Analysis of preparation methods and formation mechanisms of hydrophobized polysaccharide-based self-assembly systems

  • LI Hong ,
  • TANG Xin ,
  • WANG Xiaogang ,
  • WANG Yongde ,
  • ZHAO Bo ,
  • WU Zhen
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  • 1(National Key Laboratory of Market Supervision (Condiment Supervision Technology), Chongqing Institute for Food and Drug Control, Chongqing 401121, China)
    2(Chongqing Academy of Chinese Materia Medica, Chongqing Key Laboratory of Chinese Medicine and Health Science, Chongqing 400065, China)

Received date: 2022-09-23

  Revised date: 2022-11-22

  Online published: 2024-03-15

Abstract

As safe, non-toxic, and effective delivery carrier materials, natural polysaccharides have been widely studied in recent years, but lack of amphiphilicity and self-assembly ability and uncontrolled and unstable spatial structures limit their application. The high-level structures of polysaccharides can be changed greatly by suitable hydrophobic modification, giving more possibilities for their structural regulation and application. The research progress of hydrophobized polysaccharides (HPs) in the last five years was summarized. The preparation methods of various delivery systems (micelles, reverse micelles, polymersomes, hydrogels, etc.) formed by HPs molecules were mainly summarized. Their preconditions and molecular mechanisms were analyzed. Results showed that the structures, sizes, and morphologies of HPs self-aggregation systems could be customized by selecting the types and preparation methods of HPs to achieve specific applications. It provides the foundation and basis for the design, preparation, and application of HPs self-aggregates and their delivery systems.

Cite this article

LI Hong , TANG Xin , WANG Xiaogang , WANG Yongde , ZHAO Bo , WU Zhen . Analysis of preparation methods and formation mechanisms of hydrophobized polysaccharide-based self-assembly systems[J]. Food and Fermentation Industries, 2024 , 50(3) : 336 -344 . DOI: 10.13995/j.cnki.11-1802/ts.033748

References

[1] FAN Y Q, LIU Y Q, WU Y, et al.Natural polysaccharides based self-assembled nanoparticles for biomedical applications - A review[J].International Journal of Biological Macromolecules, 2021, 192:1240-1255.
[2] HUANG C, SUN F S, MA X X, et al.Hydrophobically modified chitosan microgels stabilize high internal phase emulsions with high compliance[J].Carbohydrate Polymers, 2022, 288:119277.
[3] ZHANG Y Z, DONG L Z, LIU L Y, et al.Recent advances of stimuli-responsive polysaccharide hydrogels in delivery systems:A review[J].Journal of Agricultural and Food Chemistry, 2022, 70(21):6300-6316.
[4] 郑荣, 李珍, 闵洁, 等.双亲性多糖胶束的制备及作为纳米药物载体应用研究进展[J].高分子通报, 2021(12):1-12.
ZHENG R, LI Z, MIN J, et al.Progress of the preparations of amphiphilic polysaccharide micelles as nanoparticle drug carriers[J].Polymer Bulletin, 2021(12):1-12.
[5] WANG X, HUANG L X, ZHANG C H, et al.Research advances in chemical modifications of starch for hydrophobicity and its applications:A review[J].Carbohydrate Polymers, 2020, 240:116292.
[6] BU X T, JI N, DAI L, et al.Self-assembled micelles based on amphiphilic biopolymers for delivery of functional ingredients[J].Trends in Food Science & Technology, 2021, 114:386-398.
[7] 吴振. 温度和pH影响OSβG胶束化及其增溶和控释β-胡萝卜素的机制研究[D].重庆:西南大学, 2021.
WU Z.Molecular mechanisms underlying the effects of temperature and pH on OSβG micellization, solubilization and controlled-release of β-carotene by the resultant micelles[D].Chongqing:Southwest University, 2021.
[8] LU A J, PETIT E, LI S M, et al.Novel thermo-responsive micelles prepared from amphiphilic hydroxypropyl methyl cellulose-block-JEFFAMINE copolymers[J].International Journal of Biological Macromolecules, 2019, 135:38-45.
[9] YANG W Y, GUO L, LI F F, et al.Hydrophobically modified glucan as an amphiphilic carbohydrate polymer for micellar delivery of myricetin[J].Molecules, 2019, 24(20):3747.
[10] LU A J, PETIT E, WANG Y D, et al.Synthesis and self-assembly of hydroxypropyl methyl cellulose-block-poly(ε-caprolactone) copolymers as nanocarriers of lipophilic drugs[J].ACS Applied Nano Materials, 2020, 3(5):4367-4375.
[11] LIU Y R, SUN C, ZHANG G Y, et al.Bio-responsive Bletilla striata polysaccharide-based micelles for enhancing intracellular docetaxel delivery[J].International Journal of Biological Macromolecules, 2020, 142:277-287.
[12] GU C H, LE V, LANG M D, et al.Preparation of polysaccharide derivates chitosan-graft-poly(ε-caprolactone) amphiphilic copolymer micelles for 5-fluorouracil drug delivery[J].Colloids and Surfaces B:Biointerfaces, 2014, 116:745-750.
[13] SHEN F, LING H, GE W J, et al.Self-assembly behavior and conformation of amphiphilic hemicellulose-graft-fatty acid micelles[J].Carbohydrate Polymers, 2021, 261:117886.
[14] STANCIU M C, NICHIFOR M, MOCANU G, et al.Block copolymers containing dextran and deoxycholic acid polyesters.Synthesis, self-assembly and hydrophobic drug encapsulation[J].Carbohydrate Polymers, 2019, 223:115118.
[15] 王彬彬, 吕白, 张琦, 等.星点设计-效应面法优化负载和厚朴酚的当归多糖-小檗碱聚合物胶束的处方工艺研究[J].中草药, 2022, 53(4):1021-1029.
WANG B B, LYU B, ZHANG Q, et al.Optimization of prescription process of Angelica sinensis polysaccharideberberine micelle loaded with honokiol by central composite design-response surface method[J].Chinese Traditional and Herbal Drugs, 2022, 53(4):1021-1029.
[16] QIU L P, SHAN X T, LONG M M, et al.Elucidation of cellular uptake and intracellular trafficking of heparosan polysaccharide-based micelles in various cancer cells[J].International Journal of Biological Macromolecules, 2019, 130:755-764.
[17] SALDÍAS C, VELÁSQUEZ L, QUEZADA C, et al.Physicochemical assessment of Dextran-g-Poly (ε-caprolactone) micellar nanoaggregates as drug nanocarriers[J].Carbohydrate Polymers, 2015, 117:458-467.
[18] LIU Q Y, YANG X L, XU H B, et al.Novel nanomicelles originating from hydroxyethyl starch-g-polylactide and their release behavior of docetaxel modulated by the PLA chain length[J].European Polymer Journal, 2013, 49(11):3522-3529.
[19] MU Y Z, FU Y M, LI J, et al.Multifunctional quercetin conjugated chitosan nano-micelles with P-gp inhibition and permeation enhancement of anticancer drug[J].Carbohydrate Polymers, 2019, 203:10-18.
[20] LI J, KONG M, CHENG X J, et al.Preparation of biocompatible chitosan grafted poly(lactic acid) nanoparticles[J].International Journal of Biological Macromolecules, 2012, 51(3):221-227.
[21] MALEKHOSSEINI S, REZAIE A, KHALEDIAN S, et al.Fabrication and characterization of hydrocortisone loaded dextran-poly lactic-co-glycolic acid micelle[J].Heliyon, 2020, 6(5):e03975.
[22] MA L, LIU R G, TAN J J, et al.Self-assembly and dual-stimuli sensitivities of hydroxypropylcellulose-graft-poly(N, N-dimethyl aminoethyl methacrylate) copolymers in aqueous solution[J].Langmuir:the ACS Journal of Surfaces and Colloids, 2010, 26(11):8697-8703.
[23] MA L, KANG H L, LIU R G, et al.Smart assembly behaviors of hydroxypropylcellulose-graft-poly(4-vinyl pyridine) copolymers in aqueous solution by thermo and pH stimuli[J].Langmuir:the ACS Journal of Surfaces and Colloids, 2010, 26(23):18519-18525.
[24] IKKENE D, ARTENI A A, OULDALI M, et al.Self-assembly of amphiphilic copolymers containing polysaccharide:PISA versus nanoprecipitation, and the temperature effect[J].Polymer Chemistry, 2020, 11(29):4729-4740.
[25] ALIBOLANDI M, ALABDOLLAH F, SADEGHI F, et al.Dextran-b-poly(lactide-co-glycolide) polymersome for oral delivery of insulin:In vitro and in vivo evaluation[J].Journal of Controlled Release, 2016, 227:58-70.
[26] ROSSELGONG J, CHEMIN M, ALMADA C C, et al.Synthesis and self-assembly of xylan-based amphiphiles:From bio-based vesicles to antifungal properties[J].Biomacromolecules, 2019, 20(1):118-129.
[27] IKKENE D, ARTENI A A, OULDALI M, et al.Direct access to polysaccharide-based vesicles with a tunable membrane thickness in a large concentration window via polymerization-induced self-assembly[J].Biomacromolecules, 2021, 22(7):3128-3137.
[28] NISHIMURA T, SHEN S S, SASAKI Y, et al.Thermoresponsive polysaccharide graft polymer vesicles with tunable size and structural memory[J].Journal of the American Chemical Society, 2020, 142(27):11784-11790.
[29] KĿODZIŃSKA S N, WAN F, JUMAA H, et al.Utilizing nanoparticles for improving anti-biofilm effects of azithromycin:A head-to-head comparison of modified hyaluronic acid nanogels and coated poly (lactic-co-glycolic acid) nanoparticles[J].Journal of Colloid and Interface Science, 2019, 555:595-606.
[30] FENG J L, QI J R, YIN S W, et al.Fabrication and characterization of stable soy β-conglycinin-dextran core-shell nanogels prepared via a self-assembly approach at the isoelectric point[J].Journal of Agricultural and Food Chemistry, 2015, 63(26):6075-6083.
[31] PILIPENKO I M, KORZHIKOV-VLAKH V A, ZAKHAROVA N V, et al.Thermo- and pH-sensitive glycosaminoglycans derivatives obtained by controlled grafting of poly(N-isopropylacrylamide)[J].Carbohydrate Polymers, 2020, 248:116764.
[32] SETAYESH A, BAGHERI F, BODDOHI S.Self-assembled formation of chondroitin sulfate-based micellar nanogel for curcumin delivery to breast cancer cells[J].International Journal of Biological Macromolecules, 2020, 161:771-778.
[33] BORAH P K, DAS A S, MUKHOPADHYAY R, et al.Macromolecular design of folic acid functionalized amylopectin-albumin core-shell nanogels for improved physiological stability and colon cancer cell targeted delivery of curcumin[J].Journal of Colloid and Interface Science, 2020, 580:561-572.
[34] SAWADA S I, YUKAWA H, TAKEDA S, et al.Self-assembled nanogel of cholesterol-bearing xyloglucan as a drug delivery nanocarrier[J].Journal of Biomaterials Science.Polymer Edition, 2017, 28(10-12):1183-1198.
[35] ZEPON K M, OTSUKA I, BOUILHAC C, et al.Glyco-nanoparticles made from self-assembly of maltoheptaose-block-poly(methyl methacrylate):Micelle, reverse micelle, and encapsulation[J].Biomacromolecules, 2015, 16(7):2012-2024.
[36] WU Z, LI H, ZHAO X W, et al.Hydrophobically modified polysaccharides and their self-assembled systems:A review on structures and food applications[J].Carbohydrate Polymers, 2022, 284:119182.
[37] ZHU J, LI L, CHEN L, et al.Nano-structure of octenyl succinic anhydride modified starch micelle[J].Food Hydrocolloids, 2013, 32(1):1-8.
[38] CHANG R R, YANG J, GE S J, et al.Synthesis and self-assembly of octenyl succinic anhydride modified short glucan chains based amphiphilic biopolymer:Micelles, ultrasmall micelles, vesicles, and lutein encapsulation/release[J].Food Hydrocolloids, 2017, 67:14-26.
[39] ITOO A M, PAUL M, GHOSH B, et al.Oxaliplatin delivery via chitosan/vitamin E conjugate micelles for improved efficacy and MDR-reversal in breast cancer[J].Carbohydrate Polymers, 2022, 282:119108.
[40] EENSCHOOTEN C, VACCARO A, DELIE F, et al.Novel self-associative and Multiphasic nanostructured soft carriers based on amphiphilic hyaluronic acid derivatives[J].Carbohydrate Polymers, 2012, 87(1):444-451.
[41] ZENG Q, ZENG W H, JIN Y G, et al.Construction and evaluation of ovalbumin-pullulan nanogels as a potential delivery carrier for curcumin[J].Food Chemistry, 2022, 367:130716.
[42] NICHIFOR M, STANCIU M C, DOROFTEI F.Self-assembly of dextran - b - deoxycholic acid polyester copolymers:Copolymer composition and self-assembly procedure tune the aggregate size and morphology[J].Carbohydrate Polymers, 2021, 252:117147.
[43] LI H, YANG H T, XU J J, et al.Novel amphiphilic carboxymethyl curdlan-based pH responsive micelles for curcumin delivery[J].LWT, 2022, 153:112419.
[44] MUHOZA B, ZHANG Y T, XIA S Q, et al.Improved stability and controlled release of lutein-loaded micelles based on glycosylated casein via Maillard reaction[J].Journal of Functional Foods, 2018, 45:1-9.
[45] ZHAO Z W, ZHANG Z, CHEN L, et al.Biodegradable stereo complex micelles based on dextran-block-polylactide as efficient drug deliveries[J].Langmuir:the ACS Journal of Surfaces and Colloids, 2013, 29(42):13072-13080.
[46] SHAHRIARI M, TAGHDISI S M, ABNOUS K, et al.Synthesis of hyaluronic acid-based polymersomes for doxorubicin delivery to metastatic breast cancer[J].International Journal of Pharmaceutics, 2019, 572:118835.
[47] 徐成. 两亲性淀粉反相聚集体对蛋白质的增溶性质研究[D].大连:大连工业大学, 2017.
XU C.Study on the solubilization properties of the amphipathic starch reverse aggregates[D].Dalian:Dalian Polytechnic University, 2017.
[48] HASANNIA M, ALIABADI A, ABNOUS K, et al.Synthesis of block copolymers used in polymersome fabrication:Application in drug delivery[J].Journal of Controlled Release:Official Journal of the Controlled Release Society, 2022, 341:95-117.
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