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:
-
[3];
[2];
- Jackson State Univ, Jackson, MS (United States)
- Univ. of Mississippi Medical Center, Jackson, MS (United States)
- Univ. of California, Riverside, CA (United States)
- 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:
- 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},
number = 1,
volume = 8,
place = {United States},
year = {2018},
month = {1}
}
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Cited by: 7 works
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Figure 1: Macrocycle L and its dinuclear copper complex 1.
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Works referenced in this record:
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
Molecular Recognition of Carboxylate Ions Based on the Metal–Ligand Interaction and Signaled through Fluorescence Quenching
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Proton MRS of human prostatic fluid: Correlations between citrate, spermine, andmyo-inositol levels and changes with disease
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Anion Recognition of Chloride and Bromide by a Rigid Dicobalt(II) Cryptate
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Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective
journal, November 2015
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- Angewandte Chemie International Edition, Vol. 55, Issue 6
Chemosensors for Pyrophosphate
journal, January 2009
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- Accounts of Chemical Research, Vol. 42, Issue 1
Di- and trinuclear copper(II) complexes of polyaza macrocycles and cryptands as anion receptors
journal, March 2013
- Mateus, Pedro; Lima, Luís M. P.; Delgado, Rita
- Polyhedron, Vol. 52
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
A highly efficient dinuclear Cu( ii ) chemosensor for colorimetric and fluorescent detection of cyanide in water
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- RSC Adv., Vol. 4, Issue 97
A europium luminescence assay of lactate and citrate in biological fluids
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Fluorescent detection of phosphate anion by a highly selective chemosensor in water
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Assessing the Accuracy of M06-L Organometallic Thermochemistry
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Cascade complexation of pseudo-halide by dicopper cryptates: a linear Cu–NNN–Cu unit
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- Harding, Charles J.; Mabbs, Frank E.; MacInnes, Eric J. L.
- J. Chem. Soc., Dalton Trans., Issue 15
Halide-Ion Encapsulation by a Flexible Dicopper(II) Bis-Tren Cryptate
journal, August 2000
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- Angewandte Chemie, Vol. 112, Issue 16
Hexaazamacrocycle Containing Pyridine and Its Dicopper Complex as Receptors for Dicarboxylate Anions
journal, October 2005
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- European Journal of Inorganic Chemistry, Vol. 2005, Issue 22
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/
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A Chemosensor for Citrate in Beverages
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Colourimetric and fluorescent detection of oxalate in water by a new macrocycle-based dinuclear nickel complex: a remarkable red shift of the fluorescence band
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Colorimetric and optical discrimination of halides by a simple chemosensor
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- RSC Advances, Vol. 5, Issue 48
Oxalate in renal stone disease: the terminal metabolite that just won't go away
journal, June 2008
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- Nature Clinical Practice Nephrology, Vol. 4, Issue 7
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
Dicopper( ii ) complexes of a new di-para-xylyldioxatetraazamacrocycle and cascade species with dicarboxylate anions: thermodynamics and structural properties
journal, January 2007
- Carvalho, Sílvia; Delgado, Rita; Drew, Michael G. B.
- Dalton Trans., Issue 23
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
High citrate diet delays progression of renal insufficiency in the ClC-5 knockout mouse model of Dent's disease
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Supramolecular Assembly of Uridine Monophosphate (UMP) and Thymidine Monophosphate (TMP) with a Dinuclear Copper(II) Receptor
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- ACS Omega, Vol. 2, Issue 11
Anion Recognition and Sensing by a New Macrocyclic Dinuclear Copper(II) Complex: A Selective Receptor for Iodide
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- Mendy, John S.; Saeed, Musabbir A.; Fronczek, Frank R.
- Inorganic Chemistry, Vol. 49, Issue 16
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
The implementation of density functional theory within the polarizable continuum model for solvation
journal, December 1994
- Fortunelli, Alessandro; Tomasi, Jacopo
- Chemical Physics Letters, Vol. 231, Issue 1
Anion Receptor Chemistry
journal, September 2016
- Gale, Philip A.; Howe, Ethan N. W.; Wu, Xin
- Chem, Vol. 1, Issue 3
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
Anion recognition by coordinative interactions: metal–amine complexes as receptors
journal, January 2013
- Fabbrizzi, Luigi; Poggi, Antonio
- Chem. Soc. Rev., Vol. 42, Issue 4
Recognition and sensing of fluoride anion
journal, January 2009
- Cametti, Massimo; Rissanen, Kari
- Chemical Communications, Issue 20
Precise absolute-structure determination in light-atom crystals
journal, August 2004
- Parsons, S.; Flack, H.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 60, Issue a1
Spectroscopic Properties of Nanotube–Chromophore Hybrids
journal, September 2011
- Huang, Changshui; Wang, Randy K.; Wong, Bryan M.
- ACS Nano, Vol. 5, Issue 10
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
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
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
Regional citrate anticoagulation in continuous venovenous hemofiltration in critically ill patients with a high risk of bleeding
journal, May 1999
- Palsson, Runolfur; Niles, John L.
- Kidney International, Vol. 55, Issue 5
On the use of least-squares restraints for origin fixing in polar space groups
journal, July 1988
- Flack, H. D.; Schwarzenbach, D.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 44, Issue 4
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
- DeBorba, Brian M.; Rohrer, Jeff S.; Bhattacharyya, Lokesh
- Journal of Pharmaceutical and Biomedical Analysis, Vol. 36, Issue 3
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
Citrate selective electrodes for the flow injection analysis of soft drinks, beers and pharmaceutical products
journal, October 2002
- Ribeiro, Cristina M. F.; Matos, Cristina Delerue; Sales, M. Goreti F.
- Analytica Chimica Acta, Vol. 471, Issue 1
Encapsulation and selectivity of sulfate with a furan-based hexaazamacrocyclic receptor in water
journal, January 2014
- Rhaman, Md Mhahabubur; Ahmed, Lucky; Wang, Jing
- Org. Biomol. Chem., Vol. 12, Issue 13
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
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
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
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
Inclusion Complexes of Halide Anions with Macrocyclic Receptors
journal, September 2008
- Hossain, Md.
- Current Organic Chemistry, Vol. 12, Issue 14
Self-assembled metalla-bowls for selective sensing of multi-carboxylate anions
journal, January 2012
- Mishra, Anurag; Vajpayee, Vaishali; Kim, Hyunuk
- Dalton Trans., Vol. 41, Issue 4
A new selective chromogenic and fluorogenic sensor for citrate ion
journal, November 2012
- Liu, Zhao-Hong; Devaraj, Soosai; Yang, Chi-Rei
- Sensors and Actuators B: Chemical, Vol. 174
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
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
Halide-Ion Encapsulation by a Flexible Dicopper(II) Bis-Tren Cryptate
journal, August 2000
- Amendola, Valeria; Bastianello, Emanuela; Fabbrizzi, Luigi
- Angewandte Chemie, Vol. 39, Issue 16
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
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
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
Halide-Ion Encapsulation by a Flexible Dicopper(II) Bis-Tren Cryptate
journal, August 2000
- Amendola, Valeria; Bastianello, Emanuela; Fabbrizzi, Luigi
- Angewandte Chemie, Vol. 112, Issue 16
Precise absolute-structure determination in light-atom crystals
journal, August 2004
- Parsons, S.; Flack, H.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 60, Issue a1
Spectroscopic Properties of Nanotube–Chromophore Hybrids
journal, September 2011
- Huang, Changshui; Wang, Randy K.; Wong, Bryan M.
- ACS Nano, Vol. 5, Issue 10
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
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
Anion Receptor Chemistry
journal, September 2016
- Gale, Philip A.; Howe, Ethan N. W.; Wu, Xin
- Chem, Vol. 1, Issue 3
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
Anion recognition by coordinative interactions: metal–amine complexes as receptors
journal, January 2013
- Fabbrizzi, Luigi; Poggi, Antonio
- Chem. Soc. Rev., Vol. 42, Issue 4
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
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
Proton MRS of human prostatic fluid: Correlations between citrate, spermine, andmyo-inositol levels and changes with disease
journal, March 1997
- Lynch, Michael J.; Nicholson, Jeremy K.
- The Prostate, Vol. 30, Issue 4
Assessing the Accuracy of M06-L Organometallic Thermochemistry
journal, July 2013
- Gusev, Dmitry G.
- Organometallics, Vol. 32, Issue 15
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
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
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
- DeBorba, Brian M.; Rohrer, Jeff S.; Bhattacharyya, Lokesh
- Journal of Pharmaceutical and Biomedical Analysis, Vol. 36, Issue 3
Recognition and sensing of fluoride anion
journal, January 2009
- Cametti, Massimo; Rissanen, Kari
- Chemical Communications, Issue 20
A highly efficient dinuclear Cu( ii ) chemosensor for colorimetric and fluorescent detection of cyanide in water
journal, January 2014
- Rhaman, Md Mhahabubur; Alamgir, Azmain; Wong, Bryan M.
- RSC Adv., Vol. 4, Issue 97
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
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
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
CCDC 1017159: Experimental Crystal Structure Determination
dataset, January 2018
- Mhahabubur, Rhaman, Md; Hasan, Mohammad H.; Alamgir, Azmain
- Cambridge Crystallographic Data Centre
Cascade complexation of pseudo-halide by dicopper cryptates: a linear Cu–NNN–Cu unit
journal, January 1996
- Harding, Charles J.; Mabbs, Frank E.; MacInnes, Eric J. L.
- J. Chem. Soc., Dalton Trans., Issue 15
Dicopper( ii ) complexes of a new di-para-xylyldioxatetraazamacrocycle and cascade species with dicarboxylate anions: thermodynamics and structural properties
journal, January 2007
- Carvalho, Sílvia; Delgado, Rita; Drew, Michael G. B.
- Dalton Trans., Issue 23
Di- and trinuclear copper(II) complexes of polyaza macrocycles and cryptands as anion receptors
journal, March 2013
- Mateus, Pedro; Lima, Luís M. P.; Delgado, Rita
- Polyhedron, Vol. 52
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
Fluorescent detection of phosphate anion by a highly selective chemosensor in water
journal, September 2010
- Saeed, Musabbir A.; Powell, Douglas R.; Hossain, Md. Alamgir
- Tetrahedron Letters, Vol. 51, Issue 37
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
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
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
Encapsulation and selectivity of sulfate with a furan-based hexaazamacrocyclic receptor in water
journal, January 2014
- Rhaman, Md Mhahabubur; Ahmed, Lucky; Wang, Jing
- Org. Biomol. Chem., Vol. 12, Issue 13
Colorimetric and optical discrimination of halides by a simple chemosensor
journal, January 2015
- Haque, Syed A.; Bolhofner, Robert L.; Wong, Bryan M.
- RSC Advances, Vol. 5, Issue 48
A new selective chromogenic and fluorogenic sensor for citrate ion
journal, November 2012
- Liu, Zhao-Hong; Devaraj, Soosai; Yang, Chi-Rei
- Sensors and Actuators B: Chemical, Vol. 174
On the use of least-squares restraints for origin fixing in polar space groups
journal, July 1988
- Flack, H. D.; Schwarzenbach, D.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 44, Issue 4
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
- Kacprzak, Karol; Gawronski, Jacek
- Chemical Communications, Issue 13
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
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
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
Self-assembled metalla-bowls for selective sensing of multi-carboxylate anions
journal, January 2012
- Mishra, Anurag; Vajpayee, Vaishali; Kim, Hyunuk
- Dalton Trans., Vol. 41, Issue 4
Inclusion Complexes of Halide Anions with Macrocyclic Receptors
journal, September 2008
- Hossain, Md.
- Current Organic Chemistry, Vol. 12, Issue 14
Chemosensors for Pyrophosphate
journal, January 2009
- Kim, Sook Kyung; Lee, Dong Hoon; Hong, Jong-In
- Accounts of Chemical Research, Vol. 42, Issue 1
Regional citrate anticoagulation in continuous venovenous hemofiltration in critically ill patients with a high risk of bleeding
journal, May 1999
- Palsson, Runolfur; Niles, John L.
- Kidney International, Vol. 55, Issue 5
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
The implementation of density functional theory within the polarizable continuum model for solvation
journal, December 1994
- Fortunelli, Alessandro; Tomasi, Jacopo
- Chemical Physics Letters, Vol. 231, Issue 1
CCDC 1401581: Experimental Crystal Structure Determination
dataset, January 2018
- Mhahabubur, Rhaman, Md; Hasan, Mohammad H.; Alamgir, Azmain
- Cambridge Crystallographic Data Centre
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
Citrate selective electrodes for the flow injection analysis of soft drinks, beers and pharmaceutical products
journal, October 2002
- Ribeiro, Cristina M. F.; Matos, Cristina Delerue; Sales, M. Goreti F.
- Analytica Chimica Acta, Vol. 471, Issue 1
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
A Chemosensor for Citrate in Beverages
journal, March 1998
- Metzger, Axel; Anslyn, Eric V.
- Angewandte Chemie International Edition, Vol. 37, Issue 5
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