Autori: Georgiana G. Surpateanu, Gautier Decock, Sophie Fourmentin, David Landy, Paul Ionut Dron, and Gheorghe Surpateanu

Editorial: Internet Electronic Journal of Molecular Design, 6 (4), p.96-105, 2007.

Rezumat:

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.

Cuvinte cheie: Cyclodextrins; inclusion compounds; allergens; docking; MM3; AM1.