1-Acetylpyrene with dual functions as an environment-sensitive fluorophore and fluorescent photoremovable protecting group

Tetrahedron

Volumn 66, Issue 52, 2010, Pages 9798-9807

  Jana, Avijit ^a   Atta, Sanghamitra ^a   Sarkar, Sujan K ^a   Singh, N D Pradeep ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

1 Acetylpyrene; Fluorescence; Photocleavage; Photoremovable protecting group

Indexed keywords

1 ACETYLPYRENE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; FLUORESCENT DYE; PYRENE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; CONTROLLED STUDY; ENVIRONMENT; FLUORESCENCE; IRRADIATION; PHOTOLYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 78649681307     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.090     Document Type: Article

References (64)

1. V.N.R. Pillai Synthesis 1 1980
2. T.W. Greene, and G.M. Wuts Protective Groups in Organic Chemistry 3rd ed. 1999 John Wiley New York, NY
3. J. Abelson, M. Simon, and G. Marriott Caged Compounds 1998 Academic New York, NY-London
4. J.M. Nerbonne Curr. Opin. Neurobiol. 6 1996 379
5. Y. Shigeri, Y. Tatsu, and N. Yumoto Pharmacol. Ther. 91 2001 85
6. A.P. Pelliccioli, and J. Wirz Photochem. Photobiol. Sci. 1 2002 441
7. C.G. Bochet J. Chem. Soc., Perkin Trans. 1 2002 125
8. C.G. Bochet Tetrahedron Lett. 41 2000 6341
9. K. Schaper, S.A.M. Mobarekah, and C. Grewer Eur. J. Org. Chem. 2002 1037
10. S. Loudwig, and M. Goeldner Tetrahedron Lett. 42 2001 7957
11. L. Peng, J. Wirz, and M. Goeldner Tetrahedron Lett. 38 1997 2961
12. C. Dinkel, O. Wichmann, and C. Schultz Tetrahedron Lett. 44 2003 1153
13. C. Dinkel, and C. Schultz Tetrahedron Lett. 44 2003 1157
14. W.-H. Li, J. Llopis, M. Whitney, G. Zlokarnik, and R.Y. Tsien Nature 392 1998 936
15. M. Lu, O.D. Fedoryak, B.R. Moister, and T.M. Dore Org. Lett. 5 2003 2119
16. P. Wang, H. Hu, and Y. Wang Org. Lett. 9 2007 1533
17. J.-Y. Yu, W.-J. Tang, H.-B. Wang, and Q.-H. Song J. Photochem. Photobiol., A 185 2007 101
18. S. Kantevari, C.V. Narasimhaji, and H.B. Mereyala Tetrahedron 61 2005 5849
19. A. Banerjee, C. Grewer, L. Ramakrishnan, J. Jäger, A. Gameiro, H.-G.A. Breitinger, K.R. Gee, B.K. Carpenter, and G.P. Hess J. Org. Chem. 68 2003 8361
20. A.K. Singh, and P.K. Khade Tetrahedron 61 2005 10007
21. C. Grewer, J. Jäger, B.K. Carpenter, and G.P. Hess Biochemistry 39 2000 2063
22. R.S. Givens, J.F.W. Weber, P.G. Conrad, G. Orosz, S.L. Donahue, and S.A. Thayer J. Am. Chem. Soc. 122 2000 2687
23. C. Ma, M.G. Steinmetz, E.J. Kopatz, and R. Rathore J. Org. Chem. 70 2005 4431
24. G. Papageorgiou, D.C. Ogden, A. Barth, and J.E.T. Corrie J. Am. Chem. Soc. 121 1999 6503
25. A.K. Singh, and P.K. Khade Tetrahedron Lett. 46 2005 5563
26. Y. Zhu, C.M. Pavlos, J.P. Toscano, and T.M. Dore J. Am. Chem. Soc. 128 2006 4267
27. M.J. Davis, C.H. Kragor, K.G. Reddie, H.C. Wilson, Y. Zhu, and T.M. Dore J. Org. Chem. 74 2009 1721
28. Y.M. Li, J. Shi, R. Cai, X.Y. Chen, Q.X. Guo, and L. Liu Tetrahedron Lett. 51 2010 1609
29. Y.M. Li, J. Shi, R. Caia, X.Y. Chen, Z.F. Luo, and Q.X. Guo J. Photochem. Photobiol., A 211 2010 129
30. V.R. Shembekar, Y. Chen, B.K. Carpenter, and G.P. Hess Biochemistry 44 2005 7107
31. V. Hagen, B. Dekowski, N. Kotzur, R. Lechler, B. Wiesner, B. Briand, and M. Beyermann Chem. - Eur. J. 14 2008 1621
32. A.M. Piloto, D. Rovira, S.P.G. Costa, and M.S.T. Gonalves Tetrahedron 62 2006 11955
33. A.S.C. Fonseca, M.S.T. Gonalves, and S.P.G. Costa Tetrahedron 63 2007 1353
34. B. Schade, V. Hagen, R. Schmidt, R. Herbrich, E. Krause, T. Eckardt, and J. Bendig J. Org. Chem. 64 1999 9109
35. V. Hagen, S. Frings, J. Bendig, D. Lorenz, B. Wiesner, and U.B. Kaupp Angew. Chem., Int. Ed. 41 2002 3625
36. M.B. Welch, C.I. Martinez, A.J. Zhang, S. Jin, R. Gibbs, and K. Burgess Chem. - Eur. J. 5 1999 951
37. T. Eckardt, V. Hagen, B. Schade, R. Schmidt, C. Schweitzer, and J. Bending J. Org. Chem. 67 2002 703
38. J.C. Politz Trends Cell Biol. 9 1999 284
39. C. Muller, P. Even, M.-L. Viriot, and M.-C. Carre Helv. Chim. Acta 84 2001 3753
40. G.H. McGall, A.D. Barone, M. Diggelmann, S.P.A. Fodor, E. Gentalen, and N. Ngo J. Am. Chem. Soc. 119 1997 5081
41. C. Muller, P. Even, M.-L. Viriot, and M.-C. Carré Helv. Chim. Acta 84 2001 3735
42. X.J. Tang, and I.J. Dmochowski Org. Lett. 7 2005 279
43. M.E. Vasquez, M. Nitz, J. Stehn, M.B. Yaffe, and B. Imperiali J. Am. Chem. Soc. 125 2003 10150
44. M. Canepari, L. Nelson, G. Papageorgiou, J.E.T. Corrie, and D. Ogden J. Neurosci. Methods 112 2001 29
45. B. Curten, H.M.P. Kullmann, M.E. Bier, K. Kandler, and B.F. Schmidt Photochem. Photobiol. 81 2005 641
46. M.J.G. Fernandes, M.S.T. Goncalves, and S.P.G. Costa Tetrahedron 63 2007 10133
47. A.J. Shah, F. Crespi, and C. Heidbreder J. Chromatogr., B 781 2002 151
48. L.J. Schwartz, and G.H. Patterson Methods Cell Biol. 85 2008 45
49. G. Ravaglia, P. Forti, F. Maioli, G. Bianchi, M. Martelli, T. Talerico, L. Servadei, M. Zoli, and E. Mariani Am. J. Clin. Nutr. 80 2004 483
50. T. Furuta, Y. Hirayama, and M. Iwamura Org. Lett. 3 2001 1809
51. M. Iwamura, C. Hodota, and M. Ishibashi Synlett 1991 35
52. M. Iwamura, T. Ishikawa, Y. Koyama, K. Sakuma, and H. Iwamura Tetrahedron Lett. 28 1987 679
53. T. Furuta, H. Torigai, T. Osawa, and M. Iwamura Chem. Lett. 1993 1179
54. S. Okada, S. Yamashita, T. Furuta, and M. Iwamura Photochem. Photobiol. 61 1995 431
55. C. Armbruster, M. Knapp, K. Rechthaler, R. Schamschule, A.B.J. Parusel, G. Köhler, and W. Wehrmann J. Photochem. Photobiol., A 125 1999 29
56. K. Szczubiałka, Ł Moczek, A. Goliszek, M. Nowakowska, A. Kotzev, and A. Laschewsky J. Fluorine Chem. 126 2005 1409
57. N.S. Bayliss, and E.G. McRae J. Phys. Chem. 58 1954 1002
58. G.C. Brealey, and M. Kasha J. Am. Chem. Soc. 77 1955 4462
59. K. Kalyanasundaram, and J.K. Thomas J. Phys. Chem. 81 1977 2176
60. A. Endo, K. Suzuki, T. Yoshihara, S. Tobita, M. Yahiro, and C. Adachi Chem. Phys. Lett. 155 2008 460
61. P. Bandyopadhyay, P.K. Bharadwaj, M. Basu Roy, R. Dutta, and S. Ghosh Chem. Phys. 255 2000 325
62. J.F. Rabek Radiometry and Actinometry: Experimental Methods in Photochemistry and Photophysics Vol. 2 1982 Wiley New York, NY p 944
63. P. Magnus, and G. Roy Organometallics 1 1982 553
64. F.F. Wong, P.W. Chang, H.C. Lin, B.J. You, J.J. Huang, and S.K. Lin J. Organomet. Chem. 694 2009 3452