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Synthesis, characterization, and in vitro evaluation of curcumin-loaded albumin nanoparticles surface-functionalized with glycyrrhetinic acid.

Li J, Chen T, Deng F, Wan J, Tang Y, Yuan P, Zhang L - Int J Nanomedicine (2015)

Bottom Line: Ccn-BNP-GA also appeared to be taken up to a greater extent by HepG2 cells than undecorated groups, which might be due to the high affinity of GA for GA receptors on the HepG2 cell surface.Further, Ccn-BNP-GA showed an approximately twofold higher rate of cell apoptosis than the other groups.Moreover, proliferation of HepG2 cells was arrested in G2/M phase based on cell cycle analysis.

View Article: PubMed Central - PubMed

Affiliation: Chongqing Medicine Engineering Research Center, Chongqing Key Laboratory of Biochemistry and Molecular Pharmacology, School of Pharmacy, Chongqing Medical University, Chongqing, People's Republic of China.

ABSTRACT
We have designed and developed curcumin (Ccn)-loaded albumin nanoparticles (BNPs) surface-functionalized with glycyrrhetinic acid (Ccn-BNP-GA) for GA receptor-mediated targeting. Ccn-BNP-GA was prepared by conjugating GA as a hepatoma cell-specific binding molecule onto the surface of BNPs. Ccn-BNP-GA showed a narrow distribution with an average size of 258.8±6.4 nm, a regularly spherical shape, an entrapment efficiency of 88.55%±5.54%, and drug loading of 25.30%±1.58%. The density of GA as the ligand conjugated to BNPs was 140.48±2.784 μg/g bovine serum albumin. Cytotoxicity assay results indicated that Ccn-BNP-GA was significantly more cytotoxic to HepG2 cells and in a concentration-dependent manner. Ccn-BNP-GA also appeared to be taken up to a greater extent by HepG2 cells than undecorated groups, which might be due to the high affinity of GA for GA receptors on the HepG2 cell surface. These cytotoxicity assay results were corroborated by analysis of cell apoptosis and the cell cycle. Further, Ccn-BNP-GA showed an approximately twofold higher rate of cell apoptosis than the other groups. Moreover, proliferation of HepG2 cells was arrested in G2/M phase based on cell cycle analysis. These results, which were supported by the GA receptor-mediated endocytosis mechanism, indicate that BNPs surface-functionalized with GA could be used in targeted cancer treatment with high efficacy, sufficient targeting, and reduced toxicity.

No MeSH data available.


Related in: MedlinePlus

Fourier transform infrared spectra for reagents.Notes: (A) GA, (B) bovine serum albumin, (C) N-hydroxysuccinimide ester of GA, and (D) albumin nanoparticles surface-functionalized with GA.Abbreviation: GA, glycyrrhetinic acid.
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f2-ijn-10-5475: Fourier transform infrared spectra for reagents.Notes: (A) GA, (B) bovine serum albumin, (C) N-hydroxysuccinimide ester of GA, and (D) albumin nanoparticles surface-functionalized with GA.Abbreviation: GA, glycyrrhetinic acid.

Mentions: The surface-functionalized groups were then observed by FT-IR spectroscopy, as shown in Figure 2, to identify the probable associations between BNPs and GA. As shown in the figure, raw GA was characterized by peaks at 1,654, 1,729, and 3,434 cm−1, which were attributed to C=O and O–H bending vibrations. The structure of oleanane pentacyclic triterpenoids was indicated by the spectral signatures at 1,387 and 1,364 cm−1 because of the C–H bending vibration at the C4 position. The absorption bands at 2,960 and 2,866 cm−1 corresponded to C-CH3 absorption and aliphatic C-H stretching. The peak intensities at 1,467, 1,392, and 1,085 cm−1 were attributed to the CH2, CH3, and C-O deformation vibrations, respectively. Considering BSA with a large number of amino bonds, evident absorption peaks of N-H bending were observed at 1,659 and 3,391 cm−1. The other major absorption peaks between 2,945 cm−1 and 2,868 cm−1 were ascribed to C–H stretching. Further, the characteristic absorption peaks of GA-NHS in the 1,741 and 1,651 cm−1 regions corresponded to C=O stretching vibration. Meanwhile, the peak intensity at 1,741 cm−1 decreased with the disappearance of the carboxylic group. For BNP-GA, the peak at 3,371 cm−1 broadened, which corresponded to O-H and N-H stretching and formation of strong intermolecular and intramolecular H-bonding. The absorption of the amide band I at 1,649 cm−1, amide band II at 1,559 cm−1, and amide band III at 1,318 cm−1 were the characteristic peaks, indicating that some specific interactions occurred between the carboxylic group of GA and the amino group of BSA. Moreover, some subtle changes were observed, ie, the intensity at 1,649 cm−1 became sharper and the vibration at 1,559 cm−1 receded markedly when compared with the spectrum for BSA. In addition, the peak of the carboxylic group in GA completely disappeared. The aforementioned results imply that GA was successfully conjugated onto the surface of the BNPs.


Synthesis, characterization, and in vitro evaluation of curcumin-loaded albumin nanoparticles surface-functionalized with glycyrrhetinic acid.

Li J, Chen T, Deng F, Wan J, Tang Y, Yuan P, Zhang L - Int J Nanomedicine (2015)

Fourier transform infrared spectra for reagents.Notes: (A) GA, (B) bovine serum albumin, (C) N-hydroxysuccinimide ester of GA, and (D) albumin nanoparticles surface-functionalized with GA.Abbreviation: GA, glycyrrhetinic acid.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4556296&req=5

f2-ijn-10-5475: Fourier transform infrared spectra for reagents.Notes: (A) GA, (B) bovine serum albumin, (C) N-hydroxysuccinimide ester of GA, and (D) albumin nanoparticles surface-functionalized with GA.Abbreviation: GA, glycyrrhetinic acid.
Mentions: The surface-functionalized groups were then observed by FT-IR spectroscopy, as shown in Figure 2, to identify the probable associations between BNPs and GA. As shown in the figure, raw GA was characterized by peaks at 1,654, 1,729, and 3,434 cm−1, which were attributed to C=O and O–H bending vibrations. The structure of oleanane pentacyclic triterpenoids was indicated by the spectral signatures at 1,387 and 1,364 cm−1 because of the C–H bending vibration at the C4 position. The absorption bands at 2,960 and 2,866 cm−1 corresponded to C-CH3 absorption and aliphatic C-H stretching. The peak intensities at 1,467, 1,392, and 1,085 cm−1 were attributed to the CH2, CH3, and C-O deformation vibrations, respectively. Considering BSA with a large number of amino bonds, evident absorption peaks of N-H bending were observed at 1,659 and 3,391 cm−1. The other major absorption peaks between 2,945 cm−1 and 2,868 cm−1 were ascribed to C–H stretching. Further, the characteristic absorption peaks of GA-NHS in the 1,741 and 1,651 cm−1 regions corresponded to C=O stretching vibration. Meanwhile, the peak intensity at 1,741 cm−1 decreased with the disappearance of the carboxylic group. For BNP-GA, the peak at 3,371 cm−1 broadened, which corresponded to O-H and N-H stretching and formation of strong intermolecular and intramolecular H-bonding. The absorption of the amide band I at 1,649 cm−1, amide band II at 1,559 cm−1, and amide band III at 1,318 cm−1 were the characteristic peaks, indicating that some specific interactions occurred between the carboxylic group of GA and the amino group of BSA. Moreover, some subtle changes were observed, ie, the intensity at 1,649 cm−1 became sharper and the vibration at 1,559 cm−1 receded markedly when compared with the spectrum for BSA. In addition, the peak of the carboxylic group in GA completely disappeared. The aforementioned results imply that GA was successfully conjugated onto the surface of the BNPs.

Bottom Line: Ccn-BNP-GA also appeared to be taken up to a greater extent by HepG2 cells than undecorated groups, which might be due to the high affinity of GA for GA receptors on the HepG2 cell surface.Further, Ccn-BNP-GA showed an approximately twofold higher rate of cell apoptosis than the other groups.Moreover, proliferation of HepG2 cells was arrested in G2/M phase based on cell cycle analysis.

View Article: PubMed Central - PubMed

Affiliation: Chongqing Medicine Engineering Research Center, Chongqing Key Laboratory of Biochemistry and Molecular Pharmacology, School of Pharmacy, Chongqing Medical University, Chongqing, People's Republic of China.

ABSTRACT
We have designed and developed curcumin (Ccn)-loaded albumin nanoparticles (BNPs) surface-functionalized with glycyrrhetinic acid (Ccn-BNP-GA) for GA receptor-mediated targeting. Ccn-BNP-GA was prepared by conjugating GA as a hepatoma cell-specific binding molecule onto the surface of BNPs. Ccn-BNP-GA showed a narrow distribution with an average size of 258.8±6.4 nm, a regularly spherical shape, an entrapment efficiency of 88.55%±5.54%, and drug loading of 25.30%±1.58%. The density of GA as the ligand conjugated to BNPs was 140.48±2.784 μg/g bovine serum albumin. Cytotoxicity assay results indicated that Ccn-BNP-GA was significantly more cytotoxic to HepG2 cells and in a concentration-dependent manner. Ccn-BNP-GA also appeared to be taken up to a greater extent by HepG2 cells than undecorated groups, which might be due to the high affinity of GA for GA receptors on the HepG2 cell surface. These cytotoxicity assay results were corroborated by analysis of cell apoptosis and the cell cycle. Further, Ccn-BNP-GA showed an approximately twofold higher rate of cell apoptosis than the other groups. Moreover, proliferation of HepG2 cells was arrested in G2/M phase based on cell cycle analysis. These results, which were supported by the GA receptor-mediated endocytosis mechanism, indicate that BNPs surface-functionalized with GA could be used in targeted cancer treatment with high efficacy, sufficient targeting, and reduced toxicity.

No MeSH data available.


Related in: MedlinePlus