Luminescence-based colorimetric discrimination of single-nucleotide transversions by the combined use of the derivatives of DOTA-conjugated naphthyridine and its terbium complex

Tetrahedron Letters

Volumn 50, Issue 19, 2009, Pages 2177-2180

  Atsumi, Hiroshi ^a   Yoshimoto, Keitaro ^a,b   Saito, Shingo ^b,c   Ohkuma, Moriya ^b   Maeda, Mizuo ^b   Nagasaki, Yukio ^a,d  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b RIKEN   (Japan)

^c SAITAMA UNIVERSITY   (Japan)

^d NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

DOTA; Fluorescence; Lanthanide energy transfer; Nucleobase; Point mutation; Terbium

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; 2 AMINO 5,7 DIMETHYL 1,8 NAPHTHYRIDINE; NAPHTHYRIDINE DERIVATIVE; TERBIUM; UNCLASSIFIED DRUG;

ARTICLE; COLORIMETRY; ENERGY TRANSFER; FLAME PHOTOMETRY; LUMINESCENCE; POINT MUTATION;

EID: 62749154588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.152     Document Type: Article

References (61)

1. Dubertret B., Calame M., and Libchaber A.J. Nat. Biotechnol. 19 (2001) 365-370
2. Tyagi S., Marras S.A.E., and Kramer F.R. Nat. Biotechnol. 18 (2000) 1191-1196
3. Tyagi S., Bratu D.P., and Kramer F.R. Nat. Biotechnol. 16 (1998) 49-53
4. Tyagi S. Nat. Biotechnol. 14 (1996) 947-948
5. Marras S.A.E., Kramer F.R., and Tyagi S. Nucleic Acids Res. 30 (2002) e122
6. Wilhelm J., and Pingoud A. ChemBioChem 4 (2003) 1120-1128
7. Song P., Li S., Meibohm B., Gaber A.O., Honaker M.R., Kotb M., and Yates C.R. AAPS J. 4 (2002) 89-94
8. Kwiatkowski R.W., Lyamichev V., de Arruda M., and Neri B. Mol. Diagn. 4 (1999) 353-364
9. Hsu T.M., Law S.M., Duan S., Neri B.P., and Kwok P.Y. Clin. Chem. 47 (2001) 1373-1377
10. Erkkila K.E., Odom D.T., and Barton J.K. Chem. Rev. 99 (1999) 2777-2796
11. Imoto S., Hirohama T., and Nagatsugi F. Bioorg. Med. Chem. Lett. 18 (2008) 5660-5663
12. Nagatsugi F., Nakahara R., Inoue K., and Sasaki S. Arch. Pharm. 341 (2008) 562-567
13. Mao L., Wang Y., Liu Y., and Hu X. J. Mol. Biol. 336 (2004) 787-807
14. Ma B., Pan Y., Zheng J., Levine A.J., and Nussinov R. Nucleic Acids Res. 35 (2007) 2986-3001
15. Kawasaki T., Nagatsugi F., Ali M.M., Maeda M., Sugiyama K., Hori K., and Sasaki S. J. Org. Chem. 70 (2005) 14-23
16. Ihara T., and Mukae M. Anal. Sci. 23 (2007) 625-629
17. Kitamura Y., Ihara T., Tsujimura Y., Osawa Y., Sasahara D., Yamamoto M., Okada K., Tazaki M., and Jyo A. J. Inorg. Biochem. 102 (2008) 1921-1931
18. Ihara T., Fujii T., Mukae M., Kitamura Y., and Jyo A. J. Am. Chem. Soc. 126 (2004) 8880-8881
19. Okamoto A., Kanatani K., Ochi Y., Saito Y., and Saito I. Tetrahedron Lett. 45 (2004) 6059-6062
20. Okamoto A., Tanabe K., and Saito I. J. Am. Chem. Soc. 124 (2002) 10262-10263
21. Ihara T., Chikaura Y., Tanaka S., and Jyo A. Chem. Commun. (2002) 2152-2153
22. Kitamura Y., Ihara T., Tsujimura Y., Tazaki M., and Jyo A. Chem. Lett. 34 (2005) 1606-1607
23. Sueda S., Ihara T., Juskowiak B., and Takagi M. Anal. Chim. Acta 365 (1998) 27-34
24. Mathies R.A. Electrophoresis 21 (2000) 2352-2358
25. Nakatani K., Sando S., and Saito I. J. Am. Chem. Soc. 122 (2001) 2172-2177
26. Hagihara S., Kumasawa H., Goto Y., Hayashi G., Kobori A., Saito I., and Nakatani K. Nucleic Acids Res. 32 (2004) 278-286
27. Nakatani K., Hagihara S., Goto Y., Kobori A., Hagihara M., Hayashi G., Kyo M., Nomura M., Mishima M., and Kojima C. Nat. Chem. Biol. 1 (2005) 39-43
28. Nakatani K. Chembiochem 5 (2004) 1623-1633
29. Morita K., Sato Y., Seino T., Nishizawa S., and Teramae N. Org. Biomol. Chem. 6 (2008) 266-268
30. Yoshimoto K., Nishizawa S., Minagawa M., and Teramae N. J. Am. Chem. Soc. 125 (2003) 8982-8983
31. Nishizawa S., Yoshimoto K., Seino T., Xu C.Y., Minagawa M., Satake H., Tong A., and Teramae N. Talanta 63 (2004) 175-179
32. Satake H., Nishizawa S., and Teramae N. Anal. Sci. 22 (2006) 195-197
33. Shao Y., Morita K., Dai Q., Nishizawa S., and Teramae N. Electrochem. Commun. 10 (2008) 438-442
34. Morita K., Sankaran N.B., Huang W., Seino T., Sato Y., Nishizawa S., and Teramae N. Chem. Commun. (2006) 2376-2378
35. Zhao C., Dai Q., Seino T., Cui Y.Y., Nishizawa S., and Teramae N. Chem. Commun. (2006) 1185-1187
36. Rajendar B., Nishizawa S., and Teramae N. Org. Biomol. Chem. 6 (2008) 670-673
37. Li C., and Wong W.T. Chem. Commun. (2002) 2034-2035
38. Iki N., Horiuchi T., Oka H., Koyama K., Morohashi N., Kabuto C., and Miyano S. J. Chem. Soc., Perkin Trans. 2 (2001) 2219-2225
39. Kitamura Y., Ihara T., Tsujimura Y., Osawa Y., Tazaki M., and Jyo A. Anal. Biochem. 359 (2006) 259-261
40. Li C., Liu X., Yang P., Zhang C., Lian H., and Lin J. J. Phys. Chem. C 112 (2008) 2904-2910
41. Iki N., Ohta M., Horiuchi T., and Hoshino H. Chem. Asian J. 3 (2008) 849-853
42. Horiuchi T., Iki N., Oka H., and Miyano S. Bull. Chem. Soc. Jpn. 75 (2002) 2615-2619
43. Kajiwara T., Katagiri K., Hasegawa M., Ishii A., Ferbinteanu M., Takaishi S., Ito T., Yamashita M., and Iki N. Inorg. Chem. 45 (2006) 4880-4882
44. Li C., and Wong W.T. Tetrahedron Lett. 45 (2004) 6055-6058
45. Li C., Law G.L., and Wong W.T. Org. Lett. 6 (2004) 4841-4844
46. Nasso I., Bedel S., Galaup C., Picard C., and Jal P. Eur. J. Inorg. Chem. (2008) 2064-2074
47. Li C., and Wong W.T. J. Org. Chem. 68 (2003) 2956-2959
48. Li C., Li Y.X., Law G.L., Man K., Wong W.T., and Lei H. Bioconjugate Chem. 17 (2006) 571-574
49. 3COOH: C, 39.69; H, 5.02; N, 10.19. Found: C, 39.73; H, 4.95; N, 10.23.
50. +): 716.20, found: 716.17.
51. The experimental details about the analysis of emission decay curve were described in Supplementary data.
52. Parker D. Coord. Chem. Rev. 205 (2000) 109-130
53. Leonard J.P., and Gunnlaugsson T. J. Fluoresc. 15 (2005) 585-595
54. Kobori A., Horie S., Suda H., Saito I., and Nakatani K. J. Am. Chem. Soc. 126 (2004) 557-562
55. Nakatani K., Sando S., Kumasawa H., Kikuchi J., and Saito I. J. Am. Chem. Soc. 123 (2001) 12650-12657
56. Nakatani K., Sando S., and Saito I. Nat. Biotechnol. 19 (2001) 51-55
57. Nakatani K., Sando S., and Saito I. Biorg. Med. Chem. 9 (2001) 2381-2385
58. Thompson A.M., Anderson T.J., Condie A., Prosser J., Chetty U., Carter D.C., Evans H.J., and Steel C.M. Int. J. Cancer 50 (1992) 528-532
59. Mizukami S., Tonai K., Kaneko M., and Kikuchi K. J. Am. Chem. Soc. 130 (2008) 14376-14377
60. Hanaoka K., Kikuchi K., Kojima H., Urano Y., and Nagano T. J. Am. Chem. Soc. 126 (2004) 12470-12476
61. Hoock C., Reichert J., and Schmidtke M. Molecules 4 (1999) 264-271