N-Methyl-d-glucamine-Calix[4]resorcinarene Conjugates: Self-Assembly and Biological Properties.

Ruslan R Kashapov,Marsil K Kadirov,Albina Y Ziganshina,Lucia Y Zakharova,Victor V Syakaev,Yuliya S Razuvayeva,Anastasiia S Sapunova,Rezeda K Mukhitova,Shamil K Latypov,Alexandra D Voloshina,Irek R Nizameev

doi:10.3390/molecules24101939

Abstract

Deep insight of the toxicity of supramolecular systems based on macrocycles is of fundamental interest because of their importance in biomedical applications. What seems to be most interesting in this perspective is the development of the macrocyclic compounds with biocompatible fragments. Here, calix[4]resorcinarene derivatives containing N-methyl- d-glucamine moieties at the upper rim and different chemical groups at the lower rim were synthesized and investigated. These macrocycles showed a tendency to self-aggregate in aqueous solution, and their self-assembly abilities depend on the structure of the lower rim. The in vitro cytotoxic and antimicrobial activity of the calix[4]resorcinarenes revealed the relationship of biological properties with the ability to aggregate. Compared to macrocycles with methyl groups on the lower rim, calix[4]resorcinarenes with sulfonate groups appear to possess very similar antibacterial properties, but over six times less hemolytic activity. In some ways, this is the first example that reveals the dependence of the observed hemolytic and antibacterial activity on the lipophilicity of the calix[4]arene structure.

Highlights

Calixarenes are one of the important and promising classes of macrocyclic host-molecules in supramolecular chemistry
This paper presents data on the presents data on the aggregation and biological properties of new calix[4]resorcinarenes, containing aggregation and biological properties of new calix[4]resorcinarenes, containing N-methyl-d-glucamine
N-methyl-diffusion coefficients (Ds)-glucamine-based calix[4]resorcinarenes (GCRs) was carried out in two twosteps steps illustrated in Scheme

Summary

Introduction

Calixarenes are one of the important and promising classes of macrocyclic host-molecules in supramolecular chemistry Thanks to their hard structure, presence of an inner cavity, wide possibilities of modification of the upper and lower rims, calixarenes have attracted considerable attention for various applications ranging from biochemistry to catalysis [1,2,3,4,5,6]. Both rims of these macrocycles can be modified for development of advanced functional molecules [7]. The non-toxicity of calixarenes allows the use of systems based on these macrocycles for delivery and to improve the bioavailability of drugs [3,11,12]

Methods

Results

Conclusion