The use of 3-aminophthalimide as a pro-chemiluminescent label in chemiluminescence and fluorescence-based cellular assays

Bioconjugate Chemistry

Volumn 20, Issue 2, 2009, Pages 266-273

  Mavri Damelin, Demetra ^a,d   Wilden, Jonathan ^b   Mani, Ali Reza ^a   Selden, Clare ^a   Hodgson, Humphrey J F ^a   Damelin, Leonard H ^a,c  

^a ROYAL FREE AND UNIVERSITY COLLEGE MEDICAL SCHOOL   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c NATIONAL INSTITUTE FOR COMMUNICABLE DISEASES   (South Africa)

^d UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE; NITROGEN COMPOUNDS; NUCLEIC ACIDS; PALMITIC ACID; SYNTHESIS (CHEMICAL);

AFTER-TREATMENT; CELLULAR ASSAYS; CELLULAR BINDING; CELLULAR TRANSPORT; CELLULARS; DUAL FLUORESCENCE; LABELLING SYSTEMS; LUMINOLS; REPORTER MOLECULES; SYNTHESISED;

CHEMILUMINESCENCE;

3 AMINOPHTHALIMIDE; FUNCTIONAL GROUP; HYDRAZINE; IMIDE; INSULIN; LUMINOL; NITROGEN; NUCLEIC ACID; PALMITIC ACID; PHTHALIMIDE DERIVATIVE; POLYSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; CELL FUNCTION; CELL TRANSPORT; CHEMOLUMINESCENCE; FLUORESCENCE; HUMAN; HUMAN CELL; LIPID METABOLISM; MITOCHONDRION; PROTEIN BINDING; PROTEIN TRANSPORT; SYNTHESIS;

APIS;

EID: 62549153506     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800361r     Document Type: Article

References (22)

1. Kessler, C. (1992) Nonradioactive Labeling and Detection of Biomolecules (Kessler, C., Ed.) Springer, New York.
2. Albrecht, H. O. (1928) Über die chemiluminescenz des aminophthalsaurehydrazids. Z. Phys. Chem. 136, 321.
3. Whitehead, T. P., Kricka, L. J., Carter, T. J. N., and Thorpe, G. H. G. (1979) Analytical luminescence: Its potential in the clinical laboratory. Clin. Chem. 25, 1531-1546.
4. Shulman, S. G. (1993) Molecular Luminescence Spectroscopy. Volume 77.Part 3: Chemical Analysis Series (Shulman, S. G., Ed.) John Wiley and Sons, New York.
5. Waseem, A., Yaqoob, M., and Nabi, A. (2004) Determination of iron in blood serum using flow injection with luminol chemiluminescence detection. Luminescence 19, 333-338.
6. Schroeder, H. R., and Yeager, F. M. (1978) Chemiluminescence yields and detection limits of some isoluminol derivatives in various oxidation systems. Anal. Chem. 50, 1114-1120.
7. Khan, M. N. (1995) Kinetic evidence for the occurrence of a stepwise mechanism in hydrazinolysis of phthalimide. J. Org. Chem. 60, 4536-4541.
8. Gulis, I. M., Komyak, A. I., Saechnikov, K. A., and Tsvirko, V. A. (1989) Fluorescent spectroscopy of 3-aminophthalimide molecules cooled in an ultrasonic jet. J. Appl. Spectrosc. 50, 257-262.
9. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olsom, B. J., and Klenk, D. C. (1985) Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76-85.
10. Hermanson, G. T. (2008) Fluorescent probes, In Bioconjugate Techniques, 2nd ed., pp 396-497, Chapter 9, Academic Press, New York.
11. Calzi, S. L., Choice, C. V., and Najjar, S. M. (1997) Differential effect of pp120 on insulin endocytosis by two variant insulin receptor isoforms. Am. J. Physiol. Endocrinol. Metab. 273, 801-808.
12. Varala, R., Nuvula, S., and Matile, S. R. (2006) Molecular iodine-catalyzed facile procedure for N-Boc protection of amines. J. Org. Chem. 71, 8282-8286.
13. Cesaretti, M., Luppi, E., Maccari, F., and Volpi, N. (2003) A 96-well assay for uronic acid carbazole reaction. Carbohydr. Polym. 54, 59-61.
14. Folch, J., Lees, M., and Sloane Stanley, G. H. (1957) A simple method for the isolation and purification of total lipides from animal tissues. J. Biol. Chem. 226, 497-509.
15. Donner, D. B. (1980) Regulation of insulin binding to isolated hepatocytes: Correction for bound hormone fragments linearizes Scatchard plots. Proc. Natl. Acad. Sci. U.S.A. 77, 3176-3180.
16. Ross, M. F., Kelso, G. F., Blaikie, F. H., James, A. M., Cocheme, H. M., Filipovska, A., Ros, T., Hurd, T. R., Smith, R. A. J., and Murphy, M. P. (2005) Lipophilic triphenylphosphonium cations as tools in mitochondrial bioenergetics and free radical biology. Biochemistry (Moscow) 70, 222-230.
17. Pallotti, F., and Lenaz, G. (2001) Isolation and subfractionation of mitochondria from animal cells and tissue culture lines. Methods in Cell Biology, Volume 65 Mitochondria. (Pon, L. A., and Schon, E. A., Eds.) pp 2-31, Chapter 1, Academic Press, London.
18. Dudás, J., Ramadori, G., Knittel, T., Neubauer, K., Raddatz, D., Egedy, K., and Kovalszky, I. (2000) Effect of heparin and liver heparan sulphate on interaction of HepG2-derived transcription factors and their cis-acting elements: altered potential of hepatocellular carcinoma heparan sulphate. Biochem, J. 350, 245-51.
19. Pohl, J., Ring, A., and Stremmel, W. (2002) Uptake of long-chain fatty acids in HepG2 cells involves caveolae: analysis of a novel pathway. J. Lipid. Res. 43, 1390-1399, http://www.ncbi.nhn.nih.gov/sites/entrez?Db= pubmed&Cmd=Search&Term=%22Pohl%20J%22%5BAuthor%5D&itool= EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_RVAbstractPlus.
20. Hentz, N. G., Richardson, J. M., Sportsman, J. R., Daijo, J., and Sittampalam, G. S. (1997) Synthesis and characterization of insulin-fluorescein derivatives for bioanalytical applications. Anal. Chem. 69, 4994-5000.
21. Rajagopal, J., Anderson, W. J., Kume, S., Martinez, O. I., and Melton, D. A. (2003) Insulin staining of ES cell progeny from insulin uptake. Science 299, 363.
22. Okamoto, H., Kohno, M., Satake, K., and Kimura, M. (2005) An azacrowned phthalimide as a metal-ion sensitive sovatof-luorochromic fluorophore: fluorescence properties and a mimic integrated logic operation. Bull. Chem. Soc. Jpn. 78, 2180-2187.