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A 1H NMR Study of Host/Guest Supramolecular Complexes of a Curcumin Analogue with β-Cyclodextrin and a β-Cyclodextrin-Conjugated Gemini Surfactant
- Source :
- Molecular Pharmaceutics. 12:2993-3006
- Publication Year :
- 2015
- Publisher :
- American Chemical Society (ACS), 2015.
-
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.
- Subjects :
- Models, Molecular
Curcumin
Magnetic Resonance Spectroscopy
Stereochemistry
Chemistry, Pharmaceutical
Supramolecular chemistry
Pharmaceutical Science
Antineoplastic Agents
02 engineering and technology
Alkenes
Conjugated system
010402 general chemistry
01 natural sciences
Pulmonary surfactant
Drug Discovery
Amphiphile
chemistry.chemical_classification
Cyclodextrins
Aqueous solution
Molecular Structure
Cyclodextrin
beta-Cyclodextrins
021001 nanoscience & nanotechnology
Combinatorial chemistry
0104 chemical sciences
Quaternary Ammonium Compounds
Solubility
chemistry
Drug delivery
Proton NMR
Molecular Medicine
0210 nano-technology
Subjects
Details
- ISSN :
- 15438392 and 15438384
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- Molecular Pharmaceutics
- Accession number :
- edsair.doi.dedup.....f1cdc17d48c8fc026912e924ef447c7f