Rules for the design of highly fluorescent nucleoside probes: 8-(substituted cinnamyl)-adenosine analogues

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 11999-12008

  Zilbershtein Shklanovsky, Lital ^a   Weitman, Michal ^a   Major, Dan Thomas ^a   Fischer, Bilha ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACCURATE PREDICTION; FLUORESCENCE PROPERTIES; FLUORESCENT MOLECULES; HAMMETT CONSTANTS; HOMO AND LUMO ENERGIES; HOMO-LUMO GAPS; LINEAR CORRELATION; MAXIMUM EMISSIONS;

FLUORESCENCE;

STRUCTURAL DESIGN;

ADENOSINE DERIVATIVE; CINNAMIC ACID DERIVATIVE; FLUORESCENT DYE; NUCLEOSIDE ANALOG; TOLUENE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL PARAMETERS; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; ELECTRON; ENERGY TRANSFER; FLUORESCENCE; HAMMETT CONSTANT; MAXIMUM EMISSION WAVELENGTH; QUANTUM YIELD; SYNTHESIS;

ADENOSINE; DRUG DESIGN; FLUORESCENT DYES; MOLECULAR STRUCTURE; OLIGONUCLEOTIDE PROBES; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE;

EID: 84890101302     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402050x     Document Type: Article

References (62)

1. Namba, K.; Osawa, A.; Ishizaka, S.; Kitamura, N.; Tanino, K. J. Am. Chem. Soc. 2011, 133, 11466-11469
2. Kricka, L. J.; Fortina, P. Clin. Chem. 2009, 55, 670-683
3. Shinar, J. Organic Light-Emitting Devices; Springer: New York, 2004.
4. Valeur, B. Molecular Fluorescence: Principles and Applications; Wiley-VCH: Weinheim, 2002.
5. Nir, E.; Kleinermanns, K.; Grace, L.; de Vries, M. S. J. Phys. Chem. A 2001, 105, 5106-5110
6. Callis, P. R. Annu. Rev. Phys. Chem. 1983, 34, 329-357
7. Daniels, M.; Hauswirth, W. Science 1971, 171, 675-677
8. Udenfriend, S.; Zaltzman, P. Anal. Biochem. 1962, 3, 49-59
9. Gallardo-Escarate, C.; Alvarez-Borrego, J.; Von, B. E.; Dupre, E.; Del, R.-P. M. A. Biol. Res. 2007, 40, 29-40
10. Milanovich, N.; Suh, M.; Jankowiak, R.; Small, G. J.; Hayes, J. M. J. Phys. Chem. 1996, 100, 9181-9186
11. Milanovich, N.; Hayes, J. M.; Small, G. J. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1996, 291, 147-154
12. Pribylova, R.; Kralik, P.; Pavlik, I. Mol. Biotechnol. 2009, 42, 30-40
13. Arvey, A.; Hermann, A.; Hsia, C. C.; Ie, E.; Freund, Y.; McGinnis, W. Nucleic Acids Res. 2010, 38, e115/111-e115/117
14. Wabuyele, M. B.; Soper, S. A. Single Mol. 2001, 2, 13-21
15. Ramshesh, V. K.; Knisley, S. B. J. Biomed. Opt. 2006, 11, 024019
16. Wilhelmsson, L. M.; Holmen, A.; Lincoln, P.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 2001, 123, 2434-2435
17. Wahba, A. S.; Damha, M. J.; Hudson, R. H. E. Nucleic Acids Symp. Ser. 2008, 52, 399-400
18. Hudson, R. H. E.; Ghorbani-Choghamarani, A. Synlett 2007, 870-873
19. Sinkeldam, R. W.; Tor, Y. Collect. Symp. Ser. 2011, 12, 101-107
20. Sinkeldam, R. W.; Wheat, A. J.; Boyaci, H.; Tor, Y. ChemPhysChem 2011, 12, 567-570
21. Dodd, D. W.; Hudson, R. H. E. Mini-Rev. Org. Chem. 2009, 6, 378-391
22. Hudson, R. H. E.; Moszynski, J. M. Synlett 2006, 2997-3000
23. Ben, G. N.; Glasser, N.; Ramalanjaona, N.; Beltz, H.; Wolff, P.; Marquet, R.; Burger, A.; Mely, Y. Nucleic Acids Res. 2005, 33, 1031-1039
24. Kodali, G.; Kistler, K. A.; Narayanan, M.; Matsika, S.; Stanley, R. J. J. Phys. Chem. A 2010, 114, 256-267
25. Sharon, E.; Levesque, S. A.; Munkonda, M. N.; Sevigny, J.; Ecke, D.; Reiser, G.; Fischer, B. ChemBioChem 2006, 7, 1361-1374
26. Major, D. T.; Fischer, B. J. Phys. Chem. A 2003, 107, 8923-8931
27. Noe, M. S.; Rios, A. C.; Tor, Y. Org. Lett. 2012, 14, 3150-3153
28. Zilbershtein, L.; Silberman, A.; Fischer, B. Org. Biomol. Chem. 2011, 9, 7763-7773
29. McClure, D. S. J. Chem. Phys. 1949, 17, 905-913
30. Takadate, A.; Masuda, T.; Murata, C.; Isobe, A.; Shinohara, T.; Irikura, M.; Goya, S. Anal. Sci. 1997, 13, 753-756
31. Matsunaga, H.; Santa, T.; Iida, T.; Fukushima, T.; Homma, H.; Imai, K. Analyst 1997, 122, 931-936
32. Cheshmedzhieva, D.; Ivanova, P.; Stoyanov, S.; Tasheva, D.; Dimitrova, M.; Ivanov, I.; Ilieva, S. Phys. Chem. Chem. Phys. 2011, 13, 18530-18538
33. Sherman, W. R.; Robins, E. Anal. Chem. 1968, 40, 803-805
34. Uchiyama, S.; Santa, T.; Suzuki, S.; Yokosu, H.; Imai, K. Anal. Chem. 1999, 71, 5367-5371
35. Butler, R. S.; Cohn, P.; Tenzel, P.; Abboud, K. A.; Castellano, R. K. J. Am. Chem. Soc. 2009, 131, 623-633
36. Butler, R. S.; Myers, A. K.; Bellarmine, P.; Abboud, K. A.; Castellano, R. K. J. Mater. Chem. 2007, 17, 1863-1865
37. Haidekker, M. A.; Theodorakis, E. A. J. Biol. Eng. 2010, 4, 11
38. Kumar Paul, B.; Samanta, A.; Kar, S.; Guchhait, N. J. Lumin. 2010, 130, 1258-1267
39. Nandy, R.; Sankararaman, S. Beilstein J. Org. Chem. 2010, 6, 992-1001 No. 1112
40. Collier, A.; Wagner, G. K. Synth. Commun. 2006, 36, 3713-3721
41. Capek, P.; Pohl, R.; Hocek, M. Org. Biomol. Chem. 2006, 4, 2278-2284
42. Lagisetty, P.; Zhang, L.; Lakshman, M. K. Adv. Synth. Catal. 2008, 350, 602-608
43. Butora, G.; Schmitt, C.; Levorse, D. A.; Streckfuss, E.; Doss, G. A.; MacCoss, M. Tetrahedron 2007, 63, 3782-3789
44. Mamos, P.; Van Aerschot, A. A.; Weyns, N. J.; Herdewijn, P. A. Tetrahedron Lett. 1992, 33, 2413-2416
45. Yvon, J. A Guide to recording fluorescence quantum yields. http://www.jobinyvon.com.
46. Lakowicz, J. R. Principles of Fluorescent Spectroscopy; Springer: Baltimore, MD, 1986.
47. McDaniel, D. S.; Brown, H. C. J. Org. Chem. 1958, 23, 420-427
48. Charton, M. Prog. Phys. Org. Chem. 1981, 13, 119-251
49. Yi, S.; Men, J.; Wu, D.; Yang, M.; Sun, H.; Chen, H.; Gao, G. Des. Monomers Polym. 2011, 14, 367-381
50. Ueno, T.; Urano, Y.; Setsukinai, K.; Takakusa, H.; Kojima, H.; Kikuchi, K.; Ohkubo, K.; Fukuzumi, S.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 14079-14085
51. Seely, G. R. J. Phys. Chem. 1969, 73, 125-129
52. Motoyoshiya, J.; Fengqiang, Z.; Nishii, Y.; Aoyama, H. Spectrochim. Acta, Part A 2008, 69A, 167-173
53. Jian, C.; Seitz, W. R. Anal. Chim. Acta 1990, 237, 265-271
54. Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 10640-10641
55. Kohyama, N.; Katashima, T.; Yamamoto, Y. Synthesis 2004, 2799-2804
56. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464
57. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
58. Isegawa, M.; Peverati, R.; Truhlar, D. G. J. Chem. Phys. 2012, 137, 244104
59. Jacquemin, D.; Perpete, E. A.; Ciofini, I.; Adamo, C.; Valero, R.; Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2010, 6, 2071-2085
60. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3094
61. Hehre, W. J. Acc. Chem. Res. 1976, 9, 399-406
62. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, J.; Foresman, B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.