Abstract
This review provides a chronological survey of over fifty fluorescent chemosensors for carbohydrates from the period between 1992 to the present. The survey contains only those sensors that are synthetic or chemosensory, utilize boronic acids and display a fluorescence response in the form of intensity changes or shifts in wavelength. With each compound listed, a description of the saccharide probe is given with regard to concentration, excitation and emission wavelengths, pH and solvent mixture proportions. In addition, the selectivity of each chemosensor is provided as well as the trends in binding constants. Where possible, a description of the fluorescence signaling mechanism is given as well as commentary on the probe's unique features within this class of sensors.
Similar content being viewed by others
REFERENCES
T. D. James, K. R. A. S. Sandanayake, and S. Shinkai (1995). Recognition of sugars and related compounds by " reading-out "-type interfaces. Supramol. Chem. 6(1/2), 141–157.
T. D. James, K. R. A. S. Sandanayake, and S. Shinkai (1996). Saccharide sensing with molecular receptors based on boronic acid. Angew. Chem., Int. Ed. 35(17), 1910–1922.
J. H. Hartley, T. D. Jame, and C. J. Ward (2000). Synthetic receptors. J. Chem. Soc., Perkin Trans. 1 (19), 3155–3184.
W. Wang, X. Gao, and B. Wang (2002). Boronic acid-based sensors. Current. Org. Chem. 6(14), 1285–1317.
T. D. James and S. Shinkai (2002). Host-Guest chemistry. Top. Curr. Chem. 218, 159–200.
J. Yoon and A. W. Czarnik (1992). Fluorescent chemosensors of carbohydrates. A means of chemically communicating the binding of polyols in water based on chelation-enhanced quenching. J. Am. Chem. Soc. 114(14), 5874–5875.
T. D. Jame, P. Linnane, and S. Shinkai (1996). Fluorescent saccharide receptors: A sweet solution to the design, assembly and evaluation of boronic acid derived PET sensors. Chem. Commun. (3), 281–288. (Original paper by Czarnik and Yoon cited in reference 7 could not be located, so review paper is listed above. Based on isomeric relation between 1and 2, conditions and saccharide binding for 2were assumed to be similar to those of 1.)
Y. Nagai, K. Kobayashi, H. Toi, and Y. Aoyama (1993). Stabilization of sugar-boronic esters of indolyboronic acid in water via sugarindole interaction: A notable selectivity in oligosaccharides. Bull. Chem. Soc. Jpn. 66(10), 2965–2971.
H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai (1993). Sugar sensing utilizing aggregation properties of a boronic-acid-appended porphyrin. Tetrahedron Lett. 34(39), 6273–6276.
T. D. Jame, K. R. A. S. Sandanayake, and S. Shinkai (1994). Novel photoinduced electron-transfer sensor for saccharides based on the interaction of boronic acid and amine. J. Chem. Soc., Chem. Commun. (4), 477–478.
T. D. Jame, K. R. A. S. Sandanayake, and S. Shinkai (1994). A glucose-selective molecular fluorescence sensor. Angew. Chem. Int. Ed. Engl. 33(21), 2207–2209.
K. R. A. S. Sandanayake, K. Nakashima, and S. Shinkai (1994).Specific recognition of disaccharides by trans-3,3-stilbenediboronic acid: Rigidification and fluorescence enhancement of the stilbene skeleton upon formation of a sugar-stilbene macrocycle. J. Chem. Soc., Chem. Commun. (14), 1621–1622.
T. D. Jame, K. R. A. S. Sandanayake, and S. Shinkai (1995). Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature (London) 347(23), 345–347.
K. R. A. S. Sandanayake, S. Imazu, T. D. Jame, M. Mikami, and S. Shinkai (1995). Molecular fluorescence sensor for saccharides based on amino coumarin. Chem. Lett. (2), 139–140.
H. Suenaga, M. Mikami, K. R. A. S. Sandanayake, S. Shinkai (1995). Screening of fluorescent boronic acids for sugar sensing which show a large fluorescence change. Tetrahedron Lett. 36(27), 4825–4828.
P. Linnane, T. D. Jame, S. Imazu, and S. Shinkai (1995). A sweet toothed saccharide (PET) sensor. Tetrahedron Lett. 36(48), 8833–8834.
T. D. Jame and S. Shinkai (1995). A diboronic acid "glucose cleft" and a biscrown ether "metal sandwich" are allosterically coupled. J. Chem. Soc., Chem. Commun. (14), 1483–1485.
P. Linnane, T. D. Jame, and S. Shinkai (1995). The synthesis and properties of a calixarene-based "sugar bowl." J. Chem. Soc., Chem. Commun. (19) 1997–1998.
K. R. A. S. Sandanayake, T. D. Jame, and S. Shinkai (1995). Two dimensional photoinduced electron transfer (PET) fluorescence sensor. Chem. Lett. (7), 503–504.
M. Takeuchi, T. Mizuno, H. Shinmori, M. Nakashima, and S. Shinkai (1996). Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe. Tetrahedron 52(4), 1195–1204.
T. D. Jame, H. Shinmori, M. Takeuchi, and S. Shinkai (1996). A saccharide "sponge." Synthesis and properties of a dendritic boronic acid. Chem. Commun. (6), 705–706.
M. Takeuchi, S. Yoda, T. Imada, and S. Shinkai (1997). Chiral sugar recognition by a diboronic-acid-appended binaphthyl derivative through rigidification effect. Tetrahedron 53(25), 8335–8348.
T. D. Jame, H. Shinmori, and S. Shinkai (1997). Novel fluorescence sensor for "small" saccharides. Chem. Commun. (1), 71–72.
H. Kijima, M. Takeuchi, and S. Shinkai (1998). Selective detection of D-lactulose by a porphyrin-based diboronic acid. Chem. Lett. (8), 781–782.
C. R. Cooper and T. D. Jame (1997). Selective D-glucosamine hydrochloride fluorescence signaling based on ammonium cation and diol recognition. Chem. Commun. (15), 1419–1420.
M. Takeuchi, M. Yamamoto, and S. Shinkai (1997). Fluorescent sensing of uronic acids based on a cooperative action of boronic acid and metal chelate. Chem. Commun. (18), 1731–1732.
C. R. Cooper and T. D. James (1998). Selective fluorescence signalling of saccharides in their furanose form. Chem. Lett. (9), 883–884.
G. P. Luis, M. Granda, R. Badia, and M. E. Díaz-García (1998). Selective fluorescent chemosensor for fructose. Analyst 123(1), 155–158.
M. J. Deetz and B. D. Smith (1998). Heteroditopic ruthenium (II) bipyridyl receptor with adjacent saccharide and phosphate binding sites. Tetrahedron Lett. 39(38), 6841–6844.
D. P. Adhikiri and M. D. Heagy (1999). Fluorescent chemosensor for carbohydrates which shows large change in chelation-enhanced quenching. Tetrahedron Lett. 40(45),7893–7896.
H. Eggert, J. Frederiksen, C. Morin, and J. C. Norrild (1999). A new glucose-selective fluorescent Bisboronic acid. First report of strong a-furanose complexation in aqueous solution at physiological pH. J. Org. Chem. 64(11), 3846–3852.
E. U. Akkaya and B. Kukrer (1999). Red to near IR fluorescent signaling of carbohydrates. Tetrahedron Lett. 40(51), 9125–9128.
W. Wang, S. Gao, and B. Wang (1999). Building fluorescent sensors by template polymerization: The preparation of a fluorescent sensor for D-fructose. Org. Lett. 1(8), 1209–1212.
W. Yang, Y. He, and D. G. Drueckhammer (2001). Computer-guided design in molecular recognition: Design and synthesis of a glucopyranose receptor. Angew. Chem., Int. Ed. 40(9), 1714–1717.
N. DiCesare and J. R. Lakowicz (2001). A new highly fluorescent probe for monosaccharides based on a donor-acceptor diphenyloxazole. Chem. Commun. (19), 2022–2023.
N. DiCesare and J. R. Lakowicz (2001). Spectral properties of fluorophores combining the boronic acid group with electron donor or withdrawing groups. Implication in the development of fluorescence probes for saccharides. J. Phys. Chem. A 105(28), 6834–6840.
N. DiCesare and J. R. Lakowicz (2001). Fluorescent probe for monosaccharides based on a functionalized boron-dipyrromethene with a boronic acid group. Tetrahedron Lett. 42(52), 9105–9108.
S. Arimori, M. L. Bell, C. S. Oh, K.A. Frimat, and T. D. Jame (2001). Modular fluorescence sensors for saccharides. Chem. Commun. (18), 1836–1837.
S. Arimori, L. I. Bosch, C. J. Ward, and T. D. Jame (2001). Fluorescent internal charge transfer (ICT) saccharide sensor. Tetrahedron Lett. 42(27), 4553–4555.
A. Tong, A. Yamauchi, T. Hayashita, Z. Zhang, B. D. Smith, and N. Teramae (2001). Boronic acid fluorophore/ß-cyclodextrin complex sensors for selective sugar recognition in water. Anal Chem. 73(7), 1530–1536.
H. Cao, D. I. Diaz, N. DiCesare, J. R. Lakowicz, and M. D. Heagy (2002). Monoboronic acid sensor that displays anomalous fluorescence sensitivity to glucose. Org. Lett. 4(9), 1503–1505.
S. Arimori, C. J. Ward, and T. D. Jame (2002). A D-glucose selective fluorescent assay. Tetrahedron Lett. 43(2), 303–305.
S. Arimori, L. I. Bosch, C. J. Ward, and T. D. Jame (2002). A D-glucose selective fluorescent internal charge transfer (ICT) sensor. Tetrahedron Lett. 43(5), 911–913.
W. Yang, S. Gao, X. Gao, V. V. R. Karnati, W. Ni, B. Wang, W. B. Hook, J. Carson, and B. Weston (2002). Diboronic acids as fluorescent probes for cells expressing sialyl lewis x. Bioorg. Med. Chem. Lett. 12(16), 2175–2177.
N. DiCesare and J. R. Lakowicz (2002). Chalcone-analogue fluorescent probes for saccharides signaling using the boronic acid group. Tetrahedron Lett. 43(14), 2615–2618.
N. DiCesare, D. P. Adhikiri, J. J. Heynekamp, M. D. Heagy, and J. R. Lakowicz (2002). Spectroscopic and photophysical characterization of fluorescent chemosensors for monosaccharides based on N-phenylboronic acid derivatives of 1,8-naphthalimide. J. Fluoresc. 12(2), 147–153.
J. N. Camara, J. T. Suri, F. E. Cappuccio, R. A. Wessling, and B. Singaram (2002). Boronic acid substituted viologen based optical sugar sensors: Modulated quenching with viologen as a method for monosaccharide detection. Tetrahedron Lett. 43(7), 1139–1141.
S. Arimori, M. L. Bell, C. S. Oh, and T. D. Jame (2002). A modular fluorescence intramolecular energy transfer saccharide sensor. Org. Lett. 4(24), 4249–4251.
S. Arimori, G. A. Consiglio, M. D. Philips, and T. D. Jame (2003).Tuning saccharide selectivity in modular fluorescent sensors. Tetrahedron Lett. 44(25), 4789–4792.
W. Yang, J. Yan, H. Fang, and B. Wang (2003). The first fluorescent sensor for D-glucarate based on the cooperative action of boronic acid and guanidinium groups. Chem. Commun. (6), 792–793.
J. T. Suri, D. B. Cordes, F. E. Cappuccio, R. A. Wessling, and B. Singaram (2003). Monosaccharide detection with 4,7-phenanthrolinium salts: Charge-induced fluorescence sensing. Langmuir 19(12), 5145–5152.
W. Yang, J. Yan, G. Springsteen, S. Deeter, W. Ni, and B. Wang (2003). A novel type of fluorescent boronic acid that shows large fluorescence intensity changes upon binding with a carbohydrate in aqueous solution at physiological pH. Bioorg. Med. Chem. Lett. 13(6), 1019–1022.
X. Gao, Y. Zhang, and B. Wang (2003). New boronic acid fluorescent reporter compounds. 2. A naphthalene-based on-off sensor functional at physiological pH. Org. Lett. 5(24), 4615–4618.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Cao, H., Heagy, M.D. Fluorescent Chemosensors for Carbohydrates: A Decade's Worth of Bright Spies for Saccharides in Review. Journal of Fluorescence 14, 569–584 (2004). https://doi.org/10.1023/B:JOFL.0000039344.34642.4c
Issue Date:
DOI: https://doi.org/10.1023/B:JOFL.0000039344.34642.4c