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Biological Applications— Supramolecular Chemistry

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Organic Photochromic and Thermochromic Compounds

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References

  1. H. Dugas, Bioorganic Chemistry—A Chemical Approach to Enzyme Action, 2nd ed., Springer-Verlag, New York (1989).

    Google Scholar 

  2. G. W. Gokel, (ed.), Advances in Supramolecular Chemistry, Vols. 1, 2, and 3, JAI, Greenwich, Conn. (1990, 1992, and 1993).

    Google Scholar 

  3. F. Vögtle, Supramolecular Chemistry, John Wiley & Sons, Chichester (1991).

    Google Scholar 

  4. H.-J. Schneider and H. Dürr (eds.), Frontiers in Supramolecular Organic Chemistry and Photochemistry, VCH, Weinheim (1991).

    Google Scholar 

  5. H.-G. Löhr and F. Vögtle, Chromo-and fluoroionophores. A new class of dye reagents, Acc. Chem. Res. 18, 65–72 (1985).

    Google Scholar 

  6. J.-M. Lehn, Supramolecular chemistry—scope and perspectives, molecules, supermolecules, and molecular devices, Angew. Chem. Int. Ed. Engl. 27, 89–112 (1988).

    Google Scholar 

  7. A. W. Czarnik, in: Frontiers in Supramolecular Organic Chemistry and Photochemistry (H.-J. Schneider and H. Dürr, eds.), pp. 109–122, VCH, Weinheim (1991).

    Google Scholar 

  8. H. Bouas-Laurent, J.-P. Desvergne, F. Fages, and P. Marsau, in: Frontiers in Supramolecular Organic Chemistry and Photochemistry (H.-J. Schneider and H. Dürr, eds.), pp. 265–286, VCH, Weinheim (1991).

    Google Scholar 

  9. V Balzani and F. Scandola, Supramolecular Photochemistry, Ellis Horwood, Chichester (1991).

    Google Scholar 

  10. T. Kaneda, in: Crown Ethers and Analogous Compounds, Studies in Organic Chemistry, Vol. 45 (M. Hiraoka, ed.), pp. 311–334, Elsevier, Amsterdam (1992).

    Google Scholar 

  11. A. W. Czarnik, in: Advances in Supramolecular Chemistry, Vol. 3 (G. W. Gokel, ed.), pp. 131–157, JAI, Greenwich, Conn. (1993).

    Google Scholar 

  12. S. Shinkai, Calixarenes—the third generation of supramolecules, Tetrahedron 49, 8933–8968 (1993).

    Article  CAS  Google Scholar 

  13. A. W. Czarnik (ed.), Fluorescent Chemosensors for Ion and Molecule Recognition, American Chemical Society, Washington, D.C. (1993).

    Google Scholar 

  14. R. J. P. Williams, On first looking into nature’s chemistry, Chem. Soc. Rev. 1980 281–364.

    Google Scholar 

  15. A. Fersht, Enzyme, Structure and Mechanism, 2nd ed., W. H. Freeman, New York (1985).

    Google Scholar 

  16. B. Albert, D. Bray, J. Lewis, M. Raff, K. Robert, and J. D. Watson, Molecular Biology of the Cell, 2nd ed., Chapters 12 and 19, Garland Publishing, New York (1989).

    Google Scholar 

  17. M. F. Perutz, Mechanisms of Cooperativity and Allosteric Regulation in Proteins, Cambridge University Press, Cambridge (1989).

    Google Scholar 

  18. G. H. Brown (ed.), Photochromism, Wiley-Interscience, New York (1971).

    Google Scholar 

  19. G. Montagnoli and B. F. Erlanger (eds.), Molecular Models of Photoresponsiveness, Plenum Press, New york (1983).

    Google Scholar 

  20. H. Dürr and H. Bouas-Laurent (eds.), Photochromism: Molecules and Systems, Elsevier, Amsterdam (1990).

    Google Scholar 

  21. D. Hug, The activation of enzymes with light, Photochem. Photobiol Rev. 3, 1–33 (1978).

    CAS  Google Scholar 

  22. F. Vögtle, Supramolecular Chemistry, pp. 207–229, John Wiley & Sons, Chichester (1991).

    Google Scholar 

  23. I. Willner and B. Willner, in: Bioorganic Photochemistry, Vol. 2: Biological Applications of Photochemical Switches (H. Morrison, ed.), pp. 1–110, John Wiley & Sons, New York (1993).

    Google Scholar 

  24. G. Smets, Photochromic phenomena in solid phase, Adv. Polym. Sci. 50, 17–44 (1983).

    CAS  Google Scholar 

  25. O. Pieroni, A. Fissi, and F. Ciardelli, Light-induced effects on photoresponsive polymers, Photochem. Photobiol. 44, 785–791 (1986).

    CAS  Google Scholar 

  26. V A. Krongauz, in: Photochromism: Molecules and Systems (H. Dürr and H. Bouas-Laurent, eds.), pp. 793–820, Elsevier, Amsterdam (1990).

    Google Scholar 

  27. O. Pieroni, J. L. Houben, A. Fissi, P. Costantino, and F. Ciardelli, Reversible conformational changes induced by light in poly(L-glutamic acid) with photochromic side chains, J. Am. Chem. Soc. 102, 5913–5915(1980).

    Article  CAS  Google Scholar 

  28. A. Ueno, K. Takahashi, J. Anzai, and T. Osa, Photocontrol of polypeptide helix sense by cis-trans isomerism of side-chain azobenzene moieties, J. Am. Chem. Soc. 103, 6410–6415 (1981).

    Article  CAS  Google Scholar 

  29. F. Ciardelli, O. Pieroni, A. Fissi, and J. L. Houben. Azobenzene-containing polypeptides: Photoregulation of conformation in solution, Biopolymers 23, 1423–1437 (1984).

    Article  CAS  Google Scholar 

  30. A. Fissi, O. Pieroni, and F. Ciardelli, Photoresponsive polymers: Azobenzene-containing poly(L-lysine), Biopolymers 26, 1993–2007 (1987).

    Article  CAS  Google Scholar 

  31. M. Sato, T. Kinoshita A. Takizawa, and Y. Tsujita, Photoinduced conformational transition of polypeptides containing azobenzenesulfonate in the side chains, Macromolecules 21, 1612–1616 (1988).

    CAS  Google Scholar 

  32. P. H. Vandeywer and G. Smets, Photochromic polypeptides, J. Polym. Sci., Part A-1 8, 2361–2374 (1970).

    Google Scholar 

  33. G. Smets, Photochromic behavior of polymeric systems and related phenomena, Pure Appl. Chem. 30, 1–24 (1972).

    CAS  Google Scholar 

  34. F. Ciardelli, D. Fabbri, O. Pieroni, and A. Fissi, Photomodulation of polypeptide conformation by sunlight in spiropyran-containing poly(L-glutamic acid), J. Am. Chem. Soc. 111, 3470–3472 (1989).

    Article  CAS  Google Scholar 

  35. O. Pieroni, A. Fissi, A. Viegi, D. Fabbri, and F. Ciardelli, Modulation of the chain conformation of spiropyran-containing poly(L-lysine) by the combined action of visible light and solvent, J. Am. Chem. Soc. 114, 2734–2736 (1992).

    Article  CAS  Google Scholar 

  36. B. F. Erlanger, Photoregulation of biologically active macromolecules, Annu. Rev. Biochem. 45, 267–283 (1979).

    Google Scholar 

  37. G. Montagnoli, O. Pieroni, and S. Suzuki, Control of peptide chain conformation by photoisomerising chromophores: Enzymes and model compounds, Polym. Photochem. 7, 279–294 (1983).

    Google Scholar 

  38. I. Willner, S. Rubin, and A. Riklin, Photoregulation of papain activity through anchoring photochromic azo groups to the enzyme backbone, J. Am. Chem. Soc. 113, 3321–3325 (1991).

    CAS  Google Scholar 

  39. I. Willner, S. Rubin, and T. Zor, Photoregulation of α-chymotrypsin by its immobilization in a photochromic azobenzene copolymer, J. Am. Chem. Soc. 113, 4013–4014 (1991).

    CAS  Google Scholar 

  40. I. Willner, S. Rubin, J. Wonner, F. Effenberger, and P. Bäuerle, Photoswitchable binding of substrates to proteins: Photoregulated binding of α-D-mannopyranose to concanavalin A modified by a thiophenefiilgide dye, J. Am. Chem. Soc. 114, 3150–3151 (1992).

    CAS  Google Scholar 

  41. I. Willner, M. Lion-Dagan, S. Rubin, J. Wonner, F. Effenberger, and P. Bäuerle, Photoregulation of α-chymotrypsin activity in organic media: Effects of bioimprinting, Photochem. Photobiol. 59, 491–496 (1994).

    CAS  Google Scholar 

  42. I. Willner, S. Rubin and Y. Cohen, Photoregulated binding of spiropyran-modified concanavalin A to monosaccharide-functionalized self-assembled monolayers on gold electrodes, J. Am. Chem. Soc. 115, 4937–4938 (1993).

    CAS  Google Scholar 

  43. I. Willner, S. Rubin, R. Shatzmiller, and T. Zor, Reversible light-stimulated activation and deactivation of α-chymotrypsin by its immobilization in photoisomerizable copolymers, J. Am. Chem. Soc. 115, 8690–8694 (1993).

    CAS  Google Scholar 

  44. M. Lion-Dagan, E. Katz, and I. Willner, Amperometric transduction of optical signals recorded by organized monolayers of photoisomerizable biomaterials on Au electrodes, J. Am. Chem. Soc. 116, 7913–7914(1994).

    Article  CAS  Google Scholar 

  45. M. Lion-Dagan, E. Katz, and I. Willner, A bifunctional monolayer electrode consisting of 4-pyridyl sulfide and photoisomerizable spiropyran: Photoswitchable electrical communication between the electrode and cytochrome c, J. Chem. Soc., Chem. Commun. 1994, 2741–2742.

    Google Scholar 

  46. I. Willner, M. Lion-Dagan, S. Marx-Tibbon, and E. Katz, Bioelectrocatalyzed amperometric transduction of recorded optical signals using monolayer-modified Au-electrodes, J. Am. Chem. Soc. 117, 6581–6592 (1995).

    CAS  Google Scholar 

  47. M. Lion-Dagan, S. Marx-Tibbon, E. Katz, and I. Willner, Photoswitchable electrical communication of glucose oxidase and glutathione reductase with electrode surfaces through photoisomerizable redox mediators, Angew. Chem. Int. Ed. Engl. 34, 1604–1606 (1995).

    Article  CAS  Google Scholar 

  48. I. Willner, R. Blonder, and A. Dagan, Reversible optical recording by a dinitrophenol antibody-catalyzed ring opening of 6,8-dinitrospiropyran, J. Am. Chem. Soc. 116, 3121–3122 (1994).

    CAS  Google Scholar 

  49. I. Willner, R. Blonder, and A. Dagan, Application of photoisomerizable antigenic monolayer electrodes as reversible amperometric immunosensors, J. Am. Chem. Soc. 116, 9365–9366 (1994).

    CAS  Google Scholar 

  50. M. Inouye, M. Ueno. T. Kitao, and K. Tsuchiya, Alkali metal recognition induced isomerization of spiropyrans, J. Am. Chem. Soc. 112, 8977–8979 (1990).

    Article  CAS  Google Scholar 

  51. M. Inouye, M. Ueno, K. Tuschiya, N. Nakayama, T. Konishi, and T. Kitao, Alkali-metal cation recognition induced isomerization of spirobenzopyrans and spironaphthoxazines possessing a crown ring as a recognition site: Multifunctional artificial receptors, J. Org. Chem. 57, 5377–5383 (1992).

    CAS  Google Scholar 

  52. M. Inouye, M. Ueno, and T. Kitao, Transmission of recognition information to other sites in a molecule: Proximity of two remote sites in the spirobenzopyran by recognition of alkali-metal cations, J. Org. Chem. 57, 1639–1641 (1992).

    CAS  Google Scholar 

  53. M. Inouye, Y. Noguchi, and K. Isagawa, Sensitive and selective coloration ofcryptand-type crown spirobenzopyrans for alkaline earth metal cations, Angew. Chem. Int. Ed. Engl. 33, 1163–1166 (1994).

    Article  Google Scholar 

  54. K. Kimura, T. Yamashita, and M. Yokoyama, Cation-specific isomerization of crowned spirobenzopyrans, J. Chem. Soc., Chem. Commun. 1991, 147–148.

    Google Scholar 

  55. K. Kimura, T. Yamashita, and M. Yokoyama, Synthesis, cation complexation, isomerization and photochemical cation-binding control of spirobenzopyrans carrying a monoazacrown moiety at the 8-position, J. Chem. Soc., Perkin Trans. 2 1992, 613–619.

    Google Scholar 

  56. K. Kimura, T. Yamashita, M. Kaneshige, and M. Yokoyama, Crowned spironaphthoxazine: Lithium ion-selective colouration and ion-regulated thermal stability of its coloured form, J. Chem. Soc., Chem. Commun. 1992, 969–970.

    Google Scholar 

  57. M. Inouye, K. Kim, and T. Kitao, Selective coloration of spiro pyridopyrans for guanosine derivatives, J. Am. Chem. Soc. 114, 778–780 (1992).

    Article  CAS  Google Scholar 

  58. M. Inouye, Artificial signaling receptors for biologically important chemical species, Coord. Chem. Rev. 148, 265–283(1996).

    Article  CAS  Google Scholar 

  59. H. Sasaki, A. Ueno, J. Azai, and T. Osa, Benzo-l 5-crown-5 linked spirobenzopyran. I. Photocontrol of cation-binding ability and photoinduced membrane potential changes, Bull. Chem. Soc. Jpn. 59, 1953–1956(1986).

    CAS  Google Scholar 

  60. K. Kimura, T. Yamashita, and M. Yokoyama, Photochemical control of ionic conduction by crowned spirobenzopyran, Chem. Lett. 1991, 965–968.

    Google Scholar 

  61. K. Kimura, T. Yamashita, and M. Yokoyama, Photochemical switching of ionic conductivity in composite films containing a crowned spirobenzopyran, J. Phys. Chem. 96, 5614–5617 (1992).

    CAS  Google Scholar 

  62. K. Kimura, M. Kaneshige, T. Yamashita, and M. Yokoyama, Cation complexation, photochromism, and reversible ion-conducting control of crowned spironaphthoxazine, J. Org. Chem. 59, 1251–1256 (1994).

    CAS  Google Scholar 

  63. J. Sunamoto, K. Iwamoto, Y. Mohri, and T. Kaominato, Liposomal membranes. 13. Transport of an amino acid across liposomal bilayers as mediated by a photoresponsive carrier, J. Am. Chem. Soc. 104, 5502–5504(1982).

    CAS  Google Scholar 

  64. J. Sunamoto, K. Iwamoto, M. Akutagawa, M. Nagase, and H. Kondo, Rate control by restricting mobility of substrate in specific reaction field. Negative photochromism of water-soluble spiropyran in AOT reversed micelles, J. Am. Chem. Soc. 104, 4904–4907 (1982).

    CAS  Google Scholar 

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Inouye, M. (2002). Biological Applications— Supramolecular Chemistry. In: Crano, J.C., Guglielmetti, R.J. (eds) Organic Photochromic and Thermochromic Compounds. Topics in Applied Chemistry. Springer, Boston, MA. https://doi.org/10.1007/0-306-46912-X_10

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  • DOI: https://doi.org/10.1007/0-306-46912-X_10

  • Publisher Name: Springer, Boston, MA

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