Development of luciferin analogues bearing an amino group and their application as BRET donors

Chemistry - An Asian Journal

Volumn 5, Issue 9, 2010, Pages 2053-2061

  Takakura, Hideo ^a,b   Sasakura, Kiyoshi ^a,b   Ueno, Tasuku ^a,b   Urano, Yasuteru ^c   Terai, Takuya ^a,b   Hanaoka, Kenjiro ^a,b   Tsuboi, Takashi ^a   Nagano, Tetsuo ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

BRET; Energy transfer; Luciferin analogues; Luminescence; Solvatochromism

Indexed keywords

AMINO GROUP; BENZOTHIAZOLES; BIOLOGICAL ASSAYS; BIOLUMINESCENCE RESONANCE ENERGY TRANSFER; BIOLUMINESCENCE SPECTRA; BRET; DONOR SUBSTRATES; ENVIRONMENTAL FACTORS; FIREFLY LUCIFERASE; LUCIFERIN ANALOGUES; RELIABLE MEASUREMENT; SOLVATOCHROMISMS; YELLOW FLUORESCENT PROTEINS;

BEARINGS (STRUCTURAL); ENERGY TRANSFER; FLUORESCENCE; NAPHTHALENE; PHOSPHORESCENCE; SUBSTRATES;

BIOLUMINESCENCE;

BACTERIAL PROTEIN; BENZOTHIAZOLE; BENZOTHIAZOLE DERIVATIVE; COUMARIN; COUMARIN DERIVATIVE; DRUG DERIVATIVE; LUCIFERASE; LUCIFERIN; LUMINESCENT AGENT; NAPHTHALENE; NAPHTHALENE DERIVATIVE; PHOTOPROTEIN; QUINOLINE; QUINOLINE DERIVATIVE; YELLOW FLUORESCENT PROTEIN, BACTERIA;

ARTICLE; CHEMISTRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; LUMINESCENCE; METABOLISM;

BACTERIAL PROTEINS; BENZOTHIAZOLES; COUMARINS; FIREFLY LUCIFERIN; FLUORESCENCE RESONANCE ENERGY TRANSFER; LUCIFERASES; LUMINESCENT AGENTS; LUMINESCENT MEASUREMENTS; LUMINESCENT PROTEINS; NAPHTHALENES; QUINOLINES;

EID: 77956473262     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000219     Document Type: Article

References (21)

1. A. Pichler, J. L. Prior, G. D. Luker, D. Piwnica-Worms, Proc. Natl. Acad. Sci. USA 2008, 105, 15932-15937.
2. J. B. Robertson, C. C. Stowers, E. Boczko, C. H. Johnson, Proc. Natl. Acad. Sci. USA 2008, 105, 17988-17993
3. A. H. Kesarwala, M. M. Samrakandi, D. Piwnica-Worms, Cancer Res. 2009, 69, 976-983.
4. E. H. White, H. Wörther, H. H. Seliger, W. D. McElroy, J. Am. Chem. Soc. 1966, 88, 2015-2019.
5. B. R. Branchini, Methods Enzymol. 2000, 305, 188-195.
6. H. H. Seliger, W. D. McElroy, Proc. Natl. Acad. Sci. USA 1964, 52, 75-81.
7. A. Ishida, T. Yoshikawa, T. Kamidate, Anal. Biochem. 2003, 316, 127-130.
8. B. R. Branchini, R. A. Magyar, M. H. Murtiashaw, S. M. Anderson, L. C. Helgerson, M. Zimmer, Biochemistry 1999, 38, 13223-13230.
9. E. Shapiro, C. Lu, F. Baneyx, Protein Eng. Des. Sel. 2005, 18, 581-587.
10. B. R. Branchini, D. M. Ablamsky, J. M. Rosenman, L. Uzasci, T. L. Southworth, M. Zimmer, Biochemistry 2007, 46, 13847-13855.
11. A. Kitayama, H. Yoshizaki, Y. Ohmiya, H. Ueda, T. Nagamune, Photochem. Photobiol. 2003, 77, 333-338.
12. V. R. Viviani, T. L. Oehlmeyer, F. G. C. Arnoldi, M. R. Brochetto-Braga, Photochem. Photobiol. 2005, 81, 843-848.
13. R. P. Haugland, Handbook of Fluorescent Probes and Research Products, 10th ed., Molecular Probes, Inc. Eugene, OR, 2005.
14. H. E. Katerinopoulos, Curr. Pharm. Des. 2004, 10, 3835-3852.
15. B. R. Branchini, M. H. Murtiashaw, R. A. Magyar, N. C. Portier, M. C. Ruggiero, J. G. Stroh, J. Am. Chem. Soc. 2002, 124, 2112-2113.
16. K. A. Eidne, K. M. Kroeger, A. C. Hanyaloglu, Trends Endocrinol. Metab. 2002, 13, 415-421.
17. X. Xu, M. Soutto, Q. Xie, S. Servick, C. Subramanian, A. G. von Arnim, C. H. Johnson, Proc. Natl. Acad. Sci. USA 2007, 104, 10264-10269.
18. K. D. G. Pfleger, J. R. Dromey, M. B. Dalrymple, E. M. L. Lim, W. G. Thomas, K. A. Eidne, Cell. Signalling 2006, 18, 1664-1670.
19. P. Iglesias, J. A. Costoya, Biosens. Bioelectron. 2009, 24, 3126-3130.
20. R. Arai, H. Nakagawa, A. Kitayama, H. Ueda, T. Nagamune, J. Biosci. Bioeng. 2002, 94, 362-364.
21. C. Reichardt, Chem. Rev. 1994, 94, 2319-2358.