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Title: Derivatives (halogen, nitro and amino) of 8-hydroxyquinoline with highly potent antimicrobial and antioxidant activities
Authors: Rungrot Cherdtrakulkiat
Somchai Boonpangrak
Nujarin Sinthupoom
Supaluk Prachayasittikul
Somsak Ruchirawat
Virapong Prachayasittikul
Mahidol University. Faculty of Medical Technology. Department of Clinical Microbiology and Applied Technology
Mahidol University. Faculty of Medical Technology. Center for Innovation Development and Technology Transfer
Mahidol University. Faculty of Medical Technology. Center of Data Mining and Biomedical Informatics
Keywords: 8-Hydroxyquinoline;Antimicrobial;Antioxidant;Clioquinol;Cloxyquin;Nitroxoline;Open Access article
Issue Date: Jul-2016
Citation: Biochemistry and Biophysics Reports. Vol.6, 2016, 135-141
Abstract: 8-Hydroxyquinoline (8HQ) compounds have been reported to possess diverse bioactivities. In recent years, drug repositioning has gained considerable attention in drug discovery and development. Herein, 8HQ (1) and its derivatives (2-9) bearing various substituents (amino, nitro, cyano and halogen) were investigated for their antimicrobial against 27 microorganisms (agar dilution method) and antioxidant (DPPH method) activities. The parent 8HQ (1) exerted a highly potent antimicrobial activity against Gram-positive bacteria including diploid fungi and yeast with MIC values in the range of 3.44-13.78 μM. Moreover, the halogenated 8HQ, especially 7-bromo-8HQ (4) and clioquinol (6), displayed a high antigrowth activity against Gram-negative bacteria compared with the parent compound (1). Apparently, the derivatives with a relatively high safely index, e.g., nitroxoline (2), exhibited strong antibacterial activity against Aeromonas hydrophila (MIC=5.26 μM) and selectively inhibited the growth of P. aeruginosa with the MIC value of 84.14 μM; cloxyquin (3) showed a strong activity against L. monocytogenes and P. shigelloides with MIC values of 5.57 and 11.14 μM, respectively. Most compounds displayed an antioxidant activity. Specifically, 5-amino-8HQ (8) was shown to be the most potent antioxidant (IC50=8.70 μM) compared with the positive control (α-tocopherol) with IC50 of 13.47 μM. The findings reveal that 8HQ derivatives are potential candidates to be further developed as antimicrobial and antioxidant agents.
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