Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin

The therapeutic application of serum albumin is determined by the relative content of the monomeric form compared to dimers, tetramers, hexamers, etc. In this paper, we propose and develop an approach to synthesize the <i>cone</i> stereoisomer of <i>p-tert</i>-butylthiacalix[...

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Main Authors: Luidmila Yakimova, Aisylu Kunafina, Olga Mostovaya, Pavel Padnya, Timur Mukhametzyanov, Alexandra Voloshina, Konstantin Petrov, Artur Boldyrev, Ivan Stoikov
Format: Article
Language:English
Published: MDPI AG 2022-09-01
Series:International Journal of Molecular Sciences
Subjects:
Online Access:https://www.mdpi.com/1422-0067/23/17/10040
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author Luidmila Yakimova
Aisylu Kunafina
Olga Mostovaya
Pavel Padnya
Timur Mukhametzyanov
Alexandra Voloshina
Konstantin Petrov
Artur Boldyrev
Ivan Stoikov
author_facet Luidmila Yakimova
Aisylu Kunafina
Olga Mostovaya
Pavel Padnya
Timur Mukhametzyanov
Alexandra Voloshina
Konstantin Petrov
Artur Boldyrev
Ivan Stoikov
author_sort Luidmila Yakimova
collection DOAJ
description The therapeutic application of serum albumin is determined by the relative content of the monomeric form compared to dimers, tetramers, hexamers, etc. In this paper, we propose and develop an approach to synthesize the <i>cone</i> stereoisomer of <i>p-tert</i>-butylthiacalix[4]arene with sulfobetaine fragments stabilization of monomeric bovine serum albumin and preventing aggregation. Spectral methods (UV-vis, CD, fluorescent spectroscopy, and dynamic light scattering) established the influence of the synthesized compounds on the content of monomeric and aggregated forms of BSA even without the formation of stable thiacalixarene/protein associates. The effect of thiacalixarenes on the efficiency of protein binding with the antibiotic ciprofloxacin was shown by fluorescence spectroscopy. The binding constant increases in the presence of the macrocycles, likely due to the stabilization of monomeric forms of BSA. Our study clearly shows the potential of this macrocycle design as a platform for the development of the fundamentally new approaches for preventing aggregation.
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spelling doaj.art-a95f0db6b6be428e941a2d812cad10532023-11-23T13:22:03ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672022-09-0123171004010.3390/ijms231710040Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with CiprofloxacinLuidmila Yakimova0Aisylu Kunafina1Olga Mostovaya2Pavel Padnya3Timur Mukhametzyanov4Alexandra Voloshina5Konstantin Petrov6Artur Boldyrev7Ivan Stoikov8A.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaA.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaA.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaA.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaA.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov Street, 420088 Kazan, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov Street, 420088 Kazan, RussiaA.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaA.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, RussiaThe therapeutic application of serum albumin is determined by the relative content of the monomeric form compared to dimers, tetramers, hexamers, etc. In this paper, we propose and develop an approach to synthesize the <i>cone</i> stereoisomer of <i>p-tert</i>-butylthiacalix[4]arene with sulfobetaine fragments stabilization of monomeric bovine serum albumin and preventing aggregation. Spectral methods (UV-vis, CD, fluorescent spectroscopy, and dynamic light scattering) established the influence of the synthesized compounds on the content of monomeric and aggregated forms of BSA even without the formation of stable thiacalixarene/protein associates. The effect of thiacalixarenes on the efficiency of protein binding with the antibiotic ciprofloxacin was shown by fluorescence spectroscopy. The binding constant increases in the presence of the macrocycles, likely due to the stabilization of monomeric forms of BSA. Our study clearly shows the potential of this macrocycle design as a platform for the development of the fundamentally new approaches for preventing aggregation.https://www.mdpi.com/1422-0067/23/17/10040sulfobetainesthiacalixareneself-assemblybovine serum albuminciprofloxacin
spellingShingle Luidmila Yakimova
Aisylu Kunafina
Olga Mostovaya
Pavel Padnya
Timur Mukhametzyanov
Alexandra Voloshina
Konstantin Petrov
Artur Boldyrev
Ivan Stoikov
Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin
International Journal of Molecular Sciences
sulfobetaines
thiacalixarene
self-assembly
bovine serum albumin
ciprofloxacin
title Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin
title_full Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin
title_fullStr Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin
title_full_unstemmed Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin
title_short Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin
title_sort albumin thiacalix 4 arene nanoparticles as potential therapeutic systems role of the macrocycle for stabilization of monomeric protein and self assembly with ciprofloxacin
topic sulfobetaines
thiacalixarene
self-assembly
bovine serum albumin
ciprofloxacin
url https://www.mdpi.com/1422-0067/23/17/10040
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