China Surfactant Detergent & Cosmetics ›› 2025, Vol. 55 ›› Issue (8): 1006-1016.doi: 10.3969/j.issn.2097-2806.2025.08.007
• Basic research • Previous Articles Next Articles
Wanping Zhang1,2,Dexu Meng1,2,Kaikai Liu1,2,Pingli Wang3,Qianjie Zhang1,2,*(),Chengliang Li3,*(
)
Received:
2024-09-19
Revised:
2025-07-29
Online:
2025-08-22
Published:
2025-08-28
Contact:
*E-mail: zhangqj_sit@126.com;richard-li@laibo.com.cn.
CLC Number:
Wanping Zhang, Dexu Meng, Kaikai Liu, Pingli Wang, Qianjie Zhang, Chengliang Li. Assembly behavior and emulsification property of dopamine modified sodium hyaluronate based on ionic coordination[J].China Surfactant Detergent & Cosmetics, 2025, 55(8): 1006-1016.
Fig. 4
TEM image of Na+-DA-HA solutions with different concentrations (a); Zeta potential values of Na+-DA-HA solutions with different concentrations (b); dynamic interfacial tension of Na+-DA-HA solution with different concentrations (c); appearance, microscopic photos and distribution of emulsion particles prepared by Na+-DA-HA solution with different concentrations after standing for 24 h (d)"
Fig. 5
TEM image of Mn2+-DA-HA solutions with different concentrations (a); dynamic interfacial tension of Mn2+-DA-HA solutions with different concentrations (b); appearance, microscopic photos and distribution of emulsion particles prepared by Mn2+-DA-HA solution with different concentrations after standing for 24 h(c)"
[1] | Kuperkar Ketan, Patel Dhruvi, et al. Atanase Leonard Ionut, Amphiphilic block copolymers: their structures, and self-assembly to polymeric micelles and polymersomes as drug delivery vehicles[J]. Polymers, 2022, 14 (21) : 4702. |
[2] |
Yi Chenglin, Yang Yiqun, Zhu Ye, et al. Self-assembly and emulsification of poly {[styrene-alt-maleic acid]-co-[styrene-alt-(N-3, 4-dihydroxyphenylethyl-maleamic acid)]}[J]. Langmuir, 2012, 28 (25) : 9211-9222.
doi: 10.1021/la301605a pmid: 22639900 |
[3] | Wang Feng, Yu Xiaoyun, Yang Zhouxiaoshuang, et al. Dual pH-and light-responsive amphiphilic random copolymer nanomicelles as particulate emulsifiers to stabilize the oil/water interface[J]. The Journal of Physical Chemistry C, 2018, 122 (33) : 18995-19003. |
[4] |
Wang Feng, Tang Juntao, Liu Hui, et al. Self-assembled polymeric micelles as amphiphilic particulate emulsifiers for controllable Pickering emulsions[J]. Materials Chemistry Frontiers, 2019, 3 (3) : 356-364.
doi: 10.1039/c8qm00540k |
[5] | Jabbari Farzaneh, Babaeipou Valiollah, Saharkhiz Saeed. Comprehensive review on biosynthesis of hyaluronic acid with different molecular weights and its biomedical applications[J]. International Journal of Biological Macromolecules, 2023, 240: 124484. |
[6] | Iaconisi Giorgia Natalia, Lunetti Paola, Gallo Nunzia, et al. Hyaluronic acid: a powerful biomolecule with wide-ranging applications: A comprehensive review[J]. International Journal of Molecular Sciences, 2023, 24 (12) : 10296. |
[7] | Luo Zhiqiang, WangYu, Li Jinbo, et al. Tailoring hyaluronic acid hydrogels for biomedical applications[J]. Advanced Functional Materials, 2023, 33 (49) : 2306554. |
[8] | Li Shangzhi, Dong Qi, Peng Xiaotong, et al. Self-healing hyaluronic acid nanocomposite hydrogels with platelet-rich plasma impregnated for skin regeneration[J]. Acs Nano, 2022, 16 (7) : 11346-11359. |
[9] |
Lee Hyukjin, Lee Kyuri, Park Tae Gwan. Hyaluronic acid-paclitaxel conjugate micelles: synthesis, characterization, and antitumor activity[J]. Bioconjugate Chemistry, 2008, 19 (6) : 1319-1325.
doi: 10.1021/bc8000485 pmid: 18481885 |
[10] | Karimi-Soflou Reza, Karkhaneh Akbar. Redox-sensitive multifunctional hyaluronic acid-based nanomicelles with fine-controlled anticancer drug release[J]. International Journal of Pharmaceutics, 2022, 629: 122402. |
[11] | Sun Jiao, Li Min, Lin Kexin, et al. Delivery of quercetin for breast cancer and targeting potentiation via hyaluronic nano-micelles[J]. International Journal of Biological Macromolecules, 2023, 242: 124736. |
[12] |
Zhao Donghua, Zhu et al. Stable emulsions prepared by self-assembly of hyaluronic acid and chitosan for Papain loading[J]. Macromolecular Bioscience, 2015, 15 (4) : 558-567.
doi: 10.1002/mabi.201400486 pmid: 25594587 |
[13] | 诸超, 朱叶, 魏玮, 等. 香豆素改性透明质酸颗粒乳化剂的制备及应用[J]. 功能高分子学报, 2016, 29 (4) : 388-396. |
[14] | Zhang Cuige, Zhang Rongli, Zhu Ye, et al. Polymer vesicles prepared from the (l-phenylalanine ethyl ester)-modified hyaluronic acid[J]. Materials Letters, 2016, 164: 15-18. |
[15] | 冉海燕, 洪慧, 诸超, 等. 肉桂酸改性透明质酸颗粒乳化剂的制备及性能[J]. 功能高分子学报, 2019, 32 (1) : 53-62. |
[16] | 张翠歌, 胡良, 孙元峰, 等. 基于透明质酸生物活性自组装胶体粒子制备及乳化性能[J]. 化学研究与应用, 2021, 33 (2) : 309-316. |
[17] | 范欣怡, 闫昕, 杨晗, 等. 基于透明质酸自组装胶体粒子功能乳液的制备及缓释性能[J]. 复合材料学报, 2023, 40 (10) : 5803-5810. |
[18] | Eenschooten Corinne, Guillaumie Fanny, Kontogeorgis Georgios M, et al. Preparation and structural characterisation of novel and versatile amphiphilic octenyl succinic anhydride-modified hyaluronic acid derivatives[J]. Carbohydrate Polymers, 2010, 79 (3) : 597-605. |
[19] |
Payne William M, Svechkarev Denis, Kyrychenko Alexander, et al. The role of hydrophobic modification on hyaluronic acid dynamics and self-assembly[J]. Carbohydrate Polymers, 2018, 182: 132-141.
doi: S0144-8617(17)31210-9 pmid: 29279107 |
[20] | Liu Wenxiu, Ding Lin, Xu Jiawen, et al. Synthesis of sinapic acid modified sodium hyaluronate particles and the one-step processing of multiple Pickering emulsion[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2022, 644: 128785. |
[21] | 包舟杰, 王小永. 肉桂酸疏水改性透明质酸的聚集及其光谱性质[J]. 华东理工大学学报(自然科学版), 2024, 50 (3) : 371-376. |
[22] | Parrado Andrea Cecilia, Salaverry Luciana Soledad, Mangone Franco Mauricio, et al. Differential response of dopamine mediated by β-adrenergic receptors in human keratinocytes and macrophages: potential implication in wound healing[J]. Neuroimmunomodulation, 2018, 24(4/5): 282-291. |
[23] |
Clancy Sean K, Sodano Antonio, Cunningham Dylan J, et al. Marine bioinspired underwater contact adhesion[J]. Biomacromolecules, 2016, 17 (5) : 1869-1874.
doi: 10.1021/acs.biomac.6b00300 pmid: 27046671 |
[24] | Zhang Qianjie, Wang Pingli, Zhang Dongmei, et al. Surface modification of sodium hyaluronate with dopamine to enhance emulsifying capacity and application performance[J]. Colloid and Polymer Science, 2024: 1-13. |
[25] | 栾途. 透明质酸粘多糖的分子表征、流变学性质及其物理凝胶的研究[D]. 上海: 上海交通大学, 2012. |
[26] | Kocourková Karolína, Musilová Lenka, Smolka Petr, et al. Factors determining self-assembly of hyaluronan[J]. Carbohydrate Polymers, 2021, 254: 117307. |
[27] |
Zhu Ye, Wang Juanqin, Li Xiaojie, et al. Self-assembly and emulsification of dopamine-modified hyaluronan[J]. Carbohydrate Polymers, 2015, 123: 72-79.
doi: 10.1016/j.carbpol.2015.01.030 pmid: 25843836 |
[28] |
Zhang Cuige, Yang Suhan, Zhu Ye, et al. Formation of bowl-shaped nanoparticles by self-assembly of cinnamic acid-modified dextran[J]. Carbohydrate Polymers, 2015, 133: 637-643.
doi: 10.1016/j.carbpol.2015.07.035 pmid: 26344322 |
[29] | 张翠歌, 朱叶, 罗静, 等. Papain/HA-Phe自组装复合纳米粒子及乳化性能[J]. 高分子学报, 2016 (7) : 963-970. |
[30] |
Wu Shengfang, Ai Lianzhong, Chen Jie, et al. Study of the mechanism of formation of hyaluronan putty at pH 2.5: Part I. Experimental measurements[J]. Carbohydrate Polymers, 2013, 98 (2) : 1677-1682.
doi: 10.1016/j.carbpol.2013.05.088 pmid: 24053856 |
[31] | Snetkov Petr, Zakharova Kseniia, Morozkina Svetlana, et al. Hyaluronic acid: the influence of molecular weight on structural, physical, physico-chemical, and degradable properties of biopolymer[J]. Polymers, 2020, 12 (8) : 1800. |
[32] | Ondreas Frantisek, Dusankova Marcela, Sita Jaroslav, et al. Self-assembly of hydrophobically modified hyaluronic acid[J]. Applied Surface Science, 2021, 546: 149161. |
[33] | 易成林. 双亲大分子自组装胶束的乳化性能研究[D]. 无锡: 江南大学, 2013. |
[34] | Pal Sunirmal, Roy Saswati Ghosh, De Priyadarsi. Synthesis via RAFT polymerization of thermo-and pH-responsive random copolymers containing cholic acid moieties and their self-assembly in water[J]. Polymer Chemistry, 2014, 5 (4) : 1275-1284. |
[35] | Sanders Connor A, Werner Arthur, Smeltzer Sandra E, et al. Amphiphilic block random copolymers: influence of pH and ionic strength on aqueous solution properties[J]. Macromolecules, 2024, 57 (8) : 3484-3495. |
[36] | 徐伟, 俞蓉欣, 张相春, 等. 多酚自组装抗菌生物材料的构建及其应用进展[J]. 茶叶科学, 2024, 44 (1) : 1-15. |
[37] | Wei J, Zhang W, Mou X, et al. Bioinspired hemostatic and anti-infective armor for wound healing assisted by metal-phenol-polyamine system[J]. Advanced Functional Materials, 2024, 34 (4) : 15. |
[38] | Lin Z, Liu H, Richardson J J, et al. Metal-phenolic network composites: from fundamentals to applications[J]. Chemical Society Reviews, 2024, 53 (22) : 28. |
[39] | Fang Xiuqin, Zhao Xinyu, Yu Gaobo, et al. Effect of molecular weight and pH on the self-assembly microstructural and emulsification of amphiphilic sodium alginate colloid particles[J]. Food Hydrocolloids, 2020, 103: 105593. |
[40] | Clayton Katherine N, Salameh Janelle W,, Wereley Steven T, et al. Physical characterization of nanoparticle size and surface modification using particle scattering diffusometry[J]. Biomicrofluidics, 2016, 10 (5) : 054107. |
[41] | Li Moting, Sun Yawen, McClements David Julian, et al. Interfacial engineering approaches to improve emulsion performance: properties of oil droplets coated by mixed, multilayer, or conjugated lactoferrin-hyaluronic acid interfaces[J]. Food Hydrocolloids, 2022, 133: 107938. |
[42] | 方秀琴. 两亲性海藻酸钠衍生物自组装行为和乳化性能的调控[D]. 海口: 海南大学, 2020. |
[43] |
Bresciani Guilherme, da Cruz Ivana Beatrice Mânica, González-Gallego Javier. Manganese superoxide dismutase and oxidative stress modulation[J]. Advances in Clinical Chemistry, 2015, 68: 87-130.
doi: 10.1016/bs.acc.2014.11.001 pmid: 25858870 |
[44] | Kantappa Halake, Seungvin Cho, Junseok Kim, et al. Applications using the metal affinity of polyphenols with mussel-inspired chemistry[J]. Macromolecular Research, 2018, 26: 93-99. |
[45] | Yan Guihua, Chen Gaofeng, Peng Zhiqing, et al. The cross-linking mechanism and applications of catechol-metal polymer materials[J]. Advanced Materials Interfaces, 2021, 8 (19) : 2100239. |
[46] | Liu Shang, Ding Ran, Yuan Jiaxin, et al. Melanin-inspired composite materials: from nanoarchitectonics to applications[J]. ACS Applied Materials & Interfaces, 2024, 16 (3) : 3001-3018. |
[47] | Zou Wenting, Liu Yan, Li Renjie, et al. Ingenious multifunctional MnO2 quantum dot nanozymes with superior catechol oxidase-like activity for highly selective sensing of redox-active dopamine based on an interfacial passivation strategy[J]. ACS Sustainable Chemistry &Engineering, 2022, 10 (30) : 10057-10067. |
[48] |
Svechkarev Denis, Kyrychenko Alexander, Payne William M, et al. Probing the self-assembly dynamics and internal structure of amphiphilic hyaluronic acid conjugates by fluorescence spectroscopy and molecular dynamics simulations[J]. Soft Matter, 2018, 14 (23) : 4762-4771.
doi: 10.1039/c8sm00908b pmid: 29799600 |
[49] | Huang Jie, Chen Yeqing, Rao Pengpeng, et al. Enhancing the electron transport, quantum yield, and catalytic performance of carbonized polymer dots via Mn-O bridges[J]. Small, 2022, 18 (13) : 2106863. |
[50] | Yi C, Yang Y, Jiang J, et al. Research and application of particle emulsifiers[J]. Progress in Chemistry, 2011, 23 (1) : 65. |
[1] | Fengqin Li, Tao Geng, Jingjie Zhou, Jinyuan Sun, Ke Zhang, Chunyu Wang. Study on the mechanism and performance of different catalysts in the reaction between dodecanol and 1, 2-epoxybutane [J]. China Surfactant Detergent & Cosmetics, 2025, 55(8): 998-1005. |
[2] | Linlin Zhao, Yutian Jiao, Li Zhao, Ce Wang, Baocai Xu. Synthesis and self-assembly of an azobenzene-containing dipeptide surfactant [J]. China Surfactant Detergent & Cosmetics, 2024, 54(5): 507-513. |
[3] | Dou Xin. Analysis of supramolecular structure diversity of gel soft matter system [J]. China Surfactant Detergent & Cosmetics, 2022, 52(9): 945-950. |
[4] | Hu Chenyu,Qu Wenjie,Guo Xueping,Xu Guixin,Zou Songyan,Wang Jing. Study on multifunctional hair care efficacy of sodium hyaluronate [J]. China Surfactant Detergent & Cosmetics, 2022, 52(4): 370-375. |
[5] | LI Jun,ZHANG Xing-fang,ZHANG Cheng-wei,XU Na. Mesoscale Brownian dynamics simulation on the self-assembly behaviors of rodlike micelles of CTAC/NaSal surfactants [J]. China Surfactant Detergent & Cosmetics, 2020, 50(4): 213-219. |
[6] | SUN Na,ZHENG Li-qiang,SUN Ji-chao. Self-assembly of surfactants regulated by weak interactions(IV)Application in ionic conduction [J]. China Surfactant Detergent & Cosmetics, 2019, 49(4): 214-219. |
[7] | Yang YU,Li-qiang ZHENG,Ji-chao SUN. Self-assembly of surfactants controlled by weak interactions(Ⅲ) Responsive surfactants [J]. China Surfactant Detergent & Cosmetics, 2019, 49(3): 141-149. |
[8] | Guan-nan SUN,Li-qiang ZHENG,Ji-chao SUN. Self-assembly of surfactants controlled by weak interactions(II)The structure and design of surfactants [J]. China Surfactant Detergent & Cosmetics, 2019, 49(2): 70-75. |
[9] | DAI Lu-xun,LIANG Shao-bin,CHEN Yao,XIE Xiang-li,LI Cun-jun,WANG Lin-jiang. Exfoliation of layered double hydroxide and montmorillonite and their self-assembly [J]. China Surfactant Detergent & Cosmetics, 2018, 48(7): 392-398. |
[10] | CHEN Yu-jia, LIU Jia-xi, ZHU Qian-qian, HU Song-qing, SUN Shuang-qing, WANG Xiu-min. Effects of sodium salicylate on the self-assembly behavior of DTAB/PAM mixed system [J]. China Surfactant Detergent & Cosmetics, 2018, 48(6): 308-313. |
[11] | REN Shu-jing, ZHENG Li-qiang, SUN Ji-chao. Self-assembly of surfactants regulated by weak interaction (Ⅰ)The classification of weak interactions [J]. China Surfactant Detergent & Cosmetics, 2018, 48(11): 611-616. |
[12] | HAO Shan-shan, ZHAI Qiao-ya, ZHAO Li, XU Bao-cai. Self-assembly and photo regulation of a supra-amphiphile based on host-guest interaction [J]. China Surfactant Detergent & Cosmetics, 2017, 47(1): 1-6. |
[13] | HAO Shan-shan,ZHAO Li,XU Bao-cai. Performance and applications of surfactants (ⅩⅩⅦ) [J]. China Surfactant Detergent & Cosmetics, 2016, 46(3): 129-135. |
[14] | KANG Lin-xia, ZHANG Jian, QIN Jie, ZHANG Sheng. Stability of alkaline protease in liquid laundry detergent [J]. China Surfactant Detergent & Cosmetics, 2014, 44(3): 139-142. |
[15] | LIU Rui, WANG Xiang-mei, HU Ya-peng. Progress in field of research work with respect to vesicles of bola-form surfactant self-assembly [J]. China Surfactant Detergent & Cosmetics, 2014, 44(10): 584-589. |
|