DFT and docking studies of rhodostreptomycins A and B and their interactions with solvated/nonsolvated Mg2+ and Ca2+ ions |
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Authors: | Christiaan Jardínez Ines Nicolás-Vázquez Julian Cruz-Borbolla Cesar A González-Ramírez Miguel Cepeda Jose Correa-Basurto Thangarasu Pandiyan Rene Miranda |
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Institution: | 1. área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Unidad Universitaria, Km 4.5 Carretera Pachuca-Tulancingo, 42184, Pachuca, Hidalgo, Mexico 2. Departamento de Ciencias Químicas de la Facultad de Estudios Superiores Cuautitlán Campo 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740, Mexico 4. Laboratorio de Modelado Molecular y Bioinformática, Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón, 11340, México City, Mexico 3. Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, Coyoacán, 04510, México D.F., Mexico
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Abstract: | The interactions of L-aminoglucosidic stereoisomers such as rhodostreptomycins A (Rho A) and B (Rho B) with cations (Mg2+, Ca2+, and H+) were studied by a quantum mechanical method that utilized DFT with B3LYP/6-311G**. Docking studies were also carried out in order to explore the surface recognition properties of L-aminoglucoside with respect to Mg2+ and Ca2+ ions under solvated and nonsolvated conditions. Although both of the stereoisomers possess similar physicochemical/antibiotic properties against Helicobacter pylori, the thermochemical values for these complexes showed that its high affinity for Mg2+ cations caused the hydration of Rho B. According to the results of the calculations, for Rho A–Ca2+(H2O)6, ΔH = ?72.21 kcal?mol?1; for Rho B–Ca2+(H2O)6, ΔH = ?72.53 kcal?mol?1; for Rho A–Mg2+(H2O)6, ΔH = ?72.99 kcal?mol?1 and for Rho B–Mg2+(H2O)6, ΔH = ?95.00 kcal?mol?1, confirming that Rho B binds most strongly with hydrated Mg2+, considering the energy associated with this binding process. This result suggests that Rho B forms a more stable complex than its isomer does with magnesium ion. Docking results show that both of these rhodostreptomycin molecules bind to solvated Ca2+ or Mg2+ through hydrogen bonding. Finally, Rho B is more stable than Rho A when protonation occurs. Figure Rho B–H showed higher stability since it is considered a proton pump inhibitor, and is therefore a stronger inhibitor of Helicobacter pylori |
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