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Open AccessArticle

Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents

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Laboratory of Applied Organic Chemistry, Faculty of Sciences and Techniques, Sidi Mohamed Ben Abdellah University, Fez 30000, Morocco
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Structural Bioinformatics Laboratory, Faculty of Science and Engineering, Biochemistry, Åbo Akademi University, FI-20520 Turku, Finland
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Pharmaceutical Sciences Laboratory, Faculty of Science and Engineering, Pharmacy, Åbo Akademi University, FI-20520 Turku, Finland
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Laboratory of Materials, Processes, Catalysis and Environment, Bioindustry and Agri-Food Technology team, Higher School of Technology, Sidi Mohamed Ben Abdellah University, Fez 30000, Morocco
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Authors to whom correspondence should be addressed.
Sci. Pharm. 2020, 88(4), 57; https://doi.org/10.3390/scipharm88040057
Received: 6 October 2020 / Revised: 1 November 2020 / Accepted: 11 November 2020 / Published: 1 December 2020
A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV. View Full-Text
Keywords: alkaline hydrolysis; amino acid derivative; antibacterial activity; DNA gyrase; enzyme inhibitor; fluorescence; molecular docking; molecular dynamics simulation; quinoline carboxamide; topoisomerase-IV alkaline hydrolysis; amino acid derivative; antibacterial activity; DNA gyrase; enzyme inhibitor; fluorescence; molecular docking; molecular dynamics simulation; quinoline carboxamide; topoisomerase-IV
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MDPI and ACS Style

Moussaoui, O.; Bhadane, R.; Sghyar, R.; El Hadrami, E.M.; El Amrani, S.; Ben Tama, A.; Kandri Rodi, Y.; Chakroune, S.; Salo-Ahen, O.M.H. Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents. Sci. Pharm. 2020, 88, 57.

AMA Style

Moussaoui O, Bhadane R, Sghyar R, El Hadrami EM, El Amrani S, Ben Tama A, Kandri Rodi Y, Chakroune S, Salo-Ahen OMH. Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents. Scientia Pharmaceutica. 2020; 88(4):57.

Chicago/Turabian Style

Moussaoui, Oussama; Bhadane, Rajendra; Sghyar, Riham; El Hadrami, El M.; El Amrani, Soukaina; Ben Tama, Abdeslem; Kandri Rodi, Youssef; Chakroune, Said; Salo-Ahen, Outi M.H. 2020. "Novel Amino Acid Derivatives of Quinolines as Potential Antibacterial and Fluorophore Agents" Sci. Pharm. 88, no. 4: 57.

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