Fluorescence enhancement of warfarin induced by interaction with β-cyclodextrin

• Published in: Biotechnology progress 2009-07, Vol.25 (4), p.906-914
• Main Authors: Vasquez, Jacob M., Vu, Andrew, Schultz, Jerome S., Vullev, Valentine I.
• Format: Article
• Language: English
• Subjects: Anticoagulants - chemistry; beta-Cyclodextrins - chemistry; Biological and medical sciences; biosensing; Biotechnology; change transfer; cyclodextrin; Fluorescence; Fundamental and applied biological sciences. Psychology; Kinetics; Viscosity; warfarin; Warfarin - chemistry
• ISSN: 8756-7938; 1520-6033; 1520-6033
• DOI: 10.1002/btpr.188

Warfarin is the most common agent used for control and prevention of venous as well as arterial thromboembolism (blood clots). In aqueous media, warfarin forms inclusion complexes with a family of cyclic oligosaccharides, α, β, γ‐cyclodextrins (CD). The formation of these complexes results in enhancement of the fluorescence of warfarin. Such spectroscopic changes offer a venue for the development of bioanalytical methodologies for warfarin quantification in biological liquids. We characterized the photophysical properties of warfarin in solvents with varying polarity and viscosity. The fluorescence quantum yield of warfarin correlated: (1) strongly with the solvent viscosity (R = 0.979) and (2) weakly with the solvent polarity (R = 0.118). These findings indicate that it is the change of the viscosity, rather than polarity, of the microenvironment that causes the fluorescence enhancement of warfarin upon binding to β‐CD. Utilizing the observed fluorescence enhancement in fluorescence titration measurements, the binding constants of warfarin to β‐CD were obtained (2.6 × 102 M−1–3.7 × 102 M−1). Using multivariable linear analysis, we extracted the stoichiometry of warfarin‐β‐CD interaction (1:1). © 2009 American Institute of Chemical Engineers Biotechnol. Prog., 2009