skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Highly selective and sensitive macrocycle-based dinuclear foldamer for fluorometric and colorimetric sensing of citrate in water

Journal Article · · Scientific Reports

The selective detection of citrate anions is essential for various biological functions in living systems. A quantitative assessment of citrate is required for the diagnosis of various diseases in the human body; however, it is extremely challenging to develop efficient fluorescence and color-detecting molecular probes for sensing citrate in water. Herein, we report a macrocycle-based dinuclear foldamer (1) assembled with eosin Y (EY) that has been studied for anion binding by fluorescence and colorimetric techniques in water at neutral pH. Results from the fluorescence titrations reveal that the 1·EY ensemble strongly binds citrate anions, showing remarkable selectivity over a wide range of inorganic and carboxylate anions. The addition of citrate anions to the 1·EY adduct led to a large fluorescence enhancement, displaying a detectable color change under both visible and UV light in water up to 2 μmol. The biocompatibility of 1·EY as an intracellular carrier in a biological system was evaluated on primary human foreskin fibroblast (HF) cells, showing an excellent cell viability. The strong binding properties of the ensemble allow it to be used as a highly sensitive, detective probe for biologically relevant citrate anions in various applications.

Research Organization:
Univ. of California, Riverside, CA (United States)
Sponsoring Organization:
USDOE
Grant/Contract Number:
SC0016269
OSTI ID:
1500015
Journal Information:
Scientific Reports, Vol. 8, Issue 1; ISSN 2045-2322
Publisher:
Nature Publishing GroupCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 25 works
Citation information provided by
Web of Science

References (60)

Thermodynamic Aspects of Dicarboxylate Recognition by Simple Artificial Receptors journal November 2001
Molecular Recognition of Carboxylate Ions Based on the Metal–Ligand Interaction and Signaled through Fluorescence Quenching journal February 1996
Proton MRS of human prostatic fluid: Correlations between citrate, spermine, andmyo-inositol levels and changes with disease journal March 1997
Anion recognition by coordinative interactions: metal–amine complexes as receptors journal January 2013
Anion Recognition of Chloride and Bromide by a Rigid Dicobalt(II) Cryptate journal April 2008
Corrigendum: Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective journal April 2016
Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective journal November 2015
Chemosensors for Pyrophosphate journal January 2009
Di- and trinuclear copper(II) complexes of polyaza macrocycles and cryptands as anion receptors journal March 2013
Does citrate prevent nephrocalcinosis in preterm neonates? journal December 2006
Inhibition of endocytic pathways impacts cytomegalovirus maturation journal April 2017
Anion binding in macrobicyclic metal cryptate complexes: copper(II)-BISTREN journal May 1984
A europium luminescence assay of lactate and citrate in biological fluids journal January 2009
Fluorescent detection of phosphate anion by a highly selective chemosensor in water journal September 2010
Assessing the Accuracy of M06-L Organometallic Thermochemistry journal July 2013
Anion Receptor Chemistry journal September 2016
Cascade complexation of pseudo-halide by dicopper cryptates: a linear Cu–NNN–Cu unit journal January 1996
On the use of least-squares restraints for origin fixing in polar space groups journal July 1988
Halide-Ion Encapsulation by a Flexible Dicopper(II) Bis-Tren Cryptate journal August 2000
Remarkable hexafunctional anion receptor with operational urea-based inner cleft and thiourea-based outer cleft: Novel design with high-efficiency for sulfate binding journal July 2017
Hexaazamacrocycle Containing Pyridine and Its Dicopper Complex as Receptors for Dicarboxylate Anions journal October 2005
Bifunctional receptor triad for efficient recognition of mono- and dicarboxylic acidsElectronic supplementary information (ESI) available: experimental details, spectrometric titration results, ESMS spectrum of the complex of 2 with (R,R)-tartaric acid. See http://www.rsc.org/suppdata/cc/b3/b302003g/ journal January 2003
Colourimetric and fluorescent detection of oxalate in water by a new macrocycle-based dinuclear nickel complex: a remarkable red shift of the fluorescence band journal January 2014
Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications journal September 2014
Spectroscopic Properties of Nanotube-Chromophore Hybrids text January 2013
A Molecular Flytrap for the Selective Binding of Citrate and Other Tricarboxylates in Water journal March 2005
Oxalate in renal stone disease: the terminal metabolite that just won't go away journal June 2008
Metal-Containing Trifurcate Receptor that Recognizes and Senses Citrate in Water journal June 2005
Dicopper( ii ) complexes of a new di-para-xylyldioxatetraazamacrocycle and cascade species with dicarboxylate anions: thermodynamics and structural properties journal January 2007
Highly Selective Oligonucleotide-Based Sensor for Mercury(II) in Aqueous Solutions journal August 2004
Pyridinium-based symmetrical diamides as chemosensors in visual sensing of citrate through indicator displacement assay (IDA) and gel formation journal January 2011
High citrate diet delays progression of renal insufficiency in the ClC-5 knockout mouse model of Dent's disease journal August 2005
Supramolecular Assembly of Uridine Monophosphate (UMP) and Thymidine Monophosphate (TMP) with a Dinuclear Copper(II) Receptor journal November 2017
Anion Recognition and Sensing by a New Macrocyclic Dinuclear Copper(II) Complex: A Selective Receptor for Iodide journal August 2010
Recognition and sensing of fluoride anion journal January 2009
Halide-Ion Encapsulation by a Flexible Dicopper(II) Bis-Tren Cryptate journal August 2000
Dicarboxylate Recognition by Two Macrobicyclic Receptors: Selectivity for Fumarate over Maleate journal April 2012
Tight Binding and Fluorescent Sensing of Oxalate in Water journal September 2008
Cholic-Acid-Based Fluorescent Sensor for Dicarboxylates and Acidic Amino Acids in Aqueous Solutions journal December 2005
Anion Sensors as Logic Gates: A Close Encounter? journal February 2016
The implementation of density functional theory within the polarizable continuum model for solvation journal December 1994
Highly Selective Oligonucleotide-Based Sensor for Mercury(II) in Aqueous Solutions journal August 2004
A highly efficient dinuclear Cu( ii ) chemosensor for colorimetric and fluorescent detection of cyanide in water journal January 2014
Anion receptor chemistry journal January 2011
A naked-eye sensing ensemble for the selective detection of citrate—but not tartrate or malate—in water based on a tris-cationic receptor journal January 2006
Precise absolute-structure determination in light-atom crystals journal August 2004
Spectroscopic Properties of Nanotube–Chromophore Hybrids journal September 2011
Self-assembled metalla-bowls for selective sensing of multi-carboxylate anions journal January 2012
Inclusion Complexes of Halide Anions with Macrocyclic Receptors journal September 2008
A Synthetic Receptor Selective for Citrate journal May 1997
Regional citrate anticoagulation in continuous venovenous hemofiltration in critically ill patients with a high risk of bleeding journal May 1999
Development and validation of an assay for citric acid/citrate and phosphate in pharmaceutical dosage forms using ion chromatography with suppressed conductivity detection journal November 2004
Recognition and Sensing of Nucleoside Monophosphates by a Dicopper(II) Cryptate journal January 2010
Citrate selective electrodes for the flow injection analysis of soft drinks, beers and pharmaceutical products journal October 2002
Encapsulation and selectivity of sulfate with a furan-based hexaazamacrocyclic receptor in water journal January 2014
Colorimetric and optical discrimination of halides by a simple chemosensor journal January 2015
Assessment of Conjunctival Microvascular Hemodynamics in Stages of Diabetic Microvasculopathy journal April 2017
A Chemosensor for Citrate in Beverages journal March 1998
A new selective chromogenic and fluorogenic sensor for citrate ion journal November 2012
Halide-Ion Encapsulation by a Flexible Dicopper(II) Bis-Tren Cryptate journal August 2000

Cited By (3)

Cleft‐Induced Ditopic Binding of Spherical Halides with a Hexaurea Receptor journal January 2020
Dinuclear complexes of Mn, Co, Zn and Cd assembled with 1,4-cyclohexanedicarboxylate: synthesis, crystal structures and acetonitrile fluorescence sensing properties journal January 2020
Current Advancements in Transdermal Biosensing and Targeted Drug Delivery journal February 2019


Figures / Tables (12)


Similar Records

Polarity-Tolerant Chloride Binding in Foldamer Capsules by Programmed Solvent-Exclusion
Journal Article · Wed Feb 17 00:00:00 EST 2021 · Journal of the American Chemical Society · OSTI ID:1500015

New Colorimetric and Fluorometric Fluoride Ion Probe Based on Anthra[1,9-cd]pyrazol-6(2H)-one
Journal Article · Wed Nov 15 00:00:00 EST 2017 · Journal of Fluorescence (Online) · OSTI ID:1500015

Applications of a single-molecule detection in early disease diagnosis and enzymatic reaction study
Thesis/Dissertation · Tue Jan 01 00:00:00 EST 2008 · OSTI ID:1500015

Related Subjects