Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide
AbstractTuberculosis 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. View Full-Text
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Palos, I.; Luna-Herrera, J.; Lara-Ramírez, E.E.; Loera-Piedra, A.; Fernández-Ramírez, E.; Aguilera-Arreola, M.G.; Paz-González, A.D.; Monge, A.; Wan, B.; Franzblau, S.; Rivera, G. Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide. Molecules 2018, 23, 1453.
Palos I, Luna-Herrera J, Lara-Ramírez EE, Loera-Piedra A, Fernández-Ramírez E, Aguilera-Arreola MG, Paz-González AD, Monge A, Wan B, Franzblau S, Rivera G. Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide. Molecules. 2018; 23(6):1453.Chicago/Turabian Style
Palos, Isidro; Luna-Herrera, Julieta; Lara-Ramírez, Edgar E.; Loera-Piedra, Alejandra; Fernández-Ramírez, Emanuel; Aguilera-Arreola, Ma. G.; Paz-González, Alma D.; Monge, Antonio; Wan, Baojie; Franzblau, Scott; Rivera, Gildardo. 2018. "Anti-Mycobacterium tuberculosis Activity of Esters of Quinoxaline 1,4-Di-N-Oxide." Molecules 23, no. 6: 1453.
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