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Synthesis and Albumin Binding of Stereoisomers of Sulfobetaine p-tert-Butylthiacalix[4]arene Derivatives

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Abstract

Sulfobetaine derivatives of p-tert-butylthiacalix[4]arene were synthesized in good yields by the reaction of p-tert-butylthiacalix[4]arenes containing terminal N,N-dimethyl fragments with 1,4-butane sultone. An effect of the stereoisomeric form of the macrocyclic platform (cone, partial cone, and 1,3-alternate) on their reactivity was established. The ability of the synthesized macrocycles to form stable nanosized associates with the model protein, human serum albumin, was studied. The partial cone stereoisomer was found to increase the thermal stability of the model protein.

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Funding

The work was financially supported by the Russian Science Foundation (project no. 18-73-10094, https://rscf.ru/en/project/18-73-10094/).

The mass spectrometric analysis of the synthesized compounds was funded from the budget of the Priority-2030 Strategic Academic Leadership Program, Kazan (Volga Region) Federal University.

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Authors and Affiliations

  1. Kazan (Volga region) Federal University, Butlerov Chemistry Institute, 420008, Kazan, Russia

    L. S. Yakimova, A. F. Kunafina, P. L. Padnya & I. I. Stoikov

Authors
  1. L. S. Yakimova
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  2. A. F. Kunafina
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  3. P. L. Padnya
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  4. I. I. Stoikov
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Corresponding authors

Correspondence to L. S. Yakimova or I. I. Stoikov.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 8, pp. 878–885 https://doi.org/10.31857/S0514749222080110.

In memory of Academician A.I. Konovalov

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Yakimova, L.S., Kunafina, A.F., Padnya, P.L. et al. Synthesis and Albumin Binding of Stereoisomers of Sulfobetaine p-tert-Butylthiacalix[4]arene Derivatives. Russ J Org Chem 58, 1154–1159 (2022). https://doi.org/10.1134/S1070428022080115

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  • DOI: https://doi.org/10.1134/S1070428022080115

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