Ester of Quinoxaline-7-carboxylate 1,4-di-N-oxide as Apoptosis Inductors in K-562 Cell Line: An in vitro, QSAR and DFT Study

Rivera, Gildardo; Andrade-Ochoa, Sergio; Ortega-Romero, Manolo; Palos, Isidro; Monge, Antonio; Sánchez-Torres, Luvia Enid

doi:10.2174/1871520616666160630175927

Cited by 6 publications

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“…All compounds from the methyl, ethyl, isopropyl, and n-propyl ester series of quinoxaline 1,4- N -oxide were obtained following the procedure previously reported by Gomez-Caro et al [ 20 ]. These compounds were analyzed by IR, 1 H-NMR and elemental analysis and have been previously reported [ 21 , 22 , 23 , 24 ].…”

Section: Methodsmentioning

confidence: 99%

Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide

et al. 2018

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Tuberculosis continues to be a public health problem in the world, and drug resistance has been a major obstacle in its treatment. Quinoxaline 1,4-di-N-oxide has been proposed as a scaffold to design new drugs to combat this disease. To examine the efficacy of this compound, this study evaluates methyl, ethyl, isopropyl, and n-propyl esters of quinoxaline 1,4-di-N-oxide derivatives in vitro against Mycobacterium tuberculosis (pansusceptible and monoresistant strains). Additionally, the inhibitory effect of esters of quinoxaline 1,4-di-N-oxide on M. tuberculosis gyrase supercoiling was examined, and a stability analysis by ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS) was also carried out. Results showed that eight compounds (T-007, T-018, T-011, T-069, T-070, T-072, T-085 and T-088) had an activity similar to that of the reference drug isoniazid (minimum inhibitory concentration (MIC) = 0.12 µg/mL) with an effect on nonreplicative cells and drug monoresistant strains. Structural activity relationship analysis showed that the steric effect of an ester group at 7-position is key to enhancing its biological effects. Additionally, T-069 showed a high stability after 24 h in human plasma at 37 °C.

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Section: Methodsmentioning

confidence: 99%

Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide

et al. 2018

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“…Flow cytometry was used to examine the mechanism of the most active molecule's induction of cell death, and an in silico analysis was carried out to optimise and generate theoretical descriptors for all quinoxaline 1,4‐di‐ N ‐oxide derivatives. The most active compound resulted in induced caspase‐dependent apoptotic cell death via the intrinsic route (Rivera et al, 2017).…”

Section: Biological Activitiesmentioning

confidence: 99%

An appraisal on synthetic and pharmaceutical perspectives of quinoxaline 1,4‐di‐N‐oxide scaffold

Agrawal

Bhardwaj

2022

Chem Biol Drug Des

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Quinoxaline 1,4‐di‐N‐oxides (QdNOs) exhibit multifaceted biological properties, wherein antimicrobial, anticancer, antitrypanosomal, and anti‐inflammatory properties are included. Because of their various activities in clinical practice and research, they have a wide spectrum of uses and possibilities. QdNOs have received a significant amount of attention, and research into their medicinal chemistry is still a part of experimental investigation and analytical studies. In this review, QdNOs are classified depending on their actions, which include antibacterial and anti‐mycobacterial, anticancer or antitumor, antimalarial, antifungal, and other activities. In a conclusion, it's important to base the development of novel synthetic techniques and the design of new QdNO derivatives on the most up‐to‐date knowledge gleaned from recent research. With the summarised structure–activity relationship of fascinating QdNOs, this review aims to provide insights into the developments in the chemistry and biological activity of QdNO derivatives.

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“…Quinoxalines have a wide spectrum of biological activities [ 28 ] as anticancer [ 29 , 30 , 31 ], antimycobacterial [ 32 , 33 ], antibacterial [ 34 , 35 ], and antiparasitic [ 36 , 37 , 38 , 39 , 40 ] agents. Various quinoxaline-1,4-di- N -oxide derivatives have demonstrated trypanocidal activity.…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Analysis of New n-Butyl and Isobutyl Quinoxaline-7-carboxylate 1,4-di-N-oxide Derivatives against Trypanosoma cruzi as Trypanothione Reductase Inhibitors

González-González

Sánchez-Sánchez

Krauth‐Siegel

et al. 2022

IJMS

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American trypanosomiasis is a worldwide health problem that requires attention due to ineffective treatment options. We evaluated n-butyl and isobutyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives against trypomastigotes of the Trypanosoma cruzi strains NINOA and INC-5. An in silico analysis of the interactions of 1,4-di-N-oxide on the active site of trypanothione reductase (TR) and an enzyme inhibition study was carried out. The n-butyl series compound identified as T-150 had the best trypanocidal activity against T. cruzi trypomastigotes, with a 13% TR inhibition at 44 μM. The derivative T-147 behaved as a mixed inhibitor with Ki and Ki’ inhibition constants of 11.4 and 60.8 µM, respectively. This finding is comparable to the TR inhibitor mepacrine (Ki = 19 µM).

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Ester of Quinoxaline-7-carboxylate 1,4-di-N-oxide as Apoptosis Inductors in K-562 Cell Line: An in vitro, QSAR and DFT Study

Abstract: Our results show that compounds C5, C7, C10, C12 and C15 had the lowest IC50 of the series. C15 was the most active compound (IC50= 3.02 μg/mL), inducing caspase-dependent apoptotic cell death via the intrinsic pathway. QSAR and QPAR studies are discussed.

Cited by 6 publications

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Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide

Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide

An appraisal on synthetic and pharmaceutical perspectives of quinoxaline 1,4‐di‐N‐oxide scaffold

In Vitro and In Silico Analysis of New n-Butyl and Isobutyl Quinoxaline-7-carboxylate 1,4-di-N-oxide Derivatives against Trypanosoma cruzi as Trypanothione Reductase Inhibitors

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