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
Czarnik, A.W. (1992) Fluorescent Chemosensors for Ion and Molecule Recognition, American Chemical Society, Washington, D.C..
Löhr, H.G. and Vögtle, F. (1985) Chromo-and Fluoroionophores, A New Class of Dye Reagents, Acc. Chem. Res. 18, 65–72.
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.
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.
Shimizu, H., Iwamoto, K., Fujimoto, K., and Shinkai, S. (1991) Chromogenic Calix[4]arene, Chem. Lett. 2147-2150.
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.
Wenz, G. (1994) Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units, Angew. Chem. Int. Engl. 33, 803–822.
Bender M. L. and Komiyama, M. (1978) Cyclodextrin Chemistry, Springer Verlag, Berlin.
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.
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.
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.
Tamaki, T. (1984) Reversible Photodimerization of Water-Soluble Anthracenes Included in y-Cyclodextrin, Chem. Lett. 53-56.
Tamaki, T., Kokubu, T., and Ichimura, K. (1987) Regio-and Stereoselective Photodimerization of Anthracene Derivatives included by Cyclodextrins, Tetrahedron 43, 1485–1494.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Suzuki, T., Institute of Tokyo Technology, Master Thesis, 1996.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Nag, A. and Bhattacharyya, K. (1988) Twisted Intramolecular Charge Transfer Emission of Dimethylaminobenzonitrile in α-Cyclodextrin, Chem. Phys. Lett. 151, 474–476.
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.
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.
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.
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.
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.
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.
Ueno, A., Kuwabara, T., Nakamura, A., and Toda, F. (1992) Modified Cyclodexlrins as a Guest Responsive Color-Change Indicator, Nature 356, 136–137.
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.
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.
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.
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.
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.
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.
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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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