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Article: Activity‐Based Sensing of Ascorbate by Using Copper‐Mediated Oxidative Bond Cleavage

TitleActivity‐Based Sensing of Ascorbate by Using Copper‐Mediated Oxidative Bond Cleavage
Authors
Keywordsascorbate
copper
fluorescent probes
oxidation
sensors
Issue Date2020
PublisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2020, v. 26 n. 40, p. 8794-8800 How to Cite?
AbstractAscorbate is an important biological reductant and enzyme cofactor. Although direct detection through ascorbate‐mediated reduction is possible, this approach suffers from poor selectivity due to the wide range of cellular reducing agents. To overcome this limitation, we leverage reduction potential of ascorbate to mediate a copper‐mediated oxidative bond cleavage of ether‐caged fluorophores. The copper(II) complexes supported by a {bis(2‐pyridylmethyl)}benzylamine or a {bis(2‐pyridylmethyl)}(2‐methoxybenzyl)amine ligand were identified as an ascorbate responsive unit and their reaction with ascorbate yields a copper‐based oxidant that enables rapid benzylic oxidation and the release of an ether‐caged dye (coumarin or fluorescein). The copper‐mediated bond cleavage is specific to ascorbate and the trigger can be readily derivatized for tuning photophysical properties of the probes. The probes were successfully applied for the fluorometric detection of ascorbate in commercial food samples, human plasma, and serum, and within live cells by using confocal microscopy and flow cytometry.
Persistent Identifierhttp://hdl.handle.net/10722/284011
ISSN
2020 Impact Factor: 5.236
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorYu, ZH-
dc.contributor.authorReinhardt, CJ-
dc.contributor.authorWong, THF-
dc.contributor.authorTong, KY-
dc.contributor.authorChan, J-
dc.contributor.authorAu Yeung, HY-
dc.date.accessioned2020-07-20T05:55:18Z-
dc.date.available2020-07-20T05:55:18Z-
dc.date.issued2020-
dc.identifier.citationChemistry - A European Journal, 2020, v. 26 n. 40, p. 8794-8800-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/284011-
dc.description.abstractAscorbate is an important biological reductant and enzyme cofactor. Although direct detection through ascorbate‐mediated reduction is possible, this approach suffers from poor selectivity due to the wide range of cellular reducing agents. To overcome this limitation, we leverage reduction potential of ascorbate to mediate a copper‐mediated oxidative bond cleavage of ether‐caged fluorophores. The copper(II) complexes supported by a {bis(2‐pyridylmethyl)}benzylamine or a {bis(2‐pyridylmethyl)}(2‐methoxybenzyl)amine ligand were identified as an ascorbate responsive unit and their reaction with ascorbate yields a copper‐based oxidant that enables rapid benzylic oxidation and the release of an ether‐caged dye (coumarin or fluorescein). The copper‐mediated bond cleavage is specific to ascorbate and the trigger can be readily derivatized for tuning photophysical properties of the probes. The probes were successfully applied for the fluorometric detection of ascorbate in commercial food samples, human plasma, and serum, and within live cells by using confocal microscopy and flow cytometry.-
dc.languageeng-
dc.publisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry-
dc.relation.ispartofChemistry - A European Journal-
dc.rightsThis is the peer reviewed version of the following article: Chemistry - A European Journal, 2020, v. 26 n. 40, p. 8794-8800, which has been published in final form at https://doi.org/10.1002/chem.202000780. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.-
dc.subjectascorbate-
dc.subjectcopper-
dc.subjectfluorescent probes-
dc.subjectoxidation-
dc.subjectsensors-
dc.titleActivity‐Based Sensing of Ascorbate by Using Copper‐Mediated Oxidative Bond Cleavage-
dc.typeArticle-
dc.identifier.emailAu Yeung, HY: hoyuay@hku.hk-
dc.identifier.authorityAu Yeung, HY=rp01819-
dc.description.naturepostprint-
dc.identifier.doi10.1002/chem.202000780-
dc.identifier.pmid32583898-
dc.identifier.scopuseid_2-s2.0-85087137597-
dc.identifier.hkuros310982-
dc.identifier.volume26-
dc.identifier.issue40-
dc.identifier.spage8794-
dc.identifier.epage8800-
dc.identifier.isiWOS:000542753800001-
dc.publisher.placeGermany-
dc.identifier.issnl0947-6539-

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