A study of boronic acid based fluorescent glucose sensors

T. Kawanishi, M. A. Romey, P. C. Zhu, M. Z. Holody, Seiji Shinkai

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Boronic acid based anthracene dyes were designed, synthesized, and immobilized to solid phase, creating a continuous glucose sensor. Glucose sensitivities of dyes can decrease drastically after immobilization, therefore how to immobilize a dye to solid phase without changing the dye property is a key issue in developing the sensor. The glucose sensitivity of the simplest 1st generation sensor, which is based on an immobilized mono-phenylboronate/single- arm type, came short of the sensitivity requirement for practical use, because of the very moderate fluorescence intensity change over the physiological glucose range. However, the 2nd generation, an immobilized bis-phenylboronate/ double-arm type sensor, which contained two boronate groups in the dye moiety in expectation of a large intensity change, brought about considerable improvement on its glucose sensitivity. We tried to introduce functional groups onto an anthracene ring in order to improve the dies' fluorescence properties. Acetyl or carboxyl substitution on anthracene contributed to shift the fluorescence wavelength into the more visible range (red-shift) and a divergence of wavelength between an excitation peak and an emission peak. This improvement is advantageous to the design of an optical detection system. Furthermore, single arm immobilization to this carboxyl group, thus linking directly to the fluorophore led to a 3rd generation sensor, an immobilized bis-phenylboronate/ single-arm type, that was twice as sensitive as that of the 2nd generation sensor, presumably due to increased mobility of the dye moiety. The results of our study advance closer toward a clinically useful continuous fluorescent glucose sensor.

Original languageEnglish
Pages (from-to)499-512
Number of pages14
JournalJournal of Fluorescence
Volume14
Issue number5
DOIs
Publication statusPublished - Sep 1 2004

Fingerprint

Boronic Acids
Glucose sensors
Coloring Agents
Glucose
Sensors
Fluorescence
Immobilization
Group
substitution
divergence
Wavelength
Optical Devices
Fluorophores
Functional groups
Substitution reactions
benzeneboronic acid
anthracene

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Clinical Biochemistry

Cite this

Kawanishi, T., Romey, M. A., Zhu, P. C., Holody, M. Z., & Shinkai, S. (2004). A study of boronic acid based fluorescent glucose sensors. Journal of Fluorescence, 14(5), 499-512. https://doi.org/10.1023/B:JOFL.0000039338.16715.48

A study of boronic acid based fluorescent glucose sensors. / Kawanishi, T.; Romey, M. A.; Zhu, P. C.; Holody, M. Z.; Shinkai, Seiji.

In: Journal of Fluorescence, Vol. 14, No. 5, 01.09.2004, p. 499-512.

Research output: Contribution to journalArticle

Kawanishi, T, Romey, MA, Zhu, PC, Holody, MZ & Shinkai, S 2004, 'A study of boronic acid based fluorescent glucose sensors', Journal of Fluorescence, vol. 14, no. 5, pp. 499-512. https://doi.org/10.1023/B:JOFL.0000039338.16715.48
Kawanishi, T. ; Romey, M. A. ; Zhu, P. C. ; Holody, M. Z. ; Shinkai, Seiji. / A study of boronic acid based fluorescent glucose sensors. In: Journal of Fluorescence. 2004 ; Vol. 14, No. 5. pp. 499-512.
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