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

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Organic & Biomolecular Chemistry

Issue 15, 2013

The international home of synthetic, physical and biomolecular organic chemistry.

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

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

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Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, S.S. 554 Bivio per Sestu, Monserrato (CA), Italy
E-mail: ccaltagirone@unica.it ;
Fax: +(39) 0706754456 ;
Tel: +(39) 0706754452

Dipartimento di Chimica “Ugo Schiff”, Università degli Studi di Firenze, Via della Lastruccia 3, Sesto Fiorentino (FI), Italy

School of Chemistry, University of Southampton, Southampton, UK
E-mail: M.E.Light@soton.ac.uk ;
Fax: +44 (0)23 8059 6805 ;
Tel: +44 (0)23 8059 6805

Org. Biomol. Chem., 2013,11, 2445-2451

DOI: 10.1039/C3OB27244C
Received 19 Nov 2012, Accepted 16 Jan 2013
First published online 16 Jan 2013

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

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

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