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Novel reversible Zn2+-assisted biological phosphate "turn-on" probing through stable aryl-hydrazone salicylaldimine conjugation that attenuates ligand hydrolysis

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Title
Novel reversible Zn2+-assisted biological phosphate "turn-on" probing through stable aryl-hydrazone salicylaldimine conjugation that attenuates ligand hydrolysis
Author(s)
Tsay O.G.; Sudesh T. Manjare; Kim H.; Lee K.M.; Lee Y.S.; Churchill D.G.
Subject
4,4 difluoro 4 bora 3a,4a diaza s indacene, ; 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, ; adenosine triphosphate, ; boron derivative, ; fluorescent dye, ; hydrazone derivative, ; ligand, ; polyphosphate, ; salicylic acid derivative, ; zinc, ; article, ; chemical structure, ; chemistry, ; hydrolysis, ; methodology, ; spectrofluorometry, ; Adenosine Triphosphate, ; Boron Compounds, ; Fluorescent Dyes, ; Hydrazones, ; Hydrolysis, ; Ligands, ; Models, Molecular, ; Polyphosphates, ; Salicylates, ; Spectrometry, Fluorescence, ; Zinc
Publication Date
2013-09
Journal
INORGANIC CHEMISTRY, v.52, no.17, pp.10052 - 10061
Publisher
AMER CHEMICAL SOC
Abstract
A novel reversible zinc(II) chemosensing ensemble (2·Zn 2+) allows for selective ""turn-on"" fluorescence sensing of ATP and PPi in aqueous media (detection limits: 2.4 and 1.0 μM, respectively) giving selective binding patterns: ATP ∼ PPi > ADP AMP > monophosphates ≈ remaining ions tested. The conjugated hydrazone [C=N - NH - R] resists hydrolysis considerably, compared to the imine [C=N - CH2 - R, pyridin-2-ylmethanamine] functionality, and generalizes to other chemosensing efforts. Prerequisite Zn2+·[O phenolNimineNpyr] binding is selective, as determined by UV-vis and NMR spectroscopy; ATP or PPi extracts Zn2+ to regenerate the ligand-fluorophore conjugate (PPi: turn-on, 512 nm; detection limit, 1.0 μM). Crystallography, 2-D NMR spectroscopy, and DFT determinations (B3LYP/631g) support the nature of compound 2. 2-Hydrazinyl-pyridine- salicylaldehyde conjugation is unknown, as such; a paucity of chemosensing-Zn2+ binding reports underscores the novelty of this modifiable dual cation/anion detection platform. A combined theoretical and experimental approach reported here allows us to determine both the potential uniqueness as well as drawbacks of this novel conjugation. © 2013 American Chemical Society.
URI
https://pr.ibs.re.kr/handle/8788114/1253
DOI
10.1021/ic4013526
ISSN
0020-1669
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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