Dansylation of hydroxyl and carboxylic acid functional groups

Bartzatt, Ronald

doi:10.1016/s0165-022x(00)00136-6

Cited by 22 publications

(18 citation statements)

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“…To address this question, aggrecan was fluorescently labeled with dansyl chloride (42,43), a conjugation that did not interfere with HA binding (Fig. 8G).…”

Section: Discussionmentioning

confidence: 99%

Extracellular Processing of the Cartilage Proteoglycan Aggregate and Its Effect on CD44-mediated Internalization of Hyaluronan

Danielson

Knudson

2015

Journal of Biological Chemistry

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In many cells hyaluronan receptor CD44 mediates the endocytosis of hyaluronan and its delivery to endosomes/lysosomes. The regulation of this process remains largely unknown. In most extracellular matrices hyaluronan is not present as a free polysaccharide but often is found in complex with other small proteins and macromolecules such as proteoglycans. This is especially true in cartilage, where hyaluronan assembles into an aggregate structure with the large proteoglycan termed aggrecan. In this study when purified aggrecan was added to FITC-conjugated hyaluronan, no internalization of hyaluronan was detected. This suggested that the overall size of the aggregate prevented hyaluronan endocytosis and furthermore that proteolysis of the aggrecan was a required prerequisite for local, cell-based turnover of hyaluronan. To test this hypothesis, limited C-terminal digestion of aggrecan was performed to determine whether a size range of aggrecan exists that permits hyaluronan endocytosis. Our data demonstrate that only limited degradation of the aggrecan monomer was required to allow for hyaluronan internalization. When hyaluronan was combined with partially degraded, dansyl chloride-labeled aggrecan, blue fluorescent aggrecan was also visualized within intracellular vesicles. It was also determined that sonicated hyaluronan of smaller molecular size was internalized more readily than high molecular mass hyaluronan. However, the addition of intact aggrecan to hyaluronan chains sonicated for 5 and 10 s reblocked their endocytosis, whereas aggregates containing 15-s sonicated hyaluronan were internalized. These data suggest that hyaluronan endocytosis is regulated in large part by the extracellular proteolytic processing of hyaluronan-bound proteoglycan.

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“…To address this question, aggrecan was fluorescently labeled with dansyl chloride (42,43), a conjugation that did not interfere with HA binding (Fig. 8G).…”

Section: Discussionmentioning

confidence: 99%

Extracellular Processing of the Cartilage Proteoglycan Aggregate and Its Effect on CD44-mediated Internalization of Hyaluronan

Danielson

Knudson

2015

Journal of Biological Chemistry

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“…On the other hand, a very sensitive detection occurs for molecules containing an abstractable proton and, therefore, undergoing dansylation. Such molecules include phenols (other than estrogens), carboxylic acids, and amines [23]. In that fashion, steroidal estrogens and phytoestrogens can be analyzed in the same assay.…”

Section: Discussionmentioning

confidence: 99%

Analysis of urinary estrogens, their oxidized metabolites, and other endogenous steroids by benchtop orbitrap LCMS versus traditional quadrupole GCMS

et al. 2011

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Estrogens and other endogenous steroids are known risk markers for cancer. Gas chromatography (GC) with mass spectrometry (MS) has traditionally predominated the analysis of estrogens and other endogenous steroids but liquid chromatography (LC) MS is increasingly favored. Direct comparisons of the two technologies have hitherto not been performed. Steroids were analyzed in urine from 232 premenopausal women in a blinded fashion by benchtop orbitrap LCMS and single quadrupole GCMS. 16 steroidal estrogens including oxidized metabolites could be analyzed by LCMS. LCMS-GCMS Spearman rank correlations of the major estrogens E1, E2, E3, 16α-OHE1, and 2-OHE1 were very high (r=0.72–0.91), and absolute concentrations also agreed (<5% difference for E1, E2, E3, 16α-OHE1). LCMS allowed reinterrogation of acquired data due to orbitrap technology, which permitted post-analysis quantitation of progesterone, cortisol, and cortisone (LCMS-GCMS Spearman rank correlations=0.80–0.84; absolute difference <7%; n=137). GCMS allows the measurement of a wide range of steroids including non-polar analytes that escape the presented LCMS assay. In contrast, orbitrap based LCMS can detect more estrogens, is faster, less costly, allows post data acquisition reinterrogation of certain analytes that had not been targeted a priori, and requires much less urine.

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“…Dansyl chloride is a reagent that reacts with some primary, secondary amines, carboxyl and phenols to yield a highly fluorescent derivatives [10][11][12]. AZH was determined spectrofluorimetrically by derivatiza tion with dansyl chloride.…”

Section: Derivatizationmentioning

confidence: 99%

Sensitive spectrofluorimetric determination of alfuzosin in pharmaceutical preparations and human urine using dansyl chloride

Karasakal

Ulu

2015

J Anal Chem

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A sensitive and selective spectrofluorimetric method was developed for the determination of alfu zosin in pharmaceutical preparations and urine. The method is based on reaction of alfuzosin with 1 dime thylaminonaphthalene 5 sulphonyl (dansyl) chloride in carbonate buffer of pH 9.7 to yield a highly fluores cent derivative that is measured at 516 nm after excitation at 405 nm. The developed method was validated according to the criteria for analytical method, showing good performances in terms of linearity, limit of detection (LOD), limit of quantification (LOQ), precision, accuracy, recovery and robustness. The fluores cence intensity versus concentration plot was rectilinear over the range of 25 to 500 ng/mL. The LOD and LOQ were found to be 8 and 25 ng/mL, respectively. The method was successfully applied to the determina tion of alfuzosin in pharmaceutical preparations and urine.

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Dansylation of hydroxyl and carboxylic acid functional groups

Cited by 22 publications

References 1 publication

Extracellular Processing of the Cartilage Proteoglycan Aggregate and Its Effect on CD44-mediated Internalization of Hyaluronan

Extracellular Processing of the Cartilage Proteoglycan Aggregate and Its Effect on CD44-mediated Internalization of Hyaluronan

Analysis of urinary estrogens, their oxidized metabolites, and other endogenous steroids by benchtop orbitrap LCMS versus traditional quadrupole GCMS

Sensitive spectrofluorimetric determination of alfuzosin in pharmaceutical preparations and human urine using dansyl chloride

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