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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 DNA gyras...
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (21), p.3959 |
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| Main Authors: | , , , , , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c493t-791658607d67b02760cdf640d47e34f453b033c9973acf54bd1f281406d0d44f3 |
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| cites | cdi_FETCH-LOGICAL-c493t-791658607d67b02760cdf640d47e34f453b033c9973acf54bd1f281406d0d44f3 |
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| container_issue | 21 |
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| container_title | Molecules (Basel, Switzerland) |
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| creator | Marc, Gabriel Araniciu, Cătălin Oniga, Smaranda Dafina Vlase, Laurian Pîrnău, Adrian Nadăș, George Cosmin Novac, Cristiana Ștefania Matei, Ioana Adriana Chifiriuc, Mariana Carmen Măruțescu, Luminița Oniga, Ovidiu |
| 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. |
| doi_str_mv | 10.3390/molecules24213959 |
| format | article |
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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.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules24213959</identifier><identifier>PMID: 31683749</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>anti-bacterial ; anti-biofilm ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacokinetics ; Anti-Infective Agents - pharmacology ; Antibacterial activity ; antibiotic resistance ; Antibiotics ; Antimicrobial activity ; Antimicrobial agents ; Binding sites ; Biofilms ; Biofilms - drug effects ; Biological properties ; Catalytic Domain ; dna gyrase ; DNA Gyrase - metabolism ; DNA topoisomerase ; Drug resistance ; Enzymes ; fluoroquinolones ; Gram-positive bacteria ; Hybrids ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular Docking Simulation ; Mutation ; Norfloxacin ; Norfloxacin - analogs & derivatives ; Pathogenicity ; Pathogens ; Permeability ; Solubility ; Strains (organisms) ; thiazolidinedione ; Thiazolidinediones - chemical synthesis ; Thiazolidinediones - chemistry ; Thiazolidinediones - pharmacokinetics ; Thiazolidinediones - pharmacology ; Water - chemistry</subject><ispartof>Molecules (Basel, Switzerland), 2019-10, Vol.24 (21), p.3959</ispartof><rights>2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). 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Docking studies and ADMET were also used in order to explain the biological properties and revealed some potential advantages over the parent molecule norfloxacin.</description><subject>anti-bacterial</subject><subject>anti-biofilm</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacokinetics</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>antibiotic resistance</subject><subject>Antibiotics</subject><subject>Antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Binding sites</subject><subject>Biofilms</subject><subject>Biofilms - drug effects</subject><subject>Biological properties</subject><subject>Catalytic Domain</subject><subject>dna gyrase</subject><subject>DNA Gyrase - metabolism</subject><subject>DNA topoisomerase</subject><subject>Drug resistance</subject><subject>Enzymes</subject><subject>fluoroquinolones</subject><subject>Gram-positive bacteria</subject><subject>Hybrids</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular Docking Simulation</subject><subject>Mutation</subject><subject>Norfloxacin</subject><subject>Norfloxacin - 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Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Marc, Gabriel</au><au>Araniciu, Cătălin</au><au>Oniga, Smaranda Dafina</au><au>Vlase, Laurian</au><au>Pîrnău, Adrian</au><au>Nadăș, George Cosmin</au><au>Novac, Cristiana Ștefania</au><au>Matei, Ioana Adriana</au><au>Chifiriuc, Mariana Carmen</au><au>Măruțescu, Luminița</au><au>Oniga, Ovidiu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2019-10-31</date><risdate>2019</risdate><volume>24</volume><issue>21</issue><spage>3959</spage><pages>3959-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>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.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>31683749</pmid><doi>10.3390/molecules24213959</doi><orcidid>https://orcid.org/0000-0001-7495-1392</orcidid><orcidid>https://orcid.org/0000-0001-6098-1857</orcidid><orcidid>https://orcid.org/0000-0001-9397-0388</orcidid><orcidid>https://orcid.org/0000-0003-2363-4041</orcidid><orcidid>https://orcid.org/0000-0002-0664-3387</orcidid><orcidid>https://orcid.org/0000-0002-8621-8662</orcidid><orcidid>https://orcid.org/0000-0002-0297-7697</orcidid><orcidid>https://orcid.org/0000-0003-3900-1433</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Molecules (Basel, Switzerland), 2019-10, Vol.24 (21), p.3959 |
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| language | eng |
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| source | Publicly Available Content (ProQuest); PubMed Central |
| subjects | anti-bacterial anti-biofilm Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacokinetics Anti-Infective Agents - pharmacology Antibacterial activity antibiotic resistance Antibiotics Antimicrobial activity Antimicrobial agents Binding sites Biofilms Biofilms - drug effects Biological properties Catalytic Domain dna gyrase DNA Gyrase - metabolism DNA topoisomerase Drug resistance Enzymes fluoroquinolones Gram-positive bacteria Hybrids Microbial Sensitivity Tests Models, Molecular Molecular Docking Simulation Mutation Norfloxacin Norfloxacin - analogs & derivatives Pathogenicity Pathogens Permeability Solubility Strains (organisms) thiazolidinedione Thiazolidinediones - chemical synthesis Thiazolidinediones - chemistry Thiazolidinediones - pharmacokinetics Thiazolidinediones - pharmacology Water - chemistry |
| title | Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents |
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