Publications by authors named "Seunho Jung"

95 Publications

Biomacromolecules, Biobased and Biodegradable Polymers: 2018-2019.

Authors:
Seunho Jung

Polymers (Basel) 2021 Jan 31;13(3). Epub 2021 Jan 31.

Department of Bioscience and Biotechnology, Department of Systems Biotechnology, Institute for Ubiquitous Information Technology and Applications (UBITA), Konkuk University, Seoul 05029, Korea.

This editorial introduces the most cited papers published in the years 2018-2019 in the section "Biomacromolecules, Biobased and Biodegradable Polymers" of the journal Polymers [...].
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http://dx.doi.org/10.3390/polym13030453DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7866781PMC
January 2021

Fabrication and Characterization of Polysaccharide Metallohydrogel Obtained from Succinoglycan and Trivalent Chromium.

Polymers (Basel) 2021 Jan 8;13(2). Epub 2021 Jan 8.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, Seoul 05029, Korea.

In the present study, a polysaccharide metallohydrogel was successfully fabricated using succinoglycan and trivalent chromium and was verified via Fourier transform infrared spectroscopy, differential scanning calorimetry analysis, thermogravimetric analysis (TGA), field emission scanning electron microscopy, and rheological measurements. Thermal behavior analysis via TGA indicated that the final mass loss of pure succinoglycan was 87.8% although it was reduced to 65.8% by forming a hydrogel with trivalent chromium cations. Moreover, succinoglycan-based metallohydrogels exhibited improved mechanical properties based on the added concentration of Cr and displayed a 10 times higher compressive stress and enhanced storage modulus (G') of 230% at the same strain. In addition, the pore size of the obtained SCx could be adjusted by changing the concentration of Cr. Gelation can also be adjusted based on the initial pH of the metallohydrogel formulation. This was attributed to crosslinking between chromium trivalent ions and hydroxyl/carboxyl groups of succinoglycan, each of which exhibits a specific pH-dependent behavior in aqueous solutions. It could be used as a soft sensor to detect Cr in certain biological systems, or as a soft matrix for bioseparation that allows control of pore size and mechanical strength by tuning the Cr concentration.
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http://dx.doi.org/10.3390/polym13020202DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7827257PMC
January 2021

Biocompatible and self-recoverable succinoglycan dialdehyde-crosslinked alginate hydrogels for pH-controlled drug delivery.

Carbohydr Polym 2020 Dec 16;250:116934. Epub 2020 Aug 16.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea; Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea. Electronic address:

We fabricated polysaccharide-based hydrogels, which are biocompatible, self-recoverable and pH-sensitive. Succinoglycan dialdehyde (SGDA) was first synthesized from bacterial succinoglycan directly isolated from Sinorhizobium meliloti and then hydrazine-functionalized alginate (HZ-Alg) was prepared to form SGDA-crosslinked alginate hydrogels (SGDA/HZ-Alg) without any catalyst. Due to structural characteristics of SGDA, SGDA/HZ-Alg were effectively obtained in a short time even at low concentrations (0.94-1.57 wt%) where they exhibited self-recoverable and tunable rheological properties corresponding to efficiency of recovery from 93.2%-97.9%. Moreover, SGDA/HZ-Alg showed the pH-responsive degradation as well as pH-controlled release behavior for 5-fluorouracil. 5-Fluorouracil was released approximately 98 % at pH 2.0 within 12 h, but not completely released even after 24 h at pH 7.4. The WST-8 assay results also demonstrated that SGDA/HZ-Alg did not show any cytotoxicity against HEK-293 cells. Since the suggested hydrogels are biocompatible, rheologically self-recoverable and tunable, and pH-controllable, they would be potential biomaterials for the hydrogel-based drug delivery systems.
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http://dx.doi.org/10.1016/j.carbpol.2020.116934DOI Listing
December 2020

Structural Characterization of Glycerophosphorylated and Succinylated Cyclic β-(1→2)-d-Glucan Produced by 1021.

Polymers (Basel) 2020 Sep 12;12(9). Epub 2020 Sep 12.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea.

produces different types of surface polysaccharides. Among them, cyclic β-(1→2)-d-glucan is located in the periplasmic space of rhizobia and plays an important role in the adaptation of bacteria to osmotic adaptation. Cyclic β-(1→2)-d-glucan (CG), synthesized from 1021, has a neutral and anionic form. In the present study, we characterized the exact chemical structures of anionic CG after purification using size exclusion s (Bio-Gel P-6 and P-2) chromatography, and DEAE-Sephadex anion exchange chromatography. The exact structure of each isolated anionic CG was characterized using various analytical methods such as nuclear magnetic resonance (NMR), attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopy and matrix associated laser desorption ionization-time of Flight (MALDI-TOF) mass spectrometry. The precise chemical structures of novel anionic CG molecules were elucidated by various NMR spectroscopic analyses, including H, C, P, and 2D HSQC NMR spectroscopy. As a result, we discovered that anionic CG molecules have either glycerophosphoryl or succinyl residues at C6 positions of a neutral CG. In addition, the results of MALDI-TOF mass spectrometric analysis confirmed that there are two types of patterns for anionic CG peaks, where one type of peak was the succinylated CG (SCG) and the other was glycerophospholated CG (GCG). In addition, it was revealed that each anionic CG has one to four substituents of the succinyl group of SCG and glycerophosphoryl group of GCG, respectively. Anionic CG could have potential as a cyclic polysaccharide for drug delivery systems and a chiral separator based on the complexation with basic target molecules.
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http://dx.doi.org/10.3390/polym12092073DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7569799PMC
September 2020

Azobenzene-grafted carboxymethyl cellulose hydrogels with photo-switchable, reduction-responsive and self-healing properties for a controlled drug release system.

Int J Biol Macromol 2020 Nov 10;163:824-832. Epub 2020 Jul 10.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea; Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea. Electronic address:

In this study, multifunctional hydrogels containing host-guest complex formation between azobenzene-grafted carboxymethyl cellulose (CMC-Azo) and β-cyclodextrin (CD) dimers connected by disulfide bonds with agarose for structural support were prepared. The obtained hydrogels exhibited self-healing properties by host-guest complexation as well as gel-sol phase transition in response to ultraviolet (UV) light and reducing agents. Photo-switchable properties of the hydrogels depend on changes in the complex formation of CD-dimers through the trans(450 nm) to cis(365 nm) photo-isomerization of azobenzene. The tensile and strain sweep tests confirmed that the hydrogel's self-healing ability was 79.44% and 81.59%, respectively. In addition, drug release from the hydrogels was controlled to accelerate to 80% in 3 h using UV light or reducing agent. Since the suggested photo-switchable, reduction-responsive, and self-healable hydrogels are non-cytotoxic, they can be potentially applied as biomedical materials in the development of hydrogel-based drug release systems.
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http://dx.doi.org/10.1016/j.ijbiomac.2020.07.071DOI Listing
November 2020

Preparation of Succinoglycan Hydrogel Coordinated With Fe Ions for Controlled Drug Delivery.

Polymers (Basel) 2020 Apr 22;12(4). Epub 2020 Apr 22.

Department of Systems Biotechnology & Dept. of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea.

Hydrogel materials with a gel-sol conversion due to external environmental changes have potential applications in a wide range of fields, including controlled drug delivery. Succinoglycans are anionic extracellular polysaccharides produced by various bacteria, including species, which have diverse applications. In this study, the rheological analysis confirmed that succinoglycan produced by Rm 1021 binds weakly to various metal ions, including Fe cations, to maintain a sol form, and binds strongly to Fe cations to maintain a gel form. The Fe-coordinated succinoglycan (Fe-SG) hydrogel was analyzed by attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopy, circular dichroism (CD), and field-emission scanning electron microscopy (FE-SEM). Our results revealed that the Fe cations that coordinated with succinoglycan were converted to Fe by a reducing agent and visible light, promoting a gel-sol conversion. The Fe-SG hydrogel was then successfully used for controlled drug delivery based on gel-sol conversion in the presence of reducing agents and visible light. As succinoglycan is nontoxic, it is a potential material for controlled drug delivery.
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http://dx.doi.org/10.3390/polym12040977DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7240483PMC
April 2020

Utilization of Water-Soluble Aminoethylamino-β-Cyclodextrin in the Pfitzinger Reaction-Catalyzed to the Synthesis of Diversely Functionalized Quinaldine.

Polymers (Basel) 2020 Feb 9;12(2). Epub 2020 Feb 9.

Department of Systems Biotechnology & Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea.

In this study we describe the use of an aminoethylamino-β-cyclodextrin (AEA-β-CD) as a supramolecular homogeneous catalyst for the synthesis of a series of diversely substituted quinaldine derivatives which are medicinally important, via Pfitzinger reaction. This supramolecular catalyst exhibited remarkable catalytic activity with high substrate scope to achieve the synthetic targets in good to excellent yield, 69-92%. The structural and morphological properties of the synthesized AEA-β-CD were determined through MALDI-TOF mass spectrometry, NMR, FT-IR, and SEM analysis. Possible reaction mechanisms were determined through molecular host-guest complexation and proposed based on 2D NMR (ROESY) spectroscopy, FT-IR, FE-SEM, and DSC.
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http://dx.doi.org/10.3390/polym12020393DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7077625PMC
February 2020

Succinoglycan dialdehyde-reinforced gelatin hydrogels with toughness and thermal stability.

Int J Biol Macromol 2020 Apr 23;149:281-289. Epub 2020 Jan 23.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea; Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, South Korea. Electronic address:

Pure gelatin hydrogel (PG) has limited practical applications due to their thermal instability and unfavorable mechanical properties. To overcome these limitations, dually crosslinked hydrogels were developed by imparting chemical crosslinking to existing physically crosslinked gelatin hydrogel networks using succinoglycan dialdehyde (SGDA) as a macromolecular crosslinker. SGDA-reinforced gelatin hydrogels (SGDA/Gels) displayed an 11 times higher compressive stress under identical deformation strain and a 1040% improvement in storage modulus (G') than PG. In addition, chemical crosslinking induced by SGDA increased the thermal stability of SGDA/Gels, such that they did not decompose at 60 °C, as confirmed by oscillatory temperature ramp experiments. The newly synthesized SGDA/Gels with reinforced networks and thermal stability exhibit potential for long-term use as controlled drug delivery carriers and 3D cell culture scaffolds for tissue engineering.
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http://dx.doi.org/10.1016/j.ijbiomac.2020.01.228DOI Listing
April 2020

Mono-6-Deoxy-6-Aminopropylamino--Cyclodextrin on Ag-Embedded SiO Nanoparticle as a Selectively Capturing Ligand to Flavonoids.

Nanomaterials (Basel) 2019 Sep 20;9(10). Epub 2019 Sep 20.

Department of Bioscience and Biotechnology, Konkuk University, Seoul 05029, Korea.

It has been increasingly important to develop a highly sensitive and selective technique that is easy to handle in detecting levels of beneficial or hazardous analytes in trace quantity. In this study, mono-6-deoxy-6-aminopropylamino--cyclodextrin (pr--CD)-functionalized silver-assembled silica nanoparticles (SiO@Ag@pr--CD) for flavonoid detection were successfully prepared. The presence of pr--CD on the surface of SiO@Ag enhanced the selectivity in capturing quercetin and myricetin among other similar materials (naringenin and apigenin). In addition, SiO@Ag@pr--CD was able to detect quercetin corresponding to a limit of detection (LOD) as low as 0.55 ppm. The relationship between the Raman intensity of SiO@Ag@pr--CD and the logarithm of the Que concentration obeyed linearity in the range 3.4-33.8 ppm (R = 0.997). The results indicate that SiO@Ag@pr--CD is a promising material for immediately analyzing samples that demand high sensitivity and selectivity of detection.
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http://dx.doi.org/10.3390/nano9101349DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6835478PMC
September 2019

Cyclodextrin functionalized agarose gel with low gelling temperature for controlled drug delivery systems.

Carbohydr Polym 2019 Oct 20;222:115011. Epub 2019 Jun 20.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul, 05029, South Korea; Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, 05029, South Korea. Electronic address:

Conventional agaroses with high gelling temperature are limited to apply to the field of drug delivery. In this study, β-cyclodextrin (βCD) functionalized agarose (CFA) with low gelling temperature was successfully prepared from ethylenediamine-functionalized agarose using mono-succinyl βCD. The gelling temperature of CFA dramatically decreased to 26.7 °C from 65 °C and the melting temperature declined from 95 °C to 66.1 °C. Upon drug loading, CFA can be used at 30 °C because of its low gelling temperature compared to agarose. CFA gel could be used both for bovine serum albumin as a full release, and for the doxorubicin (DOX) for sustained release, via inclusion complexation of βCD. Furthermore, cytotoxicity tests revealed that CFA was noncytotoxic. DOX in the CFA gel could retain the anti-cancer activity. Newly synthesized CFA with low gelling temperature offer a new means for the development of hydrogel-based delivery systems for a variety of therapeutic drugs.
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http://dx.doi.org/10.1016/j.carbpol.2019.115011DOI Listing
October 2019

Cytochrome P450 Monooxygenase-Mediated Metabolic Utilization of Benzo[]Pyrene by Species.

mBio 2019 05 28;10(3). Epub 2019 May 28.

Molecular and Environmental Toxicology Center, University of Wisconsin-Madison, Madison, Wisconsin, USA

Soil-dwelling fungal species possess the versatile metabolic capability to degrade complex organic compounds that are toxic to humans, yet the mechanisms they employ remain largely unknown. Benzo[]pyrene (BaP) is a pervasive carcinogenic contaminant, posing a significant concern for human health. Here, we report that several species are capable of degrading BaP. Exposing cells to BaP results in transcriptomic and metabolic changes associated with cellular growth and energy generation, implying that the fungus utilizes BaP as a growth substrate. Importantly, we identify and characterize the conserved gene encoding a cytochrome P450 monooxygenase that is necessary for the metabolic utilization of BaP in We further demonstrate that the fungal NF-κB-type regulators VeA and VelB are required for proper expression of in response to nutrient limitation and BaP degradation in Our study illuminates fundamental knowledge of fungal BaP metabolism and provides novel insights into enhancing bioremediation potential. We are increasingly exposed to environmental pollutants, including the carcinogen benzo[]pyrene (BaP), which has prompted extensive research into human metabolism of toxicants. However, little is known about metabolic mechanisms employed by fungi that are able to use some toxic pollutants as the substrates for growth, leaving innocuous by-products. This study systemically demonstrates that a common soil-dwelling fungus is able to use benzo[]pyrene as food, which results in expression and metabolic changes associated with growth and energy generation. Importantly, this study reveals key components of the metabolic utilization of BaP, notably a cytochrome P450 monooxygenase and the fungal NF-κB-type transcriptional regulators. Our study advances fundamental knowledge of fungal BaP metabolism and provides novel insight into designing and implementing enhanced bioremediation strategies.
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http://dx.doi.org/10.1128/mBio.00558-19DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6538779PMC
May 2019

Efficient Adsorption on Benzoyl and Stearoyl Cellulose to Remove Phenanthrene and Pyrene from Aqueous Solution.

Polymers (Basel) 2018 Sep 19;10(9). Epub 2018 Sep 19.

Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea.

Benzoyl and stearoyl acid grafted cellulose were synthesized by a simple chemical grafting method. Using these as chemical adsorbents, polycyclic aromatic hydrocarbons (PAHs), like pyrene and phenanthrene, were effectively removed from aqueous solution. The structural and morphological properties of the synthesized adsorbents were determined through X-ray diffraction analysis (XRD), thermal gravimetric analysis (TGA), Fourier transform infrared (FT-IR), FE-SEM, and NMR analyses. Through this method, it was confirmed that benzoyl and stearoyl acid were successfully grafted onto the surface of cellulose. The 5 mg of stearoyl grafted cellulose (St⁻Cell) remove 96.94% pyrene and 97.61% phenanthrene as compared to unmodified cellulose, which adsorbed 1.46% pyrene and 2.99% phenanthrene from 0.08 ppm pyrene and 0.8 ppm phenanthrene aqueous solution, suggesting that those results show a very efficient adsorption performance as compared to the unmodified cellulose.
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http://dx.doi.org/10.3390/polym10091042DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6403814PMC
September 2018

Solubility Enhancement of Atrazine by Complexation with Cyclosophoraose Isolated from biovar TA-1.

Polymers (Basel) 2019 Mar 12;11(3). Epub 2019 Mar 12.

Department of Systems Biotechnology & Dept. of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, Korea.

biovar TA-1, a kind of soil bacteria, produces cyclosophoraoses (Cys). Cyclosophoraoses contain various ring sizes with degrees of polymerization ranging from 17 to 23. Atrazine is a hardly-soluble herbicide that contaminates soil and drinking water, and remains in soil for a long time. To remove this insoluble contaminant from aqueous solutions, we have enhanced the solubility of atrazine by complexation with Cys. The complex formation of Cys and atrazine was confirmed using ¹H nuclear magnetic resonance (NMR), Fourier transform infrared (FT-IR) spectroscopy, differential scanning calorimetry (DSC), field emission scanning electron microscopy (FE-SEM), rotating frame nuclear overhauser spectroscopy (ROESY), and molecular modeling studies. The aqueous solubility of atrazine was enhanced 3.69-fold according to the added concentrations (20 mM) of Cys, compared to the 1.78-fold enhancements by β-cyclodextrin (β-CD). Cyclosophoraoses as an excellent solubility enhancer with long glucose chains that can effectively capture insoluble materials showed a potential application of microbial polysaccharides in the removal of hazardous hardly-soluble materials from aqueous solutions in the fields of biological and environmental industry.
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http://dx.doi.org/10.3390/polym11030474DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6473739PMC
March 2019

Inclusion complexes of cysteinyl β-cyclodextrin with baicalein restore collagen synthesis in fibroblast cells following ultraviolet exposure.

J Cell Biochem 2019 03 30;120(3):4032-4043. Epub 2018 Sep 30.

Department of Applied Chemistry, Dongduk Women's University, Seoul, Korea.

Baicalein, a bioactive flavonoid, has poor water solubility, thereby limiting its use in a wide range of biological applications. In the present study, we used inclusion complexes of cysteinyl β-cyclodextrin (β-CD) with baicalein to enhance the stability and solubility of baicalein in aqueous solution. We examined the effects of inclusion complexes of cysteinyl β-CD on collagen synthesis following ultraviolet (UV) irradiation, as well as the mechanisms underlying its effects. Our findings demonstrated that baicalein significantly restored collagen synthesis in the UV-exposed human fibroblast Hs68 cells. In addition, synthetic cysteine functionalized β-CDs were found to promote baicalein-induced collagen synthesis. Inclusion complexes of cysteinyl β-CDs with baicalein significantly upregulated the protein expression of type I collagen and activated the transcription of type I, II, and III collagen. Inclusion complexes of cysteinyl β-CDs with baicalein also downregulated matrix metalloproteinase -1 and -3, and α-smooth muscle actin expression. In addition, inclusion complexes of cysteinyl β-CDs with baicalein attenuated the expression of caveolin-1, but this treatment enhanced the UV-induced phosphorylation of Smad in the transforming growth factor-β pathway. These results suggested that the newly synthesized derivative of CD can be used as a complexing agent to enhance the bioavailability of flavonoids such as baicalein, especially in restoring collagen synthesis.
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http://dx.doi.org/10.1002/jcb.27687DOI Listing
March 2019

Triple-crosslinkedβ-cyclodextrin oligomer self-healing hydrogel showing high mechanical strength, enhanced stability and pH responsiveness.

Carbohydr Polym 2018 Oct 28;198:563-574. Epub 2018 Jun 28.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea; Institute for Ubiquitous Information Technology and Applications (UBITA), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 05029, South Korea. Electronic address:

A novel self-healing hydrogel was prepared from a cationic β-cyclodextrin oligomer allyl ether [C(βCD-OM)AE] using a triple cross-linking strategy combining electrostatic interaction, host-guest complexation, and CC bonds as the macrocrosslinker. Here, the C(βCD-OM)AE@Ad gel was successfully prepared by polymerization of synthesized C(βCD-OM)AE, 1-adamantyl acrylate, and acrylic acid. The triple cross-linked hydrogel shows multi-functionality of high mechanical strength, enhanced stability, cytocompatibility, pH responsiveness as well as self-healing ability. Based on the cooperative and synergetic forces of non-covalent and covalent bonds, the C(βCD-OM)AE@Ad gel shows a high tensile strain up to 1,590%, and the self-healed gel could restore up to 84% of its initial length within 24 h. Furthermore, drug release in the hydrogel was controlled by the surrounding pH and slowly released. The present work reveals the cooperativity of multiple cross-links for a 3D structured polymeric material, and the developed self-healable hydrogel can possibly be applied in various biomedical applications.
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http://dx.doi.org/10.1016/j.carbpol.2018.06.117DOI Listing
October 2018

Enhanced Solubilization of Fluoranthene by Hydroxypropyl β-Cyclodextrin Oligomer for Bioremediation.

Polymers (Basel) 2018 Jan 24;10(2). Epub 2018 Jan 24.

Center for Biotechnology Research in UBITA (CBRU), Institute for Ubiquitous Information Technology and Applications (UBITA), Konkuk University, Seoul 05029, Korea.

Fluoranthene (FT) is a polycyclic aromatic hydrocarbon (PAH), consisting of naphthalene and benzene rings connected by a five-member ring. It is widespread in the environment. The hydrophobicity of FT limits its availability for biological uptake and degradation. In this study, hydroxypropyl β-cyclodextrin oligomers (HP-β-CD-ol) were synthesized with epichlorohydrin (EP), while the solubility enhancement of FT by HP-β-CD-ol was investigated in water. The synthesized HP-β-CD-ol was characterized by MALDI-TOF mass spectrometry (MS), ¹H NMR, and C NMR spectroscopy. The solubility of FT increased 178-fold due to the complex formation with HP-β-CD oligomers. The inclusion complexes of FT/HP-β-CD-ol were analyzed using Fourier-Transform Infrared (FT-IR), Differential Scanning Calorimetry (DSC), Scanning Electron Microscope (SEM), and Nuclear Overhauser Effect Spectroscopy Nuclear magnetic resonance (NOESY NMR) spectroscopy. On the basis of these results, HP-β-CD-ol is recommended as a potential solubilizer for the development of PAH removal systems.
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http://dx.doi.org/10.3390/polym10020111DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6415056PMC
January 2018

Biotinylated Cyclooligosaccharides for Paclitaxel Solubilization.

Molecules 2018 Jan 2;23(1). Epub 2018 Jan 2.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MBRC) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

The poor water solubility of paclitaxel causes significant problems in producing cancer therapeutic formulations. Here, we aimed to solubilize paclitaxel using biocompatible cyclic carbohydrates. Generally recognized as safe, labeled β-cyclodextrin (β-CD), a cyclic α-1,4-glucan consisting of seven glucoses, was prepared, and bio-sourced cyclosophoraoses (CyS), which are unbranched cyclic β-1,2-glucans with 17-23 glucose units, were purified using various chromatographic methods from cultural broth. For effective targeting, CyS and β-CD were modified with a biotinyl moiety in a reaction of mono-6-amino CyS and mono-6-amino-β-CD with -hydroxysuccinimide ester of biotinamidohexanoic acid. Interestingly, the aqueous solubility of paclitaxel was enhanced 10.3- and 3.7-fold in the presence of biotinyl CyS and biotinyl β-CD, respectively. These findings suggest that biotin-appended cyclooligosaccharides can be applied to improve the delivery of paclitaxel.
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http://dx.doi.org/10.3390/molecules23010090DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017118PMC
January 2018

Biomolecule-Functionalized Smart Polydiacetylene for Biomedical and Environmental Sensing.

Molecules 2018 Jan 4;23(1). Epub 2018 Jan 4.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MBRC) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

Polydiacetylene (PDA) has attracted interest for use as a sensing platform in biomedical, environmental, and chemical engineering applications owing to its capacity for colorimetric and fluorescent transition in response to external stimuli. Many researchers have attempted to develop a tailor-made PDA sensor via conjugation of chemical or biological substances to PDA. Here, we review smart bio-conjugates of PDA with various biomolecules such as carbohydrates, lipids, nucleic acids, and proteins. In addition, materialization and signal amplification strategies to improve handling and sensitivity are described.
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http://dx.doi.org/10.3390/molecules23010107DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017116PMC
January 2018

Carboxymethyl cyclosophoraoses as a flexible pH-responsive solubilizer for pindolol.

Carbohydr Polym 2017 Nov 9;175:493-501. Epub 2017 Aug 9.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea. Electronic address:

In the present study, cyclosophoraoses (CyS) (β-1,2 linked cyclic glucans, with glucopyranose units ranging from 17 to 23) isolated from Rhizobium leguminosarum biovar viciae VF-39 were modified with carboxymethyl (CM) groups, and the pH-sensitive complexation of CM CyS with pindolol was investigated. The solubility of pindolol increased 32-fold by its complexation with 5mM CM CyS at pH 10, whereas it shows no significant change at pH 3. Pindolol, a β-adrenergic blocking agent, has a hydrophobic nature at non-ionized state, and CM CyS could solubilize efficiently pindolol in a high alkaline solution. The carboxymethylation of flexible CyS allows them to present a more suitable cavity for the hydrophobic pindolol at pH 10, which is differentiated from CM β-cyclodextrin (β-CD). It can be interpreted as that the anionic repulsion effectively modulates the flexible and distorted conformation of CyS rather than rigid annular shape of β-CD. Resultingly, the highly solubilized CM CyS/pindolol complex was characterized by UV-vis, T1 relaxation, ROESY, DOSY NMR spectroscopy, FT-IR spectroscopy, SEM, and molecular modeling studies. The antioxidant activity of pindolol was also improved 260% in the complex compared to free pindolol. The use of flexible host molecules with pH-responsive substituents would be applied in the development of smart systems for sensing or in biomedical fields.
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http://dx.doi.org/10.1016/j.carbpol.2017.08.026DOI Listing
November 2017

Oil-based cyclo-oligosaccharide nanodevices for drug encapsulation.

Colloids Surf B Biointerfaces 2017 Nov 25;159:259-267. Epub 2017 Jul 25.

Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057, Braga, Portugal. Electronic address:

New encapsulation nanodevices were synthesized by emulsification of cyclo-oligosaccharides fully substituted by hydrophobic palmitic chains. These highly hydrophobic compounds, acquire oily-like behaviour at moderate temperatures (∼50°C) and when submitted to ultrasound (US) can undergo emulsification. The improved emulsifying properties of modified cyclo-oligosaccharides are suitable to produce small and narrow sized nanoemulsions with ability to encapsulate amphiphilic molecules. Both encapsulation and delivery of a therapeutic drug, methotrexate (MTX), with amphiphilic character was assessed. The physicochemical properties of the cyclo-oligosaccharide nanoemulsions containing MTX were investigated by nuclear magnetic resonance (NMR), scanning transmission electron microscopy (STEM) and dynamic light scattering (DLS). The results revealed that the modified cyclo-oligosaccharides are potential platforms for the encapsulation of bio compounds for cosmetic and pharmaceutical purposes.
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http://dx.doi.org/10.1016/j.colsurfb.2017.07.055DOI Listing
November 2017

Carbohydrate-Based Host-Guest Complexation of Hydrophobic Antibiotics for the Enhancement of Antibacterial Activity.

Molecules 2017 Aug 8;22(8). Epub 2017 Aug 8.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

Host-guest complexation with various hydrophobic drugs has been used to enhance the solubility, permeability, and stability of guest drugs. Physical changes in hydrophobic drugs by complexation have been related to corresponding increases in the bioavailability of these drugs. Carbohydrates, including various derivatives of cyclodextrins, cyclosophoraoses, and some linear oligosaccharides, are generally used as host complexation agents in drug delivery systems. Many antibiotics with low bioavailability have some limitations to their clinical use due to their intrinsically poor aqueous solubility. Bioavailability enhancement is therefore an important step to achieve the desired concentration of antibiotics in the treatment of bacterial infections. Antibiotics encapsulated in a complexation-based drug delivery system will display improved antibacterial activity making it possible to reduce dosages and overcome the serious global problem of antibiotic resistance. Here, we review the present research trends in carbohydrate-based host-guest complexation of various hydrophobic antibiotics as an efficient delivery system to improve solubility, permeability, stability, and controlled release.
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http://dx.doi.org/10.3390/molecules22081311DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152325PMC
August 2017

Label-Free Colorimetric Detection of Influenza Antigen Based on an Antibody-Polydiacetylene Conjugate and Its Coated Polyvinylidene Difluoride Membrane.

Polymers (Basel) 2017 Mar 30;9(4). Epub 2017 Mar 30.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Center for Biotechnology Research in UBITA (CBRU), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

This study presents an antibody-conjugated polydiacetylene (PDA) and its coated polyvinylidene difluoride (PVDF) membrane. The M149 antibody was hybridized to nano-vesicles consisting of pentacosa-10,12-diynoic acid (PCDA) and dimyristoylphosphatidylcholine (DMPC). After photo-polymerization at 254 nm, the effects on the PDA by antigenic injection were investigated with UV-vis spectroscopy, fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. Because PDA, an alternating ene-yne molecule, induces a blue-to-red color transition and an interesting fluorescent response by the distortion of its backbone, the biomolecular recognition of an antibody⁻antigen can be converted into an optical and fluorescent signal. Thus, an influenza antigen was successfully detected with the proposed label-free method. Furthermore, the vesicular system was improved by coating it onto a membrane type sensing platform for its stability and portability. The proposed antibody-PDA composite PVDF membrane has potential for rapid, easy and selective visualization of the influenza virus.
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http://dx.doi.org/10.3390/polym9040127DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6432067PMC
March 2017

SERS-Based Flavonoid Detection Using Ethylenediamine-β-Cyclodextrin as a Capturing Ligand.

Nanomaterials (Basel) 2017 Jan 6;7(1). Epub 2017 Jan 6.

Center for Biotechnology Research in UBITA (CBRU), Institute for Ubiquitous Information Technology and Application (UBITA), Konkuk University, Seoul 05029, Korea.

Ethylenediamine-modified β-cyclodextrin (Et-β-CD) was immobilized on aggregated silver nanoparticle (NP)-embedded silica NPs (SiO₂@Ag@Et-β-CD NPs) for the effective detection of flavonoids. Silica NPs were used as the template for embedding silver NPs to create hot spots and enhance surface-enhanced Raman scattering (SERS) signals. Et-β-CD was immobilized on Ag NPs to capture flavonoids via host-guest inclusion complex formation, as indicated by enhanced ultraviolet absorption spectra. The resulting SiO₂@Ag@Et-β-CD NPs were used as the SERS substrate for detecting flavonoids, such as hesperetin, naringenin, quercetin, and luteolin. In particular, luteolin was detected more strongly in the linear range 10 to 10 M than various organic molecules, namely ethylene glycol, β-estradiol, isopropyl alcohol, naphthalene, and toluene. In addition, the SERS signal for luteolin captured by the SiO₂@Ag@Et-β-CD NPs remained even after repeated washing. These results indicated that the SiO₂@Ag@Et-β-CD NPs can be used as a rapid, sensitive, and selective sensor for flavonoids.
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http://dx.doi.org/10.3390/nano7010008DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5295198PMC
January 2017

Solubility and bioavailability enhancement of ciprofloxacin by induced oval-shaped mono-6-deoxy-6-aminoethylamino-β-cyclodextrin.

Carbohydr Polym 2017 May 22;163:118-128. Epub 2017 Jan 22.

Department of Systems Biotechnology, Microbial Carbohydrate Resource Bank (MCRB) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul, Republic of Korea. Electronic address:

Ciprofloxacin is a broad-spectrum fluoroquinolone antibiotic used to treat bacterial infections; however, its limited aqueous solubility inhibits its broader clinical uses. This study investigated the complexation effect of mono-6-deoxy-6-aminoethylamino-β-cyclodextrin on the aqueous solubility and bioavailability of ciprofloxacin. During complexation, the oval-shaped cavity induced by mono-aminoethylamine substitution on the primary rim of β-cyclodextrin, was considered to be a key factor according to NMR spectroscopy and molecular modeling studies. The ciprofloxacin with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin complex was characterized using FE-SEM, DSC, FT-IR, T1 relaxation, 2D NOESY, and DOSY NMR spectroscopy and molecular modeling studies. The solubility property of ciprofloxacin complexed with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin was enhanced by seven-fold compared to that of pure ciprofloxacin. Furthermore antibacterial activity of that complex against methicillin-resistant Staphylococcus aureus was enhanced and it clearly showed the growth inhibition. The mono-6-deoxy-6-aminoethylamino-β-cyclodextrin has the potential to be utilized for other oblong guest molecules besides ciprofloxacin based on the novel induced elliptical cavity.
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http://dx.doi.org/10.1016/j.carbpol.2017.01.073DOI Listing
May 2017

Pentynyl Ether of β-Cyclodextrin Polymer and Silica Micro-Particles: A New Hybrid Material for Adsorption of Phenanthrene from Water.

Polymers (Basel) 2017 Jan 4;9(1). Epub 2017 Jan 4.

Center for Biotechnology Research in UBITA (CBRU), Institute for Ubiquitous Information Technology and Applications (UBITA), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

A new hybrid material for the removal of polycyclic aromatic hydrocarbons (PAH) from water was prepared by the polymerization of pentynyl beta-cyclodextrin (PyβCD) and silica micro-particles (SMP). Phenanthrene, being one of the important members of the PAH family and a potential risk for environmental pollution, was selected for this study. Results show that phenanthrene removal efficiency of the SMP was improved significantly after hybridization with PyβCD-polymer. Approximately 50% of the phenanthrene was removed in the first 60 min and more than 95% was removed in less than 7 h when 25 mL of the 2 ppm aqueous phenanthrene solution was incubated with the 100 mg of SMP-PyβCD-polymer material. Infrared spectroscopy and thermal gravimetric analysis show that the enhanced efficiency of the SMP-PyβCD-polymer compared to the unmodified SMP was due to the formation of the inclusion complexation of phenanthrene with the PyβCD. These results indicate that SMP-PyβCD polymers have a potential to be applied as molecular filters in water purification systems and also for waste water treatment.
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http://dx.doi.org/10.3390/polym9010010DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6432442PMC
January 2017

Polydiacetylenyl β-cyclodextrin based smart vesicles for colorimetric assay of arginine and lysine.

Sci Rep 2016 08 9;6:31115. Epub 2016 Aug 9.

Center for Biotechnology Research in UBITA (CBRU), Institute for Ubiquitous Information Technology and Applications (UBITA), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea.

Selective visualization of arginine and lysine has been explored among 20 amino acids using the hybrid conjugate of β-cyclodextrin (β-CD) and polydiacetylene (PDA). The mono pentacosa-10,12-diynyl aminomethyl group was successfully coupled to either the primary or the secondary face of β-CD, where mono-6-amino-6-deoxy-β-CD or mono-3-amino-3-deoxy-β-CD reacted with the N-hydroxysuccinimide ester of 10,12-pentacosadiynoic acid. In this combinatorial system, the cylindrical β-cyclodextrin functions as a channel for the introduction of the cationic amino acids to the artificial membrane. The membrane perturbation and aggregation by the target amino acids could be exclusively visualized as a blue to red color change based on the responsive polydiacetylene domain. These interesting findings demonstrated that the developed β-CD conjugated PDA system may offer a new method of cell-penetrating mechanism, a promising vector system, as well as impact the production industry of arginine or lysine.
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http://dx.doi.org/10.1038/srep31115DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4977466PMC
August 2016

Enhancing bio-availability of β-naphthoflavone by supramolecular complexation with 6,6'-thiobis(methylene)-β-cyclodextrin dimer.

Carbohydr Polym 2016 Oct 18;151:40-50. Epub 2016 May 18.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MBRC) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Republic of Korea. Electronic address:

The aryl hydrocarbon receptor (AhR) is a ligand activated transcriptional regulator, which governs key biological processes including detoxification of carcinogens. β-Naphthoflavone (β-NF) is a non-toxic flavonoid, and a potent AhR agonist. Thus, β-NF can induce the representative detoxifying enzyme cytochrome P4501A1, thereby enhancing the detoxification potential. However, its low water solubility hampers the use. We found that supramolecular complexation of β-NF with the synthetic 6,6'-thiobis(methylene)-β-cyclodextrin (β-CD-S) dimer significantly enhanced β-NF's role as an AhR agonist. The water solubility of β-NF was increased to 469 fold by effective supramolecular complexation with the β-CD-S dimer, and caused significant induction of cytochrome P4501A1. Stable formation of the supramolecular complex of β-NF with β-CD-S-dimer was verified by various analyses. In summary, supramolecular complexation of β-NF with β-CD-S dimer greatly enhanced bio-availability of β-NF as an AhR agonist. Our findings provide an easy, non-destructive, and alternative approach to enhance the bio-availability of therapeutics.
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http://dx.doi.org/10.1016/j.carbpol.2016.05.046DOI Listing
October 2016

Synthesis, Characterization, and Retinol Stabilization of Fatty Amide-β-cyclodextrin Conjugates.

Molecules 2016 Jul 22;21(7). Epub 2016 Jul 22.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

Amphiphilic cyclodextrin (CD) has been the object of growing scientific attention because of its two recognition sites, the cavity and the apolar heart, formed by self-assembly. In the present study, mono[6-deoxy-6-(octadecanamido)]-β-CD and mono[6-deoxy-6-(octadecenamido)]-β-CD were successfully synthesized by reacting mono-6-amino-6-deoxy-β-CD with N-hydroxysuccinimide esters of corresponding fatty acids in DMF. The structures were analyzed using nuclear magnetic resonance spectroscopy and mass spectrometry. The amphiphilic β-CDs were able to form self-assembled nano-vesicles in water, and the supramolecular architectures were characterized using fluorescence spectroscopy, dynamic light scattering, and transmission electron microscopy. Using the cavity-type nano-vesicles, all-trans-retinol was efficiently encapsulated; it was then stabilized against the photo-degradation. Therefore, the present fatty amide-β-CD conjugate will be a potential molecule for carrier systems in cosmetic and pharmaceutical applications.
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http://dx.doi.org/10.3390/molecules21070963DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273423PMC
July 2016

Negative regulation and developmental competence in Aspergillus.

Sci Rep 2016 07 1;6:28874. Epub 2016 Jul 1.

Department of Bacteriology, The University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.

Asexual development (conidiation) in the filamentous fungus Aspergillus nidulans is governed by orchestrated gene expression. The three key negative regulators of conidiation SfgA, VosA, and NsdD act at different control point in the developmental genetic cascade. Here, we have revealed that NsdD is a key repressor affecting the quantity of asexual spores in Aspergillus. Moreover, nullifying both nsdD and vosA results in abundant formation of the development specific structure conidiophores even at 12 h of liquid culture, and near constitutive activation of conidiation, indicating that acquisition of developmental competence involves the removal of negative regulation exerted by both NsdD and VosA. NsdD's role in repressing conidiation is conserved in other aspergilli, as deleting nsdD causes enhanced and precocious activation of conidiation in Aspergillus fumigatus or Aspergillus flavus. In vivo NsdD-DNA interaction analyses identify three NsdD binding regions in the promoter of the essential activator of conidiation brlA, indicating a direct repressive role of NsdD in conidiation. Importantly, loss of flbC or flbD encoding upstream activators of brlA in the absence of nsdD results in delayed activation of brlA, suggesting distinct positive roles of FlbC and FlbD in conidiation. A genetic model depicting regulation of conidiation in A. nidulans is presented.
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http://dx.doi.org/10.1038/srep28874DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4929475PMC
July 2016

Characterization and Enhanced Antioxidant Activity of the Cysteinyl β-Cyclodextrin-Baicalein Inclusion Complex.

Molecules 2016 May 27;21(6). Epub 2016 May 27.

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, Korea.

Baicalein is a type of flavonoid isolated from the roots of a medicinal plant, Scutellaria baicalensis. Although it has attracted considerable attention due to its antiviral, anti-tumor, and anti-inflammatory activities, its limited aqueous solubility inhibits the clinical application of this flavonoid. The present study aimed to prepare and characterize a host-guest complex in an effort to improve the solubility and antioxidant activity of baicalein. The host molecule is a macrocyclic β-cyclodextrin (β-CD) functionalized with cysteine for a synergetic effect. The structure of the synthesized cysteinyl β-CD was analyzed using nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The inclusion complex with baicalein was studied by UV-vis, NMR spectroscopy, scanning electron microscopy, and X-ray powder diffractometry. The formed cysteinyl β-CD/baicalein inclusion complex efficiently improved the solubility and antioxidant ability of baicalein. Therefore, we suggest that the present cysteinyl β-CD is a potential host molecule for inclusion complexation and for bioavailability augmentation.
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http://dx.doi.org/10.3390/molecules21060703DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273330PMC
May 2016