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Molecules. 2019 May 20;24(10). pii: E1939. doi: 10.3390/molecules24101939.

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

Author information

1
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. kashapov@iopc.ru.
2
Kazan National Research Technological University, 68 K. Marks str., Kazan 420015, Russia. kashapov@iopc.ru.
3
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. julianner@mail.ru.
4
Kazan National Research Technological University, 68 K. Marks str., Kazan 420015, Russia. julianner@mail.ru.
5
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. az@iopc.ru.
6
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. rezeda@iopc.ru.
7
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. anastasiya.strobykina@iopc.ru.
8
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. microbi@iopc.ru.
9
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. vsyakaev@iopc.ru.
10
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. lsk@iopc.ru.
11
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. irek.rash@gmail.com.
12
Kazan National Research Technological University, 68 K. Marks str., Kazan 420015, Russia. irek.rash@gmail.com.
13
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. kamaka59@gmail.com.
14
Kazan National Research Technological University, 68 K. Marks str., Kazan 420015, Russia. kamaka59@gmail.com.
15
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 Arbuzov str., Kazan 420088, Russia. lucia@iopc.ru.
16
Kazan National Research Technological University, 68 K. Marks str., Kazan 420015, Russia. lucia@iopc.ru.

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.

KEYWORDS:

calixarenes; cytotoxicity; self-assembly; supramolecular chemistry

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