Predicting the free energies of complexation between cyclodextrins and guest molecules: linear versus nonlinear models.
OBJECTIVE
In the present paper, linear and nonlinear models for complexation of alpha- beta- and gamma-cyclodextrin with guest molecules are developed, with the aim of free energy prediction and interpretation of the association process.


METHODS
Linear and nonlinear regression is used to correlate experimental free energies of complexation with calculated molecular descriptors. Molecular modeling supports the interpretation of the results.


RESULTS
Highly predictive models are obtained, although the structural variability of the compounds used for their deduction is large, reaching from synthetic heterocycles to steroids and prostaglandins.


CONCLUSIONS
The scaled regression coefficients give insight to the complexation mechanisms, which appear to be different for the three types of cyclodextrins.
Klein
C T
CT
Institut für Theoretische Chemie und Molekulare Strukturbiologie, Wien.
Polheim
D
D
Viernstein
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H
Wolschann
P
P
D003505:Cyclodextrins / Q000737:chemistry*; D004735:Energy Transfer; D016014:Linear Models; D008958:Models, Molecular; D017711:Nonlinear Dynamics; D004364:Pharmaceutical Preparations / Q000737:chemistry; D017434:Protein Structure, Tertiary; D013329:Structure-Activity Relationship; D047391:alpha-Cyclodextrins; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins
D003505:Cyclodextrins; D004364:Pharmaceutical Preparations; D047391:alpha-Cyclodextrins; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins; C031215:betadex; C023792:gamma-cyclodextrin; C032613:alpha-cyclodextrin