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Quantitative relationship between 3D structure and hydrophilicity and lipophilicity of polyphenols

Quantitative structure-property relationship (QS PR) models that relate hydrophilicity and lipophilicity of nineteen polyphenols with descriptors derived from optirnized three- dimensional molecular structures were developed. The 3D structures of polyphenols were optirnized applying the HyperChem 8.0 (Hypercube Inc.) us ing AMI method. Several physico-chernical parameters were calculated with HyperChem: the energy of the highest occupied (EHOMO) and lowest unoccupied molecular orbital (ELUMO), difference between EHOMO and ELUMO (GAP), the heat of formation (Hf) , and hydration energy (EHyDR). Applying the Dragon program, different group of molecular descriptors have been calculated: geometrical, 3D-MoRSE, Randic molecular profiles, GETA WAY, RDF, WHIM, and BCUT descriptors. Selection of descriptors based on best-subset method and multiple regression analysis was performed us ing the program Statistica 7.0 (StatSoft, Inc.). The generated QSPR model s were validated by leave-one-out cross-validation procedure using the CROMRsel (Rugjer Bošković Institute, Zagreb). This study has revealed that the hydrophilicity of polyphenols is generally dependent on the 3D- distribution of atornic electronegativity, polarizability, as well as on hydration energy of molecule. QSPR study of lipophilicity indicates about importance of the three- dimensional distribution of atornic mass and shape of molecule. 3D descriptors can be used successfully for modeling of hydrophilicity and lipophilicity of polyphenols, especially for data sets that include stereoisomers and hardly available compounds.

hydrophilicity ; lipophilicity ; polyphenols ; QSPR

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