메뉴 건너뛰기




Volumn 23, Issue 3, 2012, Pages 363-371

Detection of cellular sialic acid content using nitrobenzoxadiazole carbonyl-reactive chromophores

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CARBOXYLIC ACIDS; CATALYSIS; CYTOLOGY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; GLYCOPROTEINS; POLYSACCHARIDES; SODIUM COMPOUNDS;

EID: 84863343114     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200276k     Document Type: Article
Times cited : (49)

References (45)
  • 1
    • 75149179997 scopus 로고    scopus 로고
    • Fluorescent small-molecule probes of biochemistry at the plasma membrane
    • Cairo, C. W., Key, J. A., and Sadek, C. M. (2010) Fluorescent small-molecule probes of biochemistry at the plasma membrane Curr. Opin. Chem. Biol. 14, 57-63
    • (2010) Curr. Opin. Chem. Biol. , vol.14 , pp. 57-63
    • Cairo, C.W.1    Key, J.A.2    Sadek, C.M.3
  • 2
    • 42449100481 scopus 로고    scopus 로고
    • Bright ideas for chemical biology
    • Lavis, L. D. and Raines, R. T. (2008) Bright ideas for chemical biology ACS Chem. Biol. 3, 142-55
    • (2008) ACS Chem. Biol. , vol.3 , pp. 142-155
    • Lavis, L.D.1    Raines, R.T.2
  • 3
    • 67650391443 scopus 로고    scopus 로고
    • Monitoring Biophysical Properties of Lipid Membranes by Environment-Sensitive Fluorescent Probes
    • Demchenko, A. P., Mely, Y., Duportail, G., and Klymchenko, A. S. (2009) Monitoring Biophysical Properties of Lipid Membranes by Environment-Sensitive Fluorescent Probes Biophys. J. 96, 3461-3470
    • (2009) Biophys. J. , vol.96 , pp. 3461-3470
    • Demchenko, A.P.1    Mely, Y.2    Duportail, G.3    Klymchenko, A.S.4
  • 4
    • 77950363627 scopus 로고    scopus 로고
    • Chemoselective Ligation Techniques: Modern Applications of Time-Honored Chemistry
    • Tiefenbrunn, T. K. and Dawson, P. E. (2010) Chemoselective Ligation Techniques: Modern Applications of Time-Honored Chemistry Biopolymers 94, 95-106
    • (2010) Biopolymers , vol.94 , pp. 95-106
    • Tiefenbrunn, T.K.1    Dawson, P.E.2
  • 5
    • 70349917806 scopus 로고    scopus 로고
    • Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
    • Sletten, E. M. and Bertozzi, C. R. (2009) Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality Angew. Chem., Int. Ed. 48, 6974-6998
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6974-6998
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 6
    • 0015239274 scopus 로고
    • Studies on chemical and enzymatic modification of glycoproteins - General method for tritiation of sialic acid-containing glycoproteins
    • Van lenten, L. and Ashwell, G. (1971) Studies on chemical and enzymatic modification of glycoproteins-general method for tritiation of sialic acid-containing glycoproteins J. Biol. Chem. 246, 1889-1894
    • (1971) J. Biol. Chem. , vol.246 , pp. 1889-1894
    • Van Lenten, L.1    Ashwell, G.2
  • 7
    • 0037473202 scopus 로고    scopus 로고
    • Surface engineering of living myoblasts via selective periodate oxidation
    • DOI 10.1002/bit.10525
    • De Bank, P. A., Kellam, B., Kendall, D. A., and Shakesheff, K. M. (2003) Surface engineering of living myoblasts via selective periodate oxidation Biotechnol. Bioeng. 81, 800-808 (Pubitemid 36313718)
    • (2003) Biotechnology and Bioengineering , vol.81 , Issue.7 , pp. 800-808
    • De Bank, P.A.1    Kellam, B.2    Kendall, D.A.3    Shakesheff, K.M.4
  • 8
    • 61449097424 scopus 로고    scopus 로고
    • High-efficiency labeling of sialylated glycoproteins on living cells
    • Zeng, Y., Ramya, T. N. C., Dirksen, A., Dawson, P. E., and Paulson, J. C. (2009) High-efficiency labeling of sialylated glycoproteins on living cells Nat. Methods 6, 207-209
    • (2009) Nat. Methods , vol.6 , pp. 207-209
    • Zeng, Y.1    Ramya, T.N.C.2    Dirksen, A.3    Dawson, P.E.4    Paulson, J.C.5
  • 9
    • 34547929295 scopus 로고    scopus 로고
    • Diversity in cell surface sialic acid presentations: Implications for biology and disease
    • DOI 10.1038/labinvest.3700656, PII 3700656
    • Varki, N. M. and Varki, A. (2007) Diversity in cell surface sialic acid presentations: implications for biology and disease Lab. Invest. 87, 851-857 (Pubitemid 47267816)
    • (2007) Laboratory Investigation , vol.87 , Issue.9 , pp. 851-857
    • Varki, N.M.1    Varki, A.2
  • 11
    • 71649106024 scopus 로고    scopus 로고
    • Sialic acids in T cell development and function
    • Bi, S. and Baum, L. G. (2009) Sialic acids in T cell development and function Biochim. Biophys. Acta 1790, 1599-1610
    • (2009) Biochim. Biophys. Acta , vol.1790 , pp. 1599-1610
    • Bi, S.1    Baum, L.G.2
  • 12
    • 77449115880 scopus 로고    scopus 로고
    • Advances in the Biology and Chemistry of Sialic Acids
    • Chen, X. and Varki, A. (2010) Advances in the Biology and Chemistry of Sialic Acids ACS Chem. Biol. 5, 163-176
    • (2010) ACS Chem. Biol. , vol.5 , pp. 163-176
    • Chen, X.1    Varki, A.2
  • 13
    • 0142199949 scopus 로고    scopus 로고
    • Metabolic oligosaccharide engineering as a tool for glycobiology
    • DOI 10.1016/j.cbpa.2003.08.006
    • Dube, D. H. and Bertozzi, C. R. (2003) Metabolic oligosaccharide engineering as a tool for glycobiology Curr. Opin. Chem. Biol. 7, 616-625 (Pubitemid 37315799)
    • (2003) Current Opinion in Chemical Biology , vol.7 , Issue.5 , pp. 616-625
    • Dube, D.H.1    Bertozzi, C.R.2
  • 14
    • 0004199464 scopus 로고
    • Lymphocyte stimulation by concanavalin A
    • (Bittiger, H. and Schnebli, H. P. Eds.) pp, John Wiley & Sons, New York
    • Anderson, J. and Melchers, F. (1976) Lymphocyte stimulation by concanavalin A, in Concanavalin A as a Tool (Bittiger, H. and Schnebli, H. P., Eds.) pp 505-522, John Wiley & Sons, New York.
    • (1976) Concanavalin A As A Tool , pp. 505-522
    • Anderson, J.1    Melchers, F.2
  • 15
    • 0036798862 scopus 로고    scopus 로고
    • Ah, sweet mystery of death! Galectins and control of cell fate
    • Hernandez, J. D. and Baum, L. G. (2002) Ah, sweet mystery of death! Galectins and control of cell fate Glycobiology 12, 127R-136R (Pubitemid 35214817)
    • (2002) Glycobiology , vol.12 , Issue.10
    • Hernandez, J.D.1    Baum, L.G.2
  • 16
    • 0025856887 scopus 로고
    • The biotin-(strept)avidin system: Principles and applications in biotechnology
    • Diamandis, E. P. and Christopoulos, T. K. (1991) The biotin-(strept) avidin system: principles and applications in biotechnology Clin. Chem. 37, 625-36 (Pubitemid 21892699)
    • (1991) Clinical Chemistry , vol.37 , Issue.5 , pp. 625-636
    • Diamandis, E.P.1    Christopoulos, T.K.2
  • 17
    • 79955902283 scopus 로고    scopus 로고
    • Live Cell Labeling of Native Intracellular Bacterial Receptors Using Aniline-Catalyzed Oxime Ligation
    • Rayo, J., Amara, N., Krief, P., and Meijler, M. M. (2011) Live Cell Labeling of Native Intracellular Bacterial Receptors Using Aniline-Catalyzed Oxime Ligation J. Am. Chem. Soc. 133, 7469-7475
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 7469-7475
    • Rayo, J.1    Amara, N.2    Krief, P.3    Meijler, M.M.4
  • 18
    • 79951517827 scopus 로고    scopus 로고
    • Synthesis and Spectroscopic Characterization of Fluorescent Boron Dipyrromethene-Derived Hydrazones
    • Dilek, O. and Bane, S. (2011) Synthesis and Spectroscopic Characterization of Fluorescent Boron Dipyrromethene-Derived Hydrazones J. Fluoresc. 21, 347-354
    • (2011) J. Fluoresc. , vol.21 , pp. 347-354
    • Dilek, O.1    Bane, S.2
  • 19
    • 38349123565 scopus 로고    scopus 로고
    • Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling
    • Dilek, Ö. and Bane, S. L. (2008) Synthesis of boron dipyrromethene fluorescent probes for bioorthogonal labeling Tetrahedron Lett. 49, 1413-1416
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1413-1416
    • Dilek, Ö.1    Bane, S.L.2
  • 20
    • 62549106140 scopus 로고    scopus 로고
    • Photophysical characterization of triazole-substituted coumarin fluorophores
    • Key, J. A., Koh, S., Timerghazin, Q. K., Brown, A., and Cairo, C. W. (2009) Photophysical characterization of triazole-substituted coumarin fluorophores Dyes Pigm. 82, 196-203
    • (2009) Dyes Pigm. , vol.82 , pp. 196-203
    • Key, J.A.1    Koh, S.2    Timerghazin, Q.K.3    Brown, A.4    Cairo, C.W.5
  • 21
    • 0021412136 scopus 로고
    • Fluorogenic labeling of carbonyl compounds with 7-hydrazino-4-nitrobenzo- 2-oxa-1,3,-diazole (NBD-H)
    • Gubitz, G., Wintersteiger, R., and Frei, R. W. (1984) Fluorogenic labeling of carbonyl compounds with 7-hydrazino-4-nitrobenzo-2-oxa-1,3,-diazole (NBD-H) J. Liq. Chromatogr. 7, 839-854
    • (1984) J. Liq. Chromatogr. , vol.7 , pp. 839-854
    • Gubitz, G.1    Wintersteiger, R.2    Frei, R.W.3
  • 22
    • 0025130832 scopus 로고
    • Fluorogenic reagents: 4-aminosulphonyl-7-hydrazino-2,1,3-benzoxadiazole, 4-(N,N-dimethylaminosulphonyl)-7-hydrazino-2,1,3-benzoxadiazole and 4-hydrazino-7-nitro-2,1,3-benzoxadiazole hydrazine for aldehydes and ketones
    • Uzu, S., Kanda, S., Imai, K., Nakashima, K., and Akiyama, S. (1990) Fluorogenic Reagents-4-Aminosulphonyl-7-Hydrazino-2,1,3-Benzoxadiazole, 4-(N, N -Dimethylaminosulphonyl)-7-Hydrazino-2,1,3-Benzoxadiazole and 4-Hydrazino-7-Nitro-2,1,3-Benzoxadiazole Hydrazine for Aldehydes and Ketones Analyst 115, 1477-1482 (Pubitemid 20365497)
    • (1990) Analyst , vol.115 , Issue.11 , pp. 1477-1482
    • Uzu, S.1    Kanda, S.2    Imai, K.3    Nakashima, K.4    Akiyama, S.5
  • 23
    • 0035089879 scopus 로고    scopus 로고
    • Synthesis and application of 4-(N,N-dimethylaminosulfonyl)-7-N- methylhydrazino-2,1,3-benzoxadiazole (MDBDH) as a new derivatizing agent for aldehydes
    • Jachmann, N. and Karst, U. (2001) Synthesis and application of 4-(N,N-dimethylaminosulfonyl)-7-N-methylhydrazino-2,1,3-benzoxadiazole (MDBDH) as a new derivatizing agent for aldehydes Fresenius J. Anal. Chem. 369, 47-53 (Pubitemid 33751800)
    • (2001) Analytical and Bioanalytical Chemistry , vol.369 , Issue.1 , pp. 47-53
    • Jachmann, N.1    Karst, U.2
  • 24
    • 39349114546 scopus 로고    scopus 로고
    • Synthesis of 4-[2-(N,N-dimethylamino)ethylaminosulfonyl]- 7-N-methylhydrazino-2,1,3-benzoxadiazole (DAABD-MHz) as a derivatization reagent for aldehydes in liquid chromatography/electrospray ionization-tandem mass spectrometry
    • DOI 10.1002/bmc.903
    • Santa, T., Al-Dirbashi, O. Y., Ichibangase, T., Rashed, M. S., Fukushima, T., and Imai, K. (2008) Synthesis of 4-[2-(N, N -dimethylamino) ethylaminosulfonyl]-7-N-methylhydrazino-2,1,3-benz oxadiazole (DAABD-MHz) as a derivatization reagent for aldehydes in liquid chromatography/electrospray ionization-tandem mass spectrometry Biomed. Chromatogr. 22, 115-8 (Pubitemid 351260187)
    • (2008) Biomedical Chromatography , vol.22 , Issue.2 , pp. 115-118
    • Santa, T.1    Al-Dirbashi, O.Y.2    Ichibangase, T.3    Rashed, M.S.4    Fukushima, T.5    Imai, K.6
  • 25
    • 0039204086 scopus 로고    scopus 로고
    • N-methyl-4-hydrazino-7-nitrobenzofurazan as a new reagent for air monitoring of aldehydes and ketones
    • DOI 10.1021/ac980946f
    • Buldt, A. and Karst, U. (1999) N -methyl-4-hydrazino-7-nitrobenzofurazan as a new reagent for air monitoring of aldehydes and ketones Anal. Chem. 71, 1893-1898 (Pubitemid 29222188)
    • (1999) Analytical Chemistry , vol.71 , Issue.9 , pp. 1893-1898
    • Buldt, A.1    Karst, U.2
  • 26
    • 76249129616 scopus 로고    scopus 로고
    • Direct Polymerase Synthesis of Reactive Aldehyde-Functionalized DNA and Its Conjugation and Staining with Hydrazines
    • Raindlová, V., Pohl, R., Scaronanda, M., and Hocek, M. (2010) Direct Polymerase Synthesis of Reactive Aldehyde-Functionalized DNA and Its Conjugation and Staining with Hydrazines Angew. Chem., Int. Ed. 49, 1064-1066
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 1064-1066
    • Raindlová, V.1    Pohl, R.2    Scaronanda, M.3    Hocek, M.4
  • 27
    • 0039503890 scopus 로고    scopus 로고
    • Preparation of ring-substituted phenoxylamine derivatives
    • Miyazawa, E., Sakamoto, T., and Kikugawa, Y. (1997) Preparation of ring-substituted phenoxylamine derivatives Org. Prep. Proced. Int. 29, 594-600
    • (1997) Org. Prep. Proced. Int. , vol.29 , pp. 594-600
    • Miyazawa, E.1    Sakamoto, T.2    Kikugawa, Y.3
  • 28
    • 0001453295 scopus 로고
    • O-acylhydroxylamines 0.2. o-mesitylenesulfonyl-hydroxylamine, o-para-toluenesulfonyl-hydroxylamine and o-mesitylhydroxylamine
    • Carpino, L. A. (1960) O-acylhydroxylamines 0.2. o-mesitylenesulfonyl- hydroxylamine, o-para-toluenesulfonyl-hydroxylamine and o-mesitylhydroxylamine J. Am. Chem. Soc. 82, 3133-3135
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 3133-3135
    • Carpino, L.A.1
  • 29
    • 2942689635 scopus 로고    scopus 로고
    • Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation
    • Salahuddin, S., Renaudet, O., and Reymond, J. L. (2004) Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation Org. Biomol. Chem. 2, 1471-5
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 1471-1475
    • Salahuddin, S.1    Renaudet, O.2    Reymond, J.L.3
  • 30
    • 77956094744 scopus 로고    scopus 로고
    • Identification of fluorogenic and quenched benzoxadiazole reactive chromophores
    • Key, J. A. and Cairo, C. W. (2011) Identification of fluorogenic and quenched benzoxadiazole reactive chromophores Dyes Pigm. 88, 95-102
    • (2011) Dyes Pigm. , vol.88 , pp. 95-102
    • Key, J.A.1    Cairo, C.W.2
  • 32
    • 0001002375 scopus 로고
    • The Mechanism of Hydrolysis of Schiff Bases Derived from Aliphatic Amines
    • Cordes, E. H. and Jencks, W. P. (1963) The Mechanism of Hydrolysis of Schiff Bases Derived from Aliphatic Amines J. Am. Chem. Soc. 85, 2843-2848
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2843-2848
    • Cordes, E.H.1    Jencks, W.P.2
  • 34
    • 0029693904 scopus 로고    scopus 로고
    • Identifying the glycosylation sites and site-specific carbohydrate heterogeneity of glycoproteins by matrix-assisted laser desorption/ionization mass spectrometry
    • Yang, Y. and Orlando, R. (1996) Identifying the glycosylation sites and site-specific carbohydrate heterogeneity of glycoproteins by matrix-assisted laser desorption/ionization mass spectrometry Rapid Commun. Mass Spectrom. 10, 932-936 (Pubitemid 126680202)
    • (1996) Rapid Communications in Mass Spectrometry , vol.10 , Issue.8 , pp. 932-936
    • Yang, Y.1    Orlando, R.2
  • 35
    • 0022620597 scopus 로고
    • Binding of fluorescent 7-amino-4-nitrobenzoxadiazole derivatives to bovine serum albumin
    • Matsushita, Y., Takahashi, M., and Moriguchi, I. (1986) Binding of fluorescent 7-amino-4-nitrobenzoxadiazole derivatives to bovine serum albumin Chem. Pharm. Bull. 34, 333-9 (Pubitemid 16135919)
    • (1986) Chemical and Pharmaceutical Bulletin , vol.34 , Issue.1 , pp. 333-339
    • Masushita, Y.1    Takahashi, M.2    Moriguchi, I.3
  • 36
    • 0023127085 scopus 로고
    • Use of fluorescein hydrazide and fluorescein thiosemicarbazide reagents for the fluorometric determination of protein carbonyl groups and for the detection of oxidized protein on polyacrylamide gels
    • DOI 10.1016/0003-2697(87)90448-9
    • Ahn, B., Rhee, S. G., and Stadtman, E. R. (1987) Use of fluorescein hydrazide and fluorescein thiosemicarbazide reagents for the fluorometric determination of protein carbonyl groups and for the detection of oxidized protein on polyacrylamide gels Anal. Biochem. 161, 245-57 (Pubitemid 17045972)
    • (1987) Analytical Biochemistry , vol.161 , Issue.2 , pp. 245-257
    • Ahn, B.1    Rhee, S.G.2    Stadtman, E.R.3
  • 37
    • 79952215327 scopus 로고    scopus 로고
    • A fluorometric/colorimetric dual-channel Hg2+ sensor derived from a 4-amino-7-nitro-benzoxadiazole (ANBD) fluorophore
    • Xie, Z., Wang, K., Zhang, C., Yang, Z., Chen, Y., Guo, Z., Lu, G.-Y., and He, W. (2011) A fluorometric/colorimetric dual-channel Hg2+ sensor derived from a 4-amino-7-nitro-benzoxadiazole (ANBD) fluorophore New J. Chem. 35, 607-613
    • (2011) New J. Chem. , vol.35 , pp. 607-613
    • Xie, Z.1    Wang, K.2    Zhang, C.3    Yang, Z.4    Chen, Y.5    Guo, Z.6    Lu, G.-Y.7    He, W.8
  • 38
    • 59749091961 scopus 로고    scopus 로고
    • An NBD-based colorimetric and fluorescent chemosensor for Zn2+ and its use for detection of intracellular zinc ions
    • Xu, Z., Kim, G.-H., Han, S. J., Jou, M. J., Lee, C., Shin, I., and Yoon, J. (2009) An NBD-based colorimetric and fluorescent chemosensor for Zn2+ and its use for detection of intracellular zinc ions Tetrahedron 65, 2307-2312
    • (2009) Tetrahedron , vol.65 , pp. 2307-2312
    • Xu, Z.1    Kim, G.-H.2    Han, S.J.3    Jou, M.J.4    Lee, C.5    Shin, I.6    Yoon, J.7
  • 39
    • 0019795869 scopus 로고
    • In vivo staining of cytoskeletal actin by autointernalization of nontoxic concentrations of nitrobenzoxadiazole-phallacidin
    • DOI 10.1083/jcb.89.2.368
    • Barak, L. S., Yocum, R. R., and Webb, W. W. (1981) In vivo staining of cytoskeletal actin by autointernalization of nontoxic concentrations of nitrobenzoxadiazole-phallacidin J. Cell Biol. 89, 368-372 (Pubitemid 11081461)
    • (1981) Journal of Cell Biology , vol.89 , Issue.2 , pp. 368-372
    • Barak, L.S.1    Yocum, R.R.2    Webb, W.W.3
  • 40
    • 54749084565 scopus 로고    scopus 로고
    • Hydrolytic stability of hydrazones and oximes
    • Kalia, J. and Raines, R. T. (2008) Hydrolytic stability of hydrazones and oximes Angew. Chem., Int. Ed. 47, 7523-7526
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7523-7526
    • Kalia, J.1    Raines, R.T.2
  • 41
    • 70349392086 scopus 로고    scopus 로고
    • Aniline: A catalyst for sialic acid detection
    • Kohler, J. J. (2009) Aniline: a catalyst for sialic acid detection ChemBioChem 10, 2147-2150
    • (2009) ChemBioChem , vol.10 , pp. 2147-2150
    • Kohler, J.J.1
  • 42
    • 18744401100 scopus 로고    scopus 로고
    • Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase
    • DOI 10.1038/nmeth735
    • Chen, I., Howarth, M., Lin, W., and Ting, A. Y. (2005) Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase Nat. Methods 2, 99-104 (Pubitemid 41131030)
    • (2005) Nature Methods , vol.2 , Issue.2 , pp. 99-104
    • Chen, I.1    Howarth, M.2    Lin, W.3    Ting, A.Y.4
  • 43
    • 58849110330 scopus 로고    scopus 로고
    • A General and Efficient Method for the Site-Specific Dual-Labeling of Proteins for Single Molecule Fluorescence Resonance Energy Transfer
    • Brustad, E. M., Lemke, E. A., Schultz, P. G., and Deniz, A. A. (2008) A General and Efficient Method for the Site-Specific Dual-Labeling of Proteins for Single Molecule Fluorescence Resonance Energy Transfer J. Am. Chem. Soc. 130, 17664-17665
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 17664-17665
    • Brustad, E.M.1    Lemke, E.A.2    Schultz, P.G.3    Deniz, A.A.4
  • 44
    • 80051788053 scopus 로고    scopus 로고
    • Modified GM3 gangliosides produced by metabolic oligosaccharide engineering
    • Whitman, C. M., Yang, F., and Kohler, J. J. (2011) Modified GM3 gangliosides produced by metabolic oligosaccharide engineering Bioorg. Med. Chem. Lett. 21, 5006-5010
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 5006-5010
    • Whitman, C.M.1    Yang, F.2    Kohler, J.J.3
  • 45


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.