ChemInform Abstract: Binding of Dipeptides and Tripeptides Containing Lysine or Arginine by p‐Sulfonatocalixarenes in Water: NMR and Microcalorimetric Studies.

Douteau‐Guével, Nathalie; Perret, Florent; Coleman, Anthony W.; Morel, Jean‐Pierre; Morel‐Desrosiers, Nicole

doi:10.1002/chin.200222185

Cited by 14 publications

(29 citation statements)

References 1 publication

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“…Usually, for the determination of the binding constants of cаlіxаrеne Host-Guest complexes with organic molecules, the NMR, calorimetry [4,18,19,20], UV, fluorescent spectroscopy and other methods are widely used [14,21]. However in some cases due to poor solubility of the cаlіx [4] …”

Section: Resultsmentioning

confidence: 99%

Complexation of Calix[4]arene bis-Hydroxymethylenediphosphonic Acid with Amino acids. Binding Constants Determination by RP HPLC Method

2015

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Host-Guest complexation of calixarene-bis-hydroxymethylenediphosphonic acid with 17 amino acids in water solution had been studied by the RP HPLC and molecular modelling methods. It had been shown the binding constants of the complexes are depended on the nature of the amino acid residue, log P and pKa of the acids. The complexation is mainly determined by the electrostatic interactions between the positively charged nitrogen atom of the amino acid and the negatively charged oxygen atom of phosphonic acid residue of the calixarene, the Host-Guest p-p, СН-p and solvophobic interactions.

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Section: Resultsmentioning

confidence: 99%

Complexation of Calix[4]arene bis-Hydroxymethylenediphosphonic Acid with Amino acids. Binding Constants Determination by RP HPLC Method

2015

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“…Thus, hydrophobic interaction is one influence factor for complexation process. 1 H NMR spectra NMR spectroscopy is indeed the most powerful tools for the study of formation of inclusion complex between hosts and a variety of guest molecules, especially the interaction mechanism [26,28]. Arena and coworkers [36] detailed studied of the complexation of p-SCX4 with five different amino acids not including L-Tyr using both NMR and calorimetry.…”

Section: Resultsmentioning

confidence: 99%

“…Arena et al [24] reported that the interaction between amino acids with the water soluble p-SCX4 by NMR and the studies has shown that p-SCX4 forms 1:1 complexes with these amino acids in both near neutral (pH 7.3) and acidic solutions [25]. Doutéau-Guevel et al [26] investigated the binding of dipeptides and tripeptides containing lysine or arginine with p-sulfonatocalixarenes in water by NMR and microcalorimetric studies [27]. The association constants, enthalpies and entropies of complexation have been determined.…”

Section: Introductionmentioning

confidence: 98%

“…The interactions of p-sulfonatocalixarenes with amino acids should provide important information on the mechanism of the binding of p-sulfonatocalixarenes to complex bio-macromolecules. Although there are a few reports that have focused on the interaction between them, the used study method are mostly limited NMR [24][25][26], microcalorimetric titration [27] RP-HPLC [28] and X-ray structure [29]. Arena et al [24] reported that the interaction between amino acids with the water soluble p-SCX4 by NMR and the studies has shown that p-SCX4 forms 1:1 complexes with these amino acids in both near neutral (pH 7.3) and acidic solutions [25].…”

Section: Introductionmentioning

confidence: 99%

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Study on the intermolecular complexation behavior between p-sulfonatocalix[4]arene with l-tyrosine

Zhang

Zhao

et al. 2011

J Incl Phenom Macrocycl Chem

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The formation of the complexation behavior of host molecules water-soluble p-sulfonatocalix[4]arene (p-SCX4) with L-tyrosine (L-Tyr) guest molecule has been studied by spectrophotometric including fluorescence and nuclear magnetic resonance (NMR) spectroscopy. Experimental conditions including concentration of p-SCX4 and medium acidity were investigated in detail. The results showed that p-SCX4 forms 1:1 complexes with L-Tyr in water. Their stability constant determined by spectrofluorometric titration is 15761 L mol. Moreover, to obtain information about the binding mechanism of the interaction, 1 H NMR studies were carried out showing that the water-soluble p-SCX4 was found to be able to complex the aromatic L-Tyr, and the part of benzene ring of amino acid penetrated into the hydrophobic cavity of calix[4]arene and charged aliphatic chain of L-Tyr stick out of the cavity. In addition, the thermodynamic parameters for the complexation of p-SCX4 with L-Tyr were determined through Van't Hoff analysis. The obtained data further confirmed the binding mode of p-SCX4 with L-Tyr. The related mechanism is proposed to explain the complexation processes.

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“…[87,88] CX[n]s have been shown to self-assemble in organic solvents to form large molecular capsules, [89] however, studies in aqueous solutions are limited. para-Sulfonatocalix[n]arenes (p-s-CX[n]), first synthesized in 1984, are water soluble and form inclusion complexes with a variety of bioactive molecules [86,90] to form water-soluble drugs. [91] p-s-CX [4] also form molecular capsules with 56MESS to produce a headto-tail type dimer between two intercalator molecules (Fig.…”

Section: Calix[n]arenesmentioning

confidence: 99%

Drug Delivery Devices and Targeting Agents for Platinum(II) Anticancer Complexes

et al. 2008

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An ideal platinum-based delivery device would be one that selectively targets cancerous cells, can be systemically delivered, and is non-toxic to normal cells. It would be beneficial to provide drug delivery devices for platinum-based anticancer agents that exhibit high drug transport capacity, good water solubility, stability during storage, reduced toxicity, and enhanced anticancer activity in vivo. However, the challenges for developing drug delivery devices include carrier stability in vivo, the method by which extracellular or intracellular drug release is achieved, overcoming the various mechanisms of cell resistance to drugs, controlled drug release to cancer cells, and platinum drug bioavailability. There are many potential candidates under investigation including cucurbit[n]urils, cyclodextrins, calix[n]arenes, and dendrimers, with the most promising being those that are synthetically adaptable enough to attach to targeting agents.

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ChemInform Abstract: Binding of Dipeptides and Tripeptides Containing Lysine or Arginine by p‐Sulfonatocalixarenes in Water: NMR and Microcalorimetric Studies.

Cited by 14 publications

References 1 publication

Complexation of Calix[4]arene bis-Hydroxymethylenediphosphonic Acid with Amino acids. Binding Constants Determination by RP HPLC Method

Complexation of Calix[4]arene bis-Hydroxymethylenediphosphonic Acid with Amino acids. Binding Constants Determination by RP HPLC Method

Study on the intermolecular complexation behavior between p-sulfonatocalix[4]arene with l-tyrosine

Drug Delivery Devices and Targeting Agents for Platinum(II) Anticancer Complexes

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