Application of new semisynthetic aequorins with long half-decay time of luminescence to G-protein-coupled receptor assay

Analytical Biochemistry

Volumn 407, Issue 2, 2010, Pages 247-252

  Inouye, Satoshi ^a   Iimori, Rie ^b   Sahara, Yuiko ^a   Hisada, Sunao ^c   Hosoya, Takamitsu ^b,d  

^a CHISSO CORPORATION   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c CENTRAL RESEARCH LABORATORY   (Japan)

^d TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Aequorin; Cell based GPCR assay; Coelenterazine synthesis; Fluorescent protein; High throughput screening

Indexed keywords

LUMINESCENCE; PROTEINS;

AEQUORIN; C-2 POSITIONS; CELL-BASED; FLUORESCENT PROTEIN; G-PROTEIN COUPLED RECEPTORS; HIGH THROUGHPUT SCREENING; LUMINESCENCE PROPERTIES; REPORTER ASSAY;

BIOSYNTHESIS;

AEQUORIN; CALCIUM ION; COELENTERAZINE; G PROTEIN COUPLED RECEPTOR; IMIDAZOPYRAZINE DERIVATIVE; KETONE DERIVATIVE; OXYGEN; RECOMBINANT APOAEQUORIN; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLUMINESCENCE; CELL ASSAY; CONTROLLED STUDY; FIELD EMISSION; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DETERMINATION; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN MODIFICATION; PROTEIN SYNTHESIS;

EID: 77957228720     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2010.08.025     Document Type: Article

References (35)

1. Shimomura O. The jellyfish aequorea and other luminous coelenterates. Bioluminescence 2006, 90-158. World Scientific.
2. 2+-binding photoproteins. Photochem. Photobiol. 1995, 62:657-661.
3. Head J.F., Inouye S., Teranishi K., Shimomura O. The crystal structure of the photoprotein aequorin at 2.3Å resolution. Nature 2000, 405:372-376.
4. Toma S., Chong K.T., Nakagawa A., Teranishi K., Inouye S., Shimomura O. The crystal structures of semi-synthetic aequorins. Protein Sci. 2005, 14:409-416.
5. Shimomura O. Cause of spectral variation in the luminescence of semi-synthetic aequorins. Biochem. J. 1995, 306:537-543.
6. Inouye S. Blue fluorescent protein from the calcium-sensitive photoprotein aequorin is a heat resistant enzyme, catalyzing the oxidation of coelenterazine. FEBS Lett. 2004, 577:105-110.
7. Inouye S., Sasaki S. Blue fluorescent protein from the calcium-sensitive photoprotein aequorin: catalytic properties for the oxidation of coelenterazine as an oxygenase. FEBS Lett. 2006, 580:1977-1982.
8. Inouye S., Hosoya T. Reconstitution of blue fluorescent protein from recombinant apoaequorin and synthetic coelenteramide. Biochem. Biophys. Res. Commun. 2009, 386:617-622.
9. Inouye S., Noguchi M., Sakaki Y., Takagi Y., Miyata T., Iwanaga S., Miyata T., Tsuji F.I. Cloning and sequence analysis of cDNA for the luminescent protein aequorin. Proc. Natl. Acad. Sci. USA 1985, 82:3154-3158.
10. Inouye S., Sakaki Y., Goto T., Tsuji F.I. Expression of apoaequorin complementary DNA in Escherichia coli. Biochemistry 1986, 25:8425-8429.
11. 2+-binding protein, apoaequorin. J. Biochem. 1989, 105:473-477.
12. Shimomura O., Inouye S. The in situ regeneration and extraction of recombinant aequorin from Escherichia coli cells and the purification of extracted aequorin. Protein Express. Purif. 1999, 16:91-95.
13. Teranishi K. Luminescence of imidazo[1,2-a]pyrazin-3(7H)-one compounds. Bioorg. Chem. 2007, 35:82-111.
14. Shimomura O., Musicki B., Kishi Y. Semi-synthetic aequorin: an improved tool for the measurement of calcium ion concentration. Biochem. J. 1988, 251:405-410.
15. 2+ ions. Biochem. J. 1989, 261:913-920.
16. 2+ ion indicators. Biochem. J. 1990, 270:309-312.
17. Chen F.-Q., Hirano T., Hashizume Y., Ohmiya Y., Ohashi M. Synthesis and preliminary chem- and bio-luminescence studies of a novel photolabile coelenterazine analogue with a trifluoromethyl diazirine group. J. Chem. Soc., Chem. Commun. 1994, 2405-2406.
18. Shimomura O., Musicki B., Kishi Y., Inouye S. Light-emitting properties of recombinant semi-synthetic aequorins and recombinant fluorescein-conjugated aequorin for measuring cellular calcium. Cell Calcium 1993, 14:373-378.
19. Shimomura O., Kishi Y., Inouye S. The relative rate of aequorin regeneration from apoaequorin and coelenterazine analogues. Biochem. J. 1993, 296:549-551.
20. Blinks J.R., Prendergast F.G., Allen D.G. Photoproteins as biological calcium indicators. Pharmacol. Rev. 1976, 28:1-93.
21. 2+ revealed by specifically targeted recombinant aequorin. Nature 1992, 358:325-327.
22. Stables J., Green A., Marshall F., Fraser N., Knight E., Sautel M., Milligan G., Lee M., Rees S. A bioluminescent assay for agonist activity at potentially any G-protein-coupled receptor. Anal. Biochem. 1997, 252:115-126.
23. Ungrin M.D., Singh L.M.R., Stocco R., Sas D.E., Abramovitz M. An automated aequorin luminescence-based functional calcium assay for G-protein-coupled receptors. Anal. Biochem. 1999, 272:34-42.
24. Knight P.J.K., Pfeifer T.A., Grigliatti T.A. A functional assay for G-protein-coupled receptors using stably transformed insect tissue culture cell lines. Anal. Biochem. 2003, 320:88-103.
25. Le Poul E., Hisada S., Mizuguchi Y., Dupriez V.J., Burgeon E., Detheux M. Adaptation of aequorin functional assay to high throughput screening. J. Biomol. Screening 2002, 7:57-65.
26. Kishi Y., Tanino H., Goto T. The structure confirmation of the light-emitting moiety of bioluminescent jellyfish Aequorea. Tetrahedron Lett. 1972, 13:2747-2748.
27. Adamczyk M., Johnson D.D., Mattingly P.G., Pan Y., Reddy R.E. Synthesis of coelenterazine. Org. Prep. Proced. Int. 2001, 233:477-485.
28. Adamczyk M., Johnson D.D., Mattingly P.G., Pan Y., Reddy R.E. A convenient method for the preparation of α-ketoacetals. Synth. Commun. 2002, 32:3199-3205.
29. Baganz H., May H.-J. Reaktionen von α-diazocarbonyl-verbindungen mit tert.-butylhypochlorit. Chem. Ber. 1966, 99:3766-3770.
30. Baganz H., May H.-J. Synthesis of acetals by reaction of diazoalkanes with t-butyl hypochlorite. Angew. Chem., Int. Ed. Engl. 1966, 5:420.
31. Wu C., Kawasaki K., Ohgiya S., Ohmiya Y. Syntheses and evaluation of the bioluminescent activity of (S)-Cypridina luciferin and its analogs. Tetrahedron Lett. 2006, 47:753-756.
32. Inoue S., Sugiura S., Kakoi H., Hasuzume K., Goto T., Iio H. Squid bioluminescence II. Isolation from Watasenia scintillans and synthesis of 2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one. Chem. Lett. 1975, 141-144.
33. Hirano T., Negishi R., Yamaguchi M., Chen F.-Q., Ohmiya Y., Tsuji F.I., Ohashi M. Chemi- and bio-luminescent properties of coelenterazine analogues possessing an adamantyl group. J. Chem. Soc., Chem. Commun. 1995, 1335-1336.
34. Ohmiya Y., Teranishi K., Akutagawa M., Ohashi M., Tsuji F.I. Bioluminescence activity of coelenterazine analogues after incorporation into recombinant apoaequorin. Chem. Lett. 1993, 2149-2152.
35. Shimomura O. Membrane permeability of coelenterazine analogues measured with fish eggs. Biochem. J. 1997, 326:297-298.