Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe

Masayuki Takeuchi, Toshihisa Mizuno, Hideyuki Shinmori, Michio Nakashima, Seiji Shinkai

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

A cyanine dye (4) bearing two boronic acids was designed and synthesized, expecting the selective binding of monosaccharides through the formation of 1:1 intramolecular complexes. While it aggregates in water, it exists discretely in water/methanol 1:1 mixed solvent. In the latter solvent the fluorescence spectra were scarcely affected by the medium pH but efficiently increased when it formed intramolecular 1:1 complexes with monosaccharides. This complexation mode was also corroborated by CD spectroscopy and continuous variation plots. Hence, the saccharide-induced fluorescence increase is rationalized in terms of 'rigidification' of the cyanine skeleton. The association constants (K) were estimated from plots of saccharide concentration vs. fluorescence intensity: the largest K was observed for D-fructose (1.3 x 105 M-1) and the next for D-arabinose (1.0 x 104 M-1). This is a novel system for sensitive and selective fluorescence detection of monosaccharides.

Original languageEnglish
Pages (from-to)1195-1204
Number of pages10
JournalTetrahedron
Volume52
Issue number4
DOIs
Publication statusPublished - Jan 1 1996

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Sugars
Monosaccharides
Fluorescence
Acids
Bearings (structural)
Boronic Acids
Arabinose
Water
Fructose
Complexation
Skeleton
Methanol
Spectrum Analysis
Coloring Agents
Association reactions
Spectroscopy

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Takeuchi, M., Mizuno, T., Shinmori, H., Nakashima, M., & Shinkai, S. (1996). Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe. Tetrahedron, 52(4), 1195-1204. https://doi.org/10.1016/0040-4020(95)00979-5

Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe. / Takeuchi, Masayuki; Mizuno, Toshihisa; Shinmori, Hideyuki; Nakashima, Michio; Shinkai, Seiji.

In: Tetrahedron, Vol. 52, No. 4, 01.01.1996, p. 1195-1204.

Research output: Contribution to journalArticle

Takeuchi, M, Mizuno, T, Shinmori, H, Nakashima, M & Shinkai, S 1996, 'Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe', Tetrahedron, vol. 52, no. 4, pp. 1195-1204. https://doi.org/10.1016/0040-4020(95)00979-5
Takeuchi, Masayuki ; Mizuno, Toshihisa ; Shinmori, Hideyuki ; Nakashima, Michio ; Shinkai, Seiji. / Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe. In: Tetrahedron. 1996 ; Vol. 52, No. 4. pp. 1195-1204.
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