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dc.contributor.authorMcQuade, Lindsey E.
dc.contributor.authorLippard, Stephen J.
dc.date.accessioned2012-10-18T14:59:44Z
dc.date.available2012-10-18T14:59:44Z
dc.date.issued2010-09
dc.date.submitted2010-06
dc.identifier.issn0020-1669
dc.identifier.issn1520-510X
dc.identifier.urihttp://hdl.handle.net/1721.1/74074
dc.description.abstractThe synthesis and spectroscopic characterization of two new, cell-trappable fluorescent probes for Zn(II) are presented. These probes, 2-(4,5-bis(((6-(2-ethoxy-2-oxoethoxy)quinolin-8-yl)amino)methyl)-6-hydroxy-3-oxo-3H-8 xanthen-9-yl)benzoic acid (QZ2E) and 2,2′-((8,8′-(((9-(2-carboxyphenyl)-6-hydroxy-3-oxo-3H-xanthene-4,5-diyl)bis(methylene))bis(azanediyl))bis(quinoline-8,6-diyl))bis(oxy))diacetic acid (QZ2A), are poorly emissive in the off-state but exhibit dramatic increases in fluorescence upon Zn(II) binding (120 ± 10-fold for QZ2E, 30 ± 7-fold for QZ2A). This binding is selective for Zn(II) over other biologically relevant metal cations, toxic heavy metals, and most first-row transition metals and is of appropriate affinity (K[subscript d1](QZ2E) = 150 ± 100 μM, K[subscript d2](QZ2E) = 3.5 ± 0.1 mM, K[subscript d1](QZ2A) = 220 ± 30 μM, K[subscript d2](QZ2A) = 160 ± 80 μM, K[subscript d3](QZ2A) = 9 ± 6 μM) to reversibly bind Zn(II) at physiological levels. In live cells, QZ2E localizes to the Gogli apparatus where it can detect Zn(II). It is cell-membrane-permeable until cleavage of its ester groups by intracellular esterases produces QZ2A, a negatively charged acid form that cannot cross the cell membrane.en_US
dc.description.sponsorshipNational Science Foundation (U.S.) (CHE-0907905)en_US
dc.language.isoen_US
dc.publisherAmerican Chemical Society (ACS)en_US
dc.relation.isversionofhttp://dx.doi.org/10.1021/ic1012507en_US
dc.rightsCreative Commons Attribution-Noncommercial-Share Alike 3.0en_US
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/3.0/en_US
dc.sourceProf. Lippard via Erja Kajosaloen_US
dc.titleCell-Trappable Quinoline-Derivatized Fluoresceins for Selective and Reversible Biological Zn(II) Detectionen_US
dc.typeArticleen_US
dc.identifier.citationMcQuade, Lindsey E., and Stephen J. Lippard. “Cell-Trappable Quinoline-Derivatized Fluoresceins for Selective and Reversible Biological Zn(II) Detection.” Inorganic Chemistry 49.20 (2010): 9535–9545.en_US
dc.contributor.departmentMassachusetts Institute of Technology. Department of Chemistryen_US
dc.contributor.approverLippard, Stephen J.
dc.contributor.mitauthorMcQuade, Lindsey E.
dc.contributor.mitauthorLippard, Stephen J.
dc.relation.journalInorganic Chemistryen_US
dc.eprint.versionAuthor's final manuscripten_US
dc.type.urihttp://purl.org/eprint/type/JournalArticleen_US
eprint.statushttp://purl.org/eprint/status/PeerRevieweden_US
dspace.orderedauthorsMcQuade, Lindsey E.; Lippard, Stephen J.en
dc.identifier.orcidhttps://orcid.org/0000-0002-2693-4982
mit.licenseOPEN_ACCESS_POLICYen_US
mit.metadata.statusComplete


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