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化学进展 2022, Vol. 34 Issue (10): 2267-2282 DOI: 10.7536/PC220131 前一篇   后一篇

• 综述与评论 •

蛋白质-多糖复合体系在活性物质传递中的应用

陈雅琼1,2, 宋洪东2, 吴懋1, 陆扬1, 管骁2,*()   

  1. 1 上海健康医学院药学院 上海 201318
    2 上海理工大学健康科学与工程学院 上海 200093
  • 收稿日期:2022-01-29 修回日期:2022-04-29 出版日期:2022-10-24 发布日期:2022-06-25
  • 通讯作者: 管骁
  • 基金资助:
    国家自然科学基金项目(32172247)
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Application of Protein-Polysaccharide Complex System in the Delivery of Active Ingredients

Chen Yaqiong1,2, Song Hongdong2, Wu Mao1, Lu Yang1, Guan Xiao2()   

  1. 1 School of Pharmacy, Shanghai University of Medicine & Health Sciences,Shanghai 201318, China
    2 School of Health Sciences and Engineering, University of Shanghai for Science and Technology,Shanghai 200093, China
  • Received:2022-01-29 Revised:2022-04-29 Online:2022-10-24 Published:2022-06-25
  • Contact: Guan Xiao
  • Supported by:
    National Natural Science Foundation of China(32172247)

蛋白质-多糖复合体系作为生物活性物质传递系统的壁材,有着人工合成聚合物或无机物等其他材料不可比拟的多重优势。本文就蛋白质和多糖之间的连接方式及蛋白质-多糖复合体系形成传递系统的多种形式进行了综述,以及对此领域的发展趋势进行了展望。结合蛋白质和多糖的结构特点,二者之间的链接方式分为非共价结合的物理共聚,和共价结合的美拉德偶联、化学交联、酶催化交联等方式,文中分别对各种连接方式的原理和机理,以及其影响因素做了深入阐述。以蛋白质-多糖复合体系为壁材对活性物质的传递形式大体上分成乳化系统、胶束、纳米凝胶、分子复合物以及壳核结构等系统。不同的活性物质的特征和传递需求,可针对性地选择合适结构的蛋白质和多糖种类以及二者的连接方式和传递系统的形式。并且,随着研究的逐步发展和推进,此领域的发展趋势朝着智能化和靶向性的方向进行。目前活性物质的蛋白质-多糖复合体系的传递系统,还依然面临着系统设计、评价和应用等多方面的挑战,这就要求我们在更全面更深入了解认识其对活性物质影响和功效的基础上,安全合理地设计和深入细致地评价活性成分的传递系统。

关键词： 蛋白质-多糖复合体系, 传递系统, 结合方式, 靶向性, 活性物质

Protein-polysaccharide complex system, as the wall material of bioactive ingredient delivery systems, have multiple advantages that other materials such as synthetic polymers or inorganic materials do not have. The connection mode between protein and polysaccharide, the various forms of protein-polysaccharide complex forming delivery system are reviewed, and the development trend of this field is prospected. According to the structural characteristics of proteins and polysaccharides, the linking methods between the two are divided into non-covalent binding such as physical copolymerization, and covalent binding such as Maillard coupling, chemical cross-linking, and enzyme-catalyzed cross-linking. The binding mechanism of the above connection methods and the influencing factors are expounded. The delivery forms of active ingredients with protein polysaccharide complexes as wall materials are generally divided into emulsion systems, micelles, nanogels, molecular complexes, and shell-core structure systems. According to the characteristics and delivery requirements of different active ingredients, proteins and polysaccharides with suitable structures and types, as well as their connection methods and delivery systems, can be selected in a targeted manner. Moreover, with the gradual development and advancement of research, the development trend in this field is moving towards the direction of intelligence and targeting. At present, the protein-polysaccharide complexes delivery system of active ingredients still faces many challenges in system design, evaluation and application. This requires us to design and evaluate the delivery system of active ingredients in a safe and reasonable manner based on a more comprehensive and in-depth study of its impact and efficacy on active ingredients.

Key words: protein-polysaccharide complex system, delivery system, binding method, targeted, active ingredients
()
图1 蛋白质多糖结合方式示意图
Fig. 1 Schematic diagram of the binding mode of protein and polysaccharide
图2 (a)决定蛋白质和多糖凝聚的三个pH节点:pHc、pHφ1、pHφ2;以及(b)离子强度对pH节点的影响[28]
Fig. 2 (a) Three pH nodes determining protein and polysaccharide aggregation: pHc, pHφ1, pHφ2; and (b) the effect of ionic strength on the pH node (b)[28]. Copyright 2003, ACS
图3 不同参数对复合凝聚过程的影响
Fig. 3 Effects of different parameters on the process of protein-polysaccharide complex coacervation
图4 美拉德反应形成蛋白质-多糖共价复合物示意图[32]
Fig. 4 Schematic diagram of the Maillard reaction to form protein-polysaccharide covalent complexes[32], Copyright 2003, China Agricultural University
图5 EDC/NHS偶联蛋白质和含羧基多糖反应历程图
Fig. 5 EDC/NHS coupling reaction scheme
图6 DMTMM偶联蛋白质和含羧基多糖反应历程图
Fig. 6 DMTMM coupling process of hyaluronic acid and amine-containing compounds
图7 (a)、(b) 京尼平与含伯氨化合物交联反应机理, (c)多糖和蛋白质之间通过京尼平交联的模式 (R1、R2:任一为蛋白质,另一为氨基多糖)
Fig. 7 (a),(b) Mechanism of cross-linking reaction between genipin and compounds containing primary ammonia, (c) Patterns of cross-linking between polysaccharides and proteins via genipin(R1, R2:one of them is protein, the other is aminopolysaccharide)
图8 谷氨酰胺转胺酶催化蛋白质和氨基多糖的反应历程
Fig. 8 Transglutaminase-catalyzed reaction process
图9 漆酶、过氧化物酶和酪氨酸酶对含酚结构化合物进行酶促氧化机理
Fig. 9 Laccase, peroxidase and tyrosinase enzymatic oxidation mechanism of compounds containing phenolic structures
表1 蛋白质-多糖复合体系结合方式及其影响因素
Table 1 The binding mode of protein-polysaccharide complex and its influencing factors
图10 蛋白质-多糖复合体系对生物活性物质的包埋传递形式示意图
Fig. 10 Schematic of the delivery system for active ingredients by proteoglycan-saccharide complexes
表2 蛋白质-多糖复合体系转递活性物质系统类型及其功能
Table 2 Types and functions of protein-polysaccharide complex delivery system for active ingredients
active ingredients Wall Material/Methods delivery system Function/Purpose ref
Lycopene WPI-SA/ transglutaminase cross-
linked, emulsification		 Nanoemul-sion lycopene-loaded emulsion showed better photochemical and gastrointestinal stability, strong anti-inflammatory activity against Caco-2 cells, and increased lycopene uptake by Caco-2 cells 78
Blackberry tree anthocyanins Gelatin-GA/complex coacervation Multiple emulsion Blackberry tree anthocyanins were microencapsulated by a double-emulsion system composed of gelatin and gum arabic, the structure and properties were evaluated, and the effect on the stability of anthocyanins was determined. 4
curcumin Gliadin-Chitosan/ Anti-
solvent dispersion		 Pickering emulsion The gliadin-chitosan Pickering emulsion has a high internal phase, is partially wetted, effectively adsorbed and fixed at the oil-water interface, provides steric hindrance, and has suitable viscoelasticity, while protecting curcumin. 75
Canola oil WPC- GA/complex coacervation Pickering double emulsions Pickering O/W/O double emulsion prepared from WPC- GA complex with long-term stability. 79
naringenin β-CN-dextran/ Maillard reaction,
self-assembly		 micelle Dextran-induced β-CN glycosylation to improve the stability of naringenin-loaded β-CN micelles in acidic and high calcium environments 80
curcumin OVA-Pul/Maillard reaction,
Heat treatment		 nanogel OVA-Pul nanogels have good storage stability and facilitate the controlled release of curcumin during digestion 81
cinnamaldehyde GelatiN- HMP or LMP/
complex coacervation		 Molecular complex Pectin type and gelatin conformation significantly affect the overall coordination and properties of cinnamaldehyde microcapsules 82
EGCG hordein-chitosan/Anti-solvent dispersion, Electrostatic deposition Shell-Core particle Chitosan-coated barley soluble pale white shell-structured core nanoparticles have high encapsulation efficiency of EGCG and penetrate into epithelial cells through vesicle-mediated endocytosis and macropinocytosis 22
Hyperoside SPI-SSPS/Anti-solvent dispersion, Electrostatic deposition Shell-Core particle The main forces for the formation of nanoparticles were electrostatic interaction, hydrogen bond interaction and hydrophobic interaction. The encapsulation efficiency is high, and the encapsulated HYP maintains its high antioxidant capacity. 83
图11 壳核结构的EGCG-大麦醇溶蛋白/壳聚糖(Cs-EHNs)纳米颗粒的制备示意图,以及该纳米颗粒在Caco-2/HT29细胞中的吸收和跨细胞渗透性[22]
Fig. 11 Schematic illustration of the preparation of shell-core structured EGCG-hordein/chitosan (Cs-EHNs) nanoparticles, and their uptake and transcellular permeability in Caco-2/HT29 cells[22]. Copyright 2021, Elsevier
图12 牛血清蛋白(BSA)修饰制备成热敏响应性囊泡(a)热敏感物质PNIPAAm聚合物与BSA的偶联方案;(b)皮克林乳剂形成的蛋白囊泡微室方案;(c)蛋白囊泡形成了一个热门控系统,该系统通过溶胀或脱溶胀来运行;(d)在两种反应物(2-甲氧基苯酚和H2O2)存在下,游离肌红蛋白(黑线)和蛋白体包覆肌红蛋白(红线)相应的温度依赖性催化反应速率[102]
Fig. 12 Thermoresponsive vesicles prepared by modification of bovine serum albumin(BSA)(a) Coupling scheme of thermosensitive substance PNIPAAm polymer and BSA; (b) scheme of protein vesicle microchamber formed by Pickering emulsion; (c) protein vesicle A thermally controlled system is formed that operates by swelling or de-swelling; (d) Corresponding temperature-dependent catalytic reaction rates for free myoglobin (black line) and protein body encapsulated myoglobin (red line) in the presence of two reactants (2-methoxyphenol and H2O2)[102]. Copyright 2013, Nature
图13 (a)靶向DNPs纳米颗粒的构建方案,(b)上皮细胞对胰岛素的摄取机制,以及(c)DNPs从胆汁酸途径经上皮细胞转运克服肠道上皮细胞的多重屏障的示意图[103]
Fig. 13 (a) Construction scheme of nanoparticles targeting DNPs, (b) mechanism of insulin uptake by epithelial cells, and (c) schematic diagram of the transport of DNPs from the bile acid pathway through epithelial cells to overcome the multiple barriers of intestinal epithelial cells[103]. Copyright 2013, University of Chinese Academy of Sciences
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