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Drug Delivery Systems Based on Polysaccharides: Second Edition
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Drug Delivery Systems Based on Polysaccharides: Second Edition

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Macromolecular Chemistry".

Deadline for manuscript submissions: 31 October 2024 | Viewed by 4747

Special Issue Editors

Prof. Dr. Marcel Popa

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Guest Editor
“Cristofor Simionescu” Faculty of Chemical Engineering and Environment Protection, “Gheorghe Asachi” Technical University, Iasi, Romania
Interests: polysaccharide modification; bioactive polymers; biomaterials; hydrogels; interpenetrated networks; micro- and nanoparticles (spheres and capsules); hybrid and functionalized nanoparticles for drug targeting; drug delivery; polymer–drug conjugates
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Leonard Ionut Atanase

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Guest Editor
Faculty of Medical Dentistry, “Apollonia” University of Iasi, Romania-11, Pacurari Street, 700511 Iasi, Romania
Interests: block and graft copolymers; micelles; colloids; emulsions; drug delivery; polysaccharides
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The use of polysaccharides in biomedical applications, and especially for obtaining systems capable of encapsulating, transporting, and delivering drugs in a sustained/controlled manner, is an area that has been intensely explored in recent decades, though it remains far from being exhausted. Polysaccharides, and also in large part their derivatives, are ideal supports for these applications, given their biocompatibility with living organisms and being of natural origin themselves. This Special Issue aims to present the latest aspects regarding the realization of polymer–biologically active principle systems in different formats, e.g., films, hydrogels, particles, capsules, implants, inserts, etc., that use polysaccharides and their derivatives as supports. A complementary field of interest is the creation of nanoparticles or nanocapsules for drug delivery, which are, respectively, particles functionalized on the surface with ligands recognizable by receptors that are well expressed in the cell membranes of different organs and hybrid particles containing magnetic nanoparticles encapsulated in polymeric matrices that are capable of active targeting after systemic administration by intravenous injection. Drug-carrying liposomes, stabilized by coating with polysaccharides, as well as their derivatives or copolymers with synthetic polymers, are also of interest for this Special Issue.

Prof. Dr. Marcel Popa
Prof. Dr. Leonard Ionut Atanase
Guest Editors

Manuscript Submission Information

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Keywords

  • polysaccharides
  • polysaccharide derivatives
  • hydrogels
  • micro- and nanoparticles (spheres and capsules)
  • hybrid nanoparticles
  • functionalized nanoparticles for drug targeting
  • micelles based on amphiphilic polysaccharides
  • drug delivery

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Related Special Issue

Published Papers (3 papers)

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Research

17 pages, 5620 KiB  
Article
Insulin Conformation Changes in Hybrid Alginate–Gelatin Hydrogel Particles
by Gulzhan Ye. Yerlan, Michael Shen, Bakyt B. Tyussyupova, Sagdat M. Tazhibayeva, Kuanyshbek Musabekov and Paul Takhistov
Molecules 2024, 29(6), 1254; https://doi.org/10.3390/molecules29061254 - 12 Mar 2024
Viewed by 1161
Abstract
There is a strong need to develop an insulin delivery system suitable for oral administration and preserving natural (α-helix) insulin conformation. In this work, we fabricated alginate–gelatin hydrogel beads for insulin encapsulation. Altering matrix composition and crosslinking agents has resulted in various surface [...] Read more.
There is a strong need to develop an insulin delivery system suitable for oral administration and preserving natural (α-helix) insulin conformation. In this work, we fabricated alginate–gelatin hydrogel beads for insulin encapsulation. Altering matrix composition and crosslinking agents has resulted in various surface morphologies and internal spatial organization. The structures of the insulin-loaded matrices were studied using optical and field emission electronic microscopy. We use FTIR spectroscopy to identify insulin conformation changes as affected by the hydrogel matrices. It was found that blended alginate–gelatin matrices demonstrate better encapsulation efficiency and stronger swelling resistance to a simulated gastric environment than sodium alginate beads crosslinked with the CaCl2. FTIR measurements reveal conformation changes in insulin. It is also confirmed that in the presence of gelatin, the process of insulin fibrinogenesis ceases due to intermolecular interaction with the gelatin. Performed molecular modeling shows that dipole–dipole interactions are the dominating mechanism that determines insulin behavior within the fabricated matrix. Full article
(This article belongs to the Special Issue Drug Delivery Systems Based on Polysaccharides: Second Edition)
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Figure 1

Figure 1
<p>Mechanisms of the alginate and gelatin interactions with Ca<sup>2+</sup> and GA ions: (<b>a</b>)—formation of the gelatin-glutaraldehyde complex; (<b>b</b>)—sodium alginate ionotropic gelation in presence of Ca<sup>2+</sup> ions, and (<b>c</b>)—sodium alginate glutaraldehyde complexation.</p> Full article ">Figure 2
<p>Design of the hydrogel matrices for insulin immobilization.</p> Full article ">Figure 3
<p>Effect of the ultrasound on the microparticle morphology: no ultrasound (<b>a</b>); ultrasound processing with 50% energy (<b>b</b>) and 100% energy (<b>c</b>).</p> Full article ">Figure 4
<p>Stereo images of crosslinked polymer matrices of alginate and alginate–gelatin in the absence and presence of insulin: NaAlg + CaCl<sub>2</sub> (<b>a</b>), NaAlg + Gel + CaCl<sub>2</sub> (<b>b</b>), NaAlg + Gel + CaCl<sub>2</sub> + GA (<b>c</b>), NaAlg + Gel + Ins (CaCl<sub>2</sub>) (<b>d</b>), NaAlg + Gel + Ins + CaCl<sub>2</sub> + GA (<b>e</b>), and NaAlg + Ins + CaCl<sub>2</sub> (<b>f</b>).</p> Full article ">Figure 5
<p>SEM images of crosslinked polymer matrices of sodium alginate and gelatin without (<b>a</b>–<b>c</b>) and with the embedded insulin (<b>d</b>–<b>f</b>): NaAlg + CaCl<sub>2</sub> (<b>a</b>), NaAlg + Gel + CaCl<sub>2</sub> (<b>b</b>), NaAlg + Gel + CaCl<sub>2</sub> + GA (<b>c</b>), NaAlg + Ins + CaCl<sub>2</sub> (<b>d</b>), NaAlg + Gel + Ins + CaCl<sub>2</sub> (<b>e</b>), and NaAlg + Gel + Ins + CaCl<sub>2</sub> + GA (<b>f</b>).</p> Full article ">Figure 6
<p>FTIR spectra of the raw materials (1—NaAlg; 2—Gel) and fabricated matrices (3—NaAlg (CaCl<sub>2</sub>), 4—NaAlg-Gel (CaCl<sub>2</sub>), 5—NaAlg-Gel (GA), and 6—NaAlg-Gel (CaCl<sub>2</sub>-GA)).</p> Full article ">Figure 7
<p>FTIR spectra of the insulin (1) and insulin-loaded hydrogel matrices: 1—Insulin; 2—NaAlg-Insulin (CaCl<sub>2</sub>); 3—NaAlg-Gel-Insulin (CaCl<sub>2</sub>); 4—NaAlg-Gel-Insulin (GA); 5—NaAlg-Gel-Insulin (CaCl<sub>2</sub>-GA).</p> Full article ">Figure 8
<p>Computed electrostatic potential maps of the interacting molecules and pairwise total interaction energies. The electrostatic potential map for insulin has been adapted from [<a href="#B34-molecules-29-01254" class="html-bibr">34</a>].</p> Full article ">Figure 9
<p>FTIR spectra in 1500–1700 cm<sup>−1</sup> region and corresponding band assignment of insulin.</p> Full article ">
20 pages, 15030 KiB  
Article
Angelica Sinensis Polysaccharide-Based Nanoparticles for Liver-Targeted Delivery of Oridonin
by Henglai Sun, Jijuan Nai, Biqi Deng, Zhen Zheng, Xuemei Chen, Chao Zhang, Huagang Sheng and Liqiao Zhu
Molecules 2024, 29(3), 731; https://doi.org/10.3390/molecules29030731 - 5 Feb 2024
Cited by 2 | Viewed by 1420
Abstract
The present work aimed to study the feasibility of Angelica sinensis polysaccharide (ASP) as an instinctive liver targeting drug delivery carrier for oridonin (ORI) in the treatment of hepatocellular carcinoma (HCC). ASP was reacted with deoxycholic acid (DOCA) via an esterification reaction to [...] Read more.
The present work aimed to study the feasibility of Angelica sinensis polysaccharide (ASP) as an instinctive liver targeting drug delivery carrier for oridonin (ORI) in the treatment of hepatocellular carcinoma (HCC). ASP was reacted with deoxycholic acid (DOCA) via an esterification reaction to form an ASP-DOCA conjugate. ORI-loaded ASP-DOCA nanoparticles (ORI/ASP-DOCA NPs) were prepared by the thin-film water method, and their size was about 195 nm in aqueous solution. ORI/ASP-DOCA NPs had a drug loading capacity of up to 9.2%. The release of ORI in ORI/ASP-DOCA NPs was pH-dependent, resulting in rapid decomposition and accelerated drug release at acidic pH. ORI/ASP-DOCA NPs significantly enhanced the accumulation of ORI in liver tumors through ASGPR-mediated endocytosis. In vitro results showed that ORI/ASP-DOCA NPs increased cell uptake and apoptosis in HepG2 cells, and in vivo results showed that ORI/ASP-DOCA NPs caused effective tumor suppression in H22 tumor-bearing mice compared with free ORI. In short, ORI/ASP-DOCA NPs might be a simple, feasible, safe and effective ORI nano-drug delivery system that could be used for the targeted delivery and treatment of liver tumors. Full article
(This article belongs to the Special Issue Drug Delivery Systems Based on Polysaccharides: Second Edition)
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Graphical abstract

Graphical abstract
Full article ">Figure 1
<p>The design principle of ORI/ASP-DOCA NPs and its anti-liver tumor effect. Reprinted/adapted with permission from Ref. [<a href="#B23-molecules-29-00731" class="html-bibr">23</a>]. 2021, Dan Zheng.</p> Full article ">Figure 2
<p>(<b>A</b>) UV absorption spectrum scanning results of ASP; (<b>B</b>) FT-IR spectrum of ASP; (<b>C</b>) Dextran corresponding molecular weight standard curve; (<b>D</b>) HPLC chromatogram of monosaccharide standard solution mixture; (<b>E</b>) HPLC chromatogram of ASP solution. (1: PMP; 2: <span class="html-small-caps">d</span>-mannose; 3: Rhamnose; 4: <span class="html-small-caps">d</span>-galacturonic acid; 5: <span class="html-small-caps">d</span>-glucose; 6: <span class="html-small-caps">d</span>-galactose; 7: Arabinose).</p> Full article ">Figure 3
<p>Synthetic route of the ASP-DOCA compound.</p> Full article ">Figure 4
<p>FT-IR (<b>A</b>) and <sup>1</sup>H-NMR Spectra (<b>B</b>) of ASP, DOCA and the ASP-DOCA compound; (<b>C</b>) CAC of the ASP-DOCA compound.</p> Full article ">Figure 5
<p>(<b>A</b>) ORI/ASP-DOCA NPs solution and its freeze-dried powder; (<b>B</b>) The relationship between the particle size and dispersion coefficient of ORI/ASP-DOCA NPs and storage time; (<b>C</b>) Particle size distribution of ORI/ASP-DOCA NPs; (<b>D</b>) The drug release curves of free ORI and ORI/ASP-DOCA NPs at different pH values.</p> Full article ">Figure 6
<p>TEM images of ASP-DOCA NPs (<b>Aa</b>) and ORI/ASP-DOCA NPs (<b>Ab</b>); SEM images of ASP-DOCA NPs (<b>Ba</b>) and ORI/ASP-DOCA NPs (<b>Bb</b>); (<b>C</b>) XRD patterns of ORI, ORI/ASP-DOCA NPs, ASP-DOCA NPs, ORI and ASP-DOCA NPs physical mixture; (<b>D</b>) DSC spectrum of ORI, ORI/ASP-DOCA NPs, ASP-DOCA NPs, ORI and ASP-DOCA NPs physical mixture.</p> Full article ">Figure 7
<p>Cytotoxicity of ASP-DOCA NPs on HepG2 cells for 24 h (<b>Aa</b>) and 48 h (<b>Ab</b>); Cytotoxicity of ASP-DOCA NPs on HeLa cells for 24 h (<b>Ba</b>) and 48 h (<b>Bb</b>).</p> Full article ">Figure 8
<p>Cytotoxicity of free ORI and ORI/ASP DOCA NPs on HepG2 cells for 24 h (<b>Aa</b>) and 48 h (<b>Ab</b>); Cytotoxicity of free ORI and ORI/ASP DOCA NPs on HeLa cells for 24 h (<b>Ba</b>) and 48 h (<b>Bb</b>). (Note: compared with ORI group, * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.01).</p> Full article ">Figure 9
<p>The in vitro targeting effect of ORI/ASP-DOCA NPs and ASP + ORI/ASP-DOCA NPs on HepG2 after 1 h (<b>a</b>), 2 h (<b>b</b>), 4 h (<b>c</b>) and 24 h (<b>d</b>). (Note: compared with ASP + ORI/ASP-DOCA NPs group, * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.01).</p> Full article ">Figure 10
<p>Cellular uptake of ORI, ORI/ASP-DOCA, ORI/DEX-DOCA and ASP + ORI/ASP-DOCA by HepG2 (<b>Aa</b>) and HeLa (<b>Ab</b>) cells; (<b>B</b>) Cellular uptake of C6, C6/ASP-DOCA and C6/DEX-DOCA NPs detected by flow cytometry.</p> Full article ">Figure 11
<p>(<b>A</b>) CLSM images of HepG2 cells incubated with C6/ASP-DOCA NPs for different times of 2, 4, 6 h. (<b>B</b>) CLSM images of HepG2 cells incubated with different drugs for 6 h. (<b>C</b>) CLSM images of HeLa cells incubated with different drugs for 6 h.</p> Full article ">Figure 12
<p>(<b>A</b>) Fluorescence images of DIR obtained by free DIR, DIR/ASP-DOCA and DIR/DEX-DOCA NPs at different time points of tumor-bearing mice in vivo; (<b>B</b>) DIR fluorescence imaging of the main isolated organs of tumor-bearing mice; (<b>C</b>) Tumor tissue images of tumor-bearing mice in each group; (<b>D</b>) Changes in the body weight of tumor-bearing mice in each group; (Note: compared with the ORI/ASP-DOCA NPs group, * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.01); (<b>E</b>) Changes in the tumor volume of tumor-bearing mice in each group; (<b>F</b>) Tumor tissue weight of tumor-bearing mice in each group (Note: compared with control group, * <span class="html-italic">p</span> &lt; 0.05, ** <span class="html-italic">p</span> &lt; 0.01).</p> Full article ">Figure 13
<p>H &amp; E staining on sections of hearts, spleens, lungs, kidneys and tumors in tumor-bearing mice in each group (200×).</p> Full article ">Figure 14
<p>H &amp; E staining of mouse liver sections in each group (200×).</p> Full article ">
17 pages, 4759 KiB  
Article
Anticancer Activity of Astaxanthin-Incorporated Chitosan Nanoparticles
by Eun Ju Hwang, Young-IL Jeong, Kyong-Je Lee, Young-Bob Yu, Seung-Ho Ohk and Sook-Young Lee
Molecules 2024, 29(2), 529; https://doi.org/10.3390/molecules29020529 - 21 Jan 2024
Cited by 3 | Viewed by 1710
Abstract
Astaxanthin (AST)-encapsulated nanoparticles were fabricated using glycol chitosan (Chito) through electrostatic interaction (abbreviated as ChitoAST) to solve the aqueous solubility of astaxanthin and improve its biological activity. AST was dissolved in organic solvents and then mixed with chitosan solution, followed by a dialysis [...] Read more.
Astaxanthin (AST)-encapsulated nanoparticles were fabricated using glycol chitosan (Chito) through electrostatic interaction (abbreviated as ChitoAST) to solve the aqueous solubility of astaxanthin and improve its biological activity. AST was dissolved in organic solvents and then mixed with chitosan solution, followed by a dialysis procedure. All formulations of ChitoAST nanoparticles showed small diameters (less than 400 nm) with monomodal distributions. Analysis with Fourier transform infrared (FT-IR) spectroscopy confirmed the specific peaks of AST and Chito. Furthermore, ChitoAST nanoparticles were formed through electrostatic interactions between Chito and AST. In addition, ChitoAST nanoparticles showed superior antioxidant activity, as good as AST itself; the half maximal radical scavenging concentrations (RC50) of AST and ChitoAST nanoparticles were 11.8 and 29.3 µg/mL, respectively. In vitro, AST and ChitoAST nanoparticles at 10 and 20 µg/mL properly inhibited the production of intracellular reactive oxygen species (ROSs), nitric oxide (NO), and inducible nitric oxide synthase (iNOS). ChitoAST nanoparticles had no significant cytotoxicity against RAW264.7 cells or B16F10 melanoma cells, whereas AST and ChitoAST nanoparticles inhibited the growth of cancer cells. Furthermore, AST itself and ChitoAST nanoparticles (20 µg/mL) efficiently inhibited the migration of cancer cells in a wound healing assay. An in vivo study using mice and a pulmonary metastasis model showed that ChitoAST nanoparticles were efficiently delivered to a lung with B16F10 cell metastasis; i.e., fluorescence intensity in the lung was significantly higher than in other organs. We suggest that ChitoAST nanoparticles are promising candidates for antioxidative and anticancer therapies of B16F10 cells. Full article
(This article belongs to the Special Issue Drug Delivery Systems Based on Polysaccharides: Second Edition)
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Figure 1

Figure 1
<p>(<b>a</b>) Schematic illustrations of electrostatic interaction between hydroxyl group of AST and amine group of chitosan. (<b>b</b>) Morphological observation of ChitoAST-2 nanoparticles. (<b>c</b>) Particle size distribution of ChitoAST nanoparticles.</p> Full article ">Figure 2
<p>(<b>a</b>) Fourier transform infrared (FT−IR) spectra of AST, Chito, ChitoAST-1 and ChitoAST-2 nanoparticles. NP = nanoparticles. (<b>b</b>) <sup>1</sup>H NMR spectra of AST (DMSO), Chito (D<sub>2</sub>O/DMSO), ChitoAST-2 nanoparticles (D<sub>2</sub>O) and ChitoAST-2 nanoparticles (D<sub>2</sub>O/DMSO).</p> Full article ">Figure 3
<p>UV spectrum of AST and ChitoAST-2 nanoparticles. (<b>a</b>) AST in DMSO. AST (10 μg/mL in DMSO or DMSO/water mixtures (1/9, <span class="html-italic">v</span>/<span class="html-italic">v</span>). (<b>b</b>) ChitoAST-1 nanoparticles (ChitoAST-1 NP) in DMSO/water mixtures (9/1, <span class="html-italic">v</span>/<span class="html-italic">v</span>) or water. (<b>c</b>) ChitoAST-2 nanoparticles (ChitoAST-2 NP) in DMSO/water mixtures (9/1, <span class="html-italic">v</span>/<span class="html-italic">v</span>) or water. (<b>d</b>) Empty nanoparticles (Empty NP, Chito only) in DMSO/water mixtures (100 μg/mL in DMSO/water mixtures (9/1, <span class="html-italic">v</span>/<span class="html-italic">v</span>)).</p> Full article ">Figure 4
<p>AST release from ChitoAST nanoparticles. (<b>a</b>) The effect of drug content; (<b>b</b>) The effect of media on the drug release characteristics (ChitoAST-2 nanoparticles).</p> Full article ">Figure 5
<p>(<b>A</b>) (<b>Aa</b>) The effect of UVB irradiation against B16F10 cells. The effect of ROS scavenging effect of AST or AST released from ChitoAST nanoparticles (ChitoAST-2 NP) against UVB-irradiated B16F10 cells: (<b>Ab</b>) Fluorescence images of cells (bar = 100 µm); (<b>Ac</b>) Comparison of intracellular ROS levels. **, ***: <span class="html-italic">p</span> &lt; 0.01. (<b>B</b>) (<b>Ba</b>) Inhibitory effects of AST or AST released from ChitoAST-2 nanoparticles (ChitoAST-2 NP) on nitric oxide production and (<b>Bb</b>) iNOS expression of RAW 264.7 cells. To study the effect of astaxanthin or astaxanthin released from ChitoAST-2 nanoparticles on the production of nitric oxide, cells were stimulated with LPS (1 μg/mL) for 24 h in the presence of AST or ChitoAST-2 NP. Results are expressed as percentages compared to the respective values obtained for the control. Data represent the mean ± SD over three separate experiments. <sup>##</sup>, <sup>###</sup> <span class="html-italic">p</span> &lt; 0.01 vs. the control group; ** <span class="html-italic">p</span> &lt; 0.01, *** <span class="html-italic">p</span> &lt; 0.001 vs. the LPS-treated group.</p> Full article ">Figure 6
<p>(<b>A</b>) Cytotoxicity of AST, ChitoAST nanoparticles (ChitoAST-2 NP), and empty nanoparticles (Empty NP) against (<b>Aa</b>) RAW264.7 cells, (<b>Ab</b>) B16F10 cells, and (<b>Ac</b>) HeLa cells. 2 × 10<sup>4</sup> cells/well in a 96-well plate was exposed to AST, ChitoAST NP-2, and/or empty NP (Chito only) in serum-free media for 24 h. For treatment of ChitoAST NPs, ChitoAST-2 nanoparticles were used. Empty NPs are Chito only. (<b>B</b>) Growth inhibition of AST or AST released from ChitoAST-2 nanoparticles (ChitoAST-2 NP) against (<b>Ba</b>) B16F10 human melanoma cells and (<b>Bb</b>) HeLa human cervical cancer cells. A total of 4 × 10<sup>3</sup> B16F10 or HeLa cells in a 96-well plate were exposed to AST or ChitoAST NP for 60 h. For treatment of ChitoAST-2 NPs, AST released from ChitoAST-2 nanoparticles (<a href="#molecules-29-00529-f004" class="html-fig">Figure 4</a>b) in DMEM media was used for treatment of cancer cells.</p> Full article ">Figure 7
<p>(<b>a</b>) Wound healing assay and (<b>b</b>) gelatin zymography of B16F10 cells. B16F10 cells were treated with AST or AST released from ChitoAST-2 nanoparticles (ChitoAST-2 NP). Dashed lines in wound healing assay indicated the migration of cells from 0 h to 24 h.</p> Full article ">Figure 8
<p>Pulmonary metastasis model of B16F10 cells for evaluation of targetability of ChitoAST-2 nanoparticles (ChitoAST-2 NPs). (<b>a</b>) Fluorescence images of each organ. (<b>b</b>) Comparison of lung weight. 1. Normal lung; 2. PBS; 3. Empty nanoparticles; 4. AST; 5. ChitoAST-2 NPs. For empty nanoparticles, Chito was intravenously (i.v.) administered. *, **, ***, ****: <span class="html-italic">p</span> &lt; 0.01 For pulmonary metastasis of B16F10 cells, 5 × 10<sup>5</sup> cells/0.1 mL PBS were administered intravenously (i.v.) via tail vein of nude BALb/C mice. Fluorescence dye-conjugated ChitoAST-2 nanoparticles (ChitoAST-2 NPs) were administered via tail vein of nude BALb/C mice. 1 day later, mice were sacrificed to observe fluorescence intensity of each organ, which reflects biodistribution of nanoparticles.</p> Full article ">
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