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. 2025 Aug 12;30(16):3354.
doi: 10.3390/molecules30163354.

Synthesis and Properties of Silver Nanoparticles Functionalized with β-Cyclodextrin and Their Loading with Lupinine and Its Acetyl Derivatives

Serik D Fazylov  1 , Zhangeldy S Nurmaganbetov  1 , Oralgazy A Nurkenov  1 , Akmaral Z Sarsenbekova  2 , Olzhas T Seilkhanov  3 , Roza B Seidakhmetova  4 , Anel Z Mendibayeva  1 , Ryszhan Y Bakirova  5 , Zainulla M Muldakhmetov  1
Affiliations

Synthesis and Properties of Silver Nanoparticles Functionalized with β-Cyclodextrin and Their Loading with Lupinine and Its Acetyl Derivatives

Serik D Fazylov et al. Molecules. .

Abstract

This study presents the results of a study of the synthesis and properties of 2-hydroxy-β-cyclodextrin functionalized by silver nanoparticles and its loading with a bioactive component. As a reducing agent and stabilizer, 2-Hydroxy-β-cyclodextrin (2gβCD) was used in the production of silver nanoparticles. The use of 2gβCD-AgNPs in loading molecules of the plant alkaloid lupinine (Lup) and its acetyl derivative (Lac) with bactericidal properties were studied. The formation of Lup-2gβCD-AgNPs and Lac-2gβCD-AgNPs was confirmed by UV spectroscopy and X-ray diffraction spectroscopy (XRD). Transmission electron microscopy (TEM) showed that the synthesized AgNPs had a spherical shape. 1H-, 13C-NMR nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy (FT-IR) confirmed the reduction and encapsulation of AgNPs by 2gβCD. Thermographic data show that the obtained Lup and its derivative inclusion complexes reduced energy barriers. This makes them promising components for thermosensitive functional materials. Encapsulated complexes of Lup and its acetate inclusion with silver nanoparticles demonstrated significantly (p < 0.05) higher antibacterial, cytotoxic, and moderately pronounced analgesic activity.

Keywords: 2-hydroxypropyl-β-cyclodextrin; analgetic activities; bactericidal; cytotoxic; lupinine; lupinyl acetate; nanocomposite; silver nanoparticles.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
(a)-UV-vis spectrum of Lup(Lac)-2gβCD-AgNPs; (b)-the solution of Lup-2gβCD-AgNPs; (c)-dry powder Lup-2gβCD-AgNPs.
Figure 2
Figure 2
TEM images and size distribution of the AgNPs nanoparticles. Average particle size is 8.5 ± 1.14 nm, 60 min, pH = 9.25.
Figure 3
Figure 3
XRD pattern of Lup-2gβCD-AgNPs (a—60 min after the start of the reaction; b—after 120 min from the start of the Ag+ reduction reaction).
Figure 4
Figure 4
(a)-IR Fourier spectra of Lup; (b)-β-CD; (c)-Lup-2gβCD-AgNPs.
Figure 5
Figure 5
Thermogravimetric (TG) and differential thermogravimetric (DTG) curves of thermal decomposition of the following samples: (a)—Lup; (b)—Lac; (c)—Lup-2gβCD and Lup-2gβCD-AgNPs; (d)—Lup-2gβCD and Lup-2gβCD-AgNPs/acetone.
Figure 5
Figure 5
Thermogravimetric (TG) and differential thermogravimetric (DTG) curves of thermal decomposition of the following samples: (a)—Lup; (b)—Lac; (c)—Lup-2gβCD and Lup-2gβCD-AgNPs; (d)—Lup-2gβCD and Lup-2gβCD-AgNPs/acetone.
Figure 6
Figure 6
Dependences of the logarithm of the derivative α on the inverse temperature constructed for different degrees of transformation (α = 0.1, … 0.5, … 1.0) at four heating rates (β = 2.5, 5.0, 7.5, 10.0 °C min−1): (a)—Lup; (b)—Lac; (c)—Lup-2gβCD-AgNPs; (d)—Lup-2gβCD-AgNPs/acetone inclusion complex.
Figure 6
Figure 6
Dependences of the logarithm of the derivative α on the inverse temperature constructed for different degrees of transformation (α = 0.1, … 0.5, … 1.0) at four heating rates (β = 2.5, 5.0, 7.5, 10.0 °C min−1): (a)—Lup; (b)—Lac; (c)—Lup-2gβCD-AgNPs; (d)—Lup-2gβCD-AgNPs/acetone inclusion complex.
Figure 7
Figure 7
Three-dimensional dependences of the reaction rate (da/dT) on temperature (T) and degree of transformation (α) for the studied samples: (a)—Lup; (b)—Lac; (c)—Lup-2gβCD-AgNPs inclusion complex; (d)—a similar complex synthesized in an acetone medium (Lup-2gβCD-AgNPs /acetone).
Figure 8
Figure 8
Dependences of the reaction rate (da/dT) on the degree of transformation (α) at different heating rates (β = 2.5, 5.0, 7.5 and 10.0 °C min−1) for the studied samples: (a)—Lup; (b)—Lac; (c)—inclusion complex Lup-2gβCD-AgNPs; (d)—Lup-2gβCD-AgNPs inclusion complex in acetone solution.
Figure 9
Figure 9
Synthesis of Lup acetate.
Figure 10
Figure 10
Schematic representation for the synthesis of Lup (Lac)-2gβCD-AgNPs.
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