Generation of a novel fluorescent product, monochlorofluorescein from dichlorofluorescin by photo-irradiation

Free Radical Research

Volumn 40, Issue 9, 2006, Pages 959-965

  Matsugo, Seiichi ^a   Sasai, Masaaki ^a   Shinmori, Hideyuki ^a   Yasui, Fumihiko ^a   Takeuchi, Minoru ^b   Takeuchi, Toru ^c  

^a UNIVERSITY OF YAMANASHI   (Japan)

^b KYOTO SANGYO UNIVERSITY   (Japan)

^c KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

Dichlorofluorescin; Monochlorofluorescein; Photochemical reaction; Reactive oxygen species

Indexed keywords

DICHLOROFLUORESCEIN; FLUORESCEIN DERIVATIVE; FLUORESCENT DYE; MONOCHLOROFLUORESCEIN; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT IRRADIANCE; MOLECULAR WEIGHT; OXIDATION; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCEINS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; ULTRAVIOLET RAYS;

EID: 33749245902     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760600827012     Document Type: Article

References (18)

1. Bass, DA and Parce, JW and Dechatelet, LR and Szejda, P and Seeds, MC and Thomas, M. (1983) Flow cytometric studies of oxidative product formation by neutrophils: A graded response to membrane stimulation J Immunol, 130, pp. 1910-1917.
2. Rothe, G and Valet, G. (1990) Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,′-dichlorofluorescin J Leukoc Biol, 47, pp. 440-448.
3. Takeuchi, T and Nakajima, M and Morimoto, K. (1996) Relationship between the intracellular reactive oxygen species and the induction of oxidative DNA damage in human neutrophil-like cells Carcinogenesis, 17, pp. 1543-1548.
4. Halliwell, B and Whiteman, M. (2004) Measuring reactive species and oxidative damage in vivo and in cell culture: How should you do it and what do the results mean? Br J Pharmacol, 142, pp. 231-255.
5. Setsukinai, K and Urano, Y and Kakinuma, K and Majima, HJ and Nagano, T. (2003) Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species J Biol Chem, 278, pp. 3170-3175.
6. Afzal, M and Matsugo, S and Sasai, M and Xu, BH and Aoyama, K and Takeuchi, T. (2003) Method to overcome photoreaction, a serious drawback to the use of dichlorofluorescin in evaluation of ROS Biochem Biophys Res Commun, 304, pp. 619-624.
7. Matsugo, S and Kawanishi, S and Yamamoto, K and Sugiyama, H and Matsuura, T and Saito, I. (1991) Bis (Hydroperoxy)naphthalimide as a "photo-fenton reagent"- sequence-specific photocleavage of DNA Angew Chem Int Ed Engl, 30, pp. 1351-1353.
8. LeBel, CP and Ischiropoulos, H and Bondy, SC. (1992) Evaluation of the probe 2′ ′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress Chem Res Toxicol, 5, pp. 227-231.
9. http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/73148
10. http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/D6665
11. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (National Institute of Advanced Industrial Science and Technology, Jan. 2006).
12. Takeuchi, T and Matsugo, S and Morimoto, K. (1997) Mutagenicity of oxidative DNA damage in Chinese hamster V79 cell Carcinogenesis, 18, pp. 2051-2055.
13. Gilbert, A. (1986) Aromatic compounds: Substitution and cyclisation. In Photochemistry in Organic Synthesis. (pp. 278-300). London: Royal Society of Chemistry.
14. Dekant, W. (1996) Toxicology of chlorofluorocarbon replacements Environ Health Perspect, 104, pp. 75-83.
15. Dwivedi, AH and Pande, U. (2003) Spectrophotometric study of photosensitized dechlorination of isometric mono- and di-chloronitrobenzenes J Photochem Photobiol, 154, pp. 303-309.
16. Rota, C and Chignell, CF and Mason, RP. (1999) Evidence for free radical formation during the oxidation of 2′,7′-dichlorofluorescin to the fluorescent dye 2′,7′ dichlorofluorescein by horseradish peroxidase: Possible implications for oxidative stress measurements Free Radic Biol Med, 27, pp. 873-881.
17. Ohashi, T and Mizutani, A and Murakami, A and Kojo, A and Ishii, T and Taketani, S. (2002) Rapid oxidation of dichlorodihydrofluorescin with heme and hemoproteins: Formation of the fluorescein is independent of the generation of reactive oxygen species FEBS Lett, 511, pp. 21-27.
18. Bilski, P and Belanger, AG and Chignell, CF. (2002) Photosensitized oxidation of 2′,7′-dichlorofluorescin: Singlet oxygen does not contribute to the formation of fluorescent oxidation product 2′,7′-dichlorofluorescein Free Radic Biol Med, 33, pp. 938-946.