Enhanced stability of a naringenin/2,6-dimethyl β-cyclodextrin inclusion complex: molecular dynamics and free energy calculations based on MM- and QM-PBSA/GBSA.
作者： Waratchada Sangpheak , Wasinee Khuntawee , Peter Wolschann , Piamsook Pongsawasdi , Thanyada Rungrotmongkol
DOI: 10.1016/J.JMGM.2014.03.001
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摘要: Abstract The structure, dynamic behavior and binding affinity of the inclusion complexes between naringenin two cyclodextrins (CDs), β-CD its 2,6-dimethyl derivative (DM-β-CD), were theoretically studied by multiple molecular dynamics simulations free energy calculations. Naringenin most likely prefers to bind with CDs through phenyl ring. Although a lower hydrogen bond formation 3-hydroxyl group DM-β-CD (relative β-CD) was observed, higher cavity could encapsulate almost whole molecule. In contrast for naringenin/β-CD complex, ring feasibly passed primary rim resulting in chromone inside instead. MM-PBSA/GBSA QM-PBSA/GBSA energies strongly suggested greater stability naringenin/DM-β-CD complex. Van der Waals force played an important role as key guest–host interaction complexation each cyclodextrin.
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