Journal Title
Title of Journal: J Mol Model
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Abbravation: Journal of Molecular Modeling
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Publisher
Springer Berlin Heidelberg
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Authors: M Hossein Khalilian Saber Mirzaei Avat Arman Taherpour
Publish Date: 2016/10/25
Volume: 22, Issue: 11, Pages: 270-
Abstract
The electronic features of antitumor agent temozolomide and its degradation products MTIC and metabolite AIC have been traced by means of UV absorption spectroscopy in vacuo and aqueous media For comparison electronic spectra of related structures and drugs eg dacarbazine were also investigated These investigations were carried out using timedependent density functional theory TDDFT method while the conductor like screening model COSMO were applied for the inclusion of solvent effects in electronic spectra From functional benchmarking two methods B3LYP and O3LYP were selected among several other methods with 6311+G2dp basis set aiming to get the best results in accord with the experimental values An assessment of the obtained spectra has shown that O3LYP functional gives a mean absolute error MAE from experimental absorption peaks of 43 nm compared to the 72 nm MAE value at B3LYP level in aqueous media Furthermore since the structural and tautomeric conformers affect the electronic spectra conformational preferences have been analyzed in temozolomide dacarbazine and their related structures Temozolomide structure possesses two rotamers that differ in the orientation of carboxamide moiety with a small energy difference energy difference of 139 kcal mol−1 in vacuo and 035 kcal mol−1 in aqueous media at B3LYP/6311++G2df3pd The more stable and metastable TMZ rotamer have shown their absorption maxima at 329–334 nm respectively at O3LYP level in aqueous media Applying statistical calculation according to Boltzmann population formula at 25 °C and computed weighed mean estimates the λmax of temozolomide at 331 nm which is in notable agreement with the experimental value 330 nm Moreover molecular orbital composition analysis has been conducted in order to interpret these findingsThe authors gratefully acknowledge the Research and Computational Lab of Theoretical Chemistry and Nano Structures of Razi University KermanshahIran and the Medical Biology Research Center Kermanshah University of Medical Sciences Kermanshah Iran for supporting the present work
Keywords:
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