Macrocycle-derived functional xanthenes and progress towards concurrent detection of glucose and fructose.
The detection of saccharides in biological media is of great current importance for the monitoring of disease states. We have previously reported that solutions of boronic acid-functionalized macrocycles form acyclic oligomeric materials in situ. The oligomers contain fluorescent xanthene moieties. Current efforts are aimed at modulating the spectroscopic responses of these materials for the analysis of specific sugars. We describe conditions whereby the xanthene boronic acids exhibit high colorimetric fructose selectivity. In contrast, at physiological levels selective glucose monitoring can be achieved via fluorescence. Additionally, we describe a method which exhibits promise for detecting both glucose and fructose at dual wavelengths in the UV-Vis region. Mechanistic rationale for each of these findings is presented.
Rusin
Oleksandr
O
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Alpturk
Onur
O
He
Ming
M
Escobedo
Jorge O
JO
Jiang
Shan
S
Dawan
Fareed
F
Lian
Kun
K
McCarroll
Matthew E
ME
Warner
Isiah M
IM
Strongin
Robert M
RM
D001786:Blood Glucose / Q000032:analysis; D001897:Boronic Acids / Q000737:chemistry; D047250:Calixarenes; D005456:Fluorescent Dyes / Q000737:chemistry; D005632:Fructose / Q000032:analysis* / Q000737:chemistry; D005947:Glucose / Q000032:analysis* / Q000737:chemistry; D006801:Humans; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D008991:Monitoring, Physiologic / Q000379:methods*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry; D013056:Spectrophotometry, Ultraviolet; D014966:Xanthenes / Q000737:chemistry*
D001786:Blood Glucose; D001897:Boronic Acids; D005456:Fluorescent Dyes; D047028:Macrocyclic Compounds; D014966:Xanthenes; C466160:resorcinarene; D047250:Calixarenes; D005632:Fructose; D010649:Phenylalanine; D005947:Glucose