title: A 1H NMR Study of Host/Guest Supramolecular Complexes of a Curcumin Analogue with β-Cyclodextrin and a β-Cyclodextrin-Conjugated Gemini Surfactant.
abstract: Host systems based on β-cyclodextrin (βCD) were employed as pharmaceutical carriers to encapsulate a poorly soluble drug, curcumin analogue (NC 2067), in order to increase its water solubility. βCD was chemically conjugated with an amphiphilic gemini surfactant with the ability to self-assemble and to form nanoscale supramolecular structures. The conjugated molecule, βCDgemini surfactant (βCDg), was shown to be a promising drug delivery agent. In this report, its physicochemical properties were assessed in aqueous solution using 1D and 2D 1H NMR spectroscopy. The results showed that the apolar hydrocarbon domain of the gemini surfactant was self-included within the βCD internal cavity. The host/guest complexes composed of native βCD or βCDg with NC 2067 were examined using 1D/2D ROESY NMR methods. The stoichiometry of βCD/NC 2067 complex was estimated using Job's method via 1H NMR spectroscopy. The binding geometry of NC 2067 within βCD was proposed using molecular docking and further supported by 1D and 2D ROESY NMR results. Addition of NC 2067 to βCDg revealed minimal changes to the overall structure of the βCDg system, in agreement with the formation of a βCDg/NC 2067 ternary complex.
authors.affiliation: †Drug Discovery and Development Research Group, College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5E5, Canada.
authors.forename: Masoomeh
authors.initials: M
authors.lastname: Poorghorban
authors.affiliation: ‡Department of Chemistry, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5C9, Canada.
authors.forename: Abdalla H
authors.initials: AH
authors.lastname: Karoyo
authors.affiliation: †Drug Discovery and Development Research Group, College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5E5, Canada.|§Canadian Light Source, Saskatoon, Saskatchewan, S7N 2 V3, Canada.
authors.forename: Pawel
authors.initials: P
authors.lastname: Grochulski
authors.affiliation: ‡Department of Chemistry, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5C9, Canada.
authors.forename: Ronald E
authors.initials: RE
authors.lastname: Verrall
authors.affiliation: ‡Department of Chemistry, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5C9, Canada.
authors.forename: Lee D
authors.initials: LD
authors.lastname: Wilson
authors.affiliation: †Drug Discovery and Development Research Group, College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Saskatchewan, S7N 5E5, Canada.
authors.forename: Ildiko
authors.initials: I
authors.lastname: Badea
mesh_terms: D000475:Alkenes / Q000737:chemistry* / Q000378:metabolism; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism; D002626:Chemistry, Pharmaceutical / Q000379:methods; D003474:Curcumin / Q000737:chemistry* / Q000378:metabolism; D003505:Cyclodextrins / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008958:Models, Molecular; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry* / Q000378:metabolism; D012995:Solubility; D047392:beta-Cyclodextrins / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000475:Alkenes; D000970:Antineoplastic Agents; D003505:Cyclodextrins; D000644:Quaternary Ammonium Compounds; D047392:beta-Cyclodextrins; C509664:hexamethylene-1,6-bis(dodecyldimethylammonium bromide); D003474:Curcumin; C031215:betadex
keywords: molecular docking; rotating frame Overhauser effect spectroscopy (ROESY); self-inclusion; through-space interaction