Boronic acid based modular fluorescent sensors for glucose.
Modular photoinduced electron transfer (PET) sensors bearing two phenylboronic acid groups, one or two fluorophores: pyrene(a), phenanthrene(b), anthracene(c), 1-naphthalene(d), 2-naphthalene(e) and alkylene linkers, from trimethylene(3) to octamethylene(8), have been evaluated. Systems with a single pyrene fluorophore 34a, 35a and 36a bind the strongest with D-glucose (36a also binds well with D-melibiose). Whilst 37a and 38a bind the strongest with D-galactose. Changing the fluorophore, also, influences the binding, 36a, 36b and 36c are D-glucose selective, whilst 36d and 36e are D-galactose selective. Systems with two fluorophores 36a-a and 36a-b show an overall decrease in binding efficiency. Energy transfer in 36a-b results in enhanced sensitivity and selectivity towards D-glucose.
Phillips
Marcus D
MD
Department of Chemistry, University of Bath, Bath BA2 7AY, United Kingdom.
James
Tony D
TD
D015374:Biosensing Techniques / Q000379:methods*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry; D031541:Fluorescence Resonance Energy Transfer; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D005470:Fluorometry; D005947:Glucose / Q000032:analysis*; D006801:Humans; D015394:Molecular Structure; D008991:Monitoring, Physiologic / Q000379:methods; D009005:Monosaccharides / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry; D013050:Spectrometry, Fluorescence
D001896:Boron Compounds; D001897:Boronic Acids; D004187:Disaccharides; D005456:Fluorescent Dyes; D009005:Monosaccharides; D011084:Polycyclic Aromatic Hydrocarbons; D005947:Glucose