Fluorescent labeling of cranberry proanthocyanidins with 5-([4,6-dichlorotriazin-2-yl]amino)fluorescein (DTAF)

Food Chemistry

Volumn 166, Issue , 2015, Pages 337-345

  Feliciano, Rodrigo P ^a   Heintz, Joseph A ^b   Krueger, Christian G ^a,c   Vestling, Martha M ^a   Reed, Jess D ^a,c  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b University of Wisconsin Madison Reed Research Group Dept Animal Sciences ^*  (United States)

^c Biological and Biomaterials Preparation Imaging and Characterization Facility Dept Animal Sciences ^*  (United States)

Author keywords

5 ( 4,6 Dichlorotriazin 2 yl amino)fluorescein; Cranberry; DTAF; Fluorescence; MALDI TOF MS; Microscopy; MTAF; Proanthocyanidins; TAF

Indexed keywords

ALKALINITY; ANTIGEN-ANTIBODY REACTIONS; CELL CULTURE; ESCHERICHIA COLI; FLAVONOIDS; FLUORESCENCE MICROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROSCOPIC EXAMINATION;

5-([4,6-DICHLOROTRIAZIN-2-YL]AMINO)FLUORESCEIN; CRANBERRY; DTAF; MALDI TOF MS; MTAF; PROANTHOCYANIDINS; TAF;

FLUORESCENCE;

5 [(4,6 DICHLOROTRIAZIN 2 YL)AMINO]FLUORESCEIN; CHLORINE; EPICATECHIN; FLUORESCEIN DERIVATIVE; HYDROXYL GROUP; PROANTHOCYANIDIN DERIVATIVE; UNCLASSIFIED DRUG; FLUORESCEIN; PLANT EXTRACT; PROANTHOCYANIDIN;

ALKALINITY; ANTIGEN ANTIBODY REACTION; ARTICLE; CONTROLLED STUDY; CRANBERRY; DIODE; ELECTROPHILICITY; FLUORESCENCE MICROSCOPY; FRAGMENTATION REACTION; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; NUCLEOPHILICITY; PATHOGENIC ESCHERICHIA COLI; PH; REVERSED PHASE LIQUID CHROMATOGRAPHY; SUBURETHRAL SLING; THIN LAYER CHROMATOGRAPHY; CHEMISTRY; FRUIT; MASS SPECTROMETRY; PROCEDURES;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCEIN; FRUIT; MASS SPECTROMETRY; PLANT EXTRACTS; PROANTHOCYANIDINS; VACCINIUM MACROCARPON;

EID: 84903768030     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2014.06.031     Document Type: Article

References (40)

1. T. Abitbol, A. Palermo, J.M. Moran-Mirabal, and E.D. Cranston Fluorescent labeling and characterization of cellulose nanocrystals with varying charge contents Biomacromolecules 14 9 2013 3278 3284 10.1021/bm400879x
2. G.E. Adamson, S.A. Lazarus, A.E. Mitchell, R.L. Prior, G.H. Cao, and P.H. Jacobs et al. HPLC method for the quantification of procyanidins in cocoa and chocolate samples and correlation to total antioxidant capacity Journal of Agricultural and Food Chemistry 47 10 1999 4184 4188 10.1021/jf990317m (Pubitemid 29506222)
3. F. Ahmed, P. Alexandridis, and S. Neelamegham Synthesis and application of fluorescein-labeled Pluronic block copolymers to the study of polymer-surface interactions Langmuir 17 2 2001 537 546 (Pubitemid 32159145)
4. N.P. Beard, J.B. Edel, and A.J. deMello Integrated on-chip derivatization and electrophoresis for the rapid analysis of biogenic amines Electrophoresis 25 14 2004 2363 2373 10.1002/elps.200305919 (Pubitemid 39136357)
5. D. Blakeslee, and M.G. Baines Immunofluorescence using dichlorotriazinylaminofluorescein (DTAF) I. Preparation and fractionation of labelled IgG Journal of Immunological Methods 13 3-4 1976 305 320 (Pubitemid 8010421)
6. R.P. Feliciano, C.G. Krueger, D. Shanmuganayagam, M.M. Vestling, and J.D. Reed Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins Food Chemistry 135 3 2012 1485 1493
7. R.P. Feliciano, J.J. Meudt, D. Shanmuganayagam, C.G. Krueger, and J.D. Reed Ratio of "A-type" to "B-type" proanthocyanidin interflavan bonds affects extra-intestinal pathogenic Escherichia coli invasion of gut epithelial cells Journal of Agricultural and Food Chemistry 2013 10.1021/jf403839a
8. R.P. Feliciano, M.P. Shea, D. Shanmuganayagam, C.G. Krueger, A.B. Howell, and J.D. Reed Comparison of isolated cranberry (Vaccinium macrocarpon Ait.) proanthocyanidins to catechin and procyanidins A2 and B2 for use as standards in the 4-(dimethylamino)cinnamaldehyde assay Journal of Agricultural and Food Chemistry 60 18 2012 4578 4585 10.1021/jf3007213
9. L. Gu, M. Kelm, J.F. Hammerstone, G. Beecher, D. Cunningham, and S. Vannozzi et al. Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method Journal of Agricultural and Food Chemistry 50 17 2002 4852 4860 10.1021/jf020214v (Pubitemid 34856155)
10. W. Helbert, H. Chanzy, T.L. Husum, M. Schülein, and S. Ernst Fluorescent cellulose microfibrils as substrate for the detection of cellulase activity Biomacromolecules 4 3 2003 481 487 10.1021/bm020076i (Pubitemid 36701215)
11. J.M. Herrero-Martinez, M. Sanmartin, M. Roses, E. Bosch, and C. Rafols Determination of dissociation constants of flavonoids by capillary electrophoresis Electrophoresis 26 10 2005 1886 1895 10.1002/elps.200410258 (Pubitemid 40796653)
12. B.J. Johnson, B. Lin, M.A. Dinderman, R.A. Rubin, A.P. Malanoski, and F.S. Ligler Impact of cranberry on Escherichia coli cellular surface characteristics Biochemical and Biophysical Research Communications 377 3 2008 992 994
13. K.N. Krahn, C.V.C. Bouten, S. van Tuijl, M.A.M.J. van Zandvoort, and M. Merkx Fluorescently labeled collagen binding proteins allow specific visualization of collagen in tissues and live cell culture Analytical Biochemistry 350 2 2006 177 185 (Pubitemid 43332817)
14. C.G. Krueger, N.C. Dopke, P.M. Treichel, J. Folts, and J.D. Reed Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of polygalloyl polyflavan-3-ols in grape seed extract Journal of Agricultural and Food Chemistry 48 5 2000 1663 1667 10.1021/jf990534n (Pubitemid 30331505)
15. C.G. Krueger, M.M. Vestling, and J.D. Reed Matrix-Assisted Laser Desorption-Ionization Time-Of-Flight Mass Spectrometry Of Anthocyanin-Poly- Flavan-3-ol Oligomers In Cranberry Fruit (Vaccinium macrocarpon, Ait.) and Spray-Dried Cranberry Juice Red Wine Color 2004 American Chemical Society pp. 232-246
16. E.L. Lagendijk, S. Validov, G.E.M. Lamers, S. de Weert, and G.V. Bloemberg Genetic tools for tagging Gram-negative bacteria with mCherry for visualization in vitro and in natural habitats, biofilm and pathogenicity studies FEMS Microbiology Letters 305 1 2010 81 90 10.1111/j.1574-6968.2010. 01916.x
17. S. Lalljie, and P. Sandra Practical and quantitative aspects in the analysis of FITC and DTAF amino acid derivatives by capillary electrophoresis and LIF detection Chromatographia 40 9 1995 519 526 10.1007/bf02290262
18. H.-J. Li, and M.L. Deinzer Tandem mass spectrometry for sequencing proanthocyanidins Analytical Chemistry 79 4 2007 1739 1748 10.1021/ac061823v
19. X. Liu, Y.-Q. Hu, L. Ma, and Y.-T. Lu Determination of phosphoamino acids derivatized with 5-(4,6-dichloro-s-triazin-2-ylamino)fluorescein by micellar electrokinetic chromatography Journal of Chromatography A 1049 1-2 2004 237 242 (Pubitemid 39208809)
20. Y. Liu, A.M. Gallardo-Moreno, P.A. Pinzon-Arango, Y. Reynolds, G. Rodriguez, and T.A. Camesano Cranberry changes the physicochemical surface properties of E. coli and adhesion with uroepithelial cells Colloids and Surfaces B: Biointerfaces 65 1 2008 35 42
21. Y. Liu, P.A. Pinzón-Arango, A.M. Gallardo-Moreno, and T.A. Camesano Direct adhesion force measurements between E. coli and human uroepithelial cells in cranberry juice cocktail Molecular Nutrition & Food Research 54 12 2010 1744 1752 10.1002/mnfr.200900535
22. L.N. Loh, and T.H. Ward Chapter six - Escherichia coli K1 Invasion of Human Brain Microvascular Endothelial Cells P.M. Conn, Methods in Enzymology Vol. 506 2012 Academic Press 93 113
23. D. Luensmann, and L. Jones Impact of fluorescent probes on albumin sorption profiles to ophthalmic biomaterials Journal of Biomedical Materials Research Part B: Applied Biomaterials 94B 2 2010 327 336 10.1002/jbm.b.31655
24. M. Mateos-Martín, E. Fuguet, C. Quero, J. Pérez- Jiménez, and J. Torres New identification of proanthocyanidins in cinnamon (Cinnamomum zeylanicum L.) using MALDI-TOF/TOF mass spectrometry Analytical and Bioanalytical Chemistry 402 3 2012 1327 1336 10.1007/s00216-011- 5557-3
25. M. Molina, and M. Silva Analytical potential of fluorescein analogues for ultrasensitive determinations of phosphorus-containing amino acid herbicides by micellar electrokinetic chromatography with laser-induced fluorescence detection Electrophoresis 23 7-8 2002 1096 1103 10.1002/1522-2683(200204)23:7/ 8<1096::aid-elps1096>3.0.co;2-e (Pubitemid 34537431)
26. I. Mueller-Harvey, V. Mlambo, J.L.N. Sikosana, T. Smith, E. Owen, and R.H. Brown Octanol-water partition coefficients for predicting the effects of tannins in ruminant nutrition Journal of Agricultural and Food Chemistry 55 14 2007 5436 5444 10.1021/jf070308a (Pubitemid 47092912)
27. A. Petrossian, A.B. Kantor, and J.C. Owicki Synthesis and characterization of a highly fluorescent peptidyl-phosphatidylethanolamine Journal of Lipid Research 26 6 1985 767 773 (Pubitemid 15248951)
28. J.F. Pierre, A.F. Heneghan, R.P. Feliciano, D. Shanmuganayagam, D.A. Roenneburg, and C.G. Krueger et al. Cranberry proanthocyanidins improve the gut mucous layer morphology and function in mice receiving elemental enteral nutrition Journal of Parenteral and Enteral Nutrition 2012 10.1177/ 0148607112463076
29. P. Poupard, P. Sanoner, A. Baron, C.M.G.C. Renard, and S. Guyot Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry Journal of Mass Spectrometry 46 11 2011 1186 1197 10.1002/jms.2007
30. M. Prodanov, V. Vacas, T. Hernández, I. Estrella, B. Amador, and P. Winterhalter Chemical characterisation of Malvar grape seeds (Vitis vinifera L.) by ultrafiltration and RP-HPLC-PAD-MS Journal of Food Composition and Analysis 31 2 2013 284 292 10.1016/j.jfca.2013.06.003
31. R. Schumann, and D. Rentsch Staining particulate organic matter with DTAF - a fluorescence dye for carbohydrates and protein: a new approach and application of a 2D image analysis system Marine Ecology Progress Series 163 1998 77 88 10.3354/meps163077 (Pubitemid 28178570)
32. R. Siegler, L.A. Sternson, and J.F. Stobaugh Suitability of DTAF as a fluorescent labelling reagent for direct analysis of primary and secondary amines - spectral and chemical reactivity considerations Journal of Pharmaceutical and Biomedical Analysis 7 1 1989 45 55 (Pubitemid 19018709)
33. M. Strohalm, D. Kavan, P. Novak, M. Volny, and V. Havlicek MMass 3: a cross-platform software environment for precise analysis of mass spectrometric data Analytical Chemistry 82 11 2010 4648 4651 10.1021/ac100818g
34. C. Toseland Fluorescent labeling and modification of proteins Journal of Chemical Biology 6 3 2013 85 95 10.1007/s12154-013-0094-5
35. P. Wadsworth, and R.D. Sloboda Modification of tubulin with the fluorochrome 5-(4,6-dichlorotriazin-2-yl)amino fluorescein and the interaction of the fluorescent protein with the isolated meiotic apparatus The Biological Bulletin 166 2 1984 357 367
36. W. Wang, C. Li, Y. Li, Z. Hu, and X. Chen Rapid and ultrasensitive determination of ephedrine and pseudoephedrine derivatizated with 5-(4,6-dichloro-s-triazin-2-ylamino) fluorescein by micellar electrokinetic chromatography with laser-induced fluorescence detection Journal of Chromatography A 1102 1-2 2006 273 279 (Pubitemid 41790358)
37. J. Weyermann, D. Lochmann, C. Georgens, I. Rais, J. Kreuter, and M. Karas et al. Physicochemical characterisation of cationic polybutylcyanoacrylat- nanoparticles by fluorescence correlation spectroscopy European Journal of Pharmaceutics and Biopharmaceutics 58 1 2004 25 35 (Pubitemid 38781001)
38. B.L. White, L.R. Howard, and R.L. Prior Release of bound procyanidins from cranberry pomace by alkaline hydrolysis Journal of Agricultural and Food Chemistry 58 13 2010 7572 7579 10.1021/jf100700p
39. D.A. Wicks, and P.C.H. Li Separation of fluorescent derivatives of hydroxyl-containing small molecules on a microfluidic chip Analytica Chimica Acta 507 1 2004 107 114 (Pubitemid 38224095)
40. Y. Xiao, X.-D. Yu, K. Wang, J.-J. Xu, J. Huang, and H.-Y. Chen Study on the separation of amino acids in modified poly(dimethylsiloxane) microchips Talanta 71 5 2007 2048 2055 (Pubitemid 46386196)