Modified 6-aza uridines: Highly emissive pH-sensitive fluorescent nucleosides

ChemPhysChem

Volumn 13, Issue 14, 2012, Pages 3350-3356

  Sinkeldam, Renatus W ^a   Hopkins, Patrycja A ^a   Tor, Yitzhak ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

acidity; donor acceptor systems; fluorescent probes; nucleosides; photophysics

Indexed keywords

ACIDITY; BIOMOLECULES; FLUOROPHORES; PH; PHOTOPHYSICS; PROBES; THIOPHENE; WATER ABSORPTION;

DONOR-ACCEPTOR SYSTEM; FLUORESCENCE FEATURES; FLUORESCENCE PROPERTIES; FLUORESCENCE QUANTUM YIELD; FLUORESCENT PROBES; NUCLEOSIDES; SPECTROSCOPIC PROPERTY; THIOPHENE DERIVATIVES;

FLUORESCENCE;

EID: 84866984799     PISSN: 14394235     EISSN: 14397641     Source Type: Journal    
DOI: 10.1002/cphc.201200375     Document Type: Article

References (55)

1. R. W. Sinkeldam, N. J. Greco, Y. Tor, Chem. Rev. 2010, 110, 2579-2619.
2. N. J. Greco, Y. Tor, J. Am. Chem. Soc. 2005, 127, 10784-10785.
3. D. Shin, R. W. Sinkeldam, Y. Tor, J. Am. Chem. Soc. 2011, 133, 14912-14915.
4. M. E. Hawkins, Meth. Enzym. 2008, 450, 201-231
5. D. W. Dodd, R. H. E. Hudson, Mini-Rev. Org. Chem. 2009, 6, 378-391
6. Y. Tor, Pure Appl. Chem. 2009, 81, 263-272
7. L. M. Wilhelmsson, Q. Rev. Biophys. 2010, 43, 159-183
8. M. Kimoto, R. S. I. Cox, I. Hirao, Expert Rev. Mol. Diagn. 2011, 11, 321-331.
9. D. C. Ward, E. Reich, L. Stryer, J. Biol. Chem. 1969, 244, 1228-1237
10. C. H. Liu, C. T. Martin, J. Mol. Biol. 2001, 308, 465-475
11. Y. Tor, S. Del Valle, D. Jaramillo, S. G. Srivatsan, A. Rios, H. Weizman, Tetrahedron 2007, 63, 3608-3614
12. S. G. Srivatsan, N. J. Greco, Y. Tor, Angew. Chem. 2008, 120, 6763-6767
13. Angew. Chem. Int. Ed. Angew. Chem. Int. Ed. Engl. 2008, 47, 6661-6665
14. Y. Xie, A. V. Dix, Y. Tor, J. Am. Chem. Soc. 2009, 131, 17605-17614
15. Y. Xie, T. Maxson, Y. Tor, J. Am. Chem. Soc. 2010, 132, 11896-11897
16. N. J. Greco, Y. Tor, Tetrahedron 2007, 63, 3515-3527.
17. R. W. Sinkeldam, A. J. Wheat, H. Boyaci, Y. Tor, ChemPhysChem 2011, 12, 567-570.
18. R. W. Sinkeldam, P. Marcus, D. Uchenik, Y. Tor, ChemPhysChem 2011, 12, 2260-2265.
19. rd ed., Springer, New York, 2006.
20. C. Reichardt, Chem. Rev. 1994, 94, 2319-2358.
21. M. Y. Berezin, S. Achilefu, Chem. Rev. 2010, 110, 2641-2684.
22. B. C. Lobo, C. J. Abelt, J. Phys. Chem. A 2003, 107, 10938-10943.
23. G. Oster, Y. Nishijima, J. Am. Chem. Soc. 1956, 78, 1581-1584.
24. R. O. Loutfy, B. A. Arnold, J. Phys. Chem. 1982, 86, 4205-4211.
25. L. M. Wilhelmsson, P. Sandin, A. Holmen, B. Albinsson, P. Lincoln, B. Norden, J. Phys. Chem. B 2003, 107, 9094-9101.
26. K. M. Sun, C. K. McLaughlin, D. R. Lantero, R. A. Manderville, J. Am. Chem. Soc. 2007, 129, 1894-1895.
27. R. O. Roblin, J. O. Lampen, J. P. English, Q. P. Cole, J. R. Vaughan, J. Am. Chem. Soc. 1945, 67, 290-294.
28. J. Wierzchowski, B. Wielgus-Kutrowska, D. Shugar, Biochim. Biophys. Acta Gen. Subj. 1996, 1290, 9-17.
29. C. P. Da Costa, M. J. Fedor, L. G. Scott, J. Am. Chem. Soc. 2007, 129, 3426-3432.
30. L. Liu, J. W. Cottrell, L. G. Scott, M. J. Fedor, Nat. Chem. Biol. 2009, 5, 351-357.
31. F. Seela, P. Chittepu, J. Org. Chem. 2007, 72, 4358-4366.
32. R. W. Sinkeldam, Y. Tor, Org. Biomol. Chem. 2007, 5, 2523-2528.
33. R. W. Sinkeldam, N. J. Greco, Y. Tor, ChemBioChem 2008, 9, 706-709.
34. K. Hayes, J. Med. Chem. 1964, 7, 819-820.
35. I. Basnak, P. L. Coe, R. T. Walker, Nucleosides Nucleotides 1994, 13, 163-175.
36. H. A. Burch, J. Med. Chem. 1970, 13, 288-291.
37. C. Cristescu, Rev. Roum. Chim. 1975, 20, 1287-1293.
38. W. L. Mitchell, P. Ravenscroft, M. L. Hill, L. J. S. Knutsen, B. D. Judkins, R. F. Newton, D. I. C. Scopes, J. Med. Chem. 1986, 29, 809-816.
39. R. Jin, K. J. Breslauer, Proc. Natl. Acad. Sci. USA 1988, 85, 8939-8942.
40. D. A. Barawkar, K. N. Ganesh, Biochem. Biophys. Res. Commun. 1994, 203, 53-58.
41. D. A. Barawkar, K. N. Ganesh, Nucleic Acids Res. 1995, 23, 159-164.
42. T. Kimura, K. Kawai, T. Majima, Org. Lett. 2005, 7, 5829-5832.
43. T. Kimura, K. Kawai, T. Majima, Chem. Commun. 2006, 1542-1544.
44. V. R. Jadhav, D. A. Barawkar, K. N. Ganesh, J. Phys. Chem. A 1999, 103, 7383-7385.
45. A. Okamoto, K. Tainaka, I. Saito, Bioconjugate Chem. 2005, 16, 1105-1111.
46. K. Tainaka, K. Tanaka, S. Ikeda, K. Nishiza, T. Unzai, Y. Fujiwara, I. Saito, A. Okamoto, J. Am. Chem. Soc. 2007, 129, 4776-4784.
47. D. Shugar, J. J. Fox, Biochim. Biophys. Acta. 1952, 9, 199-218.
48. J. J. Fox, D. Shugar, Biochim. Biophys. Acta 1952, 9, 369-384.
49. W. Pfleider, H. Deiss, Isr. J. Chem. 1968, 6, 603-614.
50. M. S. A. Abdel-Mottaleb, R. O. Loutfy, R. Lapouyade, J. Photochem. Photobiol. A 1989, 48, 87-93.
51. T. Förster, G. Hoffmann, Z. Phys. Chem. 1971, 75, 63-76.
52. M. A. Haidekker, E. A. Theodorakis, Org. Biomol. Chem. 2007, 5, 1669-1678.
53. DIPPR Project 801, Design Institute for Physical Properties, AIChE, 2009.
54. M. A. Haidekker, T. P. Brady, D. Lichlyter, E. A. Theodorakis, Bioorg. Chem. 2005, 33, 415-425.
55. I. Bansak, M. Sun, T. A. Hamor, F. Focher, A. Verri, S. Spadari, B. Wroblowski, P. Herdewijn, R. T. Walker, Nucleosides Nucleotides 1998, 17, 187-206.