Main Article Content
The pKa values were calculated for some acetoxy group molecules using CBS-Q method which is one of the Complete Basis Set methods to find accurate energies. The acetoxy group molecules were also planned by Quantitative Structure Activity Relationship (QSAR) to study their effect on paraoxonase1 activity.
The results of this study showed a strong relationship, (R2=0.99) between the calculated and experimental pka, also showed correlations between the activity of the enzyme and some of the studied descriptors. Moreover, the results of the study revealed that by using the SPSS program, there is a correlation between LUMO, Softness, Nucleofugality and Electrofugality as dependent variables and Cal. pKa as an independent variable.
Petersson GA, Bennett A, Tensfeldt TG, Al-Laham MA, Shirley WA, Mantzaris J. A complete basis set model chemistry. I. The total energies of closed‐shell atoms and hydrides of the first‐row elements. J Chem Phys. 1988;89:2193–2218.
Petersson GA, Al-Laham MA. A complete basis set model chemistry. II. Open‐shell systems and the total energies of the first‐row atoms. J Chem Phys. 1991;94: 6081–6090.
Petersson GA, Tenfeldt TG, Mongomery JA. A complete basis set model chemistry. III. The complete basis set‐quadratic configuration interaction family of methods. J Chem Phys. 1991;94:6091–6101.
Petersson GA, Malick DK, Wilson WG, Ochterski JW, Montgomery JA, Frisch JM. Calibration and comparison of the Gaussian-2, complete basis set, and density functional methods for computational thermochemistry. J. Chem. Phys. 1998;109:10570-10579.
Casasnovas R, Frau J, Ortega-Castro J, Salvà A, Donoso J, Muñoz F. Absolute and relative pKa calculations of mono and diprotic pyridines by quantum methods. Journal of Molecular Structure: THEO. CHEM. 2009;912:5-12.
Casasnovas R, Fernandez D, Ortega-Castro J, Frau J, Donoso J, Muñoz F. Avoiding gas-phase calculations in theoretical pKa predictions. Theor Chem Acc. 2011;130:1–13.
Khersonsky O, Tawfik DS. Structure-reactivity studies of serum paraoxonase PON1 suggest that its native activity is lactonase. Biochemistry. 2005;44:6371-6382.
Gao DQ, Svoronos P, Wong PK, Maddalena D, Hwang J, Walker H. pK(a) of acetate in water: A computational study. J. Phys. Chem. 2005;109(47):10776-85.
Mongomery JA, Ochterski JW, Petersson GA. A complete basis set model chemistry. IV. An improved atomic pair natural orbital method. J Chem Phys. 1994;101:5900–5909.
Montgomery JA, Frisch MJ, Ochterski JW, Petersson GA. A complete basis set model chemistry. VI. Use of density functional geometries and frequencies. J. Chem. Phys. 1999;110:2822-2827.
Ochterski JW, Petersson G, Montgomery JA. A complete basis set model chemistry. V. Extensions to six or more heavy atoms. J. Chem.Phys. 1998;104:2598-2619.
Liptak MD, Shields GC. Accurate pKa calculations for carboxylic acids using complete basis set and Gaussian-n models combined with CPCM continuum solvation methods. J. Am. Chem. Soc. 2001;123: 7314-7319.
Liptak MD, Gross KC, Seybold PG, Feldgus S, Shields GC. Absolute pKa determinations for substituted phenols. J. Am. Chem. Soc. 2002;124:6421-6427.
Aihara J. Reduced HOMO&LUMO gap as an index of kinetic stability for polycyclic aromatic hydrocarbons. J. Phys. Chem. 1999;103:7487–7495.
Kim KH, Han YK, Jung J. Basis set effects on relative energies and HOMO–LUMO energy gaps of fullerene C36. Theoretical Chemistry Accounts. 2005;113:233–237.
Abbaz T, Bendjeddou A, Villemin D. Molecular structure, HOMO, LUMO, MEP, natural bond orbital analysis of benzo and anthraquinodimethane derivatives. Pharmaceutical and Biological Evaluations. 2018;5(2):27-39.
Sayiner HS, Abdalrahim AAS, Başaran MA, Kovalishyn V, Kandemirli F. The quantum chemical and QSAR studies on Acinetobacter baumannii Oxphos inhibitors. Medicinal Chemistry. 2018;14: 253-268.