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Chemical Compound Review

Dansyl     5-dimethylaminonaphthalene-1- sulfonyl...

Synonyms: DNSCl, DNS], DNS chloride, AG-C-79147, CHEBI:51907, ...
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Disease relevance of Dansyl

  • Isolated sigma subunit labeled with the fluorescent probe dansyl (DNS) chloride bound stoichiometrically to core polymerase and stimulated transcription of phage T7 DNA to the same extent as did unlabeled sigma [1].
  • Using thin layer chromatography and field desorption mass spectrometry of the amine dansyl derivatives a comparative study was made of the faecal amines of 13 selected infants with gastroenteritis (diarrhoea) and of 13 healthy infants. p-Tyramine, the most abundant amine, was significantly higher (p = 0.02) in the sick infants [2].
  • Exposure of purified influenza virions to [14C]dansyl chloride resulted in the covalent attachment of the dansyl chromophore to the virion [3].
  • Functional lac carrier proteins in cytoplasmic membrane vesicles isolated from Escherichia coli. 1. Temperature dependence of dansyl galactoside binding and beta-galactoside transport [4].
  • In order to monitor the intermediates involved in nascent peptidoglycan (PG) assembly in Gaffkya homari, a pulse/chase assay utilizing UDP-MurNAc-Ala-DGlu-Lys(N epsilon-Dns)-DAla-DAla [Dns (dansyl) = 5-(dimethylamino)naphthalene-1-sulfonyl] was devised [5].

Psychiatry related information on Dansyl

  • The optimal conditions were: amine solution buffered at pH 12, 2 mM dansyl chloride (acetone-bicarbonate solution 20 mM (pH 9-9.5), 2 + 3 v/v) as reagent concentration, room temperature and 30 min reaction time [6].

High impact information on Dansyl

  • A family of chimeric immunoglobulins (Igs) bearing the murine variable region directed against the hapten dansyl linked to human IgG1, -2, -3, and -4 has been characterized with respect to binding to the human high affinity Fc gamma receptor, Fc gamma RI [7].
  • The dansyl label was subsequently immunolocalized in the epidermis, dermal connective tissue, and along the basement membrane [8].
  • One predominant glutaminyl substrate (amine acceptor) in the chondrocyte matrix is osteonectin as revealed by incorporation of the dansyl label in culture [9].
  • These results, in conjunction with the microscopic localization, suggest that the dansyl-labeled proteins are constituents of the myofibril Z line [10].
  • The structure consistent with both distance constraints and direct perturbations of the dansyl fluorophores placed the proteinase at the distal end of the serpin from the initial docking site [11].

Chemical compound and disease context of Dansyl


Biological context of Dansyl

  • For that purpose, the association of the monoclonal antibodies with either the beta 2 subunit or its isolated domains was studied by using fluorescence energy transfer between tryptophan residues of the antibodies and a dansyl group covalently linked to the antigen [14].
  • The amino acid sequence of neuropeptide Y, a 36-residue peptide recently isolated from porcine brain, has been determined by using high performance liquid chromatography for separation of its tryptic and chymotryptic fragments and subsequent sequence analysis of the isolated fragments by an improved dansyl Edman subtractive technique [15].
  • An extracellular region of DAF was joined to an antibody combining site with specificity for the hapten dansyl, at the end of either C(H)1 or C(H)3 Ig regions [16].
  • Only slight differences were also observed between lambda and kappa molecules in their kinetics of binding to and dissociation from the hapten dansyl [17].
  • The activation of platelets by NBD-PS is not attributable to the NBD moiety exclusively since acylation of the amino group with 5-dimethylaminonaphthalene-1-sulfonyl-chloride yielded a similarly active derivative [18].

Anatomical context of Dansyl

  • The covalently binding fluorescent probe 5-dimethylamino-1-naphthalenesulfonyl (dansyl) chloride was affixed directly to the plasma membrane of viable human peripheral blood lymphocytes via a solid phase transfer method utilizing Sephadex G-10 as the transfer vehicle [19].
  • Each of these 13 C alpha genes, C alpha 1-C alpha 13, was subcloned into an expression vector containing the VDJ (V, variable; D, diversity; J, joining) gene of a dansyl (DNS)-binding hybridoma antibody [20].
  • Factor IX-(1-47) bound to phospholipid membranes, as monitored by energy transfer from intrinsic fluorophores to dansyl (5-dimethylaminonaphthalene-1-sulfonyl)-phosphatidylethanolamine incorporated into a lipid bilayer composed of phosphatidylserine:phosphatidylcholine [21].
  • We have extended these studies by producing the same dansyl-specific IgG1 in cell lines deficient in attachment of sialic acid (Lec 2) and galactose (Lec 8) [22].
  • The adult frequencies for Ars and Dansyl in conventionally reared BALB/c mice are 1.5 +/- 0.3/10(5) B cells and 9.4 +/- 3.3/10(5) Bcells, respectively [23].

Associations of Dansyl with other chemical compounds

  • Oligopeptide substrates of porcine pepsin (E) of the type A-Phe-Phe-B (S) that are cleaved solely at the Phe-Phe bond under the conditions of these studies, and bearing an amino-terminal fluorescent probe group (mansyl or dansyl), have been used for stopped-flow measurements of the rate of formation of the A-Phe product [24].
  • The level of dansyl fluorescence exhibited by cells after incubation with DAAA paralleled cytosolic ALDH levels determined by Western blotting and the sensitivity of the cells to cyclophosphamide [25].
  • The binding of fVIIIa to membrane-bound Fl-A-FPR-fIXa or DEGR-fIXa did not alter the location of the active site relative to the membrane surface, but did alter both the emission intensity and anisotropy of the fluorescein and dansyl probes and hence their environments [26].
  • Autoradiographic studies and the use of inhibitors of endocytosis, such as dansyl cadaverine, confirmed that endocytosis of elastase was the secondary event after cell binding [27].
  • From the efficiency of fluorescence resonance energy transfer, distances of closest approach of approximately 63 and approximately 64 A were estimated between the dansyl on DEGR-APC and rhodamine in PC/PS/GlcCer(OR) and PC/PS(OR), respectively, assuming kappa(2) = 2/3 [28].

Gene context of Dansyl

  • The IgG3-IGF1 chimeric protein retained its specificity for the antigen dansyl [29].
  • A quantitative analysis obtained with dansyl (5-dimethylaminonaphthalene-1-sulfonyl)-calmodulin showed that myristoylated MARCKS has an affinity higher than the non-myristoylated protein [30].
  • The binding affinity between the TBD and cyclin T1 was analyzed with fluorescence spectroscopy methods, using a dansyl-based fluorescence label at position G257C [31].
  • 9. The dissociation of enolase appears to take place over a significantly smaller range (1.7 units), and dansyl conjugates of enolase show an even narrower range (0.9 unit) [32].
  • Employing the latter system, we have titrated the transglutaminase-reactive sites of vimentin and, by sequencing the dansyl-tracer-labeled segments of the protein, we have shown that residues Gln453 and Gln460 served as acceptor functionalities and Lys97, Lys104, Lys294, and Lys439 as electron donor functionalities in vimentin [33].

Analytical, diagnostic and therapeutic context of Dansyl

  • The effect of temperature from 5 degrees C to 50 degrees C on the retention of dansyl derivatives of amino acids in hydrophobic interaction chromatography (HIC) was investigated by HPLC on three stationary phases [34].
  • In the present work the COOH-terminal fragments of polypeptides containing characteristic alpha-amide groups were released enzymatically and then converted into the fluorescent dansyl derivatives, which were identified by thin-layer chromatography [35].
  • Of the 13 resulting transfectomas, 12 were shown by ELISA to secrete DNS-binding chimeric rabbit-mouse IgA molecules [20].
  • Purification of the M protein by gel filtration followed by cyanogen bromide cleavage and peptide fractionation revealed that four of six peptide peaks contained dansyl label [3].
  • The macrocyclic antibiotic A35512B was examined as a chiral selector for capillary electrophoresis (CE) using thirteen racemic dansyl amino acids as test analytes [36].


  1. Sigma cycle during in vitro transcription: demonstration by nanosecond fluorescence depolarization spectroscopy. Wu, C.W., Yarbrough, L.R., Hillel, Z., Wu, F.Y. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  2. Studies of the free faecal amines of infants with gastroenteritis and of healthy infants. Murray, K.E., Adams, R.F., Earl, J.W., Shaw, K.J. Gut (1986) [Pubmed]
  3. Selective dansylation of M protein within intact influenza virions. Robertson, B.H., Bennett, J.C., Compans, R.W. J. Virol. (1982) [Pubmed]
  4. Functional lac carrier proteins in cytoplasmic membrane vesicles isolated from Escherichia coli. 1. Temperature dependence of dansyl galactoside binding and beta-galactoside transport. Therisod, H., Letellier, L., Weil, R., Shechter, E. Biochemistry (1977) [Pubmed]
  5. Intramembranal events in the biosynthesis of peptidoglycan in Gaffkya homari. Manteuffel, R.L., Neuhaus, F.C. Biochemistry (1987) [Pubmed]
  6. Urine polyamines determination using dansyl chloride derivatization in solid-phase extraction cartridges and HPLC. Molins-Legua, C., Campíns-Falcó, P., Sevillano-Cabeza, A., Pedrón-Pons, M. The Analyst. (1999) [Pubmed]
  7. The binding affinity of human IgG for its high affinity Fc receptor is determined by multiple amino acids in the CH2 domain and is modulated by the hinge region. Canfield, S.M., Morrison, S.L. J. Exp. Med. (1991) [Pubmed]
  8. Cross-linking of the dermo-epidermal junction of skin regenerating from keratinocyte autografts. Anchoring fibrils are a target for tissue transglutaminase. Raghunath, M., Höpfner, B., Aeschlimann, D., Lüthi, U., Meuli, M., Altermatt, S., Gobet, R., Bruckner-Tuderman, L., Steinmann, B. J. Clin. Invest. (1996) [Pubmed]
  9. Transglutaminase-catalyzed matrix cross-linking in differentiating cartilage: identification of osteonectin as a major glutaminyl substrate. Aeschlimann, D., Kaupp, O., Paulsson, M. J. Cell Biol. (1995) [Pubmed]
  10. Specific fluorescent labeling of chicken myofibril Z-line proteins catalyzed by guinea pig liver transglutaminase. Gard, D.L., Lazarides, E. J. Cell Biol. (1979) [Pubmed]
  11. Formation of the covalent serpin-proteinase complex involves translocation of the proteinase by more than 70 A and full insertion of the reactive center loop into beta-sheet A. Stratikos, E., Gettins, P.G. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  12. A predictive assay for human tumor cellular response to hyperthermia using dansyl lysine staining and flow cytometry. Woo, S.Y., Rice, G.C., Kapp, D.S., Hahn, G.M. Int. J. Radiat. Oncol. Biol. Phys. (1988) [Pubmed]
  13. Factor XIII (fibrin stabilising factor) in Henoch-Schönlein's purpura. Henriksson, P., Hedner, U., Nilsson, I.M. Acta paediatrica Scandinavica. (1977) [Pubmed]
  14. Partly native epitopes are already present on early intermediates in the folding of tryptophan synthase. Blond, S., Goldberg, M. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  15. Neuropeptide Y: complete amino acid sequence of the brain peptide. Tatemoto, K. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  16. Targeting of functional antibody-decay-accelerating factor fusion proteins to a cell surface. Zhang , H., Lu, S., Morrison, S.L., Tomlinson, S. J. Biol. Chem. (2001) [Pubmed]
  17. Influence of the isotype of the light chain on the properties of IgG. Montaño, R.F., Morrison, S.L. J. Immunol. (2002) [Pubmed]
  18. Activation of human platelets by N-substituted aminophospholipids. Martin, T.W., Joist, J.H., Bauman, J.E., Lagunoff, D. J. Biol. Chem. (1985) [Pubmed]
  19. Retention of susceptibility to mitogens after direct dansylation of viable human lymphocytes. Coleman, P.S., Ewell, A.J., Good, R.A. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  20. Expression of 12 rabbit IgA C alpha genes as chimeric rabbit-mouse IgA antibodies. Schneiderman, R.D., Hanly, W.C., Knight, K.L. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  21. Membrane binding properties of the factor IX gamma-carboxyglutamic acid-rich domain prepared by chemical synthesis. Jacobs, M., Freedman, S.J., Furie, B.C., Furie, B. J. Biol. Chem. (1994) [Pubmed]
  22. Effect of C2-associated carbohydrate structure on Ig effector function: studies with chimeric mouse-human IgG1 antibodies in glycosylation mutants of Chinese hamster ovary cells. Wright, A., Morrison, S.L. J. Immunol. (1998) [Pubmed]
  23. The frequency of para-azophenylarsonate and dimethylaminonapthalene-sulfonyl-specific B cells in neonatal and adult BALB/c mice. Sigal, N.H. J. Immunol. (1977) [Pubmed]
  24. Kinetics of action of pepsin on fluorescent peptide substrates. Sachdev, G.P., Fruton, J.S. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  25. Assessment of aldehyde dehydrogenase in viable cells. Jones, R.J., Barber, J.P., Vala, M.S., Collector, M.I., Kaufmann, S.H., Ludeman, S.M., Colvin, O.M., Hilton, J. Blood (1995) [Pubmed]
  26. The active site of factor IXa is located far above the membrane surface and its conformation is altered upon association with factor VIIIa. A fluorescence study. Mutucumarana, V.P., Duffy, E.J., Lollar, P., Johnson, A.E. J. Biol. Chem. (1992) [Pubmed]
  27. Receptor-mediated binding of leukocyte elastase by chondrocytes. Bartholomew, J.S., Lowther, D.A. Arthritis Rheum. (1987) [Pubmed]
  28. Glucosylceramide, a neutral glycosphingolipid anticoagulant cofactor, enhances the interaction of human- and bovine-activated protein C with negatively charged phospholipid vesicles. Yegneswaran, S., Deguchi, H., Griffin, J.H. J. Biol. Chem. (2003) [Pubmed]
  29. Expression and characterization of an antibody binding specificity joined to insulin-like growth factor 1: potential applications for cellular targeting. Shin, S.U., Morrison, S.L. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  30. Direct involvement of protein myristoylation in myristoylated alanine-rich C kinase substrate (MARCKS)-calmodulin interaction. Matsubara, M., Titani, K., Taniguchi, H., Hayashi, N. J. Biol. Chem. (2003) [Pubmed]
  31. Identification of a cyclin T-binding domain in Hexim1 and biochemical analysis of its binding competition with HIV-1 Tat. Schulte, A., Czudnochowski, N., Barboric, M., Schönichen, A., Blazek, D., Peterlin, B.M., Geyer, M. J. Biol. Chem. (2005) [Pubmed]
  32. Dynamics and time-averaged chemical potential of proteins: importance in oligomer association. Xu, G., Weber, G. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  33. The intermediate filament protein, vimentin, in the lens is a target for cross-linking by transglutaminase. Clément, S., Velasco, P.T., Murthy, S.N., Wilson, J.H., Lukas, T.J., Goldman, R.D., Lorand, L. J. Biol. Chem. (1998) [Pubmed]
  34. Temperature effects in hydrophobic interaction chromatography. Haidacher, D., Vailaya, A., Horváth, C. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  35. Chemical determination of polypeptide hormones. Tatemoto, K., Mutt, V. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  36. Enantiomeric separations of dansyl amino acids using the macrocyclic antibiotic A35512B as a chiral selector in capillary electrophoresis. Risley, D.S., Trelli-Seifert, L., McKenzie, Q.J. Electrophoresis (1999) [Pubmed]
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