Hao Liang

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Organization: Beijing University of Chemical Technology

Department: State Key Laboratory of Chemical Resource Engineering, and School of Science

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Chemicals
References

Self-repairing metal–organic hybrid complexes for reinforcing immobilized chloroperoxidase reusability

Co-reporter:Yan Liu;Yumei Zhang;Xuejian Li;Qipeng Yuan

Chemical Communications 2017 vol. 53(Issue 22) pp:3216-3219

Publication Date(Web):2017/03/14

DOI:10.1039/C6CC10319G

A self-repairing metal–enzyme hybrid nanocatalyst with a sodium alginate (SA) coating was reported in this study. Compared with free CPO, immobilized chloroperoxidase (CPO) has similar Km and Kcat values. SA-coated CPO@Ca3(PO4)2 hybrid composites displayed robust reusability under acidic conditions, maintaining more than 85% of the catalytic activity after 12 recycles.

Multicopper Laccase Mimicking Nanozymes with Nucleotides as Ligands

Co-reporter:Hao Liang, Feifei Lin, Zijie Zhang, Biwu Liu, Shuhui Jiang, Qipeng Yuan, and Juewen Liu

ACS Applied Materials & Interfaces 2017 Volume 9(Issue 2) pp:

Publication Date(Web):December 22, 2016

DOI:10.1021/acsami.6b15124

Using nanomaterials to achieve functional enzyme mimics (nanozymes) is attractive for both applied and fundamental research. Laccases are multicopper oxidases highly important for biotechnology and environmental remediation. In this work, we report an exceptionally simple yet functional laccase mimic based on guanosine monophosphate (GMP) coordinated copper. It forms an amorphous metal–organic framework (MOF) material. The ratio of copper and GMP is 3:4 as determined by isothermal titration calorimetry. It has excellent laccase-like activity and converts a diverse range of phenol containing substrates such as hydroquinone, naphthol, catechol and epinephrine. Comparative work shows that the activity is originated from guanosine coordination instead of phosphate binding in GMP. Cu2+ is required and cannot be substituted by other metal ions. At the same mass concentration, the Cu/GMP nanozyme has a higher Vmax and similar Km compared to the protein laccase. To achieve the same catalytic efficiency, the cost of the Gu/GMP is ∼2400-fold lower than that of laccase. The Cu/GMP is much more stable at extreme pH, high salt, high temperature and for long-term storage. This is one of the first laccase-mimicking nanozymes, which will find important applications in analytical chemistry, environmental protection, and biotechnology.Keywords: copper; laccase; metal−organic frameworks; nanozymes; nucleotides;

Molecular model and in vitro antioxidant activity of a water-soluble and stable phloretin/hydroxypropyl-β-cyclodextrin inclusion complex

Co-reporter:Yongqin Wei, Jin Zhang, Amjad Hussain Memon, Hao Liang

Journal of Molecular Liquids 2017 Volume 236(Volume 236) pp:

Publication Date(Web):1 June 2017

DOI:10.1016/j.molliq.2017.03.098

•Phloretin/HP-β-CD inclusion complexes were prepared and characterized.•We deduced that the aromatic ring of phloretin was included into HP-β-CD cavity from the narrow side.•The water solubility of phloretin was increased by 5808 times.•The inclusion complex still remained an approximately DPPH radical-scavenging capacity compared to the free phloretin.•The stability of phloretin was greatly improved upon forming inclusion complex with HP-β-CD.Phloretin, a dihydrochalcone flavonoid, has been associated with a wide range of biological properties such as antioxidation, antitumor, antidiabetes, skin whiting, etc. However, the instability and aqueous insolubility in its native form decreases its bioavailability and make its usage limited in clinical application. In our study, an inclusion complex of phloretin with hydroxypropyl-β-cyclodextrin (HP-β-CD) that featured improved aqueous solubility and stability was prepared using a simple co-evaporation method. The inclusion complex prepared under a condition of 1:1, 50 °C, 2 h and 500 rpm showed a great enhancement of phloretin aqueous solubility of 54.08 ± 0.05 mg/mL, which was 5808 times higher than that of free phloretin in pure water at 25 °C. The results of phase solubility study and the characterization data from SEM, PXRD, FT-IR and NMR suggested that aromatic ring of one phloretin molecule was merged into the cavity of one HP-β-CD from the narrow side. The in vitro test showed that the inclusion complex still remained an approximately DPPH radical-scavenging capacity compared to the free phloretin at the same concentration. And the stability of phloretin was greatly improved after forming inclusion complex with HP-β-CD. Thus, the phloretin/HP-β-CD inclusion complex would be a promising approach in the clinical application of phloretin in the future.

Glucoraphenin, sulforaphene, and antiproliferative capacity of radish sprouts in germinating and thermal processes

Co-reporter:Ruimin Li;Dan Song;Frank Vriesekoop;Li Cheng

European Food Research and Technology 2017 Volume 243( Issue 4) pp:547-554

Publication Date(Web):2017 April

DOI:10.1007/s00217-016-2764-3

Glucoraphenin, the predominant glucosinolate in radish sprouts, is hydrolyzed by myrosinase to sulforaphene that is implicated to exert anticancerogenic effects. The effects of germination and subsequent cooking processes on the levels of glucoraphenin and its hydrolysis products were investigated in this research. HPLC analysis revealed that the levels of glucoraphenin and sulforaphene decreased with germination time. In agreement with the above results, the antiproliferation activity of radish sprouts extracts on human lung cancer cells was also found to decline gradually in line with the germination process. Furthermore, when we applied three traditional cooking treatments to radish sprouts, the glucoraphenin and sulforaphene were markedly decreased; while the antiproliferation activity of cooked radish sprouts was considerably decreased. This research showed that 3-day-old radish sprouts are an excellent source of bioactive compounds that could potentially benefit human health, while any cooking process appears to cause the devastation of beneficial attributes in radish sprouts.

Highly Hybridizable Spherical Nucleic Acids by Tandem Glutathione Treatment and Polythymine Spacing

Co-reporter:Jing Sun, Dennis Curry, Qipeng Yuan, Xu Zhang, and Hao Liang

ACS Applied Materials & Interfaces 2016 Volume 8(Issue 19) pp:12504

Publication Date(Web):April 29, 2016

DOI:10.1021/acsami.6b00717

Gold nanoparticle (AuNP)-templated spherical nucleic acids (SNAs) have been demonstrated as an important functional material in bionanotechnology. Fabrication of SNAs having high hybridization capacity to their complementary sequences is critical to ensure their applicability in areas such as antisense gene therapy and cellular sensing. The traditional salt-aging procedure is effective but tedious, requiring 1–3 days to complete. The rapid low-pH assisted protocol is efficient, but causes concerns related to nonspecific DNA adsorption to the AuNP core. To address these issues, we systematically compared the SNAs prepared by these two methods (salt-aging method and low-pH protocol). In terms of the number of complementary DNA that each SNA can bind and the average binding affinity of each thiolated DNA probe to its complementary strand, both methods yielded comparable hybridizability, although higher loading capacity was witnessed with SNAs made using the low-pH method. Additionally, it was found that nonspecific DNA binding could be eliminated almost completely by a simple glutathione (GSH) treatment of SNAs. Compared to conventional methods using toxic mercapto-hexanol or alkanethiols to remove nonspecific DNA adsorption, GSH is mild, cost-effective, and technically easy to use. In addition, GSH-passivated SNAs minimize the toxicity concerns related to AuNP-induced GSH depletion and therefore offer a more biocompatible alternative to previously reported SNAs. Moreover, rational design of probe sequences through inclusion of a polythymine spacer into the DNA sequences resulted in enhanced DNA loading capacity and stability against salt-induced aggregation. This work provides not only efficient and simple technical solutions to the issue of nonspecific DNA adsorption, but also new insights into the hybridizability of SNAs.Keywords: glutathione; gold nanoparticles; hybridizability; polythymine spacer; spherical nucleic acids

Magnetic Iron Oxide Nanoparticle Seeded Growth of Nucleotide Coordinated Polymers

Co-reporter:Hao Liang, Biwu Liu, Qipeng Yuan, and Juewen Liu

ACS Applied Materials & Interfaces 2016 Volume 8(Issue 24) pp:15615-15622

Publication Date(Web):June 1, 2016

DOI:10.1021/acsami.6b04038

The introduction of functional molecules to the surface of magnetic iron oxide nanoparticles (NPs) is of critical importance. Most previously reported methods were focused on surface ligand attachment either by physisorption or covalent conjugation, resulting in limited ligand loading capacity. In this work, we report the seeded growth of a nucleotide coordinated polymer shell, which can be considered as a special form of adsorption by forming a complete shell. Among all of the tested metal ions, Fe3+ is the most efficient for this seeded growth. A diverse range of guest molecules, including small organic dyes, proteins, DNA, and gold NPs, can be encapsulated in the shell. All of these molecules were loaded at a much higher capacity compared to that on the naked iron oxide NP core, confirming the advantage of the coordination polymer (CP) shell. In addition, the CP shell provides better guest protein stability compared to that of simple physisorption while retaining guest activity as confirmed by the entrapped glucose oxidase assay. Use of this system as a peroxidase nanozyme and glucose biosensor was demonstrated, detecting glucose as low as 1.4 μM with excellent stability. This work describes a new way to functionalize inorganic materials with a biocompatible shell.

Preparation and stability of astaxanthin solid lipid nanoparticles based on stearic acid

Co-reporter:Miaomiao Li;Mohamed Reda Zahi;Qipeng Yuan;Feibao Tian

European Journal of Lipid Science and Technology 2016 Volume 118( Issue 4) pp:592-602

Publication Date(Web):

DOI:10.1002/ejlt.201400650

Astaxanthin (ASTA), a natural pigment carotenoid, is endowed with remarkable antioxidant activity in food and cosmetic products. However, the utilization of ASTA is limited due to its poor water-solubility, low bioavailability, and the decomposition under light, heat, and oxygen. In order to overcome these drawbacks, ASTA was encapsulated within solid lipid nanoparticles (SLNs). ASTA-SLNs, composed of lipid nucleation (ASTA, soybean oil, solid lipid matrix) and external water phase (Tween 20, deionized water), were prepared by high pressure homogenization (HPH). The contents of three different solid matrixes (stearic acid, glycerin monostearate, and glycerol distearates) and the preparation conditions (pressure and number of cycles) were optimized. Stearic acid (1 wt%) was selected on the basis of physico-chemical properties of ASTA-SLNs, such as mean particle size, zeta potential, and polydispersivity index (PDI). Moreover, ASTA-SLNs exhibited good long-term stability at 4 and 25°C, with no significant modification in the particle size. Comparative with the free ASTA, the chemical stability of ASTA in SLNs was significantly enhanced. Finally, the release experiments of ASTA-SLNs showed that SLNs could provide prolonged release of ASTA in simulated gastric and intestinal juices.

Practical application: SLNs, a promising submicron drug delivery system, could be widely applied in food, cosmetics, drugs, and health products. In the fields of targeted delivery and controlled release of drugs, SLNs have attracted increasing attention. ASTA-SLNs can be prepared into various pharmaceutical dosage forms, such as oral tablet, intravenous infusion, and percutaneous absorption, thus achieving a long-time and stable therapeutic effect in small dosage. More importantly, based on the high pressure homogenization technology, ASTA-SLNs can be produced in large-scale.

Astaxanthin solid lipid nanoparticles (ASTA-SLNs) were produced using high pressure homogenization. Internal lipid phase was prepared by adding the solid lipid matrix and ASTA into soybean oil with heating and stirring under a nitrogen atmosphere. External aqueous phase was prepared by dispersing Tween 20 (10% w/w) in deionized water. ASTA-SLNs were obtained through dispersion, high pressure homogenization, and refrigeration. The physical characteristics, stability, release behavior of ASTA-SLNs were measured.

Preparation and stabilization of d-limonene Pickering emulsions by cellulose nanocrystals

Co-reporter:Chunxia Wen, Qipeng Yuan, Hao Liang, Frank Vriesekoop

Carbohydrate Polymers 2014 Volume 112() pp:695-700

Publication Date(Web):4 November 2014

DOI:10.1016/j.carbpol.2014.06.051

•Cellulose nanocrystals were successfully prepared by ammonium persulfate hydrolysis.•d-Liomonene Pickering emulsions prepared by cellulose nanocrystals exhibited high stability.•Electrostatic interactions and temperature had obvious effect on emulsion stability to creaming.The aim of this study was to investigate d-limonene Pickering emulsion stabilized by cellulose nanocrystals (CNCs) and factors that may affect its properties. CNCs were prepared by ammonium persulfate hydrolysis of corncob cellulose, and d-limonene Pickering emulsions were generated by ultrasonic homogenizing method. The morphology and size of the prepared emulsions with different CNCs concentrations were studied by optical microscopy and laser light diffraction. In addition, factors that may affect the stability of emulsions such as ionic concentration, pH and temperature were also studied. As indicated by the experiment data, when temperature rose, the stability to of emulsions would be increased, and the stability of emulsions was reduced with low pH or high salt concentration due to electrostatic screening of the negatively charged CNC particles. In conclusion, high stability of d-limonene Pickering emulsions could be obtained by CNCs.

Preparation of Organogel with Tea Polyphenols Complex for Enhancing the Antioxidation Properties of Edible Oil

Co-reporter:Rong Shi, Qiuyue Zhang, Frank Vriesekoop, Qipeng Yuan, and Hao Liang

Journal of Agricultural and Food Chemistry 2014 Volume 62(Issue 33) pp:8379-8384

Publication Date(Web):August 4, 2014

DOI:10.1021/jf501512y

Food-grade organogels are semisolid systems with immobilized liquid edible oil in a three-dimensional network of self-assembled gelators, and they are supposed to have a broad range of potential applications in food industries. In this work, an edible organogel with tea polyphenols was developed, which possesses a highly effective antioxidative function. To enhance the dispersibility of the tea polyphenols in the oil phase, a solid lipid–surfactant–tea polyphenols complex (organogel complex) was first prepared according to a novel method. Then, a food-grade organogel was prepared by mixing this organogel complex with fresh peanut oil. Compared with adding free tea polyphenols, the organogel complex could be more homogeneously distributed in the prepared organogel system, especially under heating condition. Furthermore, the organogel loading of tea polyphenols performed a 2.5-fold higher antioxidation compared with other chemically synthesized antioxidants (butylated hydroxytoluene and propyl gallate) by evaluating the peroxide value of the fresh peanut oil based organogel in accelerated oxidation conditions.

Formation and Stability of d-Limonene Organogel-Based Nanoemulsion Prepared by a High-Pressure Homogenizer

Co-reporter:Mohamed Reda Zahi, Pingyu Wan, Hao Liang, and Qipeng Yuan

Journal of Agricultural and Food Chemistry 2014 Volume 62(Issue 52) pp:12563-12569

Publication Date(Web):December 16, 2014

DOI:10.1021/jf5032108

d-Limonene organogel-based nanoemulsion was prepared by high-pressure homogenization technology. The organogelator type had a major role on the formation of the formulations, in which stearic acid has given nanoemulsions with the smallest droplet size. The surfactant type and concentration also had an appreciable effect on droplet formation, with Tween 80 giving a mean droplet diameter (d ≈ 112 nm) among a range of non-ionic surfactants (Tween 20, 40, 60, 80, and 85). In addition, high-pressure homogenization conditions played a key role in the nanoemulsion preparation. The stability of d-limonene organogel-based nanoemulsion was also investigated under two different temperatures (4 and 28 °C) through 2 weeks of storage. Results showed a good stability of the formulations, which is maybe due to the incorporation of d-limonene into the organogel prior to homogenization. This study may have a valuable contribution for the design and use of organogel-based nanoemulsion as a delivery system in food.

Rational surface silane modification for immobilizing glucose oxidase

Co-reporter:Feibao Tian, Yi Guo, Feifei Lin, Yumei Zhang, Qipeng Yuan, Hao Liang

International Journal of Biological Macromolecules (June 2016) Volume 87() pp:191-194

Publication Date(Web):1 June 2016

DOI:10.1016/j.ijbiomac.2016.02.055

Glucose oxidase (GOx) has many significant applications in biosensor and biocatalysis. In this study, we firstly quantitatively analyzed the binding efficiency of (3-aminopropyl) trimethoxysilane (APTES) modified onto the surface of GOx. It was found that the contents of the grafted silane did not significantly influence the relative activities and tertiary structures of all surface modified GOxs. Immobilization ratio and relative activity of all instances of APTES modified GOx increased, compared with those of native enzyme. However, good stability of immobilized GOx at extreme pH and high temperature could only be obtained when modified protein with low binding silane content. At pH 2.0, the immobilized GOx with low binding content showed a more than 600% activity, compared to the free enzyme. Therefore, rational surface modification would be beneficial to improving the activity and stability of immobilized enzyme as well as increasing loading amount.

Enhancing the antimicrobial activity of d-limonene nanoemulsion with the inclusion of ε-polylysine

Co-reporter:Mohamed Reda Zahi, Mohamed El Hattab, Hao Liang, Qipeng Yuan

Food Chemistry (15 April 2017) Volume 221() pp:

Publication Date(Web):15 April 2017

DOI:10.1016/j.foodchem.2016.10.037

•The antimicrobial activity of ε-polylysine, d-limonene and their combination were evaluated against four food-borne pathogens.•ε-Polylysine and d-limonene displayed strong synergistic and useful additive effects against the tested microorganisms.•d-limonene nanoemulsion with the inclusion of ε-polylysine, was successfully prepared by high pressure homogenization.•The formulations showed an enhanced antimicrobial activity as compared with d-limonene nanoemulsion.The objective of this research was to investigate the synergism between ε-polylysine and d-limonene and develop a novel nanoemulsion system by merging the positive effect of these two antimicrobial agents. Results from the checkerboard method showed that ε-polylysine and d-limonene exhibit strong synergistic and useful additive effects against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Saccharomyces cerevisiae. In addition, d-limonene nanoemulsion with the inclusion of ε-polylysine was successfully prepared by high pressure homogenizer technology. Its antimicrobial efficiency was compared with pure d-limonene nanoemulsion by measuring the minimal inhibitory concentration, electronic microscope observation and the leakage of the intercellular constituents. The results demonstrated a wide improvement of the antimicrobial activity of d-limonene nanoemulsion following the inclusion of ε-polylysine. Overall, the current study may have a valuable contribution to make in developing a more efficient antimicrobial system in the food industry.

Self-repairing metal–organic hybrid complexes for reinforcing immobilized chloroperoxidase reusability

Co-reporter:Yan Liu, Yumei Zhang, Xuejian Li, Qipeng Yuan and Hao Liang

Chemical Communications 2017 - vol. 53(Issue 22) pp:NaN3219-3219

Publication Date(Web):2017/02/20

DOI:10.1039/C6CC10319G