Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms
Two novel quaternary ammonium salts, bis-triazolium derivatives of fluconazole and pyridoxine, were synthesized by reaction of fluconazole with pyridoxine-based synthetic intermediates. The leading compound demonstrated pronounced antimycotic and antibacterial in vitro activity, comparable to or exc...
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| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2017-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2017/4761650 |
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| author | Marsel R. Garipov Roman S. Pavelyev Svetlana A. Lisovskaya Elena V. Nikitina Airat R. Kayumov Alina E. Sabirova Oksana V. Bondar Albina G. Malanyeva Alexander M. Aimaletdinov Alfia G. Iksanova Konstantin V. Balakin Yurii G. Shtyrlin |
| author_facet | Marsel R. Garipov Roman S. Pavelyev Svetlana A. Lisovskaya Elena V. Nikitina Airat R. Kayumov Alina E. Sabirova Oksana V. Bondar Albina G. Malanyeva Alexander M. Aimaletdinov Alfia G. Iksanova Konstantin V. Balakin Yurii G. Shtyrlin |
| author_sort | Marsel R. Garipov |
| collection | DOAJ |
| description | Two novel quaternary ammonium salts, bis-triazolium derivatives of fluconazole and pyridoxine, were synthesized by reaction of fluconazole with pyridoxine-based synthetic intermediates. The leading compound demonstrated pronounced antimycotic and antibacterial in vitro activity, comparable to or exceeding that of the reference antifungal (fluconazole, terbinafine) and antibacterial/antiseptic (miramistin, benzalkonium chloride) agents. In contrast to many antimicrobials, the leading compound was also active against biofilm-embedded staphylococci and Escherichia coli. While no biofilm structure destruction occurred, all compounds were able to diffuse into the matrix and reduce the number of colony-forming units by three orders of magnitude at 16 × MBC. The leading compound was significantly less toxic than miramistin and benzalkonium chloride and more toxic than the reference antifungal drugs. The obtained results make the described chemotype a promising starting point for the development of new broad-spectrum antimicrobial therapies with powerful effect on fungal and bacterial pathogens including their biofilm-embedded forms. |
| format | Article |
| id | doaj-art-40929ba3cba443efb485e55ce6f716f4 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2017-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-40929ba3cba443efb485e55ce6f716f42025-02-03T00:59:48ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/47616504761650Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded FormsMarsel R. Garipov0Roman S. Pavelyev1Svetlana A. Lisovskaya2Elena V. Nikitina3Airat R. Kayumov4Alina E. Sabirova5Oksana V. Bondar6Albina G. Malanyeva7Alexander M. Aimaletdinov8Alfia G. Iksanova9Konstantin V. Balakin10Yurii G. Shtyrlin11Kazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan Scientific and Research Institute of Epidemiology and Microbiology, Bolshaya Krasnaya 67, Kazan 420015, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaKazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, RussiaTwo novel quaternary ammonium salts, bis-triazolium derivatives of fluconazole and pyridoxine, were synthesized by reaction of fluconazole with pyridoxine-based synthetic intermediates. The leading compound demonstrated pronounced antimycotic and antibacterial in vitro activity, comparable to or exceeding that of the reference antifungal (fluconazole, terbinafine) and antibacterial/antiseptic (miramistin, benzalkonium chloride) agents. In contrast to many antimicrobials, the leading compound was also active against biofilm-embedded staphylococci and Escherichia coli. While no biofilm structure destruction occurred, all compounds were able to diffuse into the matrix and reduce the number of colony-forming units by three orders of magnitude at 16 × MBC. The leading compound was significantly less toxic than miramistin and benzalkonium chloride and more toxic than the reference antifungal drugs. The obtained results make the described chemotype a promising starting point for the development of new broad-spectrum antimicrobial therapies with powerful effect on fungal and bacterial pathogens including their biofilm-embedded forms.http://dx.doi.org/10.1155/2017/4761650 |
| spellingShingle | Marsel R. Garipov Roman S. Pavelyev Svetlana A. Lisovskaya Elena V. Nikitina Airat R. Kayumov Alina E. Sabirova Oksana V. Bondar Albina G. Malanyeva Alexander M. Aimaletdinov Alfia G. Iksanova Konstantin V. Balakin Yurii G. Shtyrlin Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms Journal of Chemistry |
| title | Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms |
| title_full | Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms |
| title_fullStr | Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms |
| title_full_unstemmed | Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms |
| title_short | Fluconazole-Pyridoxine Bis-Triazolium Compounds with Potent Activity against Pathogenic Bacteria and Fungi Including Their Biofilm-Embedded Forms |
| title_sort | fluconazole pyridoxine bis triazolium compounds with potent activity against pathogenic bacteria and fungi including their biofilm embedded forms |
| url | http://dx.doi.org/10.1155/2017/4761650 |
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