Crystal and molecular structure of V-amylose complexed with ibuprofen. (1st June 2021)

• Record Type: Journal Article
• Authors: Le, Cong Anh Khanh; Ogawa, Yu; Dubreuil, Frédéric; Grimaud, Florent; Mazeau, Karim; Ziegler, Gregory R.; Tanwar, Shivalika; Nishiyama, Yoshiharu; Potocki-Veronese, Gabrielle; Choisnard, Luc; Wouessidjewe, Denis; Putaux, Jean-Luc
• Is Part Of: Carbohydrate polymers. Volume 261(2021)
• Publication Date: 2021-06-01
• Subjects: Amylose -- Ibuprofen -- Inclusion compound -- Crystal structure; Polysaccharides -- Periodicals; Polysaccharides -- Periodicals; Polysaccharides -- Périodiques; Electronic journals; 547.78
• DOI: 10.1016/j.carbpol.2021.117885
• Languages: English
• ISSNs: 0144-8617

Abstract

Graphical abstract: Highlights: Amylose formed chain-folded lamellar cocrystals with racemic ibuprofen. A molecular model was refined against base-plane electron diffraction data. The orthorhombic unit cell contains antiparallel 7-fold amylose single helices. Ibuprofen molecules are located in the helical cavity and between the helices. Abstract: Rectangular V-amylose single crystals were prepared by adding racemic ibuprofen to hot dilute aqueous solutions of native and enzymatically-synthesized amylose. The lamellar thickness increased with increasing degree of polymerization of amylose and reached a plateau at about 7 nm, consistent with a chain-folding mechanism. The CP/MAS NMR spectrum as well as base-plane electron and powder X-ray diffraction patterns recorded from hydrated specimens were similar to those of V-amylose complexed with propan-2-ol. Amylose was crystallized in an orthorhombic unit cell with parameters a = 2.824 ± 0.001 nm, b = 2.966 ± 0.001 nm, and c = 0.800 ± 0.001 nm. A molecular model was proposed based on structural analogies with the Vpropan-2-ol complex and on assumptions on the stoichiometry of ibuprofen. The unit cell would contain four antiparallel 7-fold amylose single helices with ibuprofen molecules distributed inside and between the helices.