Multidisciplinary Investigation of Atypical Inclusion Complexes of β-Cyclodextrin and a Phospholipase-A2 Inhibitor

Dahlheim, C.E.; Dali, Mandar; Naringrekar, Vijay H.; Miller, Scott A.; Shukla, Rajesh B.

doi:10.1002/jps.20245

Cited by 7 publications

(1 citation statement)

References 23 publications

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“…More recently, the tight-binding QC method (GFN2-xTB) [24,25] has been applied to CD-based systems [26,27]. Within this QC approach, a new form of characterizing and obtaining supramolecular arrangements was proposed [28] in an attempt to account for many equilibria simultaneously [29][30][31][32]. This was employed to treat CDbased systems with the use of the low-cost GFN2-xTB method, known as the multi-equilibrium approach [33].…”

Section: Introductionmentioning

confidence: 99%

Structure, stability, and dynamics of the inclusion complexes formed by auranofin derivatives and hydroxypropyl-β-cyclodextrin

Santos,

Anconi

2024

Preprint

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The inclusion compounds of auranofin (AF) and its iodide derivative (AF-I) with HP-b-CD were recently identified and characterized experimentally. In the present work, classical molecular dynamics and quantum computational GFN2-xTB method were applied to investigate the inclusion processes. As a result, both approaches addressed the AF-I@HP-β-CD as the most favorable system, as observed experimentally. The higher stability of AF-I@HP-β-CD was explained by entropy and solvation factors, with the GFN2-xTB method providing stability constant (logK1:1) in good agreement with experiment: 0.21 – 1.21 for AF@HP-β-CD and 1.31 – 2.33 for AF-I@HP-β-CD (experimental values are 1.48 and 2.52, respectively). The preferred inclusion mode for AF-I@HP-β-CD has the triethylphosphine (-PEt3) group pointed toward the head portion of the HP-β-CD where the hydroxypropyl groups are attached (labeled as P2). The P2 mode showed short contacts between -CH2CH3 groups (-PEt3) and -H3 only (inside the CD cavity), which is also supported by ROESY experiments.

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