Synthesis and characterization of new chloride-sensitive indicator dyes based on dynamic fluorescence quenching

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 128, Issue 1-3, 1999, Pages 111-120

  Huber, Christian ^a   Fähnrich, Karsten ^a   Krause, Christian ^a   Werner, Tobias ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Bisacridinium derivatives; Chloride probe; Fluorescence quenching

Indexed keywords

EID: 0346244091     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1010-6030(99)00160-4     Document Type: Article

References (28)

1. Kautsky H. Quenching of luminescence by oxygen. Trans. Faraday Soc. 35:1939;216-219.
2. Papkovsky D.B., Ponomarev G.V., Trettnak W., O'Leary P. Phosphorescent complexes of porphyrin ketones: optical properties and application to oxygen sensing. Anal. Chem. 67:1995;4112-4117.
3. O.S. Wolfbeis, Oxygen Sensors, in Fiber Optic Chemical Sensors and Biosensors, Chap. 9, CRC Press, Boca Raton, FL, 1991.
4. J.R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York and London, 1983.
5. Urbano E., Offenbacher H., Wolfbeis O.S. Optical sensor for continuous determination of halides. Anal. Chem. 56:1984;427-429.
6. Biwersi J., Tulk B., Verkman A.S. Long wavelength chloride-sensitive fluorescent indicators. Anal. Biochem. 219:1994;139-143.
7. Burrows H., Formosinho S.J., Fernandia M., Paiva J.R. Halide ion induced quenching and enhancement of the fluorescence of fluoranthene solubilized in cetyltrimethylammonium bromide (CTAB) micelles. J. C. S. Faraday II. 76:1980;685-692.
8. Verkman A.S. Development and biological applications of chloride-sensitive fluorescent indicators. Am. J. Physiol. 159:1990;C375-C387.
9. Verkman A.S., Sellers M.C., Chao A.C., Leung T., Ketcham R. Synthesis and characterisation of improved chloride-sensitive fluorescent indicators for biological applications. Anal. Biochem. 178:1989;355-361.
10. Illsley N.P., Verkman A.S. Membrane chloride transport measured using a chloride-sensitive fluorescent probe. Biochemistry. 26:1987;1215-1219.
11. Calatful T.M., Dix J.A. Chloride-bicarbonate exchange through the human red cell ghost membrane monitored by the fluorescent probe, 6-methoxy-N-(3 sulfopropyl)quinolinium) (SPQ). Anal. Biochem. 230:1995;1-7.
12. Legg K., Hercules D.M. Quenching of lucigenin fluorescence. J. Phys. Chem. 74:1970;2114-2118.
13. Mantaka-Marketou A.E., Varveri F.S., Vassillopoulos G., Nikokavouras J. Some aspects of the lucigenin light reaction. J. Photochem. Photobiol. 48:1989;337-340.
14. Hünig S., Rosenthal O. Farbe und Konstitution II, Phenolbetainfarbstoffe. Justus Liebigs Annalen der Chemie. 592:1955;161-179.
15. Rapaport E., Cass M.W., White E.H. Chemiluminescence of linear hydrazides. J. Am. Chem. Soc. 94:1972;3153-3159.
16. Rauhut M., Seehan D., Clarke R.H., Roberts B.G., Semsel A.M. Chemiluminescence from the reaction of 9-Chlorocarbonyl-10-methylacridinium chloride with aqueous hydrogen peroxide. J. Org. Chem. 30:1965;3587-3592.
17. D.D. Perrin, B. Dempsey, Buffers for pH and metal ion control, Chapman and Hall Laboratory Manuals, London, 1974.
18. Gleu K., Nitzsche S., Schubert A. Die Einwirkung von Phosphoroxychlorid und Oxalchlorid auf Acridone. Chem. Ber. 72:1939;1093-1099.
19. Jaycox G.D., Gribble G.W., Hacker M.P. Potential DNA bis-intercalating agents: synthesis and antitumor activity of novel, conformationally restricted bis(9-Aminoacridines). J. Heterocyclic Chem. 24:1987;1405-1408.
20. Gleu K., Schubert A. Die Umsetzung der Phosphoroxychlorid-Acridone mit Grignard-Verbindungen. Chem. Ber. 73:1940;805-811.
21. Kyriakos P., Nikokavouras J., Dimotikali D. Reaction of lucigenin in protic solvents in the presence of amines. J. Prakt. Chem. 336:1994;506-508.
22. Nakamaru K., Niizuma S., Koizumi M. Photochemical reaction of 9-Cl-acridine in aerated and deaerated ethanol I. Bull. Chem. Soc. 44:1971;1256-1261.
23. T. Werner, K. Fähnrich, Ch. Huber, O.S. Wolfbeis, Anion induced fluorescence quenching of a zwitterionic biacridine derivative, Photochem. Photobiol. (1999), in press.
24. Kaska M. Collisional perturbation of spin orbital coupling and the mechanism of fluorescence quenching. A visional demonstration of the perturbation. J. Chem. Phys. 20:1952;71-74.
25. A. Selby, in: R.M. Acheson (Ed.), Acridines, Wiley, New York, 1973, pp. 433-443.
26. Cass M.W., Rapaport E., White E.H. Chemiluminescent reaction of 9-Caboxy-N-methylacridinium chloride with potassium peroxodisulfate. J. Am. Chem. Soc. 94:1972;3168-3175.
27. Cukier R.I. On the quencher concentration dependence of fluorescence quenching: the role of solution dielectric constant and ionic strength. J. Am. Chem. Soc. 107:1985;4115-4117.
28. Vasseur M., Frangne R. Buffer-dependent pH sensitivity of the fluorescent chloride-indicator dye SPQ. Am. J. Physiol. 264:1993;C27-C31.