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Antimalarial and antimicrobial activities of 8-Aminoquinoline-Uracils metal complexes.

Phopin K, Sinthupoom N, Treeratanapiboon L, Kunwittaya S, Prachayasittikul S, Ruchirawat S, Prachayasittikul V - EXCLI J (2016)

Bottom Line: 8-Aminoquinoline (8AQ) derivatives have been reported to have antimalarial, anticancer, and antioxidant activities.Interestingly, all of these metal complexes (1-6) showed fair antimalarial activities.The results reveal application of 8AQ and its metal complexes as potential compounds to be further developed as novel antimalarial and antibacterial agents.

View Article: PubMed Central - PubMed

Affiliation: Center for Research and Innovation, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand; Department of Clinical Microbiology and Applied Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand.

ABSTRACT
8-Aminoquinoline (8AQ) derivatives have been reported to have antimalarial, anticancer, and antioxidant activities. This study investigated the potency of 8AQ-5-substituted (iodo and nitro) uracils metal (Mn, Cu, Ni) complexes (1-6) as antimalarial and antimicrobial agents. Interestingly, all of these metal complexes (1-6) showed fair antimalarial activities. Moreover, Cu complexes 2 (8AQ-Cu-5Iu) and 5 (8AQ-Cu-5Nu) exerted antimicrobial activities against Gram-negative bacteria including P. shigelloides and S. dysenteriae. The results reveal application of 8AQ and its metal complexes as potential compounds to be further developed as novel antimalarial and antibacterial agents.

No MeSH data available.


Antimalarial activity of metal complexes (1-6) and ligands
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T2: Antimalarial activity of metal complexes (1-6) and ligands

Mentions: The synthesized 8AQ metal complexes (1-6) and free ligands were tested against chloroquine-resistant P. falciparum (K1) using artesunate as a reference drug. It was found that all of the metal complexes showed fair antimalarial activity with IC50 100-1000 µg/mL (Table 2(Tab. 2)). Similarly, the free ligands (8AQ, 5Iu and 5Nu) of such metal complexes exhibited antimalarial activity with the same IC50 values. To date, the antimalarial activity of these metal complexes (1-6) as well as 8AQ, 5Iu and 5Nu has not been reported in the literature. Quinoline-based compounds are potent chelators having high lipophilic property. The antimalarial activity of these compounds was exhibited by inhibiting the growth of parasites and glycolysis process due to the inactivation of various enzymes including metalloprotein oxidase (Scheibel and Adler, 1980[35]). The antimalarial activity of 8AQ may be derived from its formation of quinoneimine metabolite which ultimately generates hydrogen peroxides and oxidative stress in erythrocytes (Shiraki et al., 2011[37]). It is reasonable to suggest that the dissociation of lipophilic 8AQ-metal complexes (1-6) could give rise to charged complexes (8AQ-M)+/ or (5Iu/5Nu-M)+, and free ligands (8AQ, 5Iu and 5Nu) (Pingaew et al., 2013[27]) in which the 8AQ chelator can interact with parasitic enzyme in different ways such as interacting with SH or NH2 group, and with certain metal ion of the enzyme leading to the growth inhibition of P. falciparum (Owens, 1953[26]).


Antimalarial and antimicrobial activities of 8-Aminoquinoline-Uracils metal complexes.

Phopin K, Sinthupoom N, Treeratanapiboon L, Kunwittaya S, Prachayasittikul S, Ruchirawat S, Prachayasittikul V - EXCLI J (2016)

Antimalarial activity of metal complexes (1-6) and ligands
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4834669&req=5

T2: Antimalarial activity of metal complexes (1-6) and ligands
Mentions: The synthesized 8AQ metal complexes (1-6) and free ligands were tested against chloroquine-resistant P. falciparum (K1) using artesunate as a reference drug. It was found that all of the metal complexes showed fair antimalarial activity with IC50 100-1000 µg/mL (Table 2(Tab. 2)). Similarly, the free ligands (8AQ, 5Iu and 5Nu) of such metal complexes exhibited antimalarial activity with the same IC50 values. To date, the antimalarial activity of these metal complexes (1-6) as well as 8AQ, 5Iu and 5Nu has not been reported in the literature. Quinoline-based compounds are potent chelators having high lipophilic property. The antimalarial activity of these compounds was exhibited by inhibiting the growth of parasites and glycolysis process due to the inactivation of various enzymes including metalloprotein oxidase (Scheibel and Adler, 1980[35]). The antimalarial activity of 8AQ may be derived from its formation of quinoneimine metabolite which ultimately generates hydrogen peroxides and oxidative stress in erythrocytes (Shiraki et al., 2011[37]). It is reasonable to suggest that the dissociation of lipophilic 8AQ-metal complexes (1-6) could give rise to charged complexes (8AQ-M)+/ or (5Iu/5Nu-M)+, and free ligands (8AQ, 5Iu and 5Nu) (Pingaew et al., 2013[27]) in which the 8AQ chelator can interact with parasitic enzyme in different ways such as interacting with SH or NH2 group, and with certain metal ion of the enzyme leading to the growth inhibition of P. falciparum (Owens, 1953[26]).

Bottom Line: 8-Aminoquinoline (8AQ) derivatives have been reported to have antimalarial, anticancer, and antioxidant activities.Interestingly, all of these metal complexes (1-6) showed fair antimalarial activities.The results reveal application of 8AQ and its metal complexes as potential compounds to be further developed as novel antimalarial and antibacterial agents.

View Article: PubMed Central - PubMed

Affiliation: Center for Research and Innovation, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand; Department of Clinical Microbiology and Applied Technology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand.

ABSTRACT
8-Aminoquinoline (8AQ) derivatives have been reported to have antimalarial, anticancer, and antioxidant activities. This study investigated the potency of 8AQ-5-substituted (iodo and nitro) uracils metal (Mn, Cu, Ni) complexes (1-6) as antimalarial and antimicrobial agents. Interestingly, all of these metal complexes (1-6) showed fair antimalarial activities. Moreover, Cu complexes 2 (8AQ-Cu-5Iu) and 5 (8AQ-Cu-5Nu) exerted antimicrobial activities against Gram-negative bacteria including P. shigelloides and S. dysenteriae. The results reveal application of 8AQ and its metal complexes as potential compounds to be further developed as novel antimalarial and antibacterial agents.

No MeSH data available.