Electronic communication of cells with a surface mediated by boronic acid saccharide interactions

Stephenson-Brown, Alexander; Yong, Sue; Mansor, Muhammad H.; Hussein, Zarrar; Yip, Nga Chi; Mendes, Paula M.; Fossey, John S.; Rawson, Frankie J.

doi:10.1039/c5cc04311e

Cited by 12 publications

(6 citation statements)

References 39 publications

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“…1 Accurate detection of saccharides could have an impact on clinical diagnosis of several diseases. 3 In past decades progress in synthetic molecular probes (chemosensors) has shown significant promise. 2 As a result, the development of sensing techniques to target these cancer biomarkers are in high demand.…”

Section: Introductionmentioning

confidence: 99%

“Click-fluors”: triazole-linked saccharide sensors

et al. 2016

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A series of boronic acid-containing saccharide receptors was synthesised via copper catalysed azidealkyne cycloaddition (CuAAC) reactions. Their saccharide binding capacity was studied by 1 H and 11 B NMR spectroscopy titrations and isothermal titration calorimetry (ITC) techniques. Fluorescent sensors were generated by linking a phenylboronic acid (PBA) receptor with fluorophores via a triazole-linker. Fluorescence titrations with fructose revealed that the substitution pattern about the PBA influences the fluorescence response to saccharides. Titrations studied by 1 H NMR spectroscopy suggested that fructose binding is enhanced when the aromatic ring bearing the boronic acid has the triazole-containing substituent at the ortho position. No evidence of either a dative N-B bond or solvent insertion (between B and N) was observed by 11 B NMR spectroscopy. These results demonstrate that synthetic accessible triazole receptors may allow rapid sensor synthesis, screening and discovery. † Electronic supplementary information (ESI) available. CCDC 1475996 and 1475987. For ESI and crystallographic data in CIF or other electronic format see

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Section: Introductionmentioning

confidence: 99%

“Click-fluors”: triazole-linked saccharide sensors

et al. 2016

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“…Currents can polarise a) single cells and b) tissues. Black arrows indicate the direction of the electrical currents whereas red arrows indicate the direction of the resulting polarised behaviour (Chang and Minc 2014) the saccharide groups of the eukaryotic cells that facilitate electron transfer (Stephenson-Brown et al 2015). In addition, structures integrated with biological components such as enzymes, lipid bilayers or antibodies are used to transduce ions into electrical currents and vice-versa for recording and stimulation of biological reactions in both intracellular and extracellular environments (Strakosas et al 2017).…”

Section: Improving Electronic Targeting: An Electrochemical Approachmentioning

confidence: 99%

Electrochemically stimulating developments in bioelectronic medicine

et al. 2018

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Cellular homeostasis is in part controlled by biological generated electrical activity. By interfacing biology with electronic devices this electrical activity can be modulated to actuate cellular behaviour. There are current limitations in merging electronics with biology sufficiently well to target and sense specific electrically active components of cells. By addressing this limitation, researchers give rise to new capabilities for facilitating the two-way transduction signalling mechanisms between the electronic and cellular components. This is required to allow significant advancement of bioelectronic technology which offers new ways of treating and diagnosing diseases. Most of the progress that has been achieved to date in developing bioelectronic therapeutics stimulate neural communication, which ultimately orchestrates organ function back to a healthy state. Some devices used in therapeutics include cochlear and retinal implants and vagus nerve stimulators. However, all cells can be impacted by electrical inputs which gives rise to the opportunity to broaden the use of bioelectronic medicine for treating disease. Electronic actuation of non-excitable cells has been shown to lead to 'programmed' cell behaviour via application of electronic input which alter key biological processes. A neglected form of cellular electrical communication which has not yet been considered when developing bioelectronic therapeutics is faradaic currents. These are generated during redox reactions. A precedent of electrochemical technology being used to modulate these reactions, thereby controlling cell behaviour, has already been set. In this mini review we highlight the current state of the art of electronic routes to modulating cell behaviour and identify new ways in which electrochemistry could be used to contribute to the new field of bioelectronic medicine.

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Section: Boronic Acid For Imaging Carbohydratesmentioning

confidence: 99%

“…51,52 In terms of common cell attachment and detachment protocols, boronic acid derivatives can be utilised to bind with native polyand oligosaccharides which are present in the outer cellular wall or membrane. 53 By combining boronic acid with fluorescence dyes or quantum dots (QDs) or other signal reporter units, researchers have developed sensing and labelling systems for the recognition of carbohydrate biomarkers. 44 Since, the fluorescence quenching of probes is often hard to avoid, the development of effective boronic acid-based carbohydrate fluorescent sensors could be hampered.…”

Section: Boronic Acid For Imaging Carbohydratesmentioning

confidence: 99%

Boronic acids for fluorescence imaging of carbohydrates

et al. 2016

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"Fluorescence imaging" is a particularly exciting and rapidly developing area of research; the annual number of publications in the area has increased ten-fold over the last decade. The rapid increase of interest in fluorescence imaging will necessitate the development of an increasing number of molecular receptors and binding agents in order to meet the demand in this rapidly expanding area. Carbohydrate biomarkers are particularly important targets for fluorescence imaging given their pivotal role in numerous important biological events, including the development and progression of many diseases. Therefore, the development of new fluorescent receptors and binding agents for carbohydrates is and will be increasing in demand. This review highlights the development of fluorescence imaging agents based on boronic acids a particularly promising class of receptors given their strong and selective binding with carbohydrates in aqueous media.

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Electronic communication of cells with a surface mediated by boronic acid saccharide interactions

Abstract: Gold surfaces were molecularly tailored with a saccharide binding motif capable of covalently adhering cells. This facilitated communication via the macrophage membrane with implications for understanding mammalian cell signalling.

Cited by 12 publications

References 39 publications

“Click-fluors”: triazole-linked saccharide sensors

“Click-fluors”: triazole-linked saccharide sensors

Electrochemically stimulating developments in bioelectronic medicine

Boronic acids for fluorescence imaging of carbohydrates

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