Water-soluble pillar[5]arene sulfo-derivatives self-assemble into biocompatible nanosystems to stabilize therapeutic proteins

Dmitriy Shurpik, Yulia Aleksandrova, Olga Mostovaya, Viktoriya Nazmutdinova, Pavel Zelenikhin, Evgenia Subakaeva, Timur Mukhametzayanov, Peter Cragg, Ivan Stoikov

Research output: Contribution to journalArticlepeer-review


Pillar[5]arenes containing sulfonate fragments have been shown to form supramolecular complexes with therapeutic proteins to facilitate targeted transport with an increased duration of action and enhanced bioavailability. Regioselective synthesis was used to obtain a water-soluble pillar[5]arene containing the fluorescent label FITC and nine sulfoethoxy fragments. The pillar[5]arene formed complexes with the therapeutic proteins binase, bleomycin, and lysozyme in a 1:2 ratio as demonstrated by UV–vis and fluorescence spectroscopy. The formation of stable spherical nanosized macrocycle/binase complexes with an average particle size of 200 nm was established by dynamic light scattering and transmission electron microscopy. Flow cytometry demonstrated the ability of macrocycle/binase complexes to penetrate into tumor cells where they exhibited significant cytotoxicity towards A549 cells at 10 −5–10 −6 M while maintaining the enzymatic activity of binase.

Original languageEnglish
Article number105415
JournalBioorganic Chemistry
Publication statusPublished - 11 Oct 2021

Bibliographical note

Funding Information:
The work was supported by the Russian Science Foundation (Grant No 17-13-01208).

Funding Information:
The investigation of structure of the compounds by NMR spectroscopy was carried out within the framework of the grant of the President of the Russian Federation for state support of leading scientific schools of the Russian Federation (NSh-2499.2020.3).


  • pillar[5]arene
  • binase
  • bleomycin
  • lysozyme
  • A549 cells
  • macrocyclic receptors
  • Macrocyclic receptors
  • Bleomycin
  • Binase
  • Pillar[5]arene
  • Lysozyme


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