title: Evaluation of pyranine derivatives in boronic acid based saccharide sensing: significance of charge interaction between dye and quencher in solution and hydrogel.
abstract: In an ongoing program to synthesize a glucose sensing polymer that could be used for real time glucose monitoring in vivo, we have been exploring the use of boronic acid functional viologens as glucose responsive quenchers for fluorescent dyes. The present study focuses on the effect of ionic interactions between pyranine or its various sulfonamide derivatives and the viologen quenchers. Dyes bearing anionic groups were quenched more efficiently when compared to dyes with nonionic substituents. The anionic dyes in conjunction with the cationic quenchers exhibited a broader range of glucose response both in solution and when immobilized in a hydrogel. The interaction of glucose with the sensing components was similar whether they are soluble or immobilized.
authors.affiliation: Department of Chemistry and Biochemistry, University of California at Santa Cruz, 1156 High Street, Santa Cruz, California 95064, USA.
authors.forename: Frank E
authors.initials: FE
authors.lastname: Cappuccio
authors.forename: Jeff T
authors.initials: JT
authors.lastname: Suri
authors.forename: David B
authors.initials: DB
authors.lastname: Cordes
authors.forename: Ritchie A
authors.initials: RA
authors.lastname: Wessling
authors.forename: Bakthan
authors.initials: B
authors.lastname: Singaram
mesh_terms: D000465:Algorithms; D001190:Arylsulfonates / Q000138:chemical synthesis / Q000737:chemistry*; D015374:Biosensing Techniques / Q000379:methods*; D001786:Blood Glucose / Q000032:analysis; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000032:analysis* / Q000737:chemistry; D006801:Humans; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate / Q000737:chemistry; D015394:Molecular Structure; D008991:Monitoring, Physiologic / Q000379:methods; D009005:Monosaccharides / Q000032:analysis; D013050:Spectrometry, Fluorescence; D014755:Viologens / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001190:Arylsulfonates; D001786:Blood Glucose; D001896:Boron Compounds; D001897:Boronic Acids; D005456:Fluorescent Dyes; D009005:Monosaccharides; D014755:Viologens; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate; C005047:pyranine; D005947:Glucose