UNS Conference Portal, The 1st International Conference on Science, Mathematics, Environment and Education 2017

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PM3 and ONIOM Modelling on Inclusion Complex of Ibuprofen Enantiomers with Dimethyl-β-cyclodextrin
Enung Siti Nurhidayah, Muhamad Abdulkadir Martoprawiro, Muhammad Ali Zulfikar

Last modified: 2017-07-03

Abstract


Host-guest inclusion complexes between 2,6-dimethyl-ß-Cyclodextrin (DIMEB) and enantiomers of ibuprofen (R/S-IBP) were simulated using the molecular docking, semi-empirical PM3 and ONIOM2 (B3LYP/6-31g(d,p): PM3) methods. The modelling results showed that the most stable geometries of two R and S-IBP/DIMEB complexes were similar. The results showed that the binding energy of (R)-IBP/DIMEB and (S)-IBP/DIMEB complexes calculated by PM3 were -53.770 and -57.278 kJ/mol, by ONIOM2 method were -52.917 and -59.053 kJ/mol. In addition, termodynamic parameters obtained follow the same trend with binding energy value. Furthermore, indicating that (S)-IBP/DIMEB complex is more stable than (R)-IBP/DIMEB complex. DIMEB formed stronger inclusion complex with S-enantiomer than with R-enantiomer ibuprofen. The theoretical results are in agreement with the experimental parameters.

Keywords: Inclusion complex, ibuprofen, dimethyl--cyclodextrin, molecular docking, PM3, ONIOM2