Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 9, Pages 2795-2804Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200701785
Keywords
boronic acids; carbohydrates; fluorescence; sensors
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Funding
- NCI NIH HHS [CA113917, CA88343, N01-CO-27184] Funding Source: Medline
- NATIONAL CANCER INSTITUTE [R21CA088343, R33CA088343, R21CA113917] Funding Source: NIH RePORTER
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Boronic acids that change fluorescence properties upon sugar binding are very useful for the synthesis of carbohydrate sensors. Along this line, boronic acids that fluoresce beyond 500 nm are especially useful. A series of boronic acid fluorescent reporter compounds based on the 4-amino- 1,8-naphthalimide. structure have been synthesized (1a-d) and evaluated under near physiological conditions. These compounds showed good water solubility and significant changes in fluorescence properties after binding with sugars, with the emission wavelength being at around 570 nm. Analogues in this series with different substitutions showed similar properties. We have also examined the mechanism of the observed fluorescence changes for these compounds.
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