, PR China |
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| Abstract: | This work explored a novel type of potential multi-targeting antimicrobial three-component sulfanilamide hybrids in combination of pyrimidine and azoles. The hybridized target molecules were characterized by 1H NMR, 13C NMR and HRMS spectra. Some of the developed target compounds exerted promising antimicrobial activity in comparison with the reference drugs norfloxacin and fluconazole. Noticeably, sulfanilamide hybrid 5c with pyrimidine and indole could effectively inhibit the growth of E. faecalis with MIC value of 1 μg/mL. The active molecule 5c showed low cell toxicity and did not obviously trigger the development of resistance towards the tested bacteria strains. Mechanism exploration indicated that compound 5c could not only exert efficient membrane permeability, but also intercalate into DNA of resistant E. faecalis to form 5c-DNA supramolecular complex, which might be responsible for its antimicrobial action. The further investigation showed that this molecule could be effectively transported by human serum albumins through hydrogen bonds and van der Waals force. |
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| Keywords: | Sulfanilamide Pyrimidine Azole Antimicrobial DNA Mechanism |
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