Thermodynamics and fluorescence emission studies on potential molecular chemosensors for ATP recognition in aqueous solution †

Albelda, M. Teresa; Bernardo, Alexandra; Garcı́a-España, Enrique; Godino-Salido, M. Luz; Luis, Santiago V.; Melo, Maria João; Piña, Fernando; Soriano, Conxa

doi:10.1039/a904894d

Cited by 95 publications

(60 citation statements)

References 15 publications

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“…For a given pH value, if the total amount of free substrate (ΣAH (h-i) ), free receptor (ΣLH i ), and adduct formed (ΣH h LS) are known, one can define an effective stability constant by using Equation (3). [40] The use of K eff allows a direct comparison between the binding ability of the ligands, overcoming the presence in .…”

Section: Anion Binding By the Ligands L1py L4py And L5pymentioning

confidence: 99%

Selective Binding of Glyphosate by a Ditopic Cyclic–Open‐Chain Polyazaligand in Aqueous Solution

et al. 2011

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International audienceThis paper reports a study of the interaction between a ditopic cyclic–open-chain polyazaligand L1py and the herbicide glyphosate [N-(phosphonomethyl)glycine or PMG] by potentiometric titrations as well as calorimetry and NMR measurements. This nonsymmetrical ligand is composed of a cyclam unit (1,4,8,11-tetraazacyclotetradecane) and the linear tetraamine 1,4,8,11-tetraazaundecane linked by a 2,6-dimethylpyridine spacer. This ligand forms stable adducts with PMG. For comparison, two analogous symmetrical ditopic ligands, a bis-macrocycle L4py and a bis-tetraamine L5py, and two related anions, iminodiacetic acid (IDA) and iminobis(methylphosphonic acid) (IDP), were also investigated. The results unambiguously show that L1py selectively binds PMG, especially around neutral pH, whereas L4py and L5py exhibit a weaker affinity for this substrate. Calorimetic and 1H NMR measurements showed that the host–guest adducts are mainly stabilized by charge–charge interactions and hydrogen bonds involving the ammonium function of PMG and the nonprotonated nitrogen atom of the pyridine linker

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Section: Anion Binding By the Ligands L1py L4py And L5pymentioning

confidence: 99%

Selective Binding of Glyphosate by a Ditopic Cyclic–Open‐Chain Polyazaligand in Aqueous Solution

et al. 2011

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“…To obtain a needed ATP concentration it was added to starting solution stepwise by aliquots (2,4,6,10,20,50,100,200, and 600 µL) with intermediate recording of the spectra.…”

Section: Methodsmentioning

confidence: 99%

“…Both groups created fluorescent sensors for multi-charged anion concentration measurements, and tetra-charged ATP anion was one effectively determined by them. Albelda and co workers also developed and studied a series of ATP chemosensors [6]. All groups elaborated the aromatic polycathionic probes that in water solutions can bind a number of anionic species, among them phosphate, pyrophosphate, polycarboxylates, etc.…”

Section: Introductionmentioning

confidence: 99%

Fluorometric Detection of Adenosine Triphosphate with 3-Hydroxy-4′-(dimethylamino)flavone in Aqueous Solutions

2006

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An effect of appearance of new band in the excitation spectra of 3-hydroxy-4 -(dimethylamino)flavone (FME probe) in presence of adenosine triphosphate (ATP) is described. Considerable shift of new band up to the red and increase of fluorescence intensity points to the formation of FME-ATP associate, in which FME molecule undergoes to a strong electrostatic stabilization by tetra-charged ATP anion. It is shown the FME anion formation is possible under influence of ATP in the studied conditions. The dynamics of the observed effect is studied in mitochondria. The registered phenomenon allows the quantitative evaluation of ATP concentration in the range of 10 −3 -10 −5 M. In contrast to ATP, other nucleoside phosphates do not give a new band in the excitation spectra of FME probe. This implies the possibility of the in vivo determination of the ATP concentration.

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“…To overcome the presence of different equilibria present in solution at the same pH value, it can be useful to calculate effective stability constants. [30] For a given pH value, if the total amount of free substrate (ΣH (h-i) A), free receptor [H (i) L] and adduct formed (H h LA) are known, one can define an effective stability constant by using the equation…”

Section: Phosphate Anion Binding In Aqueous Solutionmentioning

confidence: 99%

A Tris‐Macrocycle with Proton Sponge Characteristics as Efficient Receptor for Inorganic Phosphate and Nucleotide Anions

Bencini¹,

Biagini²,

Giorgi³

et al. 2009

Eur J Org Chem

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International audienceSynthesis, characterisation and proton-sponge behaviour of a new linear constrained tris-macrocycle (L), containing three cyclen (cyclen = 1,4,7,10-tetraazacyclododecane) reinforced macrocycles connected by two 2,6-pyridinediylbis(methylene) linkers, is reported. Protonated forms of L are efficient receptors for inorganic phosphate and nucleotide anions (ATP and ADP). The binding properties of L toward these substrates have been investigated in aqueous solution by means of potentiometric titrations, determining the stability constants of the adducts. The interaction mode was clarified by using 1H and 31P NMR measurements in aqueous solution and by means of molecular modelling calculations carried out on differently protonated species of L as well as on several nucleotide-receptor adducts. The stability of the adducts is mainly due to charge-charge and hydrogen bonding interactions between the polyphosphate chain of nucleotides and the ammonium groups of L.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009

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Thermodynamics and fluorescence emission studies on potential molecular chemosensors for ATP recognition in aqueous solution †

Cited by 95 publications

References 15 publications

Selective Binding of Glyphosate by a Ditopic Cyclic–Open‐Chain Polyazaligand in Aqueous Solution

Selective Binding of Glyphosate by a Ditopic Cyclic–Open‐Chain Polyazaligand in Aqueous Solution

Fluorometric Detection of Adenosine Triphosphate with 3-Hydroxy-4′-(dimethylamino)flavone in Aqueous Solutions

A Tris‐Macrocycle with Proton Sponge Characteristics as Efficient Receptor for Inorganic Phosphate and Nucleotide Anions

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