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

Abstract

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.

Authors:
 [1];  [2];  [1];  [3];  [4]; ORCiD logo [3]; ORCiD logo [2];  [1]
  1. Jackson State Univ, Jackson, MS (United States)
  2. Univ. of Mississippi Medical Center, Jackson, MS (United States)
  3. Univ. of California, Riverside, CA (United States)
  4. Univ. of Oklahoma, Norman, OK (United States)
Publication Date:
Research Org.:
Univ. of California, Riverside, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1500015
Grant/Contract Number:  
SC0016269
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Scientific Reports
Additional Journal Information:
Journal Volume: 8; Journal Issue: 1; Journal ID: ISSN 2045-2322
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES

Citation Formats

Rhaman, Md Mhahabubur, Hasan, Mohammad H., Alamgir, Azmain, Xu, Lihua, Powell, Douglas R., Wong, Bryan M., Tandon, Ritesh, and Hossain, Md. Alamgir. Highly selective and sensitive macrocycle-based dinuclear foldamer for fluorometric and colorimetric sensing of citrate in water. United States: N. p., 2018. Web. doi:10.1038/s41598-017-18322-w.
Rhaman, Md Mhahabubur, Hasan, Mohammad H., Alamgir, Azmain, Xu, Lihua, Powell, Douglas R., Wong, Bryan M., Tandon, Ritesh, & Hossain, Md. Alamgir. Highly selective and sensitive macrocycle-based dinuclear foldamer for fluorometric and colorimetric sensing of citrate in water. United States. doi:10.1038/s41598-017-18322-w.
Rhaman, Md Mhahabubur, Hasan, Mohammad H., Alamgir, Azmain, Xu, Lihua, Powell, Douglas R., Wong, Bryan M., Tandon, Ritesh, and Hossain, Md. Alamgir. Wed . "Highly selective and sensitive macrocycle-based dinuclear foldamer for fluorometric and colorimetric sensing of citrate in water". United States. doi:10.1038/s41598-017-18322-w. https://www.osti.gov/servlets/purl/1500015.
@article{osti_1500015,
title = {Highly selective and sensitive macrocycle-based dinuclear foldamer for fluorometric and colorimetric sensing of citrate in water},
author = {Rhaman, Md Mhahabubur and Hasan, Mohammad H. and Alamgir, Azmain and Xu, Lihua and Powell, Douglas R. and Wong, Bryan M. and Tandon, Ritesh and Hossain, Md. Alamgir},
abstractNote = {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.},
doi = {10.1038/s41598-017-18322-w},
journal = {Scientific Reports},
issn = {2045-2322},
number = 1,
volume = 8,
place = {United States},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 4 works
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Figures / Tables:

Figure 1 Figure 1: Macrocycle L and its dinuclear copper complex 1.

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    Works referencing / citing this record:

    A Synthetic Receptor Selective for Citrate
    journal, May 1997

    • Metzger, Axel; Lynch, Vincent M.; Anslyn, Eric V.
    • Angewandte Chemie International Edition in English, Vol. 36, Issue 8
    • DOI: 10.1002/anie.199708621

    Anion Sensors as Logic Gates: A Close Encounter?
    journal, February 2016

    • Madhuprasad, ; Bhat, Mahesh P.; Jung, Ho-Young
    • Chemistry - A European Journal, Vol. 22, Issue 18
    • DOI: 10.1002/chem.201504396

    Pyridinium-based symmetrical diamides as chemosensors in visual sensing of citrate through indicator displacement assay (IDA) and gel formation
    journal, January 2011

    • Ghosh, Kumaresh; Ranjan Sarkar, Avik
    • Organic & Biomolecular Chemistry, Vol. 9, Issue 19
    • DOI: 10.1039/c1ob05707c

    Spectroscopic Properties of Nanotube–Chromophore Hybrids
    journal, September 2011

    • Huang, Changshui; Wang, Randy K.; Wong, Bryan M.
    • ACS Nano, Vol. 5, Issue 10
    • DOI: 10.1021/nn202725g

    Advances in Anion Supramolecular Chemistry: From Recognition to Chemical Applications
    journal, September 2014

    • Evans, Nicholas H.; Beer, Paul D.
    • Angewandte Chemie International Edition, Vol. 53, Issue 44
    • DOI: 10.1002/anie.201309937

    Recognition and Sensing of Nucleoside Monophosphates by a Dicopper(II) Cryptate
    journal, January 2010

    • Amendola, Valeria; Bergamaschi, Greta; Buttafava, Armando
    • Journal of the American Chemical Society, Vol. 132, Issue 1
    • DOI: 10.1021/ja9046262

    Anion Receptor Chemistry
    journal, September 2016


    Metal-Containing Trifurcate Receptor that Recognizes and Senses Citrate in Water
    journal, June 2005

    • Fabbrizzi, Luigi; Foti, Francesco; Taglietti, Angelo
    • Organic Letters, Vol. 7, Issue 13
    • DOI: 10.1021/ol0507064

    Assessment of Conjunctival Microvascular Hemodynamics in Stages of Diabetic Microvasculopathy
    journal, April 2017

    • Khansari, Maziyar M.; Wanek, Justin; Tan, Michael
    • Scientific Reports, Vol. 7, Issue 1
    • DOI: 10.1038/srep45916

    Cholic-Acid-Based Fluorescent Sensor for Dicarboxylates and Acidic Amino Acids in Aqueous Solutions
    journal, December 2005

    • Liu, Shun-Ying; Fang, Lei; He, Yong-Bing
    • Organic Letters, Vol. 7, Issue 26
    • DOI: 10.1021/ol052341t

    Assessing the Accuracy of M06-L Organometallic Thermochemistry
    journal, July 2013


    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

    • Rhaman, Md Mhahabubur; Fronczek, Frank R.; Powell, Douglas R.
    • Dalton Transactions, Vol. 43, Issue 12
    • DOI: 10.1039/c3dt53467g

    Thermodynamic Aspects of Dicarboxylate Recognition by Simple Artificial Receptors
    journal, November 2001

    • Linton, Brian R.; Goodman, M. Scott; Fan, Erkang
    • The Journal of Organic Chemistry, Vol. 66, Issue 22
    • DOI: 10.1021/jo010413y

    Development and validation of an assay for citric acid/citrate and phosphate in pharmaceutical dosage forms using ion chromatography with suppressed conductivity detection
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    • DeBorba, Brian M.; Rohrer, Jeff S.; Bhattacharyya, Lokesh
    • Journal of Pharmaceutical and Biomedical Analysis, Vol. 36, Issue 3
    • DOI: 10.1016/j.jpba.2004.07.003

    Recognition and sensing of fluoride anion
    journal, January 2009

    • Cametti, Massimo; Rissanen, Kari
    • Chemical Communications, Issue 20
    • DOI: 10.1039/b902069a

    Highly Selective Oligonucleotide-Based Sensor for Mercury(II) in Aqueous Solutions
    journal, August 2004

    • Ono, Akira; Togashi, Humika
    • Angewandte Chemie International Edition, Vol. 43, Issue 33, p. 4300-4302
    • DOI: 10.1002/anie.200454172

    Dicarboxylate Recognition by Two Macrobicyclic Receptors: Selectivity for Fumarate over Maleate
    journal, April 2012

    • Mateus, Pedro; Delgado, Rita; Brandão, Paula
    • The Journal of Organic Chemistry, Vol. 77, Issue 10
    • DOI: 10.1021/jo300320w

    Hexaazamacrocycle Containing Pyridine and Its Dicopper Complex as Receptors for Dicarboxylate Anions
    journal, October 2005

    • Li, Feng; Delgado, Rita; Félix, Vítor
    • European Journal of Inorganic Chemistry, Vol. 2005, Issue 22
    • DOI: 10.1002/ejic.200401059

    Di- and trinuclear copper(II) complexes of polyaza macrocycles and cryptands as anion receptors
    journal, March 2013


    Anion Recognition and Sensing by a New Macrocyclic Dinuclear Copper(II) Complex: A Selective Receptor for Iodide
    journal, August 2010

    • Mendy, John S.; Saeed, Musabbir A.; Fronczek, Frank R.
    • Inorganic Chemistry, Vol. 49, Issue 16
    • DOI: 10.1021/ic100686m

    Fluorescent detection of phosphate anion by a highly selective chemosensor in water
    journal, September 2010


    Does citrate prevent nephrocalcinosis in preterm neonates?
    journal, December 2006

    • Schell-Feith, Eveline A.; Moerdijk, Aukje; van Zwieten, Paul H. T.
    • Pediatric Nephrology, Vol. 21, Issue 12
    • DOI: 10.1007/s00467-006-0274-4

    A Molecular Flytrap for the Selective Binding of Citrate and Other Tricarboxylates in Water
    journal, March 2005

    • Schmuck, Carsten; Schwegmann, Michael
    • Journal of the American Chemical Society, Vol. 127, Issue 10
    • DOI: 10.1021/ja0433469

    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

    • Schmuck, Carsten; Schwegmann, Michael
    • Organic & Biomolecular Chemistry, Vol. 4, Issue 5
    • DOI: 10.1039/b516019g

    A new selective chromogenic and fluorogenic sensor for citrate ion
    journal, November 2012


    Anion binding in macrobicyclic metal cryptate complexes: copper(II)-BISTREN
    journal, May 1984

    • Motekaitis, Ramunas J.; Martell, Arthur E.; Dietrich, Bernard
    • Inorganic Chemistry, Vol. 23, Issue 11
    • DOI: 10.1021/ic00179a026

    Molecular Recognition of Carboxylate Ions Based on the Metal–Ligand Interaction and Signaled through Fluorescence Quenching
    journal, February 1996

    • De Santis, Giancarlo; Fabbrizzi, Luigi; Licchelli, Maurizio
    • Angewandte Chemie International Edition in English, Vol. 35, Issue 2
    • DOI: 10.1002/anie.199602021

    Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective
    journal, November 2015

    • Langton, Matthew J.; Serpell, Christopher J.; Beer, Paul D.
    • Angewandte Chemie International Edition, Vol. 55, Issue 6
    • DOI: 10.1002/anie.201506589


    journal, September 2008


    Chemosensors for Pyrophosphate
    journal, January 2009

    • Kim, Sook Kyung; Lee, Dong Hoon; Hong, Jong-In
    • Accounts of Chemical Research, Vol. 42, Issue 1
    • DOI: 10.1021/ar800003f

    Anion Recognition of Chloride and Bromide by a Rigid Dicobalt(II) Cryptate
    journal, April 2008

    • Chen, Jia-Mei; Zhuang, Xiao-Mei; Yang, Li-Zi
    • Inorganic Chemistry, Vol. 47, Issue 8
    • DOI: 10.1021/ic702143d

    The implementation of density functional theory within the polarizable continuum model for solvation
    journal, December 1994


    Tight Binding and Fluorescent Sensing of Oxalate in Water
    journal, September 2008

    • Tang, Lijun; Park, Jinhee; Kim, Hae-Jo
    • Journal of the American Chemical Society, Vol. 130, Issue 38
    • DOI: 10.1021/ja804753n

    Oxalate in renal stone disease: the terminal metabolite that just won't go away
    journal, June 2008

    • Marengo, Susan R.; Romani, Andrea MP
    • Nature Clinical Practice Nephrology, Vol. 4, Issue 7
    • DOI: 10.1038/ncpneph0845

    Supramolecular Assembly of Uridine Monophosphate (UMP) and Thymidine Monophosphate (TMP) with a Dinuclear Copper(II) Receptor
    journal, November 2017

    • Rhaman, Md Mhahabubur; Powell, Douglas R.; Hossain, Md. Alamgir
    • ACS Omega, Vol. 2, Issue 11
    • DOI: 10.1021/acsomega.7b01293

    High citrate diet delays progression of renal insufficiency in the ClC-5 knockout mouse model of Dent's disease
    journal, August 2005


    A europium luminescence assay of lactate and citrate in biological fluids
    journal, January 2009

    • Pal, Robert; Parker, David; Costello, Leslie C.
    • Organic & Biomolecular Chemistry, Vol. 7, Issue 8
    • DOI: 10.1039/b901251f