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. 2025 Jun 24;30(13):2718.
doi: 10.3390/molecules30132718.

Degradation of Folic Acid in the Composition of a Conjugate with Polyvinylpyrrolidone and Fullerene C60 Under UV and E-Beam Irradiation

Alina A Borisenkova  1   2 , Dmitriy V Baykov  1 , Anna V Titova  1   2 , Vadim V Bakhmetyev  3 , Maria A Markova  1   2 , Zhanna B Lyutova  1   2 , Anton V Popugaev  1   2 , Vladislav S Khaleev  4 , Victor P Sedov  2
Affiliations

Degradation of Folic Acid in the Composition of a Conjugate with Polyvinylpyrrolidone and Fullerene C60 Under UV and E-Beam Irradiation

Alina A Borisenkova et al. Molecules. .

Abstract

Folic acid (FA) is used as a targeting ligand for targeted drug delivery to tumor cells, some types of which overexpress folate receptors on their surface. However, while the preparation of conjugates containing FA may comprise a multi-step process, FA presents low photostability under UV irradiation. In addition, FA undergoes radiolysis under the action of ionizing radiation, which is utilized for drug sterilization. In this study, we investigate the stability of FA in a conjugate (FA-PVP-C60) with fullerene C60 and polyvinylpyrrolidone under the action of UV (205-400 nm) and electron irradiation (doses from 2 to 8 kGy) at different pH (4.5, 7.2, 10.7). The degradation of FA is studied using fluorescence and UV-Vis spectroscopy. It is found that the fullerene C60 in the FA-PVP-C60 conjugate suppresses the degradation of FA during both photolysis and radiolysis, which is confirmed by the decrease in the quantum yield of fluorescence and the radiation chemical yield of FA destruction accompanied by increasing fullerene content in the conjugate (from 2.8 to 10 wt.%).

Keywords: UV irradiation; folic acid; fullerene; photodegradation; radiation chemical yield; radiolysis.

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Conflict of interest statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Figure 1
Figure 1
UV (orange arrows) and radio (blue arrows) FA degradation pathways.
Figure 2
Figure 2
Absorption spectra of the FA-PVP-C60 conjugate, intermediate synthesis products FA-PVP, PVP-C60, PVP, and FA at pH 4.5 (A), pH 7.2 (B) and pH 10.7 (C).
Figure 3
Figure 3
Absorption spectra of C60-PVP conjugates with fullerene content of 2.8, 5 or 10 wt.% before and after 1 h of UV irradiation at pH 4.5 (A), pH 7.2 (B) and pH 10.7 (C).
Figure 4
Figure 4
(A) Time evolution of the absorption spectra of the FA-PVP-C60 conjugates in air-equilibrated aqueous solutions (pH 7.2) under UV irradiation (240–400 nm). Arrows indicate the isosbestic points. (B) Experimental difference (ED) spectra obtained by subtracting the spectrum after 5–60 min of photolysis from the FA-PVP-C60 conjugates initial spectrum.
Figure 5
Figure 5
Fluorescence QYs (Φx) of air-equilibrated aqueous solutions of non-irradiated and UV-irradiated FA-PVP-C60 conjugates at pH 4.5 (A), pH 7.2 (B) and pH 10.7 (C).
Figure 6
Figure 6
(A) Time evolution of the absorption spectra of the FA-PVP-C60 conjugates in air-equilibrated aqueous solutions (pH 4.5) under UV irradiation (240–400 nm). Arrows indicate the isosbestic points. (B) Experimental difference (ED) spectra obtained by subtracting the spectrum after 5–60 min of photolysis from the FA-PVP-C60 conjugates initial spectrum.
Figure 7
Figure 7
(A) Time evolution of the absorption spectra of the FA-PVP-C60 conjugates in air-equilibrated aqueous solutions (pH 10.7) under UV irradiation (240–400 nm). Arrows indicate the isosbestic points. (B) Experimental difference (ED) spectra obtained by subtracting the spectrum after 5–60 min of photolysis from the FA-PVP-C60 conjugates initial spectrum.
Figure 8
Figure 8
(A) Absorption spectra of unirradiated and irradiated (2–8 kGy) FA-PVP-C60 conjugates in 7.2 pH buffer. (B) Experimental difference (ED) spectra were obtained by subtracting the spectra of conjugates irradiated with a dose of 2–8 kGy from the initial spectrum of FA-PVP-C60.
Figure 9
Figure 9
(A) Absorption spectra of unirradiated and irradiated (2–8 kGy) FA-PVP-C60 conjugates in 4.5 pH buffer. (B) Experimental difference (ED) spectra were obtained by subtracting the spectra of conjugates irradiated with a dose of 2–8 kGy from the initial spectrum of FA-PVP-C60.
Figure 10
Figure 10
(A) Absorption spectra of unirradiated and irradiated (2–8 kGy) FA-PVP-C60 conjugates in 10.7 pH buffer. (B) Experimental difference (ED) spectra were obtained by subtracting the spectra of conjugates irradiated with a dose of 2–8 kGy from the initial spectrum of FA-PVP-C60.
Figure 11
Figure 11
Fluorescence QYs (Φx) of air-equilibrated aqueous solutions of non-irradiated and irradiated with doses of 2–8 kGy FA-PVP-C60 conjugates at pH 4.5 (A), pH 7.2 (B) and pH 10.7 (C).
Figure 12
Figure 12
Radical scavenging activity of FA-PVP-C60 and intermediate conjugates FA-PVP and PVP-C60. (A) DPPH radical scavenging activity; (B) hydroxyl radical scavenging activity. The data are presented as mean values ± SD (n = 3 independent experiments).
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