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Signal Transduction in Chemosensors of Modified Cyclodextrins

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Chemosensors of Ion and Molecule Recognition

Part of the book series: NATO ASI Series ((ASIC,volume 492))

Abstract

Signal transduction from guest binding to fluorescence response was performed with various chromophore-modified CDs (CD: cyclodextrin). Many dansyl-modified CDs were prepared as sensors for molecule detection. In the triad systems of fluorophore (dansyl), amino acid (D- or L-leucine), and CD, the chirality of the amino acid remarkably affects their molecular recognition and binding properties. Modified CDs bearing two naphthyl moieties give different responses to each guest, forming patterns that reflect the size and the shape of the guest compounds. Modified β-CDs with two pyrene moieties exhibit remarkable guest-responsive excimer emission. The effect of protein (avidin) as an environmental factor was examined in CD systems which have both fluorophore and protein binding sites. Several guest-responsive color-change indicators were also constructed on the same basis.

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References

  1. Czarnik, A.W. (1992) Fluorescent Chemosensors for Ion and Molecule Recognition, American Chemical Society, Washington, D.C..

    Google Scholar 

  2. Löhr, H.G. and Vögtle, F. (1985) Chromo-and Fluoroionophores, A New Class of Dye Reagents, Acc. Chem. Res. 18, 65–72.

    Article  Google Scholar 

  3. Cram, D.J., Carmack, R.A., and Helgeson, R.C. (1988) Host-Guest Complexation. 45. A Highly Preorganized Chromogenic Spherand Indicator System Specific for Sodium and Lithium Ions, J. Am. Chem. Soc. 110, 571–577.

    Article  CAS  Google Scholar 

  4. Kaneda, T., Umeda, S. Ishizaki, Y., Kuo, H., and Misumi, S. (1989) Azophenolic Acerands: Amine-Selective Coloration and Crystal Structure of a Piperidinium Saltex, J. Am. Chem. Soc. 111, 1881–1883.

    Article  CAS  Google Scholar 

  5. Shimizu, H., Iwamoto, K., Fujimoto, K., and Shinkai, S. (1991) Chromogenic Calix[4]arene, Chem. Lett. 2147-2150.

    Google Scholar 

  6. Inoue, M., Hashimoto, K., and Isagawa, K. (1994) Nondestructive Detection of Acetylcholine in Protic Media: Artificial-Signaling Acetylcholine Receptors, J. Am. Chem. Soc. 116, 5517–5518.

    Article  Google Scholar 

  7. Wenz, G. (1994) Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units, Angew. Chem. Int. Engl. 33, 803–822.

    Article  Google Scholar 

  8. Bender M. L. and Komiyama, M. (1978) Cyclodextrin Chemistry, Springer Verlag, Berlin.

    Book  Google Scholar 

  9. Breslow, R. (1991) How Do Imidazole Groups Catalyze the Cleavage of RNA in Enzyme Models and in Enzymes? Evidence from “Negative Catalysis”, Acc. Chem. Res. 24, 317–324.

    Article  CAS  Google Scholar 

  10. Ueno, A., Moriwaki, F., Azuma, A., and Osa, T. (1989) Preparation and Photoreaction of 6A,6B-, 6A,6C-, 6A,6D-, and 6A,6E-Bis(anihracene-9-carbonyl)-γ-cyclodextrins. A New method for Regulation of Product Stereochemistry, J. Org. Chem. 54, 295–299.

    Article  CAS  Google Scholar 

  11. Ueno, A., Moriwaki, F., Suzuki, I., Osa, T., Ohta, T., and Nozoe, S. (1991) γ-Cyclodextrin Template Method for Controlling Stereochemistry of Biomolecular Interactions and Reactions, J. Am. Chem. Soc. 113, 7034–7036.

    Article  CAS  Google Scholar 

  12. Tamaki, T. (1984) Reversible Photodimerization of Water-Soluble Anthracenes Included in y-Cyclodextrin, Chem. Lett. 53-56.

    Google Scholar 

  13. Tamaki, T., Kokubu, T., and Ichimura, K. (1987) Regio-and Stereoselective Photodimerization of Anthracene Derivatives included by Cyclodextrins, Tetrahedron 43, 1485–1494.

    Article  CAS  Google Scholar 

  14. Ueno, A., Takahashi, K., and Osa, T. (1980) One Host-Two Guests Complexation between Y-Cyclodextrin and Sodium β-Naphthylacetate as Shown by Excimer Fluorescence, J. Chem. Soc., Chem. Commun. 921-922.

    Google Scholar 

  15. Herkstroeter, W.G., Martic, P.A., Evans. T.R., and Farid, S. (1986) Cyclodextrin Inclusion Complexes of 1-Pyrenebutyrate: The Role of Coinclusion of Amphiphiles, J. Am. Chem. Soc. 108, 3275–3280.

    Article  CAS  Google Scholar 

  16. Ueno, A., Suzuki, I., and Osa, T. (1989) Association Dimers, Excimers, and Inclusion Complexes of Pyrene-Appended γ-Cyclodextrins, J. Am. Chem. Soc. 111, 6391–6397.

    Article  CAS  Google Scholar 

  17. Ueno, A., Suzuki, I., and Osa, T. (1990) Host-Guest Sensory Systems for Detecting Organic Compounds by Pyrene Excimer Fluorescence, Anal. Chem. 62, 2461–2466.

    Article  CAS  Google Scholar 

  18. Ueno, A., Moriwaki, F., Osa, T., Hamada, F., and Murai, K. (1985) Fluorescence and Circular Dichroism Studies on Host-Guest Complexation of γ-Cyclodextrin Bearing Two 2-Naphthyl Moieties, Bull. Chem. Soc. Jpn. 59, 465–470.

    Article  Google Scholar 

  19. Minato, S., Osa, T., Morita, M., Nakamura, A., Ikeda, H., Toda, F., and Ueno, A. (1991) Intramolecular Excimer Formation and Molecular Recognition of Modified Cyclodextrins Appended by Two Naphthalene Rings, Photochem. Photobiol. 54, 539–597.

    Article  Google Scholar 

  20. Ueno, A., Minato, S., and Osa, T. (1992) Detection of Organic Compounds by Guest-Responsive Monomer and Excimer Fluorescence of 6A,6B-, 6A,6C-and 6A,6D-Bis(2-naphthylsulfonyl)-β-Cyclodextrins, Anal. Chem. 64, 2562–2565.

    Article  CAS  Google Scholar 

  21. Hamada, F., Minato, S., Osa, T., and Ueno A. (1996) Fluorescent Sensors for Molecules. Guest-Responsive Monomer and Excimer Fluorescence of 6A,6B-, 6A,6C-, 6A,6D-, and 6A,6E-Bis(2-naphthylsulfonyl)-γ-Cyclodextrins, Bull. Chem. Soc. Jpn. in press.

    Google Scholar 

  22. Ueno, A., Minato, S., and Osa, T. (1992) Host-Guest Sensors of 6A,6B-, 6A,6C-, 6A,6D-, and 6A,6E-Bis(2-naphthylsulfenyl)-γ-cyclodextrins for Detecting Organic Compounds by Fluorescence Enhancement, Anal. Chem. 64, 1154–1157.

    Article  CAS  Google Scholar 

  23. Suzuki, I., Ohkubo, M., Ueno, A., and Osa, T. (1992) Detection of Organic Compounds by Dual Fluorescence of Bis(l-pyrenecarbonyl)-γ-cyclodextrins, Chem. Lett. 267-272.

    Google Scholar 

  24. Suzuki, T., Institute of Tokyo Technology, Master Thesis, 1996.

    Google Scholar 

  25. Wang, Y., Ikeda, T., Ueno, A., and Toda, F. (1992) Syntheses and Molecular Recognition Abilities of 6-O-, 2-O-, and 3-O-Dansyl-γ-Cyclodextrins, Chem. Lett. 863-866.

    Google Scholar 

  26. Wang. Y., Ikeda, T., Ikeda, H., Ueno, A., and Toda, F. (1994) Dansyl-β-Cyclodextrins as Fluorescent Sensors Responsive to Organic Compounds, Bull. Chem. Soc. Jpn. 1598-1607.

    Google Scholar 

  27. Ueno, A., Minato, S., Suzuki, I., Fukushima, M., Ohkubo, M, Osa, T., Hamada, F., and Osa, T. Host-Guest Sensory System of Dansyl-Modified β-Cyclodextrin for Detecting Steroidal Compounds by Dansyl Fluorescence, Chem. Lett. 605-608.

    Google Scholar 

  28. Hamada, F., Kondo, Y., Ishikawa, K., Ito, H., Suzuki, I., Osa, T., and Ueno, A. (1993) Dansyl-Modified γ-Cyclodextrin as a Fluorescent Sensor for Molecular Recognition, J. Inclusion Phcnom. 15, 273–279.

    Article  CAS  Google Scholar 

  29. Nakamura, M., Ikeda, A., Ise, N., Ikeda, T., Ikeda, H., Toda, F., and Ueno, A. (1995) Dansyl-Modified β-Cyclodextrin with a Monensin Residue as a Hydrohobic, Metal Responsive Cap, J. Chem. Soc., Chem. Commun. 721-722.

    Google Scholar 

  30. Nakamura, M., Ikeda, T., Nakamura, A., Ikeda, H., Ueno, A., and Toda, F. (1995) Remarkable Molecular Recognition of Dansyl-Modified Cyclodextrin Dimer, Chem. Lett. 343-344.

    Google Scholar 

  31. Ikeda, H., Nakamura, M., Ise, N., Oguma, N., Nakamura, A., Ikeda, T., Toda, F., and Ueno, A. (1996) J. Am. Chem. Soc. 116, 10980–10988.

    Article  Google Scholar 

  32. Rettig, W., (1986) Charge Separation in Exited States of Decoupled Systems-TICT Compounds and Implications Regarding the Development of New Laser Dyes and Primary Processes of Vision and Photosysthesis, Angew. Chem. Int. Ed. Engl. 25, 971–988.

    Article  Google Scholar 

  33. Cox, G.S., Hauptman, P.J., Turro, N.J. (1984) Dialkylaminobenzonitriles as Fluorescence Polarity Probes for Aqueous Solutions of Cyclodextrins, Photochem. Photobiol. 39, 597–601.

    Article  CAS  Google Scholar 

  34. Nag, A. and Bhattacharyya, K. (1988) Twisted Intramolecular Charge Transfer Emission of Dimethylaminobenzonitrile in α-Cyclodextrin, Chem. Phys. Lett. 151, 474–476.

    Article  CAS  Google Scholar 

  35. Nag, A., Dutta, R., Chattopadhyay, N., and Bhattacharyya, K. (1989) Effect of Cyclodextrin Cavity Size on Twisted Intramolecular Charge Transfer Emission: Dimethylamino Benzonitrile in β-Cyclodextrin, Chem. Phys. Lett. 157, 83–86.

    Article  Google Scholar 

  36. Nag, A. and Bhattacharyya (1990) Dual Luminescence of Dimethylamino-benzonitrile in γ-Cyclodextrin Environmental Effects on Twisted Intramolecular Charge-transfer Phenomenon, J. Chem. Soc., Faraday Trans. 86, 53–54.

    Article  CAS  Google Scholar 

  37. Hamasaki, K., Ikeda, H., Nakamura, A., Ueno, A., Toda, F., Suzuki, I., and Osa, T. (1993) Fluorescent Sensors of Molecular Recognition. Modified Cyclodextrins Capable of Exhibiting Guest-Responsive Twisted Intramolecular Charge Transfer Fluorescence, J. Am. Chem. Soc. 115, 5035–5040.

    Article  CAS  Google Scholar 

  38. Hamasaki, K., Ueno, A., Toda, F., Suzuki, I., and Osa, T. (1994) Molecular Recognition Indicators of Modified Cyclodextrins Using Twisted Intramolecular Charge Transfer Fluorescence, Bull. Chem. Soc. Jpn. 67, 516–523.

    Article  CAS  Google Scholar 

  39. Hamasaki, K., Ueno, A., and Toda, F. (1993) A Fluorescent α-Cyclodextrin as a Sensor for Detecting Aliphatic Alcohols by Dual Fluorescence arising from Normal Planar and Twisted Intramolecular Charge Transfer Excited States, J. Chem. Soc., Chem. Commun. 331-333.

    Google Scholar 

  40. Wang, J., Nakamura, A., Hamasaki, K., Ikeda, H., and Ueno, A. (1966) A Fluorescent Molecule-Recognition Sensor with a Protein as an Environmental Factor, Chem. Lett. 303-304.

    Google Scholar 

  41. Ueno, A., Kuwabara, T., Nakamura, A., and Toda, F. (1992) Modified Cyclodexlrins as a Guest Responsive Color-Change Indicator, Nature 356, 136–137.

    Article  CAS  Google Scholar 

  42. Kuwabara, T., Nakamura, A., Ueno, A., and Toda, F. (1994) Inclusion Complexes and Guest-induced Color Changes of pH-Indicator-Modified β-Cyclodextrins, J. Phys. Chem. 98, 6297–6303.

    Article  CAS  Google Scholar 

  43. Kuwabara, T., Matsushila, A., Nakamura, A., Ueno, A., and Toda, F. (1993) A Novel Color-Change Indicator for Molecules. Guest-tnduced Color-to-Colorless Change of p-Nitrophenol-Modified β-Cyclodextrin, Chem. Lett. 2081-2084.

    Google Scholar 

  44. Aoyagi, T., Nakamura, A., Ikeda, H., Ikeda, T., Mihara, H., and Ueno, A. Alizarin Yellow — Modified β-Cyclodextrin as a Guest-Responsive Absorption-Change Sensor, Anal. Chem., in press.

    Google Scholar 

  45. Kuwabara, T., Takamura, M., Matsushita, A., Ueno, A., and Toda, F. (1996) A Novel Color-changeable Host for Molecules. Guest-induced Color-to-color Change of Phenolphthalein-modified β-Cyclodextrin, Supramol. Chem. in press.

    Google Scholar 

  46. Chen, Q., Suzuki, I., Osa, T., and Ueno, A. (1991) Detection of Steroidal Compounds by Guest-induced Circular Dichroism Variations of Ferrocene-Modified β-Cyclodextrin, Makromol. Chem., Rapid Commun. 12, 113–116.

    Article  CAS  Google Scholar 

  47. Ueno, A., Chen, Q., Suzuki, I., and Osa, T. (1992) Detection of Organic Compounds by Guest-Responsive Circular Dichroism Variation of Ferrocene-Appended Cyclodextrins, Anal. Chem. 64, 1650–1655.

    Article  CAS  Google Scholar 

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Ueno, A., Ikeda, H., Wang, J. (1997). Signal Transduction in Chemosensors of Modified Cyclodextrins. In: Desvergne, J.P., Czarnik, A.W. (eds) Chemosensors of Ion and Molecule Recognition. NATO ASI Series, vol 492. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3973-1_8

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  • DOI: https://doi.org/10.1007/978-94-011-3973-1_8

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