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Derivatives (halogen, nitro and amino) of 8-hydroxyquinoline with highly potent antimicrobial and antioxidant activities.

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 ?M. 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 ?M) and selectively inhibited the growth of P. aeruginosa with the MIC value of 84.14 ?M; cloxyquin (3) showed a strong activity against Listseria monocytogenes and Plesiomonas shigelloides with MIC values of 5.57 and 11.14 ?M, respectively. Most compounds displayed an antioxidant activity. Specifically, 5-amino-8HQ (8) was shown to be the most potent antioxidant (IC50=8.70 ?M) compared with the positive control (?-tocopherol) with IC50 of 13.47 ?M. The findings reveal that 8HQ derivatives are potential candidates to be further developed as antimicrobial and antioxidant agents.

SUBMITTER: Cherdtrakulkiat R

PROVIDER: S-EPMC5689172 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Derivatives (halogen, nitro and amino) of 8-hydroxyquinoline with highly potent antimicrobial and antioxidant activities.

Cherdtrakulkiat Rungrot R Boonpangrak Somchai S Sinthupoom Nujarin N Prachayasittikul Supaluk S Ruchirawat Somsak S Prachayasittikul Virapong V

Biochemistry and biophysics reports 20160324

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 antim ...[more]

PMID: 29214226

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Project description:BackgroundAntimicrobial resistance is a serious threat against humankind and the search for new therapeutics is needed. This study aims to investigate the antimicrobial and antioxidant activities of ethanol extracts and compounds isolated from Dissotis senegambiensis and Amphiblemma monticola, two Cameroonian Melastomataceae species traditionally used for the treatment of fever, malaria and infectious diseases.MethodsThe plant extracts were prepared by maceration in ethanol. Standard chromatographic and spectroscopic methods were used to isolate and identify fourteen compounds from the two plant species [1-6 (from D. senegambiensis), 3, 4 and 7-14 (from A. monticola)]. A two-fold serial micro-dilution method was used to determine the minimum inhibitory concentration (MIC) against four bacterial strains including two resistant bacterial strains, methicillin resistant S. aureus (MRSA3) and methicillin resistant S. aureus (MRSA4) and three yeast strains.ResultsThe fractionation of EtOH extracts afforded fourteen compounds belonging to triterpenoid and phenolic derivatives. The ethanol extracts, compounds 3, 5-8, 10 and the mixture of 10 + 12 were active against all the tested bacterial and fungal species. Compound 7 (MIC = 16-32 μg/mL) and 10 (MIC = 8-16 μg/mL) displayed the largest antibacterial and antifungal activities, respectively. Compounds 7, 10 and the mixture of 10 + 12 showed prominent antibacterial activity against methicillin- resistant S. aureus (MRSA) which is in some cases equal to that of ciprofloxacin used as reference antibacterial drug. Compound 8 also showed high radical-scavenging activities and ferric reducing power when compared with vitamin C and butylated hydroxytoluene used as reference antioxidants. The tested samples were non-toxic to normal cells highlighting their good selectivity.ConclusionsThe result of this investigation reveals the potential of D. senegambiensis and A. monticola as well as the most active compounds in the search for new antimicrobial and antioxidant agents. So, further investigations are needed.

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Derivatives (halogen, nitro and amino) of 8-hydroxyquinoline with highly potent antimicrobial and antioxidant activities.

Publications

Derivatives (halogen, nitro and amino) of 8-hydroxyquinoline with highly potent antimicrobial and antioxidant activities.

Similar Datasets

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