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. 2025 Mar 17;30(6):1337.
doi: 10.3390/molecules30061337.

Synthesis of β-Cyclodextrin-Functionalized Silver Nanoparticles and Their Application for Loading Cytisine and Its Phosphorus Derivative

Serik D Fazylov  1 , Oralgazy A Nurkenov  1   2 , Zhangeldy S Nurmaganbetov  1 , Akmaral Zh Sarsenbekova  3 , Ryszhan Ye Bakirova  4 , Olzhas T Seilkhanov  5 , Alexandr K Sviderskiy  6 , Ardak K Syzdykov  1   2 , Anel Zh Mendibayeva  1   2
Affiliations

Synthesis of β-Cyclodextrin-Functionalized Silver Nanoparticles and Their Application for Loading Cytisine and Its Phosphorus Derivative

Serik D Fazylov et al. Molecules. .

Abstract

In this study, the synthesis and properties of β-cyclodextrin-functionalized silver nanoparticles and their loading with a drug component are considered. β-Cyclodextrin was used as a reducing agent and stabilizer in the preparation of silver nanoparticles. The use of β-CD-AgNPs in loading molecules of the alkaloid cytisine (Cz) and its O,O-dimethyl-N-cytisinilphosphate (CzP) derivative, which have pronounced antiviral properties, was studied. The formation of β-CD-Cz-AgNPs and β-CD-CzP-AgNPs was confirmed by UV spectroscopy and X-ray diffraction spectroscopy. Scanning electron microscopy and transmission electron microscopy showed that the obtained β-CD-Cz-AgNP and β-CD-CzP-AgNP nanocomposites were well dispersed with particle sizes in the range of 3-20 nm. 1H-, 13C-NMR and COSY, HMQC, HMBC and Fourier transform infrared spectroscopy revealed the reduction and encapsulation of AgNPs by β-Cz, and the TEM imaging results showed an increase in the size of nanoparticles after the introduction of cytisine and its phosphorus derivative. The kinetic parameters of the thermal degradation process of β-CD, Cz, CzP and their inclusion complexes Cz(CzP)-β-CD-AgNPs under isothermal conditions, which ensure the preservation of the kinetic triplet, were determined. The differences in the mechanism of thermal decomposition of the studied materials are described by the parameters of the Šesták-Berggren model (m and n), which demonstrated differences for different compounds: for β-CD, the values of the parameters m and n are 0.47 and 0.53, respectively, while for CzP-β-CD-AgNPs they reach values of 0.66 and 1.34. These results indicate differences in the mechanism of thermal decomposition of the studied materials.

Keywords: antiviral activity; cytisine; encapsulation; inclusion complex; nanocomposites; silver nanoparticles; thermal decomposition; β-cyclodextrin.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Schematic representation for the synthesis of Cz-β-CD-AgNPs and CzP-β-CD-AgNPs.
Figure 2
Figure 2
UV-vis spectrum of Cz-β-CD-AgNPs (1), CzP-β-CD-AgNPs (2) (a), the solution of optimum conditions (b).
Figure 3
Figure 3
Electron micrographs of nanocomposites Cz-β-CD-AgNPs (a) and CzP-β-CD-AgNPs (b) and diagrams of silver nanoparticles’ size distribution in the β-cyclodextrin matrix.
Figure 4
Figure 4
XRD pattern of β-CD-Cz-AgNPs.
Figure 5
Figure 5
IR Fourier spectra for β-CD (a) and Cz−β-CD−AgNPs (b). The different colors in the figure show the characteristic areas of the absorption bands of various functional groups in the structure of compounds.
Figure 6
Figure 6
TG/DTG curves in nitrogen atmosphere: (a,b) Cz; (c,d) CzP; (e,f) Czβ-CD; (g,h) Cz-β-CD-AgNPs; (i,j) CzP-β-CD-AgNPs.
Figure 6
Figure 6
TG/DTG curves in nitrogen atmosphere: (a,b) Cz; (c,d) CzP; (e,f) Czβ-CD; (g,h) Cz-β-CD-AgNPs; (i,j) CzP-β-CD-AgNPs.
Figure 7
Figure 7
Results of IR spectroscopic analysis of degradation products Cz (a), CzP (b), Cz-β-CD (1:1) (c), Cz-β-CD-AgNPs (d), CzP-β-CD-AgNPs (e).
Figure 7
Figure 7
Results of IR spectroscopic analysis of degradation products Cz (a), CzP (b), Cz-β-CD (1:1) (c), Cz-β-CD-AgNPs (d), CzP-β-CD-AgNPs (e).
Figure 8
Figure 8
Annealed cytisine at different temperatures: 90 °C (a); 160 °C (b); 250 °C (c); 315 °C (d); 360 °C (e).
Figure 9
Figure 9
Annealed CzP at different temperatures: 90 °C (a), 160 °C (b), 250 °C (c), 360 °C (d).
Figure 10
Figure 10
Annealed inclusion complex Cz-β-CD (1:1) at different temperatures: (a) 80 °C; (b) 270 °C; (c) 300 °C; (d) 350 °C; (e) 450 °C.
Figure 11
Figure 11
Annealed Cz-β-CD-AgNPs inclusion complex: (a) 90 °C; (b) 160 °C; (c) 250 °C; (d) 315 °C; (e) 360 °C.
Figure 12
Figure 12
Annealed inclusion complex CzP-β-CD-AgNPs: (a) 90 °C; (b) 160 °C; (c) 250 °C; (d) 315 °C; (e) 360 °C.
Figure 13
Figure 13
Scanned electron micrographs of samples: (I–III) Cz-β-CD (1:1); (IV–VI) CzP-β-CD (1:1); (VII–IX) Cz-β-CD-AgNPs; (X–XII) CzP-β-CD-AgNPs.
Figure 14
Figure 14
Schematic representation of the Friedman differential method: Cz (a); CzP (b); Cit-β-CD (c); Cit-β-CD-AgNPs (d); CzP-β-CD-AgNPs (e).
Figure 15
Figure 15
Three-dimensional coordinate system: (a) Cz; (b) CzP; (c) Cit-β-CD; (d) Cz-β-CD-AgNPs; (e) CzP-β-CD-AgNPs.
Figure 16
Figure 16
Graphical solution to the Šesták and Berggren model: Cz (a); CzP (b); Cz-β-CD (c); Cz-β-CD-AgNPs (d); CzP-β-CD-AgNPs (e).
Figure 17
Figure 17
Activation energy (E) indices determined using the methods of nonparametric kinetics (NPK), Šesták–Berggren (SB) and Friedman (FR): Cz (a); CzP (b); Cz-β-CD (c); Cz-β-CD-AgNPs (d); CzP-β-CD-AgNPs (e).
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