Small organic molecules as fluorescent probes for nucleotides and their derivatives

TrAC - Trends in Analytical Chemistry

Volumn 29, Issue 4, 2010, Pages 354-367

  Zhao, Xi Juan ^a   Huang, Cheng Zhi ^a,a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

Adenosine mono (di or tri) phosphate; Cytidine triphosphate; Fluorescence; Fluorescent probe; Guanosine mono (di or tri) phosphate; Nucleotide; Nucleotide derivative; Small organic molecule; Stringent alarmone; Uridine di(tri) phosphate

Indexed keywords

ADENOSINE MONO (DI OR TRI) PHOSPHATE; CYTIDINE; CYTIDINE TRIPHOSPHATE; FLUORESCENT PROBES; GUANOSINES; NUCLEOTIDE DERIVATIVES; SMALL ORGANIC MOLECULE; SMALL ORGANIC MOLECULES; TRIPHOSPHATE; URIDINE DI(TRI) PHOSPHATE;

FLUORESCENCE SPECTROSCOPY; MOLECULES; NUCLEOTIDES; PROBES;

FLUORESCENCE;

ADENOSINE DIPHOSPHATE; ADENOSINE PHOSPHATE; ADENOSINE TRIPHOSPHATE; ALARMONE; ANION; CYTIDINE TRIPHOSPHATE; FLUORESCENT DYE; GUANOSINE DIPHOSPHATE; GUANOSINE PHOSPHATE; GUANOSINE TRIPHOSPHATE; NUCLEOSIDE DIPHOSPHATE; NUCLEOSIDE PHOSPHATE; NUCLEOSIDE TRIPHOSPHATE; NUCLEOTIDE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE; URIDINE TRIPHOSPHATE;

ABSORPTION; CARBOHYDRATE METABOLISM; CHEMICAL STRUCTURE; CHEMOLUMINESCENCE; FLUORESCENCE; GLYCOSYLATION; IMAGE ANALYSIS; MONITORING; PRIORITY JOURNAL; REVIEW;

EID: 77950519617     PISSN: 01659936     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.trac.2009.12.011     Document Type: Review

References (81)

1. Lee D.H., Im J.H., Son S.U., Chung Y.K., Hong J.I. J. Am. Chem. Soc. 2003, 125:7752.
2. Nishiyabu R., Anzenbacher P. J. Am. Chem. Soc. 2005, 127:8270.
3. Nishizawa S., Kato Y., Teramae N. J. Am. Chem. Soc. 1999, 121:9463.
4. Jang Y.J., Jun E.J., Lee Y.J., Kim Y.S., Kim J.S., Yoon J. J. Org. Chem. 2005, 70:9603.
5. Lee H.N., Swamy K.M.K., Kim S.K., Kwon J.Y., Kim Y., Kim S.J., Yoon Y.J., Yoon J. Org. Lett. 2007, 9:243.
6. Singh N.J., Jun E.J., Chellappan K., Thangadurai D., Chandran R.P., Hwang I.C., Yoon J., Kim K.S. Org. Lett. 2007, 9:485.
7. Lee H.N., Xu Z.C., Kim S.K., Swamy K.M.K., Kim Y., Kim S.J., Yoon J. J. Am. Chem. Soc. 2007, 129:3828.
8. Swamy K.M.K., Kwon S.K., Lee H.N., Kumar S.M.S., Kim J.S., Yoon J. Tetrahedron Lett. 2007, 48:8683.
9. Gunnlaugsson T., Davis A.P., O'Brien J.E., Glynn M. Org. Lett. 2002, 4:2449.
10. Lee D.H., Kim S.Y., Hong J.I. Tetrahedron Lett. 2007, 48:4477.
11. Fabbrizzi L., Marcotte N., Stomeo F., Taglietti A. Angew. Chem., Int. Ed. Engl. 2002, 41:3811.
12. Aldakov D., Anzenbacher P. Chem. Commun. 2003, 1394.
13. Cho H.K., Lee D.H., Hong J.I. Chem. Commun. 2005, 1690.
14. Kim S.K., Singh N.J., Kwon J., Hwang I.C., Park S.J., Kimb K.S., Yoon J. Tetrahedron 2006, 62:6065.
15. Kim S.K., Seo D., Han S.J., Son G., Lee I.J., Lee C., Lee K.D., Yoon J. Tetrahedron 2008, 64:6402.
16. McDonough M.J., Reynolds A.J., Lee W.Y.G., Jolliffe K.A. Chem. Commun. 2006, 2971.
17. Nakamura H., Tanaka H., Hasegawa M., Masuda Y., Arikawa Y., Nomura Y., Ikebukuro K., Karube I. Talanta 1999, 50:799.
18. Ryder J.M. J. Agric. Food Chem. 1985, 33:678.
19. Tomiya N., Ailor E., Lawrence S.M., Betenbaugh M.J., Lee Y.C. Anal. Biochem. 2001, 293:129.
20. Huang D., Zhang Y.Z., Chen X.G. J. Chromatogr., B 2003, 784:101.
21. Bolin C., Cardozo-Pelaez F. J. Chromatogr., B 2007, 856:121.
22. Coolen E.J.C.M., Arts I.C.W., Swennen E.L.R., Bast A., Stuart M.A.C., Dagnelie P.C. J. Chromatogr., B 2008, 864:43.
23. The Aptamer Handbook 2006, Wiley-VCH, Malden, MA, USA. S. Klussmann (Ed.).
24. Stojanovic M.N., Prada P., Landry D.W. J. Am. Chem. Soc. 2000, 122:11547.
25. Yamana K., Ohtani Y., Nakano H., Saito I. Bioorg. Med. Chem. Lett. 2003, 13:3429.
26. Wang J., Jiang Y.X., Zhou C.S., Fang X.H. Anal. Chem. 2005, 77:3542.
27. Su S.X., Nutiu R., Filipe C.D.M., Li Y.F., Pelton R. Langmuir 2007, 23:1300.
28. Li N., Ho C.M. J. Am. Chem. Soc. 2008, 130:2380.
29. Su S.X., Ali M.M., Filipe C.D.M., Li Y.F., Pelton R. Biomacromolecules 2008, 9:935.
30. Wang J., Wang L.H., Liu X.F., Liang Z.Q., Song S.P., Li W.X., Li G.X., Fan C.H. Adv. Mater. 2007, 19:3943.
31. Zuo X.L., Song S.P., Zhang J., Pan D., Wang L.H., Fan C.H. J. Am. Chem. Soc. 2007, 129:1042.
32. Lu Y., Li X.C., Zhang L.M., Yu P., Su L., Mao L.Q. Anal. Chem. 2008, 80:1883.
33. Xu J.G., Wang Z.B. Method of Fluorescence Analysis 2006, Science Press, Beijing, China. Third edition.
34. Beer P.D., Gale P.A. Angew. Chem., Int. Ed. Engl. 2001, 40:486.
35. Martínez-Máñez R., Sancenón F. Chem. Rev. 2003, 103:4419.
36. Yoon J., Kim S.K., Singh N.J., Kim K.S. Chem. Soc. Rev. 2006, 35:355.
37. Spangler C., Schaeferling M., Wolfbeis O.S. Microchim. Acta 2008, 161:1.
38. Kim S.K., Lee D.H., Hong J.I., Yoon J. Acc. Chem. Res. 2009, 42:23.
39. Zheng J., Chen J.H. General Biochemistry 1996, Higher Education Press, Beijing, China. Third edition.
40. Trajkovska S., Dzhekova-Stojkova S., Kostovska S. Anal. Chim. Acta 1994, 290:246.
41. Ci Y.X., Li Y.Z., Chang W.B. Fresenius' J. Anal. Chem. 1992, 342:91.
42. Wang D.Y., Zhao Y.B., Xu J.G., Guo X.Q. Fresenius' J. Anal. Chem. 1997, 358:514.
43. Miao Y., Liu J., Hou F., Jiang C. J. Lumin. 2006, 116:67.
44. Spangler C.M., Spangler C., Göttle M., Shen Y.Q., Tang W.J., Seifert R., Schäferling M. Anal. Biochem. 2008, 381:86.
45. Hou F.J., Miao Y.H., Jiang C.Q. Spectrochim. Acta, Part A 2005, 61:2891.
46. Hou F.J., Wang X.L., Jiang C.Q. Anal. Sci. 2005, 21:231.
47. Schäferling M., Wolfbeis O.S. Chem. Eur. J. 2007, 13:4342.
48. Schneider S.E., O'Neil S.N., Anslyn E.V. J. Am. Chem. Soc. 2000, 122:542.
49. Marquez C., Pischel U., Nau W.M. Org. Lett. 2003, 5:3911.
50. Abe H., Mawatari Y., Teraoka H., Fujimoto K., Inouye M. J. Org. Chem. 2004, 69:495.
51. Vial L., Dumy P. J. Am. Chem. Soc. 2007, 129:4884.
52. Li S.H., Yuan W.T., Zhu C.Q., Xu J.G. Anal. Biochem. 2004, 331:235.
53. Li S.H., Yu C.W., Yuan W.T., Xu J.G. Anal. Sci. 2004, 20:1375.
54. Mizukami S., Nagano T., Urano Y., Odani A., Kikuchi K. J. Am. Chem. Soc. 2002, 124:3920.
55. Ojida A., Park S., Mito-oka Y., Hamachi I. Tetrahedron Lett. 2002, 43:6193.
56. Yamaguchi S., Yoshimura I., Kohira T., Tamaru S., Hamachi I. J. Am. Chem. Soc. 2005, 127:11835.
57. Ojida A., Miyahara Y., Wongkongkatep J., Tamaru S., Sada K., Hamachi I. Chem. Asian J. 2006, 1:555.
58. Jose D.A., Mishra S., Ghosh A., Shrivastav A., Mishra S.K., Das A. Org. Lett. 2007, 9:1979.
59. Ojida A., Takashima I., Kohira T., Nonaka H., Hamachi I. J. Am. Chem. Soc. 2008, 130:12095.
60. Carolan J.V., Butler S.J., Jolliffe K.A. J. Org. Chem. 2009, 74:2992.
61. Bazzicalupi C., Biagini S., Bencini A., Faggi E., Giorgi C., Matera I., Valtancoli B. Chem. Commun. 2006, 4087.
62. Pivovarenko V.G., Vadzyuk O.B., Kosterin S.O. J. Fluoresc. 2006, 16:9.
63. Xu Z.C., Singh N.J., Lim J., Pan J., Kim H.N., Park S., Kim K.S., Yoon J. J. Am. Chem. Soc. 2009, 131:15528.
64. Li C., Numata M., Takeuchi M., Shinkai S. Angew. Chem., Int. Ed. Engl. 2005, 44:6371.
65. Tang Y.L., Feng F.D., Yu M.H., An L.L., He F., Wang S., Li Y.L., Zhu D.B., Bazan G.C. Adv. Mater. 2008, 20:703.
66. B. Lewin (Author), L. Yu, S.M. Jiang, S.Y. Zhao (Translators), Genes VIII, Science Press, Beijing, China, 2005.
67. Artsimovitch I., Patlan V., Sekine S., Vassylyeva M.N., Hosaka T., Ochi K., Yokoyama S., Vassylyev D.G. Cell 2004, 117:299.
68. Kwon J.Y., Singh N.J., Kim H.N., Kim S.K., Kim K.S., Yoon J. J. Am. Chem. Soc. 2004, 126:8892.
69. Kim S.K., Moon B.S., Park J.H., Seo Y.I., Koh H.S., Yoon Y.J., Lee K.D., Yoon J. Tetrahedron Lett. 2005, 46:6617.
70. Neelakandan P.P., Hariharan M., Ramaiah D. Org. Lett. 2005, 7:5765.
71. Neelakandan P.P., Hariharan M., Ramaiah D. J. Am. Chem. Soc. 2006, 128:11334.
72. Nair A.K., Neelakandan P.P., Ramaiah D. Chem. Commun. 2009, 6352.
73. Wang S., Chang Y.T. J. Am. Chem. Soc. 2006, 128:10380.
74. Malcolm A.D.B. Anal. Biochem. 1977, 77:532.
75. Vuojola J., Lamminmäki U., Soukka T. Anal. Chem. 2009, 81:5033.
76. Krohn M., Wagner R. Anal. Biochem. 1995, 225:188.
77. Akinyanju J., Smith R.J. FEBS Lett. 1979, 107:173.
78. Ferullo D.J., Lovett S.T. PLoS Genet. 2008, 4:1.
79. Jain V., Kumar M., Chatterji D. J. Microbiol. 2006, 44:1.
80. Rhee H.W., Lee C.R., Cho S.H., Song M.R., Cashel M., Choy H.E., Seok Y.J., Hong J.I. J. Am. Chem. Soc. 2008, 130:784.
81. Chen X.Q., Jou M.J., Yoon J. Org. Lett. 2009, 11:2181.