Highly sensitive and selective detection of the pyrophosphate anion biomarker under physiological conditions

Sánchez, Guzmán; Curiel, David; Tatkiewcz, Witold; Ratera, Imma; Tárraga, Alberto; Veciana, Jaume; Molina, Pedro

doi:10.1039/c3sc53058b

Cited by 18 publications

(12 citation statements)

References 111 publications

(11 reference statements)

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“…Langton et al 32 demonstrated the utility of halogen bonding and its potential superiority to hydrogen bonding in achieving anion binding in water in a series of cyclodextrin-functionalized acyclic (57)(58)(59) and rotaxane (60-62) hosts ( Figure 20). Rotaxane 60, which bound anions via a combination of halogen bonding and hydrogen bonding, displayed a remarkably high affinity of 2,200 M À1 for I À and a selectivity of I À > Br À > Cl À > SO 4 2À in D 2 O.…”

Section: Halogen and Chalcogen Bondingmentioning

confidence: 98%

“…Apart from using Lewis acid metal complexes, Sanchez et al 57 have demonstrated an alternative approach to sensing pyrophosphate in water. A bis(carbazolyl)urea receptor 113 was immobilized onto a gold surface to produce self-assembled monolayers of 113 (113-SAM; Figure 36), which functioned as an extremely sensitive sensor for HP 2 Recently, the use of supramolecular assemblies instead of small-molecule probes has become an increasingly popular approach to creating highly responsive sensory materials.…”

Section: Sensingmentioning

confidence: 99%

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Anion Receptor Chemistry

Gale

Howe

2016

Chem

364

228

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Section: Halogen and Chalcogen Bondingmentioning

confidence: 98%

Section: Sensingmentioning

confidence: 99%

Anion Receptor Chemistry

Gale

Howe

2016

Chem

364

228

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“…Furthermore, a high level of HP 2 O 7 3− in synovial fluids is correlated to calcium pyrophosphate dehydrate disease (CPDD); a rheumatologic disorder . Therefore, the detection and discrimination of this anion has been the main focus of efforts by several research groups . However, only one example of an effective, selective, redox chemosensor has been reported so far .…”

Section: Resultsmentioning

confidence: 99%

“…[39] Therefore, the detection and discrimination of this anion has been the main focus of efforts by severalr esearch groups. [40] However,o nly one example of an effective, Chem.E ur.J.2016, 22,7533 -7544 www.chemeurj.org selective, redox chemosensor has been reported so far. [41] Moreover,t he creation of effective HP 2 O 7 3À chemosensorsi s also ad emanding task as ac onsequence of the similarity of this anion to the H 2 PO 4 À anion.…”

Section: Electrochemical Studiesmentioning

confidence: 99%

Host–Guest Chemistry: Oxoanion Recognition Based on Combined Charge‐Assisted C−H or Halogen‐Bonding Interactions and Anion⋅⋅⋅Anion Interactions Mediated by Hydrogen Bonds

González

Zapata

Caballero

et al. 2016

Chemistry A European J

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Several bis-triazolium-based receptors have been synthesized and their anion-recognition capabilities have been studied. The central chiral 1,1'-bi-2-naphthol (BINOL) core features either two aryl or ferrocenyl end-capped side arms with central halogen- or hydrogen-bonding triazolium receptors. NMR spectroscopic data indicate the simultaneous occurrence of several charge-assisted aliphatic and heteroaromatic C-H noncovalent interactions and combinations of C-H hydrogen and halogen bonding. The receptors are able to selectively interact with HP2 O7 (3-) , H2 PO4 (-) , and SO4 (2-) anions, and the value of the association constant follows the sequence: HP2 O7 (3-) >SO4 (2-) >H2 PO4 (-) . The ferrocenyl end-capped 7(2+) ⋅2 BF4 (-) receptor allows recognition and differentiation of H2 PO4 (-) and HP2 O7 (3-) anions by using different channels: H2 PO4 (-) is selectively detected through absorption and emission methods and HP2 O7 (3-) by using electrochemical techniques. Significant structural results are the observation of an anion⋅⋅⋅anion interaction in the solid state (2:2 complex, 6(2+) ⋅[H2 P2 O7 ](2-) ), and a short C-I⋅⋅⋅O contact is observed in the structure of the complex [8(2+) ][SO4 ]0.5 [BF4 ].

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“…Solutions of AuNPs containing tetracationic resorcinarene-derived cavitands were, for example, also shown to respond to the presence of diphosphate by a color change [27] due to the known diphosphate affinity of such cavitands [28]. Self-assembled monolayers on gold containing a bis(carbazolyl)urea-derived receptor allowed the sensitive detection of diphosphate in water by surface plasmon resonance (SPR) [29]. Silica nanoparticles containing a dye coordinated to a bis(zinc(II)-DPA) receptor released the dye upon diphosphate binding [30], and thus producing an optical signal.…”

Section: Introductionmentioning

confidence: 99%

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

Reinke¹,

Bartl²,

Koch³

et al. 2020

Beilstein J. Org. Chem.

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Gold nanoparticles covered with a mixture of ligands of which one type contains solubilizing triethylene glycol residues and the other peripheral zinc(II)–dipicolylamine (DPA) complexes allowed the optical detection of hydrogenphosphate, diphosphate, and triphosphate anions in water/methanol 1:2 (v/v). These anions caused the bright red solutions of the nanoparticles to change their color because of nanoparticle aggregation followed by precipitation, whereas halides or oxoanions such as sulfate, nitrate, or carbonate produced no effect. The sensitivity of phosphate sensing depended on the nature of the anion, with diphosphate and triphosphate inducing visual changes at significantly lower concentrations than hydrogenphosphate. In addition, the sensing sensitivity was also affected by the ratio of the ligands on the nanoparticle surface, decreasing as the number of immobilized zinc(II)–dipicolylamine groups increased. A nanoparticle containing a 9:1 ratio of the solubilizing and the anion-binding ligand showed a color change at diphosphate and triphosphate concentrations as low as 10 μmol/L, for example, and precipitated at slightly higher concentrations. Hydrogenphosphate induced a nanoparticle precipitation only at a concentration of ca. 400 μmol/L, at which the precipitates formed in the presence of diphosphates and triphosphates redissolved. A nanoparticle containing fewer binding sites was more sensitive, while increasing the relative number of zinc(II)–dipicolylamine complexes beyond 25% had a negative impact on the limit of detection and the optical response. Transmission electron microscopy provided evidence that the changes of the nanoparticle properties observed in the presence of the phosphates were due to a nanoparticle crosslinking, consistent with the preferred binding mode of zinc(II)–dipicolylamine complexes with phosphate anions which involves binding of the anion between two metal centers. This work thus provided information on how the behavior of mixed monolayer-protected gold nanoparticles is affected by multivalent interactions, at the same time introducing a method to assess whether certain biologically relevant anions are present in an aqueous solution within a specific concentration range.

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Highly sensitive and selective detection of the pyrophosphate anion biomarker under physiological conditions

Abstract: Self-assembled monolayers on gold of a multidentate adsorbate bearing a bis(carbazolyl)urea unit are prepared and used as a surface resonance plasmon sensor for the detection of hydrogen pyrophosphate anions under physiological conditions.

Cited by 18 publications

References 111 publications

Anion Receptor Chemistry

Anion Receptor Chemistry

Host–Guest Chemistry: Oxoanion Recognition Based on Combined Charge‐Assisted C−H or Halogen‐Bonding Interactions and Anion⋅⋅⋅Anion Interactions Mediated by Hydrogen Bonds

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

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