A new family of bis-ureidic receptors for pyrophosphate optical sensing

Claudia Caltagirone; Carla Bazzicalupi; Francesco Isaia; Mark E. Light; Vito Lippolis; Riccardo Montis; Sergio Murgia; Martina Olivari; Giacomo Picci

doi:10.1039/c3ob27244c

A new family of bis-ureidic receptors for pyrophosphate optical sensing

Claudia Caltagirone^*, Carla Bazzicalupi, Francesco Isaia, Mark E. Light, Vito Lippolis, Riccardo Montis, Sergio Murgia, Martina Olivari, Giacomo Picci

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

A new family of bis-ureidic receptors (L¹-L⁶) has been synthesised. The binding properties of L¹-L⁶ towards different anions (acetate, benzoate, glutarate, malonate, dihydrogen phosphate, hydrogen pyrophosphate, triphosphate, AMP and ADP) have been studied by means of ¹H-NMR, UV-Vis and fluorescence spectroscopies and a remarkable affinity for HPpi^3- has been observed in the case L³ (in DMSO-d₆ and DMSO-d₆-5% H₂O) which also acts as a fluorimetric chemosensor, even to the naked eye, for this anion. Theoretical calculations helped us explain the binding properties observed.

Original language	English
Pages (from-to)	2445-2451
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	15
DOIs	https://doi.org/10.1039/c3ob27244c
Publication status	Published - 16 Jan 2013

Keywords

Binding properties
Chemosensor
Dihydrogen phosphate
Fluorimetric
Optical sensing
Synthesised
Theoretical calculations
Triphosphate
Fluorescence spectroscopy
Negative ions
Binding energy
diphosphoric acid
pyrophosphoric acid derivative
urea
article
chemical analysis
chemical structure
chemistry
conformation
equipment
light related phenomena
Chemistry Techniques, Analytical
Diphosphates
Models, Molecular
Molecular Conformation
Optical Processes

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title = "A new family of bis-ureidic receptors for pyrophosphate optical sensing",

abstract = "A new family of bis-ureidic receptors (L1-L6) has been synthesised. The binding properties of L1-L6 towards different anions (acetate, benzoate, glutarate, malonate, dihydrogen phosphate, hydrogen pyrophosphate, triphosphate, AMP and ADP) have been studied by means of 1H-NMR, UV-Vis and fluorescence spectroscopies and a remarkable affinity for HPpi3- has been observed in the case L3 (in DMSO-d6 and DMSO-d6-5% H2O) which also acts as a fluorimetric chemosensor, even to the naked eye, for this anion. Theoretical calculations helped us explain the binding properties observed.",

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author = "Claudia Caltagirone and Carla Bazzicalupi and Francesco Isaia and Light, {Mark E.} and Vito Lippolis and Riccardo Montis and Sergio Murgia and Martina Olivari and Giacomo Picci",

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doi = "10.1039/c3ob27244c",

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AU - Caltagirone, Claudia

AU - Bazzicalupi, Carla

AU - Isaia, Francesco

AU - Light, Mark E.

AU - Lippolis, Vito

AU - Montis, Riccardo

AU - Murgia, Sergio

AU - Olivari, Martina

AU - Picci, Giacomo

PY - 2013/1/16

Y1 - 2013/1/16

N2 - A new family of bis-ureidic receptors (L1-L6) has been synthesised. The binding properties of L1-L6 towards different anions (acetate, benzoate, glutarate, malonate, dihydrogen phosphate, hydrogen pyrophosphate, triphosphate, AMP and ADP) have been studied by means of 1H-NMR, UV-Vis and fluorescence spectroscopies and a remarkable affinity for HPpi3- has been observed in the case L3 (in DMSO-d6 and DMSO-d6-5% H2O) which also acts as a fluorimetric chemosensor, even to the naked eye, for this anion. Theoretical calculations helped us explain the binding properties observed.

AB - A new family of bis-ureidic receptors (L1-L6) has been synthesised. The binding properties of L1-L6 towards different anions (acetate, benzoate, glutarate, malonate, dihydrogen phosphate, hydrogen pyrophosphate, triphosphate, AMP and ADP) have been studied by means of 1H-NMR, UV-Vis and fluorescence spectroscopies and a remarkable affinity for HPpi3- has been observed in the case L3 (in DMSO-d6 and DMSO-d6-5% H2O) which also acts as a fluorimetric chemosensor, even to the naked eye, for this anion. Theoretical calculations helped us explain the binding properties observed.

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KW - Dihydrogen phosphate

KW - Fluorimetric

KW - Optical sensing

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KW - Theoretical calculations

KW - Triphosphate

KW - Fluorescence spectroscopy

KW - Negative ions

KW - Binding energy

KW - diphosphoric acid

KW - pyrophosphoric acid derivative

KW - urea

KW - article

KW - chemical analysis

KW - chemical structure

KW - chemistry

KW - conformation

KW - equipment

KW - light related phenomena

KW - Chemistry Techniques, Analytical

KW - Diphosphates

KW - Models, Molecular

KW - Molecular Conformation

KW - Optical Processes

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SN - 1477-0520

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

A new family of bis-ureidic receptors for pyrophosphate optical sensing

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Keywords

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