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Internet Electronic Journal of Molecular Design - IEJMD, ISSN 1538-6414, CODEN IEJMAT
| ABSTRACT - Internet Electron. J. Mol. Des. July 2006, Volume 5, Number 7, 376-386 |
Theoretical Study on the Inclusion of Allergens with β-Cyclodextrin
and Randomly-Methylated-β-Cyclodextrin
Gauthier Decock, Sophie Fourmentin, David Landy, Georgiana Surpateanu, Patrick Decock, and Gheorghe Surpateanu
Internet Electron. J. Mol. Des. 2006, 5, 376-386
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Abstract:
Some compounds used in fragrance are suspected to be allergens and
thus has to be extracted and analyzed. Since cyclodextrins are known
to form inclusion complexes with a large variety of organic
compounds, we have investigated the interactions occurring between
two cyclodextrins and 21 compounds suspected to be allergens by a
theoretical study. The computed complexation energies, ΔE, have been
calculated for the inclusion of 21 allergens with β-cyclodextrin (βCD)
and Randomly Methylated β-cyclodextrin (RAMEB). Our docking
strategy involves four dummy atoms, two variable parameters and two
regiochemical ways using MM3 method. The ΔE energies measured
for the formation and stabilization of the inclusion complexes and the
solvation energies calculated by AM1 (COSMO solvent field) allows
the definition of the most probable structure in each pair of
regioconformers, even if both forms may exist in solution in most
cases. The complexation behaviors of βCD and RAMEB are
analogous, but a slightly greater stabilization is generally obtained
with RAMEB. A better recognition is also generally observed for
cyclic allergens than for acyclic ones. The use of complexation and
solvation energies as computed by the MM3 and AM1-COSMO
methods could be considered as a measure of the inclusion ability of
allergens in βCD and RAMEB, and allows the determination of the
most stable conformer. The filling of the inner cyclodextrin cavity
with the allergens seems to be a key factor for the recognition.
According to the restrained range of stabilization that have been
observed, it seems that all allergens could be complexed and thus
extracted by cyclodextrins, especially the cyclic allergens and
preferably with RAMEB.
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