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Abstract <p>For the first time, water-soluble triazole derivatives of pillar[5]arene were synthesized. UV-Vis spectroscopy has revealed the formation of associates between pillar[5]arenes with 1,2,3-thiotriazole moieties and antitumor fluoropyrimidine drugs in a macrocycle : drug = 1 : 2 stoichiometric ratio in water. The association constant of the macrocycle with 5-fluorouracil was 5.46 and with floxuridine it was 7.04. Dynamic light scattering demonstrated the self-assembly of the macrocycle containing 1,2,4-thiotriazole fragments into stable associates in water, with a size of 180 nm over the entire concentration range studied (1–100 μM), in contrast to the isomeric pillar[5]arene. The critical aggregation concentration (CAC) for the macrocycle with 1,2,4-thiotriazole was 43 μM and for the pillar[5]arene with 1,2,3-thiothiothriazole it was 110 μM. At the same time, both macrocycles did not show toxicity towards model adenocarcinoma cells (A549) <i>in vitro</i>.</p>

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Synthesis of Triazole Derivatives of Pillar[5]arene and Their Self-Assembly with Antitumor Fluoropyrimidine Drugs

  • 期刊论文

  • 发表日期：

    2026年7月24日

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  • Yulia I. Aleksandrova,
  • Dmitriy N. Shurpik,
  • Arseniy I. Igumnov,
  • Arina V. Pergat,
  • Evgeniya V. Subakaeva,
  • Pavel V. Zelenikhin,
  • Ivan I. Stoikov

摘要

Abstract

For the first time, water-soluble triazole derivatives of pillar[5]arene were synthesized. UV-Vis spectroscopy has revealed the formation of associates between pillar[5]arenes with 1,2,3-thiotriazole moieties and antitumor fluoropyrimidine drugs in a macrocycle : drug = 1 : 2 stoichiometric ratio in water. The association constant of the macrocycle with 5-fluorouracil was 5.46 and with floxuridine it was 7.04. Dynamic light scattering demonstrated the self-assembly of the macrocycle containing 1,2,4-thiotriazole fragments into stable associates in water, with a size of 180 nm over the entire concentration range studied (1–100 μM), in contrast to the isomeric pillar[5]arene. The critical aggregation concentration (CAC) for the macrocycle with 1,2,4-thiotriazole was 43 μM and for the pillar[5]arene with 1,2,3-thiothiothriazole it was 110 μM. At the same time, both macrocycles did not show toxicity towards model adenocarcinoma cells (A549) in vitro.