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Quantum Mechanical Study on the Mechanistic, Energetic, and Structural Properties of Adsorption of 6‐Thioguanine onto γ‐ Fe 2 O 3 Nanoparticles
Author(s) -
Teymoori Monir,
Morsali Ali,
Bozorgmehr Mohammad Reza,
Beyramabadi S. Ali
Publication year - 2017
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11187
Subject(s) - chemistry , nanoparticle , covalent bond , density functional theory , gibbs free energy , non covalent interactions , ring (chemistry) , reactivity (psychology) , computational chemistry , adsorption , exothermic reaction , natural bond orbital , surface modification , nanotechnology , molecule , organic chemistry , thermodynamics , materials science , hydrogen bond , medicine , physics , alternative medicine , pathology
Using density functional theory, noncovalent interactions and four mechanisms of covalent functionalization of 6‐thioguanine anticancer drug onto γ‐ Fe 2 O 3 nanoparticles have been investigated. Quantum molecular descriptors of noncovalent configurations were studied. It was specified that binding of 6‐thioguanine onto γ‐ Fe 2 O 3 nanoparticles is thermodynamically suitable. Hardness and the gap of energy between LUMO and HOMO of 6‐thioguanine are higher than the noncovalent configurations, showing the reactivity of 6‐thioguanine increases in the presence of γ‐ Fe 2 O 3 nanoparticles. 6‐thioguanine can bond to γ‐ Fe 2 O 3 nanoparticles through NH 2 ( k 1 mechanism), NH in six‐membered ring ( k 2 mechanism), NH in five‐membered ring ( k 3 mechanism), and S ( k 4 mechanism) groups. The activation energies, the activation enthalpies and the activation Gibbs free energies of these reactions were calculated. Thermodynamic data indicate that k 3 mechanism is exothermic and spontaneous and can take place at room temperature. These results could be generalized to other similar drugs.