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A CuII-Salicylidene Glycinato Complex for the Selective Fluorometric Detection of Homocysteine over 20 Proteinogenic Amino Acids


Li, Xuecong; Yadav, Prerna; Spingler, Bernhard; Zelder, Felix Hubertus (2022). A CuII-Salicylidene Glycinato Complex for the Selective Fluorometric Detection of Homocysteine over 20 Proteinogenic Amino Acids. ChemistryOpen, 11(6):e202200106.

Abstract

Homocysteine (Hcy) is a sulfur-containing α-amino acid that differs by one methylene (CH2) subunit from homologous cysteine (Cys). Elevated levels of Hcy are diagnostic markers of cardiovascular disease and other medical conditions. We present a new CuII-salicylidene glycinato complex 1 for the selective fluorometric detection of Hcy in water. In the presence of this analyte, the non-fluorescent copper-complex demetallates and disassembles into its building blocks. This process liberates a 3-chloro-5-sulfosalicylaldehyde signaling unit and is accompanied by a 51-fold turn-on fluorescence at 485 nm (λex=350 nm). Out of twenty proteinogenic amino acids, only histidine (12-fold turn-on fluorescence) and Cys (8-fold turn-on fluorescence) trigger some disassembly of probe 1. In comparison with important pioneering work on the detection of biothiols, this study strikingly demonstrates that structural modifications of chelate core structures steer substrate selectivity of metal-based probes. Importantly, probe 1 has proven suitable for the detection of Hcy in artificial urine.

Abstract

Homocysteine (Hcy) is a sulfur-containing α-amino acid that differs by one methylene (CH2) subunit from homologous cysteine (Cys). Elevated levels of Hcy are diagnostic markers of cardiovascular disease and other medical conditions. We present a new CuII-salicylidene glycinato complex 1 for the selective fluorometric detection of Hcy in water. In the presence of this analyte, the non-fluorescent copper-complex demetallates and disassembles into its building blocks. This process liberates a 3-chloro-5-sulfosalicylaldehyde signaling unit and is accompanied by a 51-fold turn-on fluorescence at 485 nm (λex=350 nm). Out of twenty proteinogenic amino acids, only histidine (12-fold turn-on fluorescence) and Cys (8-fold turn-on fluorescence) trigger some disassembly of probe 1. In comparison with important pioneering work on the detection of biothiols, this study strikingly demonstrates that structural modifications of chelate core structures steer substrate selectivity of metal-based probes. Importantly, probe 1 has proven suitable for the detection of Hcy in artificial urine.

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Additional indexing

Item Type:Journal Article, not_refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:General Chemistry
Language:English
Date:1 June 2022
Deposited On:21 Jun 2022 15:30
Last Modified:29 Jan 2024 02:41
Publisher:Wiley Open Access
ISSN:2191-1363
OA Status:Gold
Free access at:PubMed ID. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/open.202200106
PubMed ID:35723424
Project Information:
  • : FunderSNSF
  • : Grant ID206021_164018
  • : Project TitleDual X-ray Wavelength Single-Crystal Diffractometer
  • : FunderSNSF
  • : Grant ID200021_169216
  • : Project TitleA stimuli responsive disassembly strategy as versatile tool for analytical applications
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)