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Internet Electronic Journal of Molecular Design - IEJMD, ISSN 1538-6414, CODEN IEJMAT
| ABSTRACT - Internet Electron. J. Mol. Des. April 2007, Volume 6, Number 4, 96-105 |
Theoretical Study on the Inclusion of Allergens with Partially Methylated Crystallized
β-Cyclodextrin and Hydroxypropyl β-Cyclodextrin
Georgiana G. Surpateanu, Gautier Decock, Sophie Fourmentin, David Landy, Paul Ionut Dron, and Gheorghe Surpateanu
Internet Electron. J. Mol. Des. 2007, 6, 96-105
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Abstract:
Several compounds used in fragrance are suspected to be allergens and thus has to
be extracted and analyzed. Cyclodextrins are well known to form inclusion
complexes with a wide range of organic compounds. This is why we investigated,
by a theoretical study, the interactions that occur between two modified
cyclodextrins and 21 compounds suspected to be allergens. The computed
complexation energies, ΔE, have been calculated for the inclusion of 21 allergens
with hydroxyl-propyl-β-cyclodextrin (HPBCD) and partially methylated
crystallized β-cyclodextrin (CRYSMEB). Our docking strategy involves three
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 salvation 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 HPBCD and CRYSMEB are analogous, but a notable
greater stabilization is generally obtained with HPBCD. A better recognition is
also generally observed for cyclic allergens than for acyclic ones. The computed
complexation energies ΔE calculated by the MM3 method could be considered as
a measure of the inclusion ability of allergens in CRYSMEB and HPBCD. The
filling of the inner cyclodextrin cavity with allergens could be taken into
consideration with complexation energy. The solvation energy in water permits
the choice of the most stable regioconformer in each pair of conformers. In
respect to β-cyclodextrin, the hydroxypropyl β-cyclodextrin (HPBCD) seems to
be the most interesting in the fixation of allergens. The specific affinities
cyclodextrin-allergen could be explored from experimental point of view.
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