两亲胆固醇壳聚糖碳酸酯的合成及其单分子膜的形成与性能研究
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摘要
本文从壳聚糖结构特点出发,利用甲磺酸保护壳聚糖氨基,在羟基上引入胆固醇合成两亲性胆固醇壳聚糖碳酸酯(ACCC),利用FT-IR和~(13)C-NMR方法证明碳酸酯基的生成。采用Langmuir膜技术跟踪探究不同取代度ACCC的单分子膜在空气/水界面上的形成过程及膜性能,由表面压-单分子层表观面积(π-A)等温曲线得知,从气相到固相变化过程中两亲壳聚糖衍生物单分子经历从分散到集中,在空气/水界面上逐渐形成单分子膜,单分子膜稳定性和强度取决于胆固醇取代度的变化。取代度分别是2.6和3.9的ACCC的膜平均极限面积(A*)达到346.76和652.65cm~2,相应塌陷压值分别等于46.13和47.48mN/m,表明这两种胆固醇壳聚糖碳酸酯Langmuir膜具有良好的性能和稳定性。通过Langmuir-Blogett技术将单分子膜转移制备多层膜修饰的ITO电极。
引文
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[33] Li X L, Tong Y J, Jia L, et al. Fabrication of molecularly cholesterol-imprinted polymer particles based on chitin and their adsorption ability[J]. Monatshefte für Chemie, 2015, 146,423-430.
[34] El-Knidri H, Belaabed R, Addaou A, et al.Extraction, chemical modification and characterization of chitin and chitosan[J].International Journal of Biological Macromolecules, 2018, 120(Part A):1181-1189.
[35] Hirano S, Osaka T. Some O-Stearoyl Derivatives of Chitosan Prepared via Its Schiff’s Base Intermediates[J]. Agricultural and Biological Chemistry, 1983, 47(6):1389-1391.
[36] Khalil M, Abdel-Monem R A, Darwesh O M, et al.Synthesis, characterization, and evaluation of antimicrobial activities of chitosan and carboxymethyl chitosan Schiff-base/silver nanoparticles[J]. Journal of Chemistry, 2017,1434320/1-1434320/11.
[37] Ahmed I, Dildar L, Haque A. Chitosan-fatty acid interaction mediated growth of Langmuir monolayer and Langmuir-Blodgett films[J]. Journal of Colloid and Interface Science, 2018, 514:433-442.
[38] Li X F, Yuan W Z, Gu S Y, et al. Synthesis and self-assembly of tunable thermosensitive chitosan amphiphilic copolymers by click chemistry[J].Materials Letters, 2010, 64(24):2663-2666.
[39] Krajewska B, Kyziol A, Wydro P. Chitosan as a subphase disturbant of membrane lipid monolayers.The effect of temperature at varying pH:II. DPPC and cholesterol[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects, 2013,434:359-364.
[2] Stefaniu C, Brezesinski G, M?hwald H. Langmuir monolayers as models to study processes at membrane surfaces[J]. Advances in Colloid and Interface Science, 2014, 208:197-213.
[3] Giner-Casares J J, Brezesinski G, M?hwald H.Langmuir monolayers as unique physical models[J].Current Opinion in Colloid Interface Science, 2014,19(3):176-182.
[4] Li T, Lilja K, Morris R J, et al. Langmuir–Blodgett technique for anisotropic colloids:Young investigator perspective[J]. Journal of Colloid and Interface Sci., 2019, 540:420-438.
[5] Nobre T M, Pavinatto F J, Caseli L, et al.Interactions of bioactive molecules&nanomaterials with Langmuir monolayers as cell membrane models[J]. Thin Solid Films, 2015, 593:158-188.
[6] Wnetrzak A, Maky?a-Juzaka K, Chachaj-Brekiesz A,et al. Cyclosporin A distribution in cholesterolsphingomyelin artificial membranes modeled as Langmuir monolayers[J]. Colloids and Surfaces B:Biointerfaces, 2018, 166:286-294.
[7] Elderdfi M, Sikorski A F. Langmuir monolayer methodologies for characterizing protein-lipid interactions[J]. Chemistry and Physics of Lipids,2018, 212:61-72.
[8] Ariga K, Yamauchi Y, Mori T, et al. 25Th anniversary article:what can be done with the Langmuir–Blodgett method? Recent developments and its critical role in materials science[J].Advanced Materials., 2013, 25:6477-6512.
[9] Hussain S A, Dey B, Bhattacharjee D, et al. Unique supramolecular assembly through LangmuirBlodgett(LB)technique[J]. Heliyon, 2018, 4(12):Article e 01038.
[10] Kausar A. Survey on Langmuir-Blodgett films of polymer and polymeric composite[J]. PolymerPlastics Technology and Engineering., 2017, 56:932-945.
[11] Su Z F, Leitch J J, Lipkowski J. Electrodesupported biomimetic membranes:An electrochemical and surface science approach for characterizing biological cellmembranes[J].Current Opinion Electrochemistry, 2018, 12:60-72.
[12] Xu Y J, Hao Q L, Mandler D. Electrochemical detection of dopamine by a calixarene-cellulose acetate mixed Langmuir-Blodgett monolayer[J].Analytica Chimica Acta, 2018, 1042:29-36.
[13] Giancane G, Valli L. State of art in porphyrin Langmuir–Blodgett films as chemical sensors[J].Advances in Colloid and Interface Science, 2012,171-172:17-35.
[14] Zhavnerko G, Marletta G. Developing Langmuir–Blodgett strategies towards practical devices[J].Materials Science and Engineering:B, 2010,169(1-3):43-48.
[15] Yen M T, Yang J H, Mau J L. Physicochemical characterization of chitin and chitosan from crab shells[J]. Carbohydrate Polymers, 2009, 75(1):15-21.
[16] Hamed I,?zogul F, Regenstein J M. Industrial applications of crustacean by-products(chitin,chitosan, and chitooligosaccharides):A review[J].Trends in Food Science&Technology, 2016,48(Suppl. C):40-50.
[17] Shariatinia Z. Pharmaceutical applications of chitosan[J]. Advances inColloid and Interface Science, 2019, 263:131-194.
[18] Mittal H, Ray S S, Kaith B S, et al. Recent progress in the structural modification of chitosan for applications in diversified biomedical fields[J].European Polymer Journal., 2018, 109:102-434.
[19] Kumaraswamy R V, Kumari S, Choudhary R C, et al.Engineered chitosan based nanomaterials:Bioactivities, mechanisms and perspectives in plant protection and growth[J]. International Journal of Biological Macromolecules, 2018, 113:494-506.
[20] Kusaoke H, Shinya S, Fukamizo T, et al.Biochemical and biotechnological trends in chitin,chitosan, and related enzymes produced by Paenibacillus IK-5 Strain[J]. International Journal of Biological Macromolecules, Part B, 2017,104:1633-1640.
[21] Unlu D, Hilmioglu N D. Pervaporation catalytic membrane reactor application over functional chitosan membrane[J]. Jounal of Membrane Science,2018, 559:138-147.
[22] Mourya V K, Inamdar N N. Chitosan-modifications and applications:Opportunities galore[J].Reactive and Functional Polymers, 2008, 68(6):1013-1051.
[23] Petit C, Reynaud S, Desbrieres J. Amphiphilic derivatives of chitosan using microwave irradiation. Toward an eco-friendly process to chitosan derivatives[J]. Carbohydrate Polymers,2015, 116:26-33.
[24] Choi C Y, Nam J P, Nah J W. Application of chitosan and chitosan derivatives as biomaterials[J].Journal of Industrial and Engineering Chemistry,2016, 33:1-10.
[25] Verlee A, Mincke S, Stevens C V. Recent developments in antibacterial and antifungal chitosan and its derivatives[J]. Carbohydrate Polymers, 2017, 164:268-283.
[26] Luo J, Ling Y, Li X, et al. Combining amphiphilic chitosan and bioglass for mediating cellular osteogenic growth peptide gene[J]. RSC Advances,2015, 5(97):79239-79248.
[27] Motiei M, Kashanian S. Preparation of amphiphilic chitosan nanoparticles for controlled release of hydrophobic drugs[J]. Journal of Nanoscience Nanotechnology, 2017, 17(8):5226-5232.
[28] Motiei M, Kashanian S, Lucia L A, et al. Intrinsic parameters for the synthesis and tuned properties of amphiphilic chitosan drug delivery nanocarriers[J]. Journal of Controlled Release, 2017, 260,213-225.
[29] Wu M M, Dong H W, Guo K, et al. Self-assemblied nanocomplexes based on biomimetic amphiphilic chitosan derivatives for protein delivery[J].Carbohydrate Polymers, 2015, 121:115-121.
[30] Zhang X, Xu G J, Gadora K. Dual-sensitive chitosan derivative micelles for site-specific drug release in the treatment of chicken coccidiosis[J].RSC Advances, 2018, 8(26):14515-14526.
[31] Tong Y J, Wang S F, Xu J W, et al. Synthesis of O, O'-dipalmitoyl chitosan andits amphiphilic properties and capability of cholesterol absorption[J]. Carbohydrate Polymers, 2005, 60(2):229-233.
[32]邹行.基于两亲壳聚糖单/双组份Langmuir膜的形成及其单分子层行为的研究[D].福州:福建师范大学,2014.
[33] Li X L, Tong Y J, Jia L, et al. Fabrication of molecularly cholesterol-imprinted polymer particles based on chitin and their adsorption ability[J]. Monatshefte für Chemie, 2015, 146,423-430.
[34] El-Knidri H, Belaabed R, Addaou A, et al.Extraction, chemical modification and characterization of chitin and chitosan[J].International Journal of Biological Macromolecules, 2018, 120(Part A):1181-1189.
[35] Hirano S, Osaka T. Some O-Stearoyl Derivatives of Chitosan Prepared via Its Schiff’s Base Intermediates[J]. Agricultural and Biological Chemistry, 1983, 47(6):1389-1391.
[36] Khalil M, Abdel-Monem R A, Darwesh O M, et al.Synthesis, characterization, and evaluation of antimicrobial activities of chitosan and carboxymethyl chitosan Schiff-base/silver nanoparticles[J]. Journal of Chemistry, 2017,1434320/1-1434320/11.
[37] Ahmed I, Dildar L, Haque A. Chitosan-fatty acid interaction mediated growth of Langmuir monolayer and Langmuir-Blodgett films[J]. Journal of Colloid and Interface Science, 2018, 514:433-442.
[38] Li X F, Yuan W Z, Gu S Y, et al. Synthesis and self-assembly of tunable thermosensitive chitosan amphiphilic copolymers by click chemistry[J].Materials Letters, 2010, 64(24):2663-2666.
[39] Krajewska B, Kyziol A, Wydro P. Chitosan as a subphase disturbant of membrane lipid monolayers.The effect of temperature at varying pH:II. DPPC and cholesterol[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects, 2013,434:359-364.