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Thiazolidinedione and thiazole derivatives potentiate norfloxacin activity against NorA efflux pump over expression in Staphylococcus aureus 1199B strains
[Display omitted] Thiazol and thiazolidinedione derivatives are known in the literature for presenting several biological activities, such as anti-diabetic, anti-inflammatory, antiparasitic, antifungal and antimicrobial activity. With this in mind, this study reports on the synthesis and antibacteri...
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Published in: | Bioorganic & medicinal chemistry 2019-09, Vol.27 (17), p.3797-3804 |
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creator | Pereira, Pedro Silvino Lima, Maria do Carmo Alves de Neto, Pedro Paulo Marcelino Oliveira-Tintino, Cícera Datiane de Morais Tintino, Saulo Relison Menezes, Irwin Rose de Alencar de Oliveira, Jamerson Ferreira Marchand, Pascal Coutinho, Henrique Douglas Melo Rodrigues, Maria do Desterro da Silva, Teresinha Gonçalves |
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Thiazol and thiazolidinedione derivatives are known in the literature for presenting several biological activities, such as anti-diabetic, anti-inflammatory, antiparasitic, antifungal and antimicrobial activity. With this in mind, this study reports on the synthesis and antibacterial activity of thiazole (NJ) and thiazolidinedione (NW) derivatives, as well as their effects in association with norfloxacin, against NorA efflux pumps in the Staphylococcus aureus 1199B (SA-1199B) strain. Among the 14 compounds evaluated, 9 were found to potentiate norfloxacin activity, with 4 compounds from the NJ series promoting a threefold norfloxacin MIC reduction. Molecular docking assays were used to confirm the binding mode of most active compounds. In the in silico study, the efficiency of the interaction of NJ series compounds with the NorA pump were evaluated. Derivatives from both series did not show considerable intrinsic antibacterial activity (MIC > 1024 μg/mL) against any of the tested strains. However, the NJ16 and NJ17 compounds, when associated with norfloxacin, reduced the MIC of this drug threefold and inhibited NorA pumps in the 1199B strain. Moreover, some NW (05, 10, 18, 19 and 21) and NJ compounds (16, 17, 18 and 20) presented low to moderate cytotoxicity against normal cells. Molecular docking studies supported the potent in vitro inhibitory activity of NJ16 and NJ17, which showed NJ16 and NJ17 possessed more favorable binding energies of −9.03 Kcal/mol and −9.34 Kcal/mol, respectively. In addition, NJ16 showed different types of interactions involved in complex stabilization. In conclusion, NJ16 and NJ17, in combination with norfloxacin, were able to completely restore the antibacterial activity of norfloxacin against S. aureus SA-1199B, the norA-overexpressing strain, with low cytotoxicity in normal cells. |
doi_str_mv | 10.1016/j.bmc.2019.07.006 |
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Thiazol and thiazolidinedione derivatives are known in the literature for presenting several biological activities, such as anti-diabetic, anti-inflammatory, antiparasitic, antifungal and antimicrobial activity. With this in mind, this study reports on the synthesis and antibacterial activity of thiazole (NJ) and thiazolidinedione (NW) derivatives, as well as their effects in association with norfloxacin, against NorA efflux pumps in the Staphylococcus aureus 1199B (SA-1199B) strain. Among the 14 compounds evaluated, 9 were found to potentiate norfloxacin activity, with 4 compounds from the NJ series promoting a threefold norfloxacin MIC reduction. Molecular docking assays were used to confirm the binding mode of most active compounds. In the in silico study, the efficiency of the interaction of NJ series compounds with the NorA pump were evaluated. Derivatives from both series did not show considerable intrinsic antibacterial activity (MIC > 1024 μg/mL) against any of the tested strains. However, the NJ16 and NJ17 compounds, when associated with norfloxacin, reduced the MIC of this drug threefold and inhibited NorA pumps in the 1199B strain. Moreover, some NW (05, 10, 18, 19 and 21) and NJ compounds (16, 17, 18 and 20) presented low to moderate cytotoxicity against normal cells. Molecular docking studies supported the potent in vitro inhibitory activity of NJ16 and NJ17, which showed NJ16 and NJ17 possessed more favorable binding energies of −9.03 Kcal/mol and −9.34 Kcal/mol, respectively. In addition, NJ16 showed different types of interactions involved in complex stabilization. In conclusion, NJ16 and NJ17, in combination with norfloxacin, were able to completely restore the antibacterial activity of norfloxacin against S. aureus SA-1199B, the norA-overexpressing strain, with low cytotoxicity in normal cells.</description><identifier>ISSN: 0968-0896</identifier><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2019.07.006</identifier><identifier>PMID: 31320212</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antimicrobial resistance ; Bacteriology ; Biochemistry, Molecular Biology ; Docking ; Efflux pump ; Gram-positive ; Human health and pathology ; Infectious diseases ; Life Sciences ; Microbiology and Parasitology ; Molecular biology</subject><ispartof>Bioorganic & medicinal chemistry, 2019-09, Vol.27 (17), p.3797-3804</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c496t-dd94c5a95afe395dae37862581990ead3b68474b15de40b7c90f9e2a3f32358c3</citedby><cites>FETCH-LOGICAL-c496t-dd94c5a95afe395dae37862581990ead3b68474b15de40b7c90f9e2a3f32358c3</cites><orcidid>0000-0001-7773-8642</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31320212$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03794769$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Pereira, Pedro Silvino</creatorcontrib><creatorcontrib>Lima, Maria do Carmo Alves de</creatorcontrib><creatorcontrib>Neto, Pedro Paulo Marcelino</creatorcontrib><creatorcontrib>Oliveira-Tintino, Cícera Datiane de Morais</creatorcontrib><creatorcontrib>Tintino, Saulo Relison</creatorcontrib><creatorcontrib>Menezes, Irwin Rose de Alencar</creatorcontrib><creatorcontrib>de Oliveira, Jamerson Ferreira</creatorcontrib><creatorcontrib>Marchand, Pascal</creatorcontrib><creatorcontrib>Coutinho, Henrique Douglas Melo</creatorcontrib><creatorcontrib>Rodrigues, Maria do Desterro</creatorcontrib><creatorcontrib>da Silva, Teresinha Gonçalves</creatorcontrib><title>Thiazolidinedione and thiazole derivatives potentiate norfloxacin activity against NorA efflux pump over expression in Staphylococcus aureus 1199B strains</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
Thiazol and thiazolidinedione derivatives are known in the literature for presenting several biological activities, such as anti-diabetic, anti-inflammatory, antiparasitic, antifungal and antimicrobial activity. With this in mind, this study reports on the synthesis and antibacterial activity of thiazole (NJ) and thiazolidinedione (NW) derivatives, as well as their effects in association with norfloxacin, against NorA efflux pumps in the Staphylococcus aureus 1199B (SA-1199B) strain. Among the 14 compounds evaluated, 9 were found to potentiate norfloxacin activity, with 4 compounds from the NJ series promoting a threefold norfloxacin MIC reduction. Molecular docking assays were used to confirm the binding mode of most active compounds. In the in silico study, the efficiency of the interaction of NJ series compounds with the NorA pump were evaluated. Derivatives from both series did not show considerable intrinsic antibacterial activity (MIC > 1024 μg/mL) against any of the tested strains. However, the NJ16 and NJ17 compounds, when associated with norfloxacin, reduced the MIC of this drug threefold and inhibited NorA pumps in the 1199B strain. Moreover, some NW (05, 10, 18, 19 and 21) and NJ compounds (16, 17, 18 and 20) presented low to moderate cytotoxicity against normal cells. Molecular docking studies supported the potent in vitro inhibitory activity of NJ16 and NJ17, which showed NJ16 and NJ17 possessed more favorable binding energies of −9.03 Kcal/mol and −9.34 Kcal/mol, respectively. In addition, NJ16 showed different types of interactions involved in complex stabilization. In conclusion, NJ16 and NJ17, in combination with norfloxacin, were able to completely restore the antibacterial activity of norfloxacin against S. aureus SA-1199B, the norA-overexpressing strain, with low cytotoxicity in normal cells.</description><subject>Antimicrobial resistance</subject><subject>Bacteriology</subject><subject>Biochemistry, Molecular Biology</subject><subject>Docking</subject><subject>Efflux pump</subject><subject>Gram-positive</subject><subject>Human health and pathology</subject><subject>Infectious diseases</subject><subject>Life Sciences</subject><subject>Microbiology and Parasitology</subject><subject>Molecular biology</subject><issn>0968-0896</issn><issn>0960-894X</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAURi0EokPhAdggb1kk2HH-LFZDBRRpVBZt19aNfcN4lIkj24lmeBSeFo8CXXZ1pevvfNbVIeQ9ZzlnvP50yLujzgvGZc6anLH6Bdnwsi4zISR_STZM1m3GWllfkTchHBhjRSn5a3IluChYwYsN-fOwt_DbDdbYEY11I1IYDY3rFqlBbxeIdsFAJxdxjBYi0tH5fnAn0HakoNOzjWcKv8COIdI757cU-36YT3SajxN1C3qKp8ljCOkLmqD7CNP-PDjttJ4DhdljGpxL-YWG6C9Fb8mrHoaA7_7Na_L47evDzW22-_n9x812l-lS1jEzRpa6AllBj0JWBlA0bV1UbepiCEZ0dVs2ZccrgyXrGi1ZL7EA0YtCVK0W1-Tj2ruHQU3eHsGflQOrbrc7ddkx0ciyqeXCU5avWe1dCB77J4AzdXGiDio5URcnijUqOUnMh5WZ5u6I5on4LyEFPq8BTFcuFr0K2uKokw-POirj7DP1fwHnmqAy</recordid><startdate>20190901</startdate><enddate>20190901</enddate><creator>Pereira, Pedro Silvino</creator><creator>Lima, Maria do Carmo Alves de</creator><creator>Neto, Pedro Paulo Marcelino</creator><creator>Oliveira-Tintino, Cícera Datiane de Morais</creator><creator>Tintino, Saulo Relison</creator><creator>Menezes, Irwin Rose de Alencar</creator><creator>de Oliveira, Jamerson Ferreira</creator><creator>Marchand, Pascal</creator><creator>Coutinho, Henrique Douglas Melo</creator><creator>Rodrigues, Maria do Desterro</creator><creator>da Silva, Teresinha Gonçalves</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-7773-8642</orcidid></search><sort><creationdate>20190901</creationdate><title>Thiazolidinedione and thiazole derivatives potentiate norfloxacin activity against NorA efflux pump over expression in Staphylococcus aureus 1199B strains</title><author>Pereira, Pedro Silvino ; Lima, Maria do Carmo Alves de ; Neto, Pedro Paulo Marcelino ; Oliveira-Tintino, Cícera Datiane de Morais ; Tintino, Saulo Relison ; Menezes, Irwin Rose de Alencar ; de Oliveira, Jamerson Ferreira ; Marchand, Pascal ; Coutinho, Henrique Douglas Melo ; Rodrigues, Maria do Desterro ; da Silva, Teresinha Gonçalves</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c496t-dd94c5a95afe395dae37862581990ead3b68474b15de40b7c90f9e2a3f32358c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antimicrobial resistance</topic><topic>Bacteriology</topic><topic>Biochemistry, Molecular Biology</topic><topic>Docking</topic><topic>Efflux pump</topic><topic>Gram-positive</topic><topic>Human health and pathology</topic><topic>Infectious diseases</topic><topic>Life Sciences</topic><topic>Microbiology and Parasitology</topic><topic>Molecular biology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pereira, Pedro Silvino</creatorcontrib><creatorcontrib>Lima, Maria do Carmo Alves de</creatorcontrib><creatorcontrib>Neto, Pedro Paulo Marcelino</creatorcontrib><creatorcontrib>Oliveira-Tintino, Cícera Datiane de Morais</creatorcontrib><creatorcontrib>Tintino, Saulo Relison</creatorcontrib><creatorcontrib>Menezes, Irwin Rose de Alencar</creatorcontrib><creatorcontrib>de Oliveira, Jamerson Ferreira</creatorcontrib><creatorcontrib>Marchand, Pascal</creatorcontrib><creatorcontrib>Coutinho, Henrique Douglas Melo</creatorcontrib><creatorcontrib>Rodrigues, Maria do Desterro</creatorcontrib><creatorcontrib>da Silva, Teresinha Gonçalves</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pereira, Pedro Silvino</au><au>Lima, Maria do Carmo Alves de</au><au>Neto, Pedro Paulo Marcelino</au><au>Oliveira-Tintino, Cícera Datiane de Morais</au><au>Tintino, Saulo Relison</au><au>Menezes, Irwin Rose de Alencar</au><au>de Oliveira, Jamerson Ferreira</au><au>Marchand, Pascal</au><au>Coutinho, Henrique Douglas Melo</au><au>Rodrigues, Maria do Desterro</au><au>da Silva, Teresinha Gonçalves</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiazolidinedione and thiazole derivatives potentiate norfloxacin activity against NorA efflux pump over expression in Staphylococcus aureus 1199B strains</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2019-09-01</date><risdate>2019</risdate><volume>27</volume><issue>17</issue><spage>3797</spage><epage>3804</epage><pages>3797-3804</pages><issn>0968-0896</issn><issn>0960-894X</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
Thiazol and thiazolidinedione derivatives are known in the literature for presenting several biological activities, such as anti-diabetic, anti-inflammatory, antiparasitic, antifungal and antimicrobial activity. With this in mind, this study reports on the synthesis and antibacterial activity of thiazole (NJ) and thiazolidinedione (NW) derivatives, as well as their effects in association with norfloxacin, against NorA efflux pumps in the Staphylococcus aureus 1199B (SA-1199B) strain. Among the 14 compounds evaluated, 9 were found to potentiate norfloxacin activity, with 4 compounds from the NJ series promoting a threefold norfloxacin MIC reduction. Molecular docking assays were used to confirm the binding mode of most active compounds. In the in silico study, the efficiency of the interaction of NJ series compounds with the NorA pump were evaluated. Derivatives from both series did not show considerable intrinsic antibacterial activity (MIC > 1024 μg/mL) against any of the tested strains. However, the NJ16 and NJ17 compounds, when associated with norfloxacin, reduced the MIC of this drug threefold and inhibited NorA pumps in the 1199B strain. Moreover, some NW (05, 10, 18, 19 and 21) and NJ compounds (16, 17, 18 and 20) presented low to moderate cytotoxicity against normal cells. Molecular docking studies supported the potent in vitro inhibitory activity of NJ16 and NJ17, which showed NJ16 and NJ17 possessed more favorable binding energies of −9.03 Kcal/mol and −9.34 Kcal/mol, respectively. In addition, NJ16 showed different types of interactions involved in complex stabilization. In conclusion, NJ16 and NJ17, in combination with norfloxacin, were able to completely restore the antibacterial activity of norfloxacin against S. aureus SA-1199B, the norA-overexpressing strain, with low cytotoxicity in normal cells.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>31320212</pmid><doi>10.1016/j.bmc.2019.07.006</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-7773-8642</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Antimicrobial resistance Bacteriology Biochemistry, Molecular Biology Docking Efflux pump Gram-positive Human health and pathology Infectious diseases Life Sciences Microbiology and Parasitology Molecular biology |
title | Thiazolidinedione and thiazole derivatives potentiate norfloxacin activity against NorA efflux pump over expression in Staphylococcus aureus 1199B strains |
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