Folic acid-modified β-cyclodextrin nanoparticles as drug delivery to load DOX for liver cancer therapeutics

Fan, Wenbo; Xu, Yuedi; Li, Zheng; Li, Qiang

doi:10.1080/1539445x.2019.1624265

Cited by 33 publications

(18 citation statements)

References 40 publications

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“…The result intuitively shows that the uptake of FA-AmCS-TPP nanoparticles by tumor cells was significantly higher than that of AmCS-TPP nanoparticles. This confirms that the introduction of FA into the carriers can increase the uptake rate by cancer cells, which is consistent with previous reports [65,66,67,68,69].…”

Section: Resultssupporting

confidence: 93%

Fabrication of Ion-Crosslinking Aminochitosan Nanoparticles for Encapsulation and Slow Release of Curcumin

Sun

Ying

et al. 2019

Pharmaceutics

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Curcumin (Cur) has anticancer activities but has poor stability, which can be improved using carrier materials. In this study, chitosan was aminated to increase the number of amino groups on its surface, modified with folic acid (FA), and then made into nanoparticles by ionic crosslinking. Owing to ion interaction, the negatively charged, non-toxic tripolyphosphate (TPP) interacted with the positively charged amino group on the aminated chitosan (AmCS) surface, producing FA-AmCS-TPP nanoparticles, which were then characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), Fourier transform infrared spectrophotometry (FT-IR), and thermogravimetric analysis (TGA). Their small particle size (175.2 ± 0.99 nm) and good surface positive potential (+42.4 mV) are beneficial for carrying antitumor drugs. We subsequently investigated whether coating of Cur by AmCS allows slow drug release by FA-AmCS-TPP nanoparticles in different pH environments, and estimated the Cur loading efficiency (EE-Cur). Our results showed that the cumulative release rate of Cur at 48 h was 56.2%, and that the EE-Cur reached 94.26 ± 0.91% with nanoparticles composed of 0.10 g AmCS, 10.0 mg FA, 10.0 mg TPP, and 15.0 mg Cur. Additionally, cytotoxicity experiments showed that the Cur/FA-AmCS-TPP nanoparticles had good targeting ability for tumor cells. Therefore, the non-toxic targeted composite nanoparticles had potential as a new antitumor agent that can overcome the limitations of Cur.

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Section: Resultssupporting

confidence: 93%

Fabrication of Ion-Crosslinking Aminochitosan Nanoparticles for Encapsulation and Slow Release of Curcumin

Sun

Ying

et al. 2019

Pharmaceutics

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“…Nowadays, there is a growing interest in the application of host-guest interactions of CDs/drugs with a combination of hydrophilic PEG macromolecules in the preparation of polymeric nanoassemblies for DOX delivery. Both the covalent conjugation [ 132 , 133 , 134 ] and supramolecular complexation [ 135 , 136 , 137 ] were used. The first strategy was focused on the conjugation of targeting molecules along with hydrophilic PEG macromolecules applying two types of targeting molecules: folic acid (FA) and d -α-tocopheryl (α-TC).…”

Section: Poly(ethylene Glycol)/cyclodextrin Systems For Biomedicalmentioning

confidence: 99%

“…The FA is a vitamin which exhibits remarkable tumor targeting ability because it is overexpressed on the surfaces of a variety of human cancers such as breast, nasopharyngeal, cervical, ovarian, and colorectal cancers [ 154 ]. Therefore, folic acid–polyethylene glycol–β-cyclodextrin (FA–PEG–β-CD) was prepared to improve DOX delivery to targeted lines human liver cancer cells (HepG2) [ 133 ] and breast cancer (MCF-7) [ 134 ], as shown in Figure 11 . The desired FA–PEG–β-CD was obtained by the reaction of carboxyl-functionalized FA-PEG-COOH [ 133 ] or amine-functionalized FA-PEG-NH 2 with β-CD [ 134 ].…”

Section: Poly(ethylene Glycol)/cyclodextrin Systems For Biomedicalmentioning

confidence: 99%

Biocompatible Polymers Combined with Cyclodextrins: Fascinating Materials for Drug Delivery Applications

et al. 2020

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Cyclodextrins (CD) are a group of cyclic oligosaccharides with a cavity/specific structure that enables to form inclusion complexes (IC) with a variety of molecules through non-covalent host-guest interactions. By an elegant combination of CD with biocompatible, synthetic and natural polymers, different types of universal drug delivery systems with dynamic/reversible properties have been generated. This review presents the design of nano- and micro-carriers, hydrogels, and fibres based on the polymer/CD supramolecular systems highlighting their possible biomedical applications. Application of the most prominent hydrophobic aliphatic polyesters that exhibit biodegradability, represented by polylactide and polycaprolactone, is described first. Subsequently, particular attention is focused on materials obtained from hydrophilic polyethylene oxide. Moreover, examples are also presented for grafting of CD on polysaccharides. In summary, we show the application of host-guest interactions in multi-component functional biomaterials for controlled drug delivery.

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“…They possess a remarkable ability to incorporate various guest molecules, via noncovalent interactions, into their hydrophobic cavities [17]. Several FA-CD systems for anticancer drugs have been reported [18][19][20] with a recent development of folic acid-polyethylene glycol-β-cyclodextrin (FA-PEG-β-CD) nanoparticles (NPs) by Fan et al [21], as a drug-delivery system for doxorubicin for liver cancer therapy. The in vitro drug release results showed that the FA-PEG-β-CD NPs improved doxorubicin's solubility and could also control the drug release.…”

Section: Introductionmentioning

confidence: 99%

Conjugated β-Cyclodextrin Enhances the Affinity of Folic Acid towards FRα: Molecular Dynamics Study

et al. 2021

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Drug targeting is a progressive area of research with folate receptor alpha (FRα) receiving significant attention as a biological marker in cancer drug delivery. The binding affinity of folic acid (FA) to the FRα active site provides a basis for recognition of FRα. In this study, FA was conjugated to beta-cyclodextrin (βCD) and subjected to in silico analysis (molecular docking and molecular dynamics (MD) simulation (100 ns)) to investigate the affinity and stability for the conjugated system compared to unconjugated and apo systems (ligand free). Docking studies revealed that the conjugated FA bound into the active site of FRα with a docking score (free binding energy < −15 kcal/mol), with a similar binding pose to that of unconjugated FA. Subsequent analyses from molecular dynamics (MD) simulations, root mean square deviation (RMSD), root mean square fluctuation (RMSF), and radius of gyration (Rg) demonstrated that FA and FA–βCDs created more dynamically stable systems with FRα than the apo-FRα system. All systems reached equilibrium with stable RMSD values ranging from 1.9–2.4 Å and the average residual fluctuation values of the FRα backbone atoms for all residues (except for terminal residues ARG8, THR9, THR214, and LEU215) were less than 2.1 Å with a consistent Rg value of around 16.8 Å throughout the MD simulation time (0–100 ns). The conjugation with βCD improved the stability and decreased the mobility of all the residues (except residues 149–151) compared to FA–FRα and apo-FRα systems. Further analysis of H-bonds, binding free energy (MM-PBSA), and per residue decomposition energy revealed that besides APS81, residues HIS20, TRP102, HIS135, TRP138, TRP140, and TRP171 were shown to have more favourable energy contributions in the holo systems than in the apo-FRα system, and these residues might have a direct role in increasing the stability of holo systems.

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Folic acid-modified β-cyclodextrin nanoparticles as drug delivery to load DOX for liver cancer therapeutics

Cited by 33 publications

References 40 publications

Fabrication of Ion-Crosslinking Aminochitosan Nanoparticles for Encapsulation and Slow Release of Curcumin

Fabrication of Ion-Crosslinking Aminochitosan Nanoparticles for Encapsulation and Slow Release of Curcumin

Biocompatible Polymers Combined with Cyclodextrins: Fascinating Materials for Drug Delivery Applications

Conjugated β-Cyclodextrin Enhances the Affinity of Folic Acid towards FRα: Molecular Dynamics Study

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