Modeling the chiral resolution ability of highly sulfated β-cyclodextrin for basic compounds in electrokinetic chromatography

Enantioresolution in electrokinetic chromatography-complete filling technique using sulfated gamma-cyclodextrin. Software-free topological anticipation

“…A first group of variables (subset-1, 20 variables) corresponds to molecular descriptors predicted by ACD/Labs and ChemAxon calculations: logarithm of octanol-water partition coefficient estimated at pH 7.4, polar surface area, hydrogen bond donors and acceptors, polarizability, molar refractivity, molar volume, freely rotatable bonds, surface tension, molecular mass, molecular surface area, van der Waals volume, Dreiding energy, orbital electronegativity of the chiral carbon atom, maximal and minimal projection area, maxima and minimal z length, charge and Huckel analysis-pi energy. A similar set of variables has been successfully used in a previous paper to model HS--CD enantioresolution ability [22]. Additionally, a new set of topological parameters (subset-3, 7 variables) have been introduced in this work.…”

“…However, this low pH does not allow the use of EKC-PFT or EKC-CFT. Our research group has demonstrated that the combination of sulfated CDs and EKC-CFT at normal polarity mode is a good choice for the enantioseparation of basic compounds at neutral or basic pHs [22]. Under these conditions, cationic or neutral compounds move through the anionic chiral selector plug that migrates in the opposite direction, allowing interaction and enantioseparation.…”

“…Mathematical models relating structural parameters of certain compounds with their electrophoretic parameters can be used to describe and predict compounds separation (quantitative-structure property relationship, QSPR). Different strategies have been used in the literature for developing QSPR for modelling enantioresolution-related information in EKC [16][17][18][19][20][21][22].…”

“…In a previous paper [22], the enantioresolution level (Rs-level) in EKC-CFT, using highly sulfated β-CD (HS-β-CD) as chiral selector of forty structurally unrelated basic drugs and pesticides has been modelled as a function of structural parameters. The model allows to predict the Rs-level of new compounds from four structural descriptors: logarithm of octanol-water partition coefficient estimated at pH 7.4 (LogD), polar surface area (PSA) and number of hydrogen bond donors and acceptors.…”

Study on the separation of ofloxacin enantiomers by hydroxyl-propyl-β-cyclodextrin as a chiral selector in capillary electrophoresis: a computational approach

“…Semiempirical methods are attracting lots of attention in the simulation of CD-inclusion compounds due to their reasonable accuracy and less computational demands. These studies were directed to unravel the nature of interaction between the host and the guest molecules to help in understanding the mechanism of complexation [4,18,[22][23][24][25][27][28][29][30][31]. These calculations have also been used to investigate the mechanistic characteristics of chiral recognition using supramolecular systems.…”