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<p>Cannabidiol (CBD) is a non-psychoactive component extracted from the Moraceae plant cannabis and possesses various pharmacological activities, including anti-tumor effects. However, its poor stability, low water solubility, and insufficient drug targeting have limited its application in tumor treatment. In this study, folic acid (FA) was grafted onto O-carboxymethyl chitosan-g-cholesterol succinate monoester (CCMC) through an amidation reaction. In order to improve the stability, apparent solubility, and targeting ability of CBD, CBD/CCMC-FA nanomicelles were prepared by loading CBD. Firstly, the synthesis of polymer CCMC-FA was evaluated by Fourier transform infrared (FT-IR) and nuclear magnetic resonance hydrogen spectrum (<sup>1</sup>H-NMR). The physicochemical properties of CBD/CCMC-FA nanomicelles were characterized by detecting critical micelle concentration (CMC), particle size, polydispersity index (PDI), drug loading, encapsulation efficiency, morphology, and in vitro drug release. Stability and apparent solubility were assessed. The CCK-8 method was used to evaluate the inhibitory effect of CBD/CCMC-FA nanomicelles on SKOV3 cells. And coumarin 6 (C6) was used as a fluorescent probe to observe the cell uptake to initially evaluate the targeting ability of CBD/CCMC-FA nanomicelles. The results of FT-IR and <sup>1</sup>H-NMR indicated that CCMC-FA was successfully synthesized, and its CMC was 0.0044&#xa0;mg/mL. The average particle size of the prepared CBD/CCMC-FA nanomicelles was 121.9 ± 1.8&#xa0;nm, the PDI was good (0.21 ± 0.05), the drug loading was 10.26 ± 0.18%, the encapsulation efficiency was 78.63 ± 0.48%, and they were spherical under transmission electron microscopy (TEM). The cumulative release rate&#xa0;of CBD/CCMC-FA nanomicelles at acidic pH (5.4) was 37.16%, which was higher than 24.53% at physiological pH (7.4), indicating that the release of CBD/CCMC-FA nanomicelles was pH-sensitive. The particle size of micelles is stable during storage for 168&#xa0;h, and the apparent solubility is 355 times that of free CBD. The results of cell experiments showed that CBD/CCMC-FA nanomicelles had a stronger inhibitory effect on the viability rate of SKOV3 cells than free CBD. In SKOV3 cells, the fluorescence intensity of C6-labeled CCMC-FA nanomicelles was higher than that of C6/CCMC nanomicelles and free C6 dyes, preliminarily suggesting the improvement of the anti-tumor and targeting effects of FA-modified CBD/CCMC-FA nanomicelles. CCMC-FA nanomicelles can enhance the stability and apparent solubility of CBD and have potential in targeted drug delivery.</p>

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O-carboxymethyl chitosan-g-cholesterol derivative nanomicelles functionalized with folic acid for targeted cannabidiol delivery to ovarian cancer cells

  • 期刊论文

  • 发表日期：

    2025年11月3日

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  • Rui Li,
  • Zhijuan Wu,
  • Liyan Lu,
  • Yanlin Kang,
  • Jue Chen,
  • Yingli Wang,
  • Wenhui Ruan

摘要

Cannabidiol (CBD) is a non-psychoactive component extracted from the Moraceae plant cannabis and possesses various pharmacological activities, including anti-tumor effects. However, its poor stability, low water solubility, and insufficient drug targeting have limited its application in tumor treatment. In this study, folic acid (FA) was grafted onto O-carboxymethyl chitosan-g-cholesterol succinate monoester (CCMC) through an amidation reaction. In order to improve the stability, apparent solubility, and targeting ability of CBD, CBD/CCMC-FA nanomicelles were prepared by loading CBD. Firstly, the synthesis of polymer CCMC-FA was evaluated by Fourier transform infrared (FT-IR) and nuclear magnetic resonance hydrogen spectrum (1H-NMR). The physicochemical properties of CBD/CCMC-FA nanomicelles were characterized by detecting critical micelle concentration (CMC), particle size, polydispersity index (PDI), drug loading, encapsulation efficiency, morphology, and in vitro drug release. Stability and apparent solubility were assessed. The CCK-8 method was used to evaluate the inhibitory effect of CBD/CCMC-FA nanomicelles on SKOV3 cells. And coumarin 6 (C6) was used as a fluorescent probe to observe the cell uptake to initially evaluate the targeting ability of CBD/CCMC-FA nanomicelles. The results of FT-IR and 1H-NMR indicated that CCMC-FA was successfully synthesized, and its CMC was 0.0044 mg/mL. The average particle size of the prepared CBD/CCMC-FA nanomicelles was 121.9 ± 1.8 nm, the PDI was good (0.21 ± 0.05), the drug loading was 10.26 ± 0.18%, the encapsulation efficiency was 78.63 ± 0.48%, and they were spherical under transmission electron microscopy (TEM). The cumulative release rate of CBD/CCMC-FA nanomicelles at acidic pH (5.4) was 37.16%, which was higher than 24.53% at physiological pH (7.4), indicating that the release of CBD/CCMC-FA nanomicelles was pH-sensitive. The particle size of micelles is stable during storage for 168 h, and the apparent solubility is 355 times that of free CBD. The results of cell experiments showed that CBD/CCMC-FA nanomicelles had a stronger inhibitory effect on the viability rate of SKOV3 cells than free CBD. In SKOV3 cells, the fluorescence intensity of C6-labeled CCMC-FA nanomicelles was higher than that of C6/CCMC nanomicelles and free C6 dyes, preliminarily suggesting the improvement of the anti-tumor and targeting effects of FA-modified CBD/CCMC-FA nanomicelles. CCMC-FA nanomicelles can enhance the stability and apparent solubility of CBD and have potential in targeted drug delivery.