A mechanism for the fluorogenic reaction of amino groups with fluorescamine and MDPF

Acta Histochemica

Volumn 110, Issue 4, 2008, Pages 333-340

  Stockert, Juan C ^a,b   Blázquez, Alfonso ^a   Galaz, Sergio ^c   Juarranz, Angeles ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^c UNIVERSIDAD DE TARAPACÁ   (Chile)

Author keywords

Amino groups; Cytochemistry; Fluorescence microscopy; Fluorogenic reactions; Furanones

Indexed keywords

2 METHOXY 2,4 DIPHENYL 3(2H) FURANONE; BUTYLAMINE; FLUORESCAMINE; FURANONE DERIVATIVE; METHANOL; SULFONIC ACID DERIVATIVE;

ALKALINITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SPECTRAL SENSITIVITY;

AMINES; FLUORESCAMINE; FLUORESCENT DYES; FURANS; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EQUIDAE; MICROMESISTIUS POUTASSOU;

EID: 49949151936     PISSN: 00651281     EISSN: 16180372     Source Type: Journal    
DOI: 10.1016/j.acthis.2007.10.011     Document Type: Article

References (46)

1. Alba F.J., and Daban J.R. Nonenzymatic chemiluminescent detection and quantitation of total protein on Western and slot blots allowing subsequent immunodetection and sequencing. Electrophoresis 18 (1997) 1960-1966
2. Barger B.O., White F.C., Pace J.L., Kemper D.L., and Ragland W.L. Estimation of molecular weight by polyacrylamide gel electrophoresis using heat stable fluorophors. Anal Biochem 70 (1976) 327-335
3. Bodhe A.M., Vartak H.G., Rele M.V., and Dhamankar V.S. Location and purification of enzymes on polyacrylamide gels using dialyzable fluorescent markers. Anal Biochem 164 (1987) 39-43
4. Bruni A., Fasulo M.P., Tosi B., Dall'Olio G., and Vannini G.L. Fluorogenic detection of primary amines in plant histochemistry with fluorescamine: a comparative study on the effects of coagulant and non-coagulant fixatives. Histochemistry 48 (1976) 269-281
5. Budavari S. The Merck index. An encyclopedia of chemicals, drugs and biologicals. 11th ed (1989), Merck & Co, Rahway, NJ
6. Cross J.W., and Briggs W.R. Labeling of membranes from erythrocytes and corn with fluorescamine. Biochim Biophys Acta 471 (1977) 67-77
7. Cuéllar T., Gosálvez J., Del Castillo P., and Stockert J.C. Fluram induces species-dependent C and G bands in mammalian chromosomes, revealing heterogeneous distribution of chromosomal proteins. Genome 34 (1991) 772-776
8. De Bernardo S., Weigele M., Toome V., Manhart K., Leimgruber W., Böhlen P., et al. Studies on the reaction of fluorescamine with primary amines. Arch Biochem Biophys 163 (1974) 390-399
9. Falk B.W., and Elliott C. Fluorescent monitoring of proteins during sodium dodecyl sulfate-polyacrylamide gel electrophoresis and Western blotting. Anal Biochem 144 (1985) 537-541
10. Felix A.M., and Jimenez M.H. Usage of fluorescamine as a spray reagent for thin-layer chromatography. J Chromatogr 89 (1974) 361-364
11. Fieser L., and Fieser M. Reagents for organic synthesis (1967), Wiley, New York
12. Fishman M.A., Hagen S., Trotter J.L., O'Connell K., and Agrawal H.C. Use of a stable fluorescent reagent, 2-methoxy-2,4-diphenyl-3(2H)-furanone, for the visualization and purification of myelin proteins. J Neurochem 32 (1979) 1077-1083
13. Hahn F.E., and Ciak J. Berberine. In: Corcoran J.W., and Hahn F.E. (Eds). Antibiotics (1975), Springer, Heidelberg, Berlin, New York 577-584
14. Håkanson R., Larsson L.I., and Sundler F. Fluorescamine: a novel reagent for the histochemical detection of amino groups. Histochemistry 39 (1974) 15-23
15. Hawkes S.P., Meehan T.D., and Bissell M.J. The use of fluorescamine as a probe for labeling the outer surface of the plasma membrane. Biochem Biophys Res Commun 68 (1976) 1226-1233
16. Horobin R.W., and Kiernan J.A. Conn's biological stains. A handbook of dyes, stains and fluorochromes for use in biology and medicine. 10th ed (2002), Bios Scientific Publishers, Oxford
17. Horobin R.W., Stockert J.C., and Rashid-Doubell F. Fluorescent cationic probes for nuclei of living cells: why are they selective? A quantitative structure-activity relations analysis. Histochem Cell Biol 126 (2006) 165-175
18. Jackson P., Urwin V.E., and Mackay C.D. Rapid imaging, using a cooled charge-coupled-device, of fluorescent two-dimensional polyacrylamide gels produced by labeling proteins in the first-dimensional isoelectric focusing gel with the fluorophore 2-methoxy-2,4-diphenyl-3(2H)furanone. Electrophoresis 9 (1988) 330-339
19. Kasai H., Hayami H., Yamaizumi Z., Saito H., and Nishimura S. Detection and identification of mutagens and carcinogens as their adducts with guanosine derivatives. Nucleic Acid Res 12 (1984) 2127-2136
20. Larsson L.I., Sundler F., and Håkanson R. Fluorescamine as a histochemical reagent: demonstration of polypeptide hormone-secreting cells. Histochemistry 44 (1975) 245-251
21. Lorch-Jorgensen L., Ingemansson S., and Larsson L.I. Formaldehyde-fluorescamine-induced fluorescence as a property of carcinoma cells. Virch Arch B Cell Pathol 30 (1979) 125-130
22. Miedel M.C., Hulmes J.D., and Pan Y.C. The use of fluorescamine as a detection reagent in protein microcharacterization. J Biochem Biophys Methods 18 (1989) 37-52
23. Nakamura H., Takagi K., Tamura Z., Yoda R., and Yamamoto Y. Stepwise fluorometric determination of primary and secondary amines by liquid chromatography after derivatization with 2-methoxy-2,4-diphenyl-3(2H)-furanone. Anal Chem 56 (1984) 919-922
24. Parry G., Blenis J., and Hawkes S.P. Detection of transformed cells using a fluorescent probe: the molecular basis for the differential reaction of fluorescamine with normal and transformed cells. Cytometry 3 (1982) 97-103
25. Sciorra L.J., Lee M.L., and Wynnyckyj H. Study of human chromosomes. IV. Labeling of chromosomal proteins with the amino group specific fluorescent reagent fluorescamine. J Histochem Cytochem 33 (1985) 1252-1255
26. Sprinzl M., and Faulhammer H.G. Participation of X47-fluorescamine modified E. coli tRNAs in in vitro protein biosynthesis. Nucleic Acid Res 5 (1978) 4837-4853
27. Stockert J.C. Cytochemistry of mast cells: new fluorescent methods selective for sulfated glycosaminoglycans. Acta Histochem 102 (2000) 259-272
28. Stockert J.C. The horse eosinophil as a model leucocyte for morphological and cytochemical studies. Braz J Morphol Sci 22 (2005) 73-84
29. Stockert J.C., and Trigoso C.I. Fluorescence of eosinophil leukocyte granules induced by the fluorogenic reagent 2-methoxy-2,4-diphenyl-3(2H)-furanone. Blood Cells 19 (1993) 423-430
30. Stockert J.C., and Trigoso C.I. Selective fluorescence reaction of indigocarmine stained eosinophil leucocyte granules induced by alkaline reduction of the bound dye to its leuco derivative. Acta Histochem 96 (1994) 8-14
31. Stockert J.C., Del Castillo P., Llorente A.R., Rasskin D.M., Romero J.B., and Gómez A. New fluorescence reactions in DNA cytochemistry. 1. Microscopic and spectroscopic studies on nonrigid fluorochromes. Anal Quant Cytol Histol 12 (1990) 1-10
32. Stockert J.C., Espada J., Trigoso C.I., and Del Castillo P. Fluorescence reaction of the anionic triaryl-methane dye fast green FCF. Appl Fluor Technol 3 (1991) 14-15
33. Stockert J.C., Pelling C., and Espada J. New cationic fluorochromes from diaryloxazole scintillators: fluorescence of chromatin DNA induced by N-quaternary POPOP derivatives. Acta Histochem 99 (1997) 195-205
34. Stockert J.C., Pinna-Senn E., Bella J.L., and Lisanti J.A. DNA-binding fluorochromes: correlation between C-banding of mouse metaphase chromosomes and hydrogen bonding to adenine-thymine base pairs. Acta Histochem 106 (2005) 413-420
35. Sundler F., Uddman R., Larsson L.I., Telenius-Berg M., Berg B., and Håkanson R. Fluorescamine in diagnosis of thyroid carcinomas. Acta Cytol 22 (1978) 54-56
36. Tata S.J., and Moir G.F.J. Fluorescamine as a reagent for location of proteins after electrophoresis in starch gel or on paper. Anal Biochem 70 (1976) 495-498
37. Toome V., and Wegrzynski B. Application of MDPF and fluorescamine. XV. Chiroptical properties of MDPF condensation compounds with dipeptides in situ. Biochem Biophys Res Commun 114 (1983) 433-439
38. Trigoso C.I., Del Castillo P., and Stockert J.C. Influence of inorganic salts on the staining reaction of eosinophil lecocyte granules by anionic dyes. Acta Histochem 93 (1992) 313-318
39. Tu S.I., and Grosso L. Fluorescent labeling of proteins in sodium dodecyl sulfate complexes with fluorescamine. Biochem Biophys Res Commun 72 (1976) 9-14
40. Uddman R., Larsson L.I., and Sundler F. Fluorescamine as a cytochemical detection reagent for mammary carcinoma cells. Acta Cytol 22 (1978) 273-275
41. Udenfriend S. Fluorescence assay in biology and medicine (1962), Academic Press, New York, London pp. 250-251
42. Udenfriend S., Stein S., Böhlen P., Dairman W., Leimgruber W., and Weigele M. Fluorescamine: a reagent for assay of amino acids, peptides, proteins and primary amines in the picomole range. Science 178 (1972) 871-872
43. Weigele M., De Bernardo S.L., Tengi J.P., and Leimgruber W. A novel reagent for the fluorometric assay of primary amines. J Am Chem Soc 94 (1972) 5927-5928
44. Weigele M., De Bernardo S.L., Leimgruber W., Cleeland R., and Grunberg E. Fluorescent labeling of proteins. A new methodology. Biochem Biophys Res Commun 54 (1973) 899-906
45. Weigele M., Tengi J.P., De Bernardo S., Czajkowski R., and Leimgruber W. Fluorometric reagents for primary amines. Synthesis of 2-alkoxy- and 2-acyloxy-3(2H)-furanones. J Org Chem 41 (1976) 388-389
46. Zhu R., and Kok W.T. Postcolumn derivatization of peptides with fluorescamine in capillary electrophoresis. J Chromatogr A 814 (1998) 213-221