Pyrene-based heparin sensors in competitive aqueous media – the role of self-assembled multivalency (SAMul)

Chan, Ching Wan; Smith, David K.

doi:10.1039/c6cc00163g

Cited by 39 publications

(21 citation statements)

References 46 publications

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“…Samples with 10 % plasma suffer from insignificant differences between different heparin concentrations and from the most prominent standard deviations. Similar disruption by increasing plasma concentration in heparin binding has previously been detected in other heparin sensing systems 18 . From the minor standard deviations in 0 and 5 % plasma samples, it can be concluded that large deviations observed in the DLS data do not prevent accurate sensing.…”

supporting

confidence: 77%

“…From these results, it can be concluded that R16+ and P10+ are the most promising alternatives for heparin binding and sensing. Overall, based on the differences observed here and in the previous studies on the electrostatic binding of heparin 16,18 , multivalency has a high importance in the competitive heparin binding. ITC measurements were conducted to further understand the thermodynamics of the host-heparin binding.…”

contrasting

confidence: 49%

“…Many colorimetric [10][11][12][13][14] and fluorescent [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] heparin sensors with different functionalities and varying structures from small molecules 11,14,[18][19][20][21][22] and host-guest complexes 16,24 to synthetic polymers 12,[27][28][29] and peptides 31,32 have been developed. For instance, a boronic acid based receptor utilizing preorganization of the structure provided a colorimetric heparin indication system capable in selective heparin binding.…”

Section: Introductionmentioning

confidence: 99%

“…57 The increased heparin binding affinity could, for instance, be achieved by further enhancing the multivalency or by increasing the sensor concentration. 18 Binding affinity can also be enhanced by increasing the binding surface allowing more simultaneous interactions with heparin. 15 On the other hand, by lowering the hostguest binding affinity, which based on the ITC measurement is high, one could more easily release the guest from the host cavity upon heparin binding.…”

mentioning

confidence: 99%

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A supramolecular host–guest complex for heparin binding and sensing

et al. 2018

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Heparin is an anionic polysaccharide widely used in clinics as an anticoagulant. However, heparin usage requires an antidote and sensors for safe operation during and after surgeries. In this study, a host-guest complex capable of selective heparin binding and sensing is presented. Heparin binding affinity was studied in solution with a variety of polycationic macrocyclic hosts, a pillar[5]arene and multiple resorcin[4]arenes, by dynamic light scattering, dye displacement assay, isothermal titration calorimetry, and anti-Xa assay. The measurements reveal the significant importance of multivalency in electrostatic host-heparin binding in competitive, application-relevant media. Additionally, to monitor the heparin concentration, a host-guest indicator displacement assay was performed by following the free and bound state of the methyl orange dye in UV-Vis spectroscopic experiments. Furthermore, this colorimetric sensing based on the tertiary host-guest-heparin supramolecular assembly was utilized in the construction of a calibration curve in a range of blood plasma concentrations.

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supporting

confidence: 77%

contrasting

confidence: 49%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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A supramolecular host–guest complex for heparin binding and sensing

et al. 2018

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“…We therefore developed a heparin sensor incorporating pyrene. 61 In buffered water, the sensor formed self-assembled multivalent (SAMul) nanostructures providing it with a significant (order of magnitude) improvement in dynamic range. Further, it gave a naked eye response unlike other pyrene derivatives.…”

Section: How Major Surgery Inspired Samul Heparin Binders and Sensorsmentioning

confidence: 99%

From fundamental supramolecular chemistry to self-assembled nanomaterials and medicines and back again – how Sam inspired SAMul

Smith

2018

Chem. Commun.

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This feature article provides a personal insight into the research from my group over the past 10 years. In particular, the article explains how, inspired in 2005 by meeting my now-husband, Sam, who had cystic fibrosis, and who in 2011 went on to have a double lung transplant, I took an active decision to follow a more applied approach to some of our research, attempting to use fundamental supramolecular chemistry to address problems of medical interest. In particular, our strategy uses self-assembly to fabricate biologically-active nanosystems from simple low-molecular-weight building blocks. These systems can bind biological polyanions in highly competitive conditions, allowing us to approach applications in gene delivery and coagulation control. In the process, however, we have also developed new fundamental principles such as self-assembled multivalency (SAMul), temporary 'on-off' multivalency, and adaptive/shape-persistent multivalent binding. By targeting materials with applications in drug formulation and tissue engineering, we have discovered novel self-assembling low-molecular-weight hydrogelators based on the industrially-relevant dibenzylidenesorbitol framework and developed innovative approaches to spatially-resolved gels and functional multicomponent hybrid hydrogels. In this way, taking an application-led approach to research has also delivered significant academic value and conceptual advances. Furthermore, beginning to translate fundamental supramolecular chemistry into real-world applications, starts to demonstrate the power of this approach, and its potential to transform the world around us for the better.

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Glycosaminoglycan‐Induced Emissive J‐Aggregate Formation in a meso‐Ester BODIPY Dye

Kim

Lee

Bouffard

et al. 2020

Advanced Optical Materials

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The analyte‐directed formation of emissive J‐aggregates of a meso‐ester BODIPY dye is explored in the design of fluorescence “light‐up” probes. The heparin‐specific pyridinium‐functionalized meso‐ester BODIPY dye C10‐Py+ self‐assembles in aqueous buffer into spherical aggregated nanostructures with spectroscopic features indistinguishable from the monomeric dye (signal off). In the presence of heparin, the aggregated assemblies rearrange and associate with heparin through charge‐pairing interactions, triggering the spontaneous formation of emissive J‐type aggregates (signal on). The heparin‐induced J‐aggregate formation of C10‐Py+ provides an excellent “turn‐on” signal with large spectral shifts. The response is highly selective for heparin over other closely related glycosaminoglycan (GAG) analogues, sensitive, fast, and operationally simple. Assays for heparin in human serum, and for the adulterant OSCS in heparin are demonstrated, confirming the reliability and robustness of the J‐aggregation approach using meso‐ester BODIPY dyes in the design of aggregation‐induced emission (AIE)‐based fluorogenic probes.

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Pyrene-based heparin sensors in competitive aqueous media – the role of self-assembled multivalency (SAMul)

Cited by 39 publications

References 46 publications

A supramolecular host–guest complex for heparin binding and sensing

A supramolecular host–guest complex for heparin binding and sensing

From fundamental supramolecular chemistry to self-assembled nanomaterials and medicines and back again – how Sam inspired SAMul

Glycosaminoglycan‐Induced Emissive J‐Aggregate Formation in a meso‐Ester BODIPY Dye

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