Receptors for Biologically Relevant Anions

Kubik, Stefan

doi:10.1002/9783527639502.ch7

Cited by 6 publications

(7 citation statements)

References 386 publications

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“…4 Receptors for the recognition of organic and inorganic phosphates have been reported and the supramolecular interactions which are the basis of the mechanisms of recognition fall into two categories: H-bonding or coordination bonds. 5 Amine-, amide-and urea-based compounds depend on hydrogen-bonding interactions between the phosphate oxygen atoms and proton donors appropriately spatially orientated. A drawback is that these often work best in organic solvents since water will compete for hydrogen bonding sites.…”

Section: Introductionmentioning

confidence: 99%

The selectivity of water-based pyrophosphate recognition is tuned by metal substitution in dimetallic receptors

et al. 2015

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The three dimetallic compounds [Ga2(bpbp)(OH)2(H2O)2](ClO4)3, [In2(bpbp)(CH3CO2)2](ClO4)3 and [Zn2(bpbp)(HCO2)2](ClO4) (bpbp(-) = 2,6-bis((N,N'-bis(2-picolyl)amino)methyl)-4-tertbutylphenolate) were evaluated as stable solid state precursors for reactive solution state receptors to use for the recognition of the biologically important anion pyrophosphate in water at neutral pH. Indicator displacement assays using in situ generated complex-pyrocatechol violet adducts, {M2(bpbp)(HxPV)}(n+) M = Ga(3+), In(3+), Zn(2+), were tested for selectivity in their reactions with a series of common anions: pyrophosphate, phosphate, ATP, arsenate, nitrate, perchlorate, chloride, sulfate, formate, carbonate and acetate. The receptor employing Ga(3+) showed a slow but visually detectable response (blue to yellow) in the presence of one equivalent of pyrophosphate but no response to any other anion, even when they were present in much higher concentrations. The systems based on In(3+) or Zn(2+) show less selectivity in accord with visibly discernible responses to several of the anions. These results demonstrate a facile method for increasing anion selectivity without modification of an organic dinucleating ligand scaffold. The comfortable supramolecular recognition of pyrophosphate by the dimetallic complexes is demonstrated by the single crystal X-ray structure of [Ga2(bpbp)(HP2O7)](ClO4)2 in which the pyrophosphate is coordinated to the two gallium ions via four of its oxygen atoms.

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Section: Introductionmentioning

confidence: 99%

The selectivity of water-based pyrophosphate recognition is tuned by metal substitution in dimetallic receptors

et al. 2015

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“…Developing sensors for the detection and quantification of anions is a major area of interest in supramolecular chemistry. This is due to the pivotal roles that these sensors play in many arenas including environmental, biological and medicinal arenas [ 1 , 2 , 3 , 4 , 5 , 6 ]. Lanthanide-based complexes have been developed and used extensively as sensors for a variety of analytes; many of these sensors are now used in commercial settings [ 7 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Terpyridine-Functionalized Calixarenes: Synthesis, Characterization and Anion Sensing Applications

et al. 2020

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Lanthanide complexes have been developed and are reported herein. These complexes were derived from a terpyridine-functionalized calix[4]arene ligand, chelated with Tb3+ and Eu3+. Synthesis of these complexes was achieved in two steps from a calix[4]arene derivative: (1) amide coupling of a calix[4]arene bearing carboxylic acid functionalities and (2) metallation with a lanthanide triflate salt. The ligand and its complexes were characterized by NMR (1H and 13C), fluorescence and UV-vis spectroscopy as well as MS. The photophysical properties of these complexes were studied; high molar absorptivity values, modest quantum yields and luminescence lifetimes on the ms timescale were obtained. Anion binding results in a change in the photophysical properties of the complexes. The anion sensing ability of the Tb(III) complex was evaluated via visual detection, UV-vis and fluorescence studies. The sensor was found to be responsive towards a variety of anions, and large binding constants were obtained for the coordination of anions to the sensor.

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“…[ 23 , 24 , 25 , 26 , 27 ] The formation of macrochelates was clearly defined for adenine nucleotides, thanks to the coordination of both the phosphate chains and the nitrogen N-7 of the purine residue. [ 28 , 29 ] Since then, different types of molecular receptors have been used for the recognition of phosphorylated anions in aqueous media [ 1 ]: (1) Linear or macrocyclic positively charged receptors, generally polyammonium systems [ 30 , 31 , 32 , 33 ] or receptors containing guanidinium or imidazolium groups [ 34 , 35 ]; (2) Metal complexes, generally coordinatively unsaturated Cu 2+ or Zn 2+ complexes, with acyclic (i.e., dipicolyl or terpyridyl derivatives [ 36 , 37 , 38 , 39 , 40 , 41 , 42 ] or Schiff base ligands [ 43 ]) or macrocyclic ligands [ 44 , 45 , 46 ]; (3) Ditopic receptors that combine a metal coordinating unit and hydrogen-bond donors to reinforce anion binding [ 47 , 48 ].…”

Section: Introductionmentioning

confidence: 99%

Recognition of AMP, ADP and ATP through Cooperative Binding by Cu(II) and Zn(II) Complexes Containing Urea and/or Phenylboronic—Acid Moieties

et al. 2018

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We report a series of Cu(II) and Zn(II) complexes with different ligands containing a dipicolyl unit functionalized with urea groups that may contain or not a phenylboronic acid function. These complexes were designed for the recognition of phosphorylated anions through coordination to the metal ion reinforced by hydrogen bonds involving the anion and NH groups of urea. The complexes were isolated and several adducts with pyrophosphate were characterized using X-ray diffraction measurements. Coordination of one of the urea nitrogen atoms to the metal ion promoted the hydrolysis of the ligands containing 1,3-diphenylurea units, while ligands bearing 1-ethyl-3-phenylurea groups did not hydrolyze significantly at room temperature. Spectrophotometric titrations, combined with 1H and 31P NMR studies, were used in investigating the binding of phosphate, pyrophosphate (PPi), and nucleoside 5′-polyphosphates (AMP, ADP, ATP, CMP, and UMP). The association constants determined in aqueous solution (pH 7.0, 0.1 M MOPS) point to a stronger association with PPi, ADP, and ATP as compared with the anions containing a single phosphate unit. The [CuL4]2+ complex shows important selectivity for pyrophosphate (PPi) over ADP and ATP.

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Receptors for Biologically Relevant Anions

Cited by 6 publications

References 386 publications

The selectivity of water-based pyrophosphate recognition is tuned by metal substitution in dimetallic receptors

The selectivity of water-based pyrophosphate recognition is tuned by metal substitution in dimetallic receptors

Terpyridine-Functionalized Calixarenes: Synthesis, Characterization and Anion Sensing Applications

Recognition of AMP, ADP and ATP through Cooperative Binding by Cu(II) and Zn(II) Complexes Containing Urea and/or Phenylboronic—Acid Moieties

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