Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 May 20;24(10):1939.
doi: 10.3390/molecules24101939.

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

Ruslan R Kashapov  1   2 , Yuliya S Razuvayeva  3   4 , Albina Y Ziganshina  5 , Rezeda K Mukhitova  6 , Anastasiia S Sapunova  7 , Alexandra D Voloshina  8 , Victor V Syakaev  9 , Shamil K Latypov  10 , Irek R Nizameev  11   12 , Marsil K Kadirov  13   14 , Lucia Y Zakharova  15   16
Affiliations

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

Ruslan R Kashapov et al. Molecules. .

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.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of GCR-1 and GCR-2.
Figure 1
Figure 1
Concentration dependence of specific conductivity (χ) of water solutions of CR-1, GCR-1 and GCR-2, 25 °C.
Figure 2
Figure 2
Isotherm of surface tension (γ) of calix[4]resorcinarenes solutions, 25 °C: 1 - water solution of GCR-1; 2 - water solutions of GCR-2 in the presence of two-fold excess of MG.
Figure 3
Figure 3
(a) UV absorption spectrum of water solution of 0.4 mM GCR-1 and 0.5 mM GCR-2, optical way 0.1 cm. (b) Concentration dependence of absorption at 500 nm: 1, water solution of GCR-1; 2, Sudan I in water solution of GCR-1; 3, water solutions of GCR-2 in the presence of two-fold excess of MG; 4, Sudan I in water solutions of GCR-2 in the presence of two-fold excess of MG, optical way 0.1 cm.
Figure 4
Figure 4
Particle size distribution and zeta-potential value of GCR solutions: (a) water solution of 1 mM and 50 mM GCR-1; (b) water solution of 1 and 15 mM GCR-2 in the presence of two-fold excess MG.
Figure 5
Figure 5
TEM image of aqueous solutions of GCR-1 (a), GCR-2 and two-fold excess of MG (b).
Figure 6
Figure 6
Proposed self-assembly structures of GCR-1 (a) and GCR-2 (b) formed in aqueous solutions.
Figure 7
Figure 7
Dependence of the self-diffusion coefficients Ds of GCR-1 and GCR-2 on their inverse concentration in 50% DMSO-d6–50% D2O, 25 °C.
Figure 8
Figure 8
Isotherms of surface tension (γ) of calix[4]resorcinarenes GCR-1 and GCR-2 in 50% DMSO–50% water, 25 °C.
Figure 9
Figure 9
Particle size distribution of GCR-1 (a) and GCR-2 (b) in 50% DMSO–50% water, 25 °C.
See this image and copyright information in PMC

References

    1. Grumezescu A.M. Design and Development of New Nanocarriers. William Andrew Publishing; Norwich, UK: 2018.
    1. Yu G., Jie K., Huang F. Supramolecular amphiphiles based on host − guest molecular recognition motifs. Chem. Rev. 2015;115:7240–7303. doi: 10.1021/cr5005315. - DOI - PubMed
    1. Perret F., Coleman A.W. Biochemistry of anionic calix[n]arenes. Chem. Commun. 2011;47:7303–7319. doi: 10.1039/c1cc11541c. - DOI - PubMed
    1. Wang J.F., Huang L.Y., Bu J.H., Li S.Y., Qin S., Xu Y.W., Liu J.M., Su C.Y. A fluorescent calixarene-based dimeric capsule constructed: Via a MII-terpyridine interaction: Cage structure, inclusion properties and drug release. RSC Adv. 2018;8:22530–22535. doi: 10.1039/C8RA02146E. - DOI - PMC - PubMed
    1. Nimse S.B., Kim T. Biological applications of functionalized calixarenes. Chem. Soc. Rev. 2013;42:366–386. doi: 10.1039/C2CS35233H. - DOI - PubMed

LinkOut - more resources