Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents
In an effort to improve the antimicrobial activity of norfloxacin, a series of hybrid norfloxacin−thiazolidinedione molecules were synthesized and screened for their direct antimicrobial activity and their anti-biofilm properties. The new hybrids were intended to have a new binding mode to...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/21/3959 |
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| author | Gabriel Marc Cătălin Araniciu Smaranda Dafina Oniga Laurian Vlase Adrian Pîrnău George Cosmin Nadăș Cristiana Ștefania Novac Ioana Adriana Matei Mariana Carmen Chifiriuc Luminița Măruțescu Ovidiu Oniga |
| author_facet | Gabriel Marc Cătălin Araniciu Smaranda Dafina Oniga Laurian Vlase Adrian Pîrnău George Cosmin Nadăș Cristiana Ștefania Novac Ioana Adriana Matei Mariana Carmen Chifiriuc Luminița Măruțescu Ovidiu Oniga |
| author_sort | Gabriel Marc |
| collection | DOAJ |
| description | In an effort to improve the antimicrobial activity of norfloxacin, a series of hybrid norfloxacin−thiazolidinedione molecules were synthesized and screened for their direct antimicrobial activity and their anti-biofilm properties. The new hybrids were intended to have a new binding mode to DNA gyrase, that will allow for a more potent antibacterial effect, and for activity against current quinolone-resistant bacterial strains. Moreover, the thiazolidinedione moiety aimed to include additional anti-pathogenicity by preventing biofilm formation. The resulting compounds showed promising direct activity against Gram-negative strains, and anti-biofilm activity against Gram-positive strains. Docking studies and ADMET were also used in order to explain the biological properties and revealed some potential advantages over the parent molecule norfloxacin. |
| first_indexed | 2024-12-11T09:31:57Z |
| format | Article |
| id | doaj.art-5ac05925ab0e4f4a8061e74057cb136a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T09:31:57Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5ac05925ab0e4f4a8061e74057cb136a2022-12-22T01:12:59ZengMDPI AGMolecules1420-30492019-10-012421395910.3390/molecules24213959molecules24213959Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial AgentsGabriel Marc0Cătălin Araniciu1Smaranda Dafina Oniga2Laurian Vlase3Adrian Pîrnău4George Cosmin Nadăș5Cristiana Ștefania Novac6Ioana Adriana Matei7Mariana Carmen Chifiriuc8Luminița Măruțescu9Ovidiu Oniga10Faculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 8 Victor Babes Street, 400012 Cluj-Napoca, RomaniaFaculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 8 Victor Babes Street, 400012 Cluj-Napoca, RomaniaFaculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 8 Victor Babes Street, 400012 Cluj-Napoca, RomaniaFaculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 8 Victor Babes Street, 400012 Cluj-Napoca, RomaniaNational Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donath Street, 400293 Cluj-Napoca, RomaniaDepartment of Microbiology, Faculty of Veterinary Medicine, University of Agricultural Sciences and Veterinary Medicine, 3-5 Mănăștur Street, 400372 Cluj-Napoca, RomaniaDepartment of Microbiology, Faculty of Veterinary Medicine, University of Agricultural Sciences and Veterinary Medicine, 3-5 Mănăștur Street, 400372 Cluj-Napoca, RomaniaDepartment of Microbiology, Faculty of Veterinary Medicine, University of Agricultural Sciences and Veterinary Medicine, 3-5 Mănăștur Street, 400372 Cluj-Napoca, RomaniaDepartment of Microbiology, Faculty of Biology, University of Bucharest, 1-3 Portocalelor Street, 60101 Bucharest, RomaniaDepartment of Microbiology, Faculty of Biology, University of Bucharest, 1-3 Portocalelor Street, 60101 Bucharest, RomaniaFaculty of Pharmacy, “Iuliu Hațieganu” University of Medicine and Pharmacy, 8 Victor Babes Street, 400012 Cluj-Napoca, RomaniaIn an effort to improve the antimicrobial activity of norfloxacin, a series of hybrid norfloxacin−thiazolidinedione molecules were synthesized and screened for their direct antimicrobial activity and their anti-biofilm properties. The new hybrids were intended to have a new binding mode to DNA gyrase, that will allow for a more potent antibacterial effect, and for activity against current quinolone-resistant bacterial strains. Moreover, the thiazolidinedione moiety aimed to include additional anti-pathogenicity by preventing biofilm formation. The resulting compounds showed promising direct activity against Gram-negative strains, and anti-biofilm activity against Gram-positive strains. Docking studies and ADMET were also used in order to explain the biological properties and revealed some potential advantages over the parent molecule norfloxacin.https://www.mdpi.com/1420-3049/24/21/3959norfloxacinthiazolidinedioneanti-biofilmanti-bacterialdna gyraseantibiotic resistancefluoroquinolones |
| spellingShingle | Gabriel Marc Cătălin Araniciu Smaranda Dafina Oniga Laurian Vlase Adrian Pîrnău George Cosmin Nadăș Cristiana Ștefania Novac Ioana Adriana Matei Mariana Carmen Chifiriuc Luminița Măruțescu Ovidiu Oniga Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents Molecules norfloxacin thiazolidinedione anti-biofilm anti-bacterial dna gyrase antibiotic resistance fluoroquinolones |
| title | Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents |
| title_full | Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents |
| title_fullStr | Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents |
| title_full_unstemmed | Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents |
| title_short | Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents |
| title_sort | design synthesis and biological evaluation of new piperazin 4 yl acetyl thiazolidine 2 4 dione norfloxacin analogues as antimicrobial agents |
| topic | norfloxacin thiazolidinedione anti-biofilm anti-bacterial dna gyrase antibiotic resistance fluoroquinolones |
| url | https://www.mdpi.com/1420-3049/24/21/3959 |
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