Synthesis and antileishmanial activity of styrylquinoline-type compounds: &lt;em&gt;in vitro&lt;/em&gt; and &lt;em&gt;in vivo&lt;/em&gt; studies

Petro-Buelvas, F. A.; Guzmán, Camilo; Villa, H. S.; Robledo, Sara M.; Vélez, Iván Darío; Santafé, Gílmar

doi:10.4038/cjs.v50i2.7880

Cited by 3 publications

(1 citation statement)

References 23 publications

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“…Likewise, antimalarial based on 8-aminoquinolines such as chloroquine, mefloquine, tanefoquine and primaquine have been reported as effective leishmanicides against several species of Leishmania 14 , with quinoline-derived formulations showing promising activity against L. (V.) panamensis and L. braziliensis 15 . Likewise, 2-styrylquinolines have showed leishmanicidal activity against L. (V.) panamensis strains and against in vivo animal infection as well as against P. falciparum strains FCB-2 and NF-54 16 – 18 . Under this scheme, the main objective of this study was to synthesize 2-arylquinoline-like compounds and to evaluate their in silico , in vitro and in vivo leishmanicidal, antiplasmodial and hemolytic activities, with aims of developing into new, effective, safe, and easy-administering treatments for CL and Malaria.…”

Section: Introductionmentioning

confidence: 99%

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Espinosa-Saez,

Robledo,

Pineda

et al. 2023

Sci Rep

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In this study, six analogs of 2-arylquinoline were synthesized and evaluated for their in vitro and in vivo antiplasmodial and leishmanicidal activity. At a later stage, hemolytic activity and druggability were tested in vitro and in silico, respectively, observing as a result: firstly, compounds showed half-maximal effective concentration (EC50) values between 3.6 and 19.3 µM. Likewise, a treatment using the compounds 4a–f caused improvement in most of the treated hamsters and cured some of them. Regarding the antiplasmodial activity, the compounds showed moderate to high activity, although they did not show hemolytic activity. Furthermore, 4e and 4f compounds were not able to control P. berghei infection when administered to animal models. Molecular dynamic simulations, molecular docking and ligand binding affinity indicate good characteristics of the studied compounds, which are expected to be active. And lastly, the compounds are absorbable at the hematoencephalic barrier but not in the gastrointestinal tract. In summary, ADMET properties suggest that these molecules may be used as a safe treatment against Leishmania.

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Section: Introductionmentioning

confidence: 99%

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Espinosa-Saez,

Robledo,

Pineda

et al. 2023

Sci Rep

View full text Add to dashboard Cite

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Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Espinosa-Saez,

Robledo,

Pineda

et al. 2023

Preprint

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In this study, six analogs of 2-arylquinoline were synthesized and evaluated for their in vitro and in vivo antiplasmodial and leishamanicidal activity. Also, hemolytic activity and drugability were tested in vitro and in silico, respectively. In relationship to leishmanicidal activity, the compounds showed half maximal effective concentration (EC50) values between 3.6µM and 19.3µM. Likewise, treatment using compounds 4a-f caused improvement in most of treated hamsters and cured some of them. Regarding antiplasmodial activity, the compounds showed moderate to high activity, did not show hemolytic activity. Furthermore, 4e and 4f compounds were not able to control P. berghei infection when administered to animal models. Molecular dynamic simulations, molecular docking and ligand binding affinity indicate good bioavailability and absorption characteristics of the studied compounds, which are expected to be active when administered orally. The compounds are absorbable at the hematoencephalic barrier but not in the gastrointestinal tract. ADMET properties suggest that these molecules may be used as a safe treatment for Leishmania.

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Synthesis and In vitro Evaluation of Hydrazonomethyl-Quinolin–8–ol and Pyrazol–3–yl-Quinolin–8–ol Derivatives for Antimicrobial and Antimalarial Potential

Kumar

Shah

Tripathi

et al. 2022

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Background: Quinoline is a well-established nucleus displaying various biological activities. Quinoline-8-ol containing compounds are reported for antimicrobial as well as antimalarial activity. Hydrazone and pyrazole containing compounds are also reported for antimicrobial activity. In this work, we have synthesized hydrazonomethyl-quinolin–8–ol and pyrazol–3–yl-quinolin–8–ol derivatives retaining quinoline 8-ol along with hydrazone/pyrazole pharmacophores. Objective: Objective of this work is synthesis and in vitro evaluation of hydrazonomethyl-quinolin–8–ol and pyrazol–3–yl-quinolin–8–ol derivatives for antifungal, antibacterial and antimalarial activity. Method: Designed and synthesized hydrazonomethyl-quinolin–8–ol and pyrazol–3–yl-quinolin–8–ol derivatives were evaluated for antifungal (against Candida albicans, Aspergillus fumigatus and Cryptococcus neoformans), antibacterial (against methicillin resistant Staphylococcus aureus (MRSA), Escherichia Coli, Pseudomonas aeruginosa and Klebsillae pneumoniae) as well as antimalarial (against Plasmodium falciparum D6 and W2 strains) activity. Result: Hydrazonomethyl-quinolin–8–ol (15.1-15.28) and pyrazol–3–yl-quinolin–8–ol derivatives (16.1-16.21 and 20.1-20.18) were synthesized in good to moderate yield. One pot synthesis of pyrazol–3–yl-quinolin–8–ol derivatives (16.1-16.21 and 20.1-20.18) was achieved. Compounds 15.3, 15.6, 15.7, 15.9-15.14, 15.16-15.19, 15.22 and 15.24 were found more potent than reference standard fluconazole (IC50 = 3.20 µM) against C. albicans with IC50 value less than 3 µM. Compounds 15.1, 15.2, 15.21 and 15.23 showed almost similar activity with reference standard fluconazole against C. albicans. Compounds 15.1-15.3, 15.9-15.12, 15.14-15.17, and 15.21-15.23 also showed good activity against fluconazole resistant strain A. fumigatus with IC50 value less than 3 µM. Compounds 15.2-15.4, 15.7, 15.9, 15.17, 15.20 showed good antimalarial activity against P. falciparum D6 as well as P. falciparum W2 with IC50 values of 1.84, 1.83, 1.56, 1.49, 1.45, 1.97, 1.68 µM and 1.86, 1.40, 1.19, 1.71, 1.16, 1.34, 1.61 µM, respectively. 5-Pyrazol–3–yl-quinolin–8–ol derivatives such as 16.3, 16.5, 16.11, 16.13, 16.19, 16.20 also showed antimalarial activity against P. falciparum D6 and W2 strains with IC50 values 2.23, 2.16, 2.99, 2.99, 2.73, 2.12 µM and 2.91, 3.60, 4.61, 2.71, 2.31, 2.66 µM, respectively. Conclusion: Most of the 5-hydrazonomethyl-quinolin–8–ol derivatives showed good antifungal activity against C. albicans, A. fumigatus and C. neoformans. Most of the 5-hydrazonomethyl-quinolin–8–ol derivatives were found more potent than reference standard fluconazole. These derivatives may be considered as leads for further development of antifungal agents.

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Synthesis and antileishmanial activity of styrylquinoline-type compounds: <em>in vitro</em> and <em>in vivo</em> studies

Cited by 3 publications

References 23 publications

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Synthesis and In vitro Evaluation of Hydrazonomethyl-Quinolin–8–ol and Pyrazol–3–yl-Quinolin–8–ol Derivatives for Antimicrobial and Antimalarial Potential

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