Synthesis and properties of chiral nanoparticles based on (pS)- and (pR)-decasubstituted pillar[5]arenes containing secondary amide fragments

Shurpik, D. N.; Padnya, Pavel L.; Evtugyn, Vladimir G.; Mukhametzyanov, Timur A.; Khannanov, Artur; Кутырева, М. П.; Stoikov, Ivan I.

doi:10.1039/c5ra25562g

Cited by 26 publications

(13 citation statements)

References 40 publications

(82 reference statements)

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“…Pillar[n]arenes are capable of anion recognition [12], forming supramolecular complexes [13], and they may serve as components of sensors [14,15]. They form inclusion complexes and associates with aromatic compounds [16], which makes them suitable structure blocks for receptor systems working on the dye-displacement principle for inorganic anions [17] and biologically relevant anion substrates, e.g., adenosine triphosphate [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

et al. 2019

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A multicyclophane with a core based on tris(2-aminoethyl)amine (TREN) linked by amide spacers to three fragments of pillar[5]arene was synthesized. The choice of the tris-amide core allowed the multicyclophane to bind to anion guests. The presence of three terminal pillar[5]arene units provides the possibility of effectively binding the colorimetric probe N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine (PhTz). It was established that the multicyclophane complexed PhTz in chloroform with a 1:1 stoichiometry (lgKa = 5.2 ± 0.1), absorbing at 650 nm. The proposed structure of the complex was confirmed by 1H-NMR spectroscopy: the amide group linking the pillar[5]arene to the TREN core forms a hydrogen bond with the PhTz imino-group while the pillararenes surround PhTz. It was established that the PhTz:tris-pillar[5]arene complex could be used as a colorimetric probe for fluoride, acetate, and dihydrogen phosphate anions due to the anion binding with proton donating amide groups which displaced the PhTz probe. Dye displacement resulted in a color change from blue to pink, lowering the absorption band at 650 nm and increasing that at 533 nm.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

et al. 2019

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“…The analysis of the experimental data obtained by 1 Н NMR spectroscopy unfortunately did not allow us to determine the nature of the interaction by changing the position of the host and guest chemical shifts. The changes that were recorded in the 1 H NMR spectrum of the 3/Ag + system (1:1, 10 −3 M) were related to the broadening of the macrocycle signals, which indirectly indicates the aggregation process and the formation of 3/Ag + associates [34][35][36]. Therefore, we used the 2D 1 H, 1 H-nuclear Overhauser effect spectroscopy (NOESY) NMR methods (Figure 3), 2D 1 H, 1 H-rotational frame nuclear Overhauser effect spectroscopy (ROESY) NMR and 2D diffusion ordered spectroscopy (DOSY) NMR methods to confirm the formation of associates.…”

Section: Synthesis Of Decasubstituted Pillar[5]arenes Containing Sulfmentioning

confidence: 97%

Nanoparticles based on the zwitterionic pillar[5]arene and Ag⁺: synthesis, self-assembly and cytotoxicity in the human lung cancer cell line A549

Shurpik

Sevastyanov

Zelenikhin

et al. 2020

Beilstein J. Nanotechnol.

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For the first time, stable pillar[5]arene/Ag+ nanoparticles, consisting of water-soluble pillar[5]arene containing γ-sulfobetaine fragments and Ag+ ions without Ag–Ag bonds, were synthesized and characterized. The pillar[5]arene/Ag+ (ratio 1:10) nanoparticles obtained were cubic with a rib length of 100 nm and are less cytotoxic than Ag+ ions. The survival of the A549 model cells in the presence of pillar[5]arene/Ag+ (1:10) nanoparticles at a concentration of 30 and 40 μM was 76% and 55%, while in the absence of pillar[5]arene, the cell survival for free Ag+ ions at the same concentration was 30% and 10%, respectively. The results can be used to create new antibacterial materials and 2D biomedical coatings.

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“…Earlier in our research group, [21][22][23][24][25][26] it was shown that the functionalization of the pillar [5]arene with amide fragments increases the solubility of compounds in water and promotes self-association and aggregation of the resulting macrocycles. So, we proposed approach to the introduction of ten amide fragments into the pillar [5]arene structure for the purpose of selective recognition of metal ions, by varying the substituents in the amide fragment (-C(O)-NH-R and -C(O)-NR 2 ).…”

Section: Introductionmentioning

confidence: 96%

Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

Shurpik¹,

Yakimova²,

Stoikov³

et al. 2017

MHC

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Pillar[5]arenes bearing amide and carboxylic groups have demonstrated recognition performance for some representative alkali metal ions including Li + , Na + , K + and Cs + in series cations of sand d-metals compared to pillar[5] arenes with hydroxyl, methoxy and acetone fragments. Their complexation abilities toward these cations were evaluated by UV-Vis technique. The complexation results revealed that pillar[5]arene, containing glicylglicyne groups, were the most efficient cation receptors for Li + , Na + , K + and Cs + over other synthesized and studied pillar[5]arenes. Introduction of long glycylglycide fragments into macrocycle structure allowed to increase the association constant logarithm in the case of Li + by 2 orders. In addition, in the set of macrocycles, incorporation of the additional amide fragments and carboxyl group into macrocycle structure leads to increasing the binding efficiency with alkali metal cations.

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Synthesis and properties of chiral nanoparticles based on (pS)- and (pR)-decasubstituted pillar[5]arenes containing secondary amide fragments

Abstract: Employing induced asymmetric synthesis, new decasubstituted pillar[5]arenes containing (R)-(+)- or (S)-(−)-1-phenylethane-1-acetamide fragments have been obtained and characterized.

Cited by 26 publications

References 40 publications

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Nanoparticles based on the zwitterionic pillar[5]arene and Ag⁺: synthesis, self-assembly and cytotoxicity in the human lung cancer cell line A549

Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

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Synthesis and properties of chiral nanoparticles based on (pS)- and (pR)-decasubstituted pillar[5]arenes containing secondary amide fragments

Abstract: Employing induced asymmetric synthesis, new decasubstituted pillar[5]arenes containing (R)-(+)- or (S)-(−)-1-phenylethane-1-acetamide fragments have been obtained and characterized.

Cited by 26 publications

References 40 publications

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Nanoparticles based on the zwitterionic pillar[5]arene and Ag+: synthesis, self-assembly and cytotoxicity in the human lung cancer cell line A549

Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

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Nanoparticles based on the zwitterionic pillar[5]arene and Ag⁺: synthesis, self-assembly and cytotoxicity in the human lung cancer cell line A549