A blue-to-red energy-transfer thymidine analogue that functions in DNA

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1701-1704

  Jiao, Guan Sheng ^a   Kim, Taeg Gyum ^b   Topp, Michael R ^b   Burgess, Kevin ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; NUCLEIC ACID BASE; OLIGONUCLEOTIDE; THYMIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENERGY TRANSFER; FLUORESCENCE; RADIATION ABSORPTION; ULTRAVIOLET RADIATION;

BASE SEQUENCE; DNA; ENERGY TRANSFER; MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; SPECTROMETRY, FLUORESCENCE; THYMIDINE;

EID: 2942568550     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049684w     Document Type: Article

References (23)

1. Daniels, M.; Hauswirth, W. Science 1971, 171, 675. Pecourt, J.-M. L.; Peon, J.; Kohler, B. J. Am. Chem. Soc. 2000, 122, 9348.
2. Daniels, M.; Hauswirth, W. Science 1971, 171, 675. Pecourt, J.-M. L.; Peon, J.; Kohler, B. J. Am. Chem. Soc. 2000, 122, 9348.
3. Okamoto, A.; Tanaka, K.; Fukuta, T.; Saito, I. J. Am. Chem. Soc. 2003, 125, 9296. Seela, F.; Becher, G. Helv. Chim. Acta 2000, 83, 928. Singleton, S. F.; Shan, F.; Kanan, M. W.: McIntosh, C. M.; Stearmann, C. J.; Helm, J. S.; Webb, K. J. Org. Lett. 2001, 3, 3919.
4. Okamoto, A.; Tanaka, K.; Fukuta, T.; Saito, I. J. Am. Chem. Soc. 2003, 125, 9296. Seela, F.; Becher, G. Helv. Chim. Acta 2000, 83, 928. Singleton, S. F.; Shan, F.; Kanan, M. W.: McIntosh, C. M.; Stearmann, C. J.; Helm, J. S.; Webb, K. J. Org. Lett. 2001, 3, 3919.
5. Okamoto, A.; Tanaka, K.; Fukuta, T.; Saito, I. J. Am. Chem. Soc. 2003, 125, 9296. Seela, F.; Becher, G. Helv. Chim. Acta 2000, 83, 928. Singleton, S. F.; Shan, F.; Kanan, M. W.: McIntosh, C. M.; Stearmann, C. J.; Helm, J. S.; Webb, K. J. Org. Lett. 2001, 3, 3919.
6. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes: Eugene, OR, 1996. Lee, L. G. Method for Detecting Oligonucleotides Using UV Light Source; PE Corporation: Foster City, CA, 2001.
7. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes: Eugene, OR, 1996. Lee, L. G. Method for Detecting Oligonucleotides Using UV Light Source; PE Corporation: Foster City, CA, 2001.
8. Burghart, A.; Thoresen, L. H.; Chen, J.; Burgess, K.; Bergström, F.; Johansson, L. B.-A. Chem. Commun. 2000, 2203. Burgess, K.; Burghart, A.; Chen, J.; Wan, C.-W. New Chemistry of BODIPY Dyes, and BODIPY Dye Cassettes Featuring Through-Bond Energy Transfer. San Jose, CA, 2000. Thoresen, L. H.; Jiao, G. S.; Haaland, W. C.; Metzker, M. L.; Burgess, K. Chem. Eur. J. 2003, 9, 4603. Jiao, G.-S.; Thoresen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668.
9. Burghart, A.; Thoresen, L. H.; Chen, J.; Burgess, K.; Bergström, F.; Johansson, L. B.-A. Chem. Commun. 2000, 2203. Burgess, K.; Burghart, A.; Chen, J.; Wan, C.-W. New Chemistry of BODIPY Dyes, and BODIPY Dye Cassettes Featuring Through-Bond Energy Transfer. San Jose, CA, 2000. Thoresen, L. H.; Jiao, G. S.; Haaland, W. C.; Metzker, M. L.; Burgess, K. Chem. Eur. J. 2003, 9, 4603. Jiao, G.-S.; Thoresen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668.
10. Burghart, A.; Thoresen, L. H.; Chen, J.; Burgess, K.; Bergström, F.; Johansson, L. B.-A. Chem. Commun. 2000, 2203. Burgess, K.; Burghart, A.; Chen, J.; Wan, C.-W. New Chemistry of BODIPY Dyes, and BODIPY Dye Cassettes Featuring Through-Bond Energy Transfer. San Jose, CA, 2000. Thoresen, L. H.; Jiao, G. S.; Haaland, W. C.; Metzker, M. L.; Burgess, K. Chem. Eur. J. 2003, 9, 4603. Jiao, G.-S.; Thoresen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668.
11. Burghart, A.; Thoresen, L. H.; Chen, J.; Burgess, K.; Bergström, F.; Johansson, L. B.-A. Chem. Commun. 2000, 2203. Burgess, K.; Burghart, A.; Chen, J.; Wan, C.-W. New Chemistry of BODIPY Dyes, and BODIPY Dye Cassettes Featuring Through-Bond Energy Transfer. San Jose, CA, 2000. Thoresen, L. H.; Jiao, G. S.; Haaland, W. C.; Metzker, M. L.; Burgess, K. Chem. Eur. J. 2003, 9, 4603. Jiao, G.-S.; Thoresen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668.
12. Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759. Tour, J. M. Chem. Rev. 1996, 96, 537. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
13. Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759. Tour, J. M. Chem. Rev. 1996, 96, 537. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
14. Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759. Tour, J. M. Chem. Rev. 1996, 96, 537. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
15. Speiser, S. Chem. Rev. 1996, 96, 1953.
16. Shi, J.; Zhang, X.; Neckers, D. C. J. Org. Chem. 1992, 57, 4418.
17. Donor control compound 3 shows 114 nm of Stokes' shift and 200 times greater quantum yield than native thymidine.
18. Jiao, G.-S.; Burgess, K. Bioorg. Med. Chem. Lett. 2003, 13, 2785. This paper also reports thermal denaturation data that show 1 has a slight destabilizing effect on annulation with complementary oligonucleotide sequences, though not as much as A:A mismatches.
19. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Malakhov, A. D.; Perepelov, A. V.; Sokolova, T. A.; Berlin, Y. A. Nucleosides Nucleotides 1998, 17, 1809. Korshun, V. A.; Prokhorenko, I. A.; Gontarev, S. V.; Skorobogatyi, M. V.; Balakin, K. V.; Manasova, E. V.; Malakhov, A. D.; Berlin, Y. A. Nucleosides Nucleotides 1997, 16, 1461. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Prokhorenko, I. A.; Buchatskii, A. G.; Berlin, Y. A. Bioorganicheskaya Khimiya 1996, 22, 923.
20. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Malakhov, A. D.; Perepelov, A. V.; Sokolova, T. A.; Berlin, Y. A. Nucleosides Nucleotides 1998, 17, 1809. Korshun, V. A.; Prokhorenko, I. A.; Gontarev, S. V.; Skorobogatyi, M. V.; Balakin, K. V.; Manasova, E. V.; Malakhov, A. D.; Berlin, Y. A. Nucleosides Nucleotides 1997, 16, 1461. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Prokhorenko, I. A.; Buchatskii, A. G.; Berlin, Y. A. Bioorganicheskaya Khimiya 1996, 22, 923.
21. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Malakhov, A. D.; Perepelov, A. V.; Sokolova, T. A.; Berlin, Y. A. Nucleosides Nucleotides 1998, 17, 1809. Korshun, V. A.; Prokhorenko, I. A.; Gontarev, S. V.; Skorobogatyi, M. V.; Balakin, K. V.; Manasova, E. V.; Malakhov, A. D.; Berlin, Y. A. Nucleosides Nucleotides 1997, 16, 1461. Korshun, V. A.; Manasova, E. V.; Balakin, K. V.; Prokhorenko, I. A.; Buchatskii, A. G.; Berlin, Y. A. Bioorganicheskaya Khimiya 1996, 22, 923.
22. Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L. J. Am. Chern. Soc. 1989, 111, 6966.
23. Others have noted this would be valuable. Hurley, D. J.; Seaman, S. E.; Mazura, J. C.; Tor, Y. Org. Lett. 2002, 4, 2305.