Pentakis-Amidothiacalix[4]arene Stereoisomers: Synthesis and Effect of Central Core Conformation on Their Aggregation Properties

Nosov, Roman; Stoikov, Ivan I.

doi:10.6060/mhc140929s

Cited by 9 publications

(9 citation statements)

References 28 publications

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“…Several approaches to the synthesis of multicyclophanes based on thiacalixarene [20,21], pillararene [22], and of hybrid structures containing both fragments [23] in high yields have been developed previously in our group. It was shown that synthesized multicyclophanes are capable of forming stable supramolecular associates [20,21] and also can participate in oxidative polymerization reactions with supramolecular assistance [23]. TREN as a convenient platform for the design of anion receptors and sensors [24,25] has been chosen as a core of the synthesized multicyclophane.…”

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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“…Additional control of the purity of compounds and monitoring of the reaction were carried out by thin-layer chromatography using Silica G, 200 µm plates, UV 254. 4a-b, 5a-d, 6a-d Compounds 1 and 2 were synthesized according to published procedures [44][45][46]. Compounds 3a and 3b were synthesized according to published procedures.…”

Section: Chemistrymentioning

confidence: 99%

Fluorescein-Labeled Thiacalix[4]arenes as Potential Theranostic Molecules: Synthesis, Self-Association, and Antitumor Activity

et al. 2022

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In this paper, a series of thiacalix[4]arenes were synthesized as potential theranostic molecules for antitumor therapy. We propose an original strategy for the regioselective functionalization of thiacalix[4]arene with a fluorescent label to obtain antiangiogenic agent mimetics. The aggregation properties of the synthesized compounds were determined using the dynamic light scattering. The average hydrodynamic diameter of self-associates formed by the macrocycles in 1,3-alternate conformation is larger (277–323 nm) than that of the similar macrocycle in cone conformation (185–262 nm). The cytotoxic action mechanism of the obtained compounds and their ability to penetrate into of human lung adenocarcinoma and human duodenal adenocarcinoma cells were established using the MTT-test and flow cytometry. Thiacalix[4]arenes in 1,3-alternate conformation did not have a strong toxic effect. The toxicity of macrocycles in cone conformations on HuTu-80 and A549 cells (IC50 = 21.83–49.11 µg/mL) is shown. The resulting macrocycles are potential theranostic molecules that combine both the pharmacophore fragment for neoplasmas treatment and the fluorescent fragment for monitoring the delivery and biodistribution of nanomedicines.

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“…249 °C, 248.8 °C. [11] MALDI-TOF MS m/z C 45 H 50 O 10 : calculated 750. Pillar [5]arenes 3-7 were synthesized by literature method.…”

Section: Synthesesmentioning

confidence: 99%

“…[1][2][3][4][5][6] As a rule, a key role in these processes is played by macrocyclic compounds. [7][8][9][10][11][12][13] Depending on the size of the cavity, they are able to form host-guest systems, [14][15][16] leading to the formation of various supramolecular assembles.…”

Section: Introductionmentioning

confidence: 99%

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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Pentakis-Amidothiacalix[4]arene Stereoisomers: Synthesis and Effect of Central Core Conformation on Their Aggregation Properties

Abstract: New monosubstituted pentakisthiacalix [4]arenes in three different configurations (cone, partial cone and 1,3-

Cited by 9 publications

References 28 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

Fluorescein-Labeled Thiacalix[4]arenes as Potential Theranostic Molecules: Synthesis, Self-Association, and Antitumor Activity

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

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