Molecular switch based on a biologically important redox reaction

Journal of Physical Chemistry B

Volumn 109, Issue 1, 2005, Pages 130-137

  Yan, Ping ^a   Holman, Michael W ^a   Robustelli, Paul ^a   Chowdhury, Arindam ^a   Ishak, Fady I ^a   Adams, David M ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC PATHWAYS; MOLECULAR SWITCHES; NICOTINAMIDE; REDOX CENTERS;

CATALYSIS; ELECTRONS; ENZYMES; FLUORESCENCE; ORGANIC COMPOUNDS; OXIDATION; PROTONS; QUENCHING; REDOX REACTIONS; REDUCTION;

MOLECULAR STRUCTURE;

ALCOHOL DEHYDROGENASE; BENZOQUINONE; BENZOQUINONE DERIVATIVE; BORANE DERIVATIVE; CYANOBOROHYDRIDE SODIUM; DRUG DERIVATIVE; NICOTINAMIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE; PERYLENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; FLUORESCENCE; OXIDATION REDUCTION REACTION; SYNTHESIS; TIME;

ALCOHOL DEHYDROGENASE; BENZOQUINONES; BOROHYDRIDES; ELECTROCHEMISTRY; FLUORESCENCE; MOLECULAR STRUCTURE; NAD; NIACINAMIDE; OXIDATION-REDUCTION; PERYLENE; TIME FACTORS;

EID: 12344255122     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp045793g     Document Type: Article

References (60)

1. Zang, L.; Liu, R.; Holman, M. W.; Nguyen, K. T.; Adams, D. M. J. Am. Chem. Soc. 2002, 124, 10640.
2. Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
3. Feringa, B. L.; Jager, W. F.; de Lange, B. Tetrahedron 1993, 49, 8267.
4. Irie, M., Ed. Special Issue: Photochromism: Memories and Switches. Chem. Rev. 2000, 100, 1683-1890.
5. Hernandez, R.; Tseng, H.; Wong, J. W.; Stoddart, J. F.; Zink, J. I. J. Am. Chem. Soc. 2004, 126, 3370.
6. de Silva, A. P.; Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
7. Brasselet, S.; Moerner, W. E. Single Mol. 2000, 1, 17.
8. Weiss, S. Science 1999, 283, 1676.
9. Xie, X. S.; Trautman, J. K. Annu. Rev. Phys. Chem. 1998, 49, 441.
10. Bissell, R. A.; de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; McCoy, C. P.; Sandanayake, K. R. A. S. Top. Curr. Chem. 1993, 168, 223.
11. Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277.
12. Carroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4378.
13. Adams, D. M.; Brus, L.; Chidsey, C. E. D.; Creager, S.; Creutz, C.; Kagan, C. R.; Kamat, P. V.; Lieberman, M.; Lindsay, S.; Marcus, R. A.; Metzger, R. M.; Michel-Beyerle, M. E.; Miller, J. R.; Newton, M. D.; Rolison, D. R.; Sankey, O.; Schanze, K. S.; Yardley, J.; Zhu, X. J. Phys. Chem. B 2003, 107, 6668.
14. Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; ACS Symposium Series 538; American Chemical Society: Washington, DC, 1993.
15. Probe Design and Chemical Sensing. Topics in Fluorescence Spectroscopy, Lakowicz, J. R.; Ed.; Plenum: New York, 1994; Vol. 4.
16. de Silva, A. P.; Fox, D. B.; Moody, T. S.; Weir, S. M. TRENDS Biotechnol. 2001, 19, 29.
17. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P. Acc. Chem. Res. 1999, 32, 846.
18. Fabbrizzi, L.; Licchelli, M.; Rabaioli, G.; Taglietti, A. Coord. Chem. Rev. 2000, 205, 85.
19. Tsien, R. Y. Chem. Eng. News 1994, 72, 34.
20. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910.
21. Tsien, R. Y. Biochemistry 1980, 19, 2396.
22. Burdette, S. C.; Walkup, G. K.; Spingler, B.; Tsien, R. Y.; Lippard, S. J. J. Am. Chem. Soc. 2001, 123, 7831.
23. Walkup, G. K.; Burdette, S. C.; Lippard, S. J.; Tsien, R. Y. J. Am. Chem. Soc: 2000, 122, 5644.
24. Guo, X.; Qian, X.; Jia, L. J. Am. Chem. Soc. 2004, 126, 2272.
25. Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 14270.
26. Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397.
27. Fabbrizzi, L.; Pallavicini, P.; Parodi, L.; Taglietti, A. Inorg. Chim. Acta 1995, 238, 5.
28. Fabbrizzi, L.; Francese, G.; Licchelli, M.; Perotti, A.; Taglietti, A. Chem. Commun. 1997, 581.
29. Nakata, E.; Nagase, T.; Shinkai, S.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 490.
30. Haugland, R. P. Handbook of Fluorescent Probes and Research Products; 9th ed.; Molecular Probes: Eugene, OR, 2002.
31. Fabbrizzi, L.; Licchelli, M.; Mascheroni, S.; Poggi, A.; Sacchi, D.; Zema, M. Inorg. Chem. 2002, 41, 6129.
32. Goulle, V.; Harriman, A.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1993, 1034.
33. Daub, J.; Martin, B.; Knorr, A.; Spreitzer, H. Pure Appl. Chem. 1996, 68, 1399.
34. Li. H.; Jeppesen, J. O.; Levillain, E.; Becher, J. Chem. Commun. 2003, 846.
35. Suzuki, T.; Migita, A.; Higuchi, H.; Kawai, H.; Fujiwara, K.; Tsuji, T. Tetrahedron Lett. 2003, 44, 6837.
36. Yee, D. J.; Balsanek, V.; Sames, D. J. Am. Chem. Sac. 2004, 126, 2282.
37. Underwood, A. L.; Burnett, R. W. Electrochemistry of Biological Compounds. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel Dekker: New York, 1973; Vol. 6, p 1.
38. Langhals, H. Heterocycles 1995, 40, 477.
39. England, P. A.; Harford-Cross, C. F.; Stevenson, J.-A.; Rouch, D. A., Wong. L.-L. FEBS Lett. 1998, 424, 271.
40. Imanishi, T.; Hamano, Y.; Yoshikawa, H.; Iwata, C. J. Chem. Soc., Chem. Commun. 1988, 473.
41. Rathore, R.; Le Magueres, P.; Lindeman, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. 2000, 39, 809.
42. Gorton, L.; Dominguez, E. Electrochemistry of NAD(P)+/NAD(P)H. In Encyclopedia of Electrochemistry, Bard, A. J., Stratmann, M., Eds.; Wiley-VCH: New York, 2002; Vol. 9, p 67.
43. Elving, P. J. In Topics in Bioelectrochemistiy and Bioenergetics; Milazzo, G., Ed.; Wiley: New York, 1976; p 179.
44. Moracci, F. M.; Liberatore, F.; Carelli, V.; Arnone, A.; Carelli, I.; Cardinali, M. E. J. Org. Chem. 1978, 43, 3420.
45. Anne, A.; Hapiot, P.; Moiroux, J.; Savéant, J.-M. J. Electroanal. Chem. 1992, 331, 959.
46. Salbeck, J.; Kunkely, H.; Langhals, H.; Saalfrank, R. W.; Daub, J. Chimia 1989, 43, 6.
47. Onoda, M.; Uchiyama, S.; Santa, T.; Imai, K. Anal. Chem. 2002, 74, 4089.
48. Miura, T.; Urano, Y.; Tanaka, K.; Nagano, T.; Ohkubo, K.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 8666.
49. Tanaka, K.; Miura, T.; Umezawa, N.; Urano, Y.; Kikuchi, K.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2001, 123, 2530.
50. Langhals, H.; Demmig, S.; Huber, H. Spectrochim. Acta 1988, 44A, 1189.
51. Kaiser, H.; Lindner, J.; Langhals, H. Chem. Ber. 1991, 124, 529.
52. Holman, M. W.; Liu, R.; Adams, D. M. J. Am. Chem. Soc. 2003, 125, 12649.
53. Brewster, M. E.; Kaminski, J. J.; Gabanyi, Z.; Czako, K.; Simay, A.; Bodor, N. Tetrahedron 1989, 45, 4395.
54. Brewster, M. E.; Simay, A.; Czako, K.; Winwood, D.; Farag, H.; Bodor, N. J. Org. Chem. 1989, 54, 3721.
55. Park, K. K.; Han, D.; Shin, D. Bull. Korean Chem. Soc. 1986, 7, 201.
56. Lettre, H.; Haede, W.; Ruhbaum, E. Liebigs Ann. Chem. 1953, 579, 123.
57. Halasz, A.; Cohen, D. U.S. Patent 4 021 486 1977.
58. Langhals, H.; Karolin, J.; Johansson, L. B.-A. J. Chem. Soc., Faraday Trans. 1998, 94, 2919.
59. Giaimo, J. M.; Gusev, A. V.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 8530.
60. Jaguar; 4.1, Schrödinger, Inc.: Portland, OR, 2000.