Chemosensors for Water Contaminants Based on Chromophore-Appended Cyclodextrins

Ikeda, Hiroshi

doi:10.1007/978-3-319-76162-6_5

Chemosensors for Water Contaminants Based on Chromophore-Appended Cyclodextrins

Hiroshi Ikeda⁷

Chapter
First Online: 23 June 2018

727 Accesses
1 Citations

Part of the book series: Environmental Chemistry for a Sustainable World ((ECSW,volume 17))

Abstract

The development of new chemical sensing methods for the recognition of molecules or ions in water is an important theme in many fields including environmental, biological, and clinical applications and simple methods for detecting organic molecules in water is desired. Chemosensors have been attracting considerable attention among the variety of methods for detecting chemical species. Many kinds of chromophore-appended cyclodextrins have been reported for chemosensors. Here, we review the molecule-sensing abilities of chromophore-appended cyclodextrins as chemosensors. First, turn-off fluorescent chemosensors using chromophore-appended cyclodextrins are discussed. The fluorescence intensities of turn-off fluorescent cyclodextrin chemosensors always decrease upon analyte addition, and the analyte-induced variation of the fluorescence intensities of the turn-off fluorescent cyclodextrin chemosensors depend on a analyte. The sensitivities of the turn-off cyclodextrin chemosensors roughly only depend on the binding affinity for a analyte. Next, dye-appended cyclodextrins are discussed as color-change chemosensors, which are effective for detection by the naked eye. Then, turn-on fluorescent chemosensors using chromophore-appended cyclodextrins are discussed. The fluorescence intensities of turn-on fluorescent cyclodextrin chemosensors increase upon addition of special analytes, which have a comparatively spherical shape. The turn-on fluorescent β-cyclodextrin chemosensor is not sensitive to bile acids, which are strongly bound by β-cyclodextrin. The shape and size of analytes have a greater influence on the fluorescence intensity than the binding affinity. Finally, chromophore-appended cyclodextrins for detection of anion or cation species are discussed.

This is a preview of subscription content, log in via an institution.

Chapter: USD 29.95; Price excludes VAT (USA)

eBook: USD 84.99; Price excludes VAT (USA)

Softcover Book: USD 109.99; Price excludes VAT (USA)

Hardcover Book: USD 109.99; Price excludes VAT (USA)

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Abbreviations

AdCOOH:: Adamantanecarboxylic acid
AdOH:: Adamantanol
AdNH₂ :: Adamantanamine
Bor:: Borneol
CA:: Cholic acid
Cam:: Camphor
CD:: Cyclodextrin
CDCA:: Chenodeoxycholic acid
c-HexOH:: Cyclohexanol
c-OctOH:: Cyclooctanol
DCA:: Deoxycholic acid
DNS-l-Leu-βCD:: N-dansyl-l-leucine-appended β-cyclodextrin
DNS-d-Leu-βCD:: N-dansyl-d-leucine-appended β-cyclodextrin
DNS-l-Phe-βCD:: N-dansyl-l-phenylalanine-appended β-cyclodextrin
DNS-d-Phe-βCD:: N-dansyl-d-phenylalanine-appended β-cyclodextrin
DNS-l-Val-βCD:: N-dansyl-l-valine-appended β-cyclodextrin
DNS-d-Val-βCD:: N-dansyl-d-valine-appended β-cyclodextrin
Fen:: Fenchone
Ger:: Geraniol
HDCA:: Hyodeoxycholic acid
LCA:: Lithocholic acid
Men:: Menthol
NC0αCD:: (7-nitrobenz-2-oxa-1,3-diazol-4-yl)amine-appended α-cyclodextrin
NC0βCD:: (7-nitrobenz-2-oxa-1,3-diazol-4-yl)amine-appended β-cyclodextrin
NC0γCD:: (7-nitrobenz-2-oxa-1,3-diazol-4-yl)amine-appended γ-cyclodextrin
NC4βCD:: (7-nitrobenz-2-oxa-1,3-diazol-4-yl)aminobutylamine-appended β-cyclodextrin
NC4γCD:: (7-nitrobenz-2-oxa-1,3-diazol-4-yl)aminobutylamine-appended γ-cyclodextrin
Ner:: Nerol
UDCA:: Ursodeoxycholic acid

References

Anslyn EV (2007) Supramolecular analytical chemistry. J Org Chem 72:687–699. https://doi.org/10.1021/jo0617971
Article CAS Google Scholar
Aoyagi T, Nakamura A, Ikeda H, Ikeda T, Mihara H, Ueno A (1997) Alizarin yellow-modified β-cyclodextrin as a guest-responsive absorption change sensor. Anal Chem 69:659–663. https://doi.org/10.1021/ac960727z
Article CAS Google Scholar
Azath IA, Suresh P, Pitchumani K (2011) Per-6-ammonium-β-cyclodextrin/p-nitrophenol complex as a colorimetric sensor for phosphate and pyrophosphate anions in water. Sens Actuators B: Chem 155:909–914. doi.org/10.1016/j.snb.2011.01.041
Article CAS Google Scholar
Czarnik AW (ed) (1993) Fluorescent chemosensors for ion and molecule recognition. American Chemical Society, Washington, DC
Google Scholar
de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566. https://doi.org/10.1021/cr960386p
Article Google Scholar
Desvergne JP, Czarnik AW (eds) (1997) Chemosensors of ion and molecule recognition, NATO ASI Series C492. Kluwer Academic, Dordrecht
Google Scholar
Dunbar RA, Bright FV (1994) Comparison of inter- and intramolecular cyclodextrin complexes. Supramol Chem 3:93–99. doi.org/10.1080/10610279408029847
Article CAS Google Scholar
Fourmentin S, Outirite M, Blach P, Landy D, Ponchel A, Monflier E, Surpateanu G (2007) Solubilisation of chlorinated solvents by cyclodextrin derivatives: a study by static headspace gas chromatography and molecular modelling. J Hazard Mater 141:92–97. doi.org/10.1016/j.jhazmat.2006.06.090
Article CAS Google Scholar
Hall KS, Nissan RA, Quintana RL, Hollins RA (1988) Inclusion complexes of diisopropylfluorophosphate with cyclodextrins. J Catal 112:464–468. doi.org/10.1016/0021-9517(88)90161-3
Article CAS Google Scholar
Hashimoto S, Thomas JK (1985) Fluorescence study of pyrene and naphthalene in cyclodextrin-amphiphile complex systems. J Am Chem Soc 107:4655–4662. https://doi.org/10.1021/ja00302a010
Article CAS Google Scholar
Huang J, Bright FV (1990) Unimodal Lorentzian lifetime distributions for the 2-anilinonaphthalene-6-sulfonate-β-cyclodextrin inclusion complex recovered by multifrequency phase-modulation fluorometry. J Phys Chem 94:8457–8463. https://doi.org/10.1021/j100385a019
Article CAS Google Scholar
Ikeda H (2011) Fluorescent cyclodextrins as chemosensors for molecule detection in water. In: Mirsky VM, Yatsimirsky AK (eds) Artificial receptors for chemical sensors. Wiley-VCH, Weinheim, pp 113–134
Google Scholar
Ikeda H, Ueno A (2009) Fluorescent α-cyclodextrin as a chemosensor for halomethanes. Chem Commun 4281–4283. https://doi.org/10.1039/B907629H
Ikeda H, Nakamura M, Ise N, Oguma N, Nakamura A, Ikeda T, Toda F, Ueno A (1996) Fluorescent cyclodextrins for molecule sensing: fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins. J Am Chem Soc 118:10980–10988. https://doi.org/10.1021/ja960183i
Article CAS Google Scholar
Ikeda H, Nakamura M, Ise N, Toda F, Ueno A (1997) NMR studies of conformations of N-dansyl-l-leucine-appended and N-dansyl-d-leucine-appended β-cyclodextrin as fluorescent indicators for molecular recognition. J Org Chem 62:1411–1418. https://doi.org/10.1021/jo960425x
Article CAS Google Scholar
Ikeda H, Murayama T, Ueno A (2005) Skeleton-selective fluorescent chemosensor based on cyclodextrin bearing a 4-amino-7-nitrobenz-2-oxa-1,3-diazole moiety. Org Biomol Chem 3:4262–4267. https://doi.org/10.1039/B508477F
Article CAS Google Scholar
Ikeda H, Li Q, Ueno A (2006a) Chiral recognition by fluorescent chemosensors based on N-dansyl-amino acid-modified cyclodextrins. Bioorg Med Chem Lett 16:5420–5423. doi.org/10.1016/j.bmcl.2006.07.069
Article CAS Google Scholar
Ikeda H, Murayama T, Ueno A (2006b) Bile acids-selective chemosensors based on NBD-amine-modified cyclodextrins. J Incl Phenom Macrocycl Chem 56:101–105. https://doi.org/10.1007/s10847-006-9069-2
Article CAS Google Scholar
Kuwabara T, Matsushita A, Nakamura A, Ueno A, Toda F (1993) A novel color-change indicator for molecules. Guest-induced color-to-colorless change of p-nitrophenol-modified β-cyclodextrin. Chem Lett 22:2081–2084. https://doi.org/10.1246/cl.1993.2081
Article Google Scholar
Kuwabara T, Nakamura A, Ueno A, Toda F (1994) Inclusion complexes and guest-induced color changes of pH-indicator-modified β-cyclodextrins. J Phys Chem 98:6297–6303. https://doi.org/10.1021/j100076a011
Article CAS Google Scholar
Kuwabara T, Takamura M, Matsushita A, Ueno A, Toda F (1996) A novel color-changeable host for molecules. Guest-induced colorless-to-color change of phenolphthalein-modified β-cyclodextrin. Supramol Chem 8:13–15. doi.org/10.1080/10610279608233963
Article CAS Google Scholar
Kuwabara T, Takamura M, Matsushita A, Ikeda H, Nakamura A, Ueno A, Toda F (1998) Phenolphthalein-modified β-cyclodextrin as a molecule-responsive colorless-to-color change indicator. J Org Chem 63:8729–8735. https://doi.org/10.1021/jo980613i
Article CAS Google Scholar
Kuwabara T, Nakajima H, Nanasawa M, Ueno A (1999) Color change indicators for molecules using methyl red-modified cyclodextrins. Anal Chem 71:2844–2849. https://doi.org/10.1021/ac9814041
Article CAS Google Scholar
Lavigne JJ, Anslyn EV (2001) Sensing a paradigm shift in the field of molecular recognition: from selective to differential receptors. Angew Chem Int Ed 40:3118–3130. https://doi.org/10.1002/1521-3773(20010903)40:17<3118::AID-ANIE3118>3.0.CO;2-Y
Article CAS Google Scholar
Li YH, Chan LM, Tyer L, Moody RT, Himel CM, Hercules DM (1975) Study of solvent effects on the fluorescence of 1-(dimethylamino)-5-naphthalenesulfonic acid and related compounds. J Am Chem Soc 97:3118–3126. https://doi.org/10.1021/ja00844a033
Article CAS Google Scholar
Matsushita A, Kuwabara T, Nakamura A, Ikeda H, Ueno A (1997) Guest-induced colour changes and molecule-sensing abilities of p-nitrophenol-modified cyclodextrins. J Chem Soc Perkin Trans 2:1705–1710. https://doi.org/10.1039/A701220I
Article Google Scholar
Mirsky VM, Yatsimirsky AK (eds) (2011) Artificial receptors for chemical sensors. Wiley-VCH, Weinheim
Google Scholar
Müller A, Wenz G (2007) Thickness recognition of bolaamphiphiles by α-cyclodextrin. Chem Eur J 13:2218–2223. https://doi.org/10.1002/chem.200600764
Article CAS Google Scholar
Nelson G, Patonay G, Warner IM (1988) Effects of selected alcohols on cyclodextrin inclusion complexes of pyrene using fluorescence lifetime measurements. Anal Chem 60:274–279. https://doi.org/10.1021/ac00154a018
Article CAS Google Scholar
Prodi L, Montalti M, Zaccheroni N (eds) (2011) Luminescence applied in sensor science. Springer, Heidelberg
Google Scholar
Saenger W (1980) Cyclodextrin inclusion compounds in research and industry. Angew Chem Int Ed Engl 19:344–362. https://doi.org/10.1002/anie.198003441
Article Google Scholar
Suresh P, Azath IA, Pitchumani K (2010) Naked-eye detection of Fe³⁺ and Ru³⁺ in water: colorimetric and ratiometric sensor based on per-6-amino-β-cyclodextrin/p-nitrophenol. Sens Actuators B: Chem 146:273–277. doi.org/10.1016/j.snb.2010.02.047
Article CAS Google Scholar
Suzuki I, Ui M, Yamauchi A (2006) Supramolecular probe for bicarbonate exhibiting anomalous pyrene fluorescence in aqueous media. J Am Chem Soc 128:4498–4499. https://doi.org/10.1021/ja055772f
Article CAS Google Scholar
Uchiyama S, Santa T, Okiyama N, Fukushima T, Imai K (2001) Fluorogenic and fluorescent labeling reagents with a benzodfurazan skeleton. Biomed Chromatogr 15:295–318. https://doi.org/10.1002/bmc.75
Article CAS Google Scholar
Ueno A, Minato S, Suzuki I, Fukushima M, Ohkubo M, Osa T, Hamada F, Murai K (1990) Host-guest sensory system of dansyl-modified β-cyclodextrin for detecting steroidal compounds by dansyl fluorescence. Chem Lett 19:605–608. https://doi.org/10.1246/cl.1990.605
Article Google Scholar
Ueno A, Kuwabara T, Nakamura A, Toda F (1992) A modified cyclodextrin as a guest responsive colour-change indicator. Nature 356:136–137. https://doi.org/10.1038/356136a0
Article CAS Google Scholar
You L, Zha D, Anslyn EV (2015) Recent advances in supramolecular analytical chemistry using optical sensing. Chem Rev 115:7840–7892. https://doi.org/10.1021/cr5005524
Article CAS Google Scholar

Download references

Author information

Authors and Affiliations

School of Life Science and Technology, Tokyo Institute of Technology, Yokohama, Japan
Hiroshi Ikeda

Authors

Hiroshi Ikeda
View author publications
You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hiroshi Ikeda .

Editor information

Editors and Affiliations

UCEIV, Dunkerque, France
Sophie Fourmentin
Université de Bourgogne Franche-Comté, Besançon, France
Grégorio Crini
Aix-Marseille Univ, CEREGE, CNRS, IRD, INRA, Coll France, Europole Mediterraneen de l’Arbois, Aix en Provence, France
Eric Lichtfouse

Rights and permissions

Reprints and permissions

Copyright information

About this chapter

Cite this chapter

Ikeda, H. (2018). Chemosensors for Water Contaminants Based on Chromophore-Appended Cyclodextrins. In: Fourmentin, S., Crini, G., Lichtfouse, E. (eds) Cyclodextrin Applications in Medicine, Food, Environment and Liquid Crystals. Environmental Chemistry for a Sustainable World, vol 17. Springer, Cham. https://doi.org/10.1007/978-3-319-76162-6_5

Download citation

DOI: https://doi.org/10.1007/978-3-319-76162-6_5
Published: 23 June 2018
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-76161-9
Online ISBN: 978-3-319-76162-6
eBook Packages: Earth and Environmental ScienceEarth and Environmental Science (R0)

Publish with us

Policies and ethics