Pattern‐Based Recognition of Heparin Contaminants by an Array of Self‐Assembling Fluorescent Receptors

Jagt, Richard B. C.; Gómez‐Biagi, Rodolfo F.; Nitz, Mark

doi:10.1002/anie.200805238

Cited by 68 publications

(50 citation statements)

References 28 publications

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“…In contrast, fluorescent/colorimetric assays are more direct, efficient and convenient in operation. Some typical fluorescent/colorimetric heparin assays reported recently are summarized in Table 1 [63][64][65][66][67][68][69][70][71]. In general, CPE-based methods generally have a boarder detecting window, allowing for quantification of heparin over the whole therapeutic dosing level.…”

Section: Comparison With Other Methodsmentioning

confidence: 99%

Conjugated polyelectrolytes for label-free visual detection of heparin

Zhan

Liang

et al. 2011

Sci. China Chem.

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Conjugated polyelectrolytes (CPEs), with electron-delocalized backbones and charged ionic side chains, are unique sensory materials for the construction of optical biosensors. In this feature article, CPE-based visual detection of heparin is summarized. Three CPE-based heparin probes, including ratiometric, light-up and colormetric probes, are discussed in terms of molecular design, detection selectivity and quantification capability. The work summarized here provides fundamental guidelines for CPE-based label-free visual sensing. conjugated polyelectrolyte, heparin, fluorescence resonance energy transfer, sensor

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Section: Comparison With Other Methodsmentioning

confidence: 99%

Conjugated polyelectrolytes for label-free visual detection of heparin

Zhan

Liang

et al. 2011

Sci. China Chem.

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“…[1] The formation of b-CD host-guest complexes have been applied in av ariety of areas including drug delivery,a sc omponents in commercial products and for enantiomeric separations. [1][2][3][4][5][6][7] While native bCDs possess this innate property, their applications are limited due to their lack of functionality.I nc ontrast, derivatized CDs feature ab roaderr ange of applications including catalysis, [1,8] polymer assembly, [9] molecular recognition of organic and biomacromolecules, [10][11][12] and targeted drug/DNA delivery. [2] While am ultitude of applications exist for functionalized b-CDs, access to complex heterofunctionalized derivativesi sc urrently hindered by the lack of efficient synthetic methods.…”

Section: Introductionmentioning

confidence: 99%

“…Amine-functionalized CD 1 is av ersatile scaffold, which has been used for the design of fluorescent sensors, [10,45] synthetic receptors, [46] investigated as ap recursor to forming glycoclusters, [47] controlling protein self-assembly, [48] DNA transfection, [49] and as an inhibitor of anthraxl ethal toxin. [50][51][52][53] In these examples, the amine groups of 1 were either per-functionalized, or monofunctionalized nonselectively with desired reagents.…”

Section: Introductionmentioning

confidence: 99%

Access to Versatile β‐Cyclodextrin Scaffolds through Guest‐Mediated Monoacylation

Vurgun

Gómez‐Biagi

Nitz

2015

Chemistry A European J

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Herein, we report the selective mono-derivatization of heptakis[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD (1) through a guest-mediated covalent capture strategy. The use of guests functionalized with cleavable linkers enables the installation of an amine-orthogonal thiol group on the primary rim of 1 as a handle for further transformations to the β-CD scaffold. Applying this methodology, two novel monoderivatized β-CDs were obtained in good yield and high purity. Both of these monoacylated CDs were amenable to facile linker cleavage and further modification at the resulting thiol group. This methodology can be applied towards the synthesis heterofunctionalized β-CD constructs for analyte sensing, drug delivery, and other applications.

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“…12,13 However, development of additional, orthogonal assays that can rapidly and sensitively detect the presence of potential contaminants, if present, is warranted. To this end, there have been several reports of potential methods, including ion exchange HPLC, 10 quantitative capillary electrophoresis, 14 inhibition of Taq polymerase in a real-time PCR, 15 a fluorescent receptor array, 16 and use of potentiometric polyanion sensors. 17 …”

mentioning

confidence: 99%

Competitive Inhibition of Heparinase by Persulfonated Glycosaminoglycans: A Tool to Detect Heparin Contamination

et al. 2011

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Heparin and the low molecular weight heparins are extensively used as medicinal products to prevent and treat the formation of venous and arterial thrombi. In early 2008, administration of some heparin lots was associated with the advent of severe adverse effects, indicative of an anaphylactoid-like response. Application of orthogonal analytical tools enabled detection and identification of the contaminant as oversulfated chondroitin sulfate (OSCS) was reported in our earlier report. Herein, we investigate whether enzymatic depolymerization using the bacterially derived heparinases, given the structural understanding of their substrate specificity, can be used to identify the presence of OSCS in heparin. We also extend this analysis to examine the effect of other persulfonated glycosaminoglycans (GAGs) on the action of the heparinases. We find that all persulfonated GAGs examined were effective inhibitors of heparinase I, with IC50 values ranging from approximately 0.5–2 µg/mL. Finally, using this biochemical understanding, we develop a rapid, simple assay to assess the purity of heparin using heparinase digestion followed by size-exclusion HPLC analysis to identify and quantify digestion products. In the context of the assay, we demonstrate that less than 0.1% (w/w) of OSCS (and other persulfonated polysaccharides) can routinely be detected in heparin.

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Pattern‐Based Recognition of Heparin Contaminants by an Array of Self‐Assembling Fluorescent Receptors

Cited by 68 publications

References 28 publications

Conjugated polyelectrolytes for label-free visual detection of heparin

Conjugated polyelectrolytes for label-free visual detection of heparin

Access to Versatile β‐Cyclodextrin Scaffolds through Guest‐Mediated Monoacylation

Competitive Inhibition of Heparinase by Persulfonated Glycosaminoglycans: A Tool to Detect Heparin Contamination

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