TY - JOUR
T1 - DFT and docking studies of rhodostreptomycins A and B and their interactions with solvated/nonsolvated Mg2+ and Ca2+ ions
AU - Jardínez, Christiaan
AU - Nicolás-Vázquez, Ines
AU - Cruz-Borbolla, Julian
AU - González-Ramírez, Cesar A.
AU - Cepeda, Miguel
AU - Correa-Basurto, Jose
AU - Pandiyan, Thangarasu
AU - Miranda, Rene
PY - 2013/11
Y1 - 2013/11
N2 - 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+(H 2O)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 Mg 2+ through hydrogen bonding. Finally, Rho B is more stable than Rho A when protonation occurs.
AB - 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+(H 2O)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 Mg 2+ through hydrogen bonding. Finally, Rho B is more stable than Rho A when protonation occurs.
KW - DFT study
KW - Mg, Ca and H ions
KW - Rhodostreptomycins A and B
UR - http://www.scopus.com/inward/record.url?scp=84888308281&partnerID=8YFLogxK
U2 - 10.1007/s00894-013-1952-3
DO - 10.1007/s00894-013-1952-3
M3 - Artículo
C2 - 24026575
SN - 1610-2940
VL - 19
SP - 4823
EP - 4836
JO - Journal of Molecular Modeling
JF - Journal of Molecular Modeling
IS - 11
ER -