Citation: ZHANG Ming-Rui, HAN Xiao-Jun. Construction of Phospholipid Analogue Vesicle and Study of Its Artificial Cell Functions[J]. Chinese Journal of Analytical Chemistry, ;2023, 51(5): 884-891. doi: 10.19756/j.issn.0253-3820.221630 shu

Construction of Phospholipid Analogue Vesicle and Study of Its Artificial Cell Functions

ZHANG Ming-Rui ,
HAN Xiao-Jun ^,

State Key Laboratory of Urban Water Resource, Environment School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China

Corresponding author: HAN Xiao-Jun, hanxiaojun@hit.edu.cn
Received Date: 21 December 2022
Revised Date: 15 February 2023

Fund Project: Supported by the National Natural Science Foundation of China (Nos. 21929401, 22174031, 22111540252), the Natural Science Foundation of Heilongjiang Province (No. ZD2022B001) and the Heilongjiang Touyan Team Project (No. HITTY- 20190034).

Phospholipids, as natural components of cell membrane systems, are widely used to construct artificial cells. However, the synthesis and purification of natural phospholipids are complicated. Chemically synthesized phospholipid analogues are structurally similar to natural phospholipids, so they can be used to mimic phospholipids to construct artificial cells. In this work, a novel phospholipid analogue 2 was synthesized by the azide-alkyne click reaction, which could form vesicles. The membrane was fluid, which indicated the vesicles could mimic cell membranes. The vesicles were capable to encapsulate small molecule of calcein and macromolecule of rhodamine B isothiocyanate-dextran. Melittins were embedded in the membrane to form pores, which allowed the transmembrane transport of calcein. When the concentrations of melittin were 1.0, 2.0, 3.0, 4.0 and 5.0 μg/mL, the transmembrane diffusion coefficients of calcein were 0.33, 0.46, 0.70, 1.37 and 1.91 μm²/s, respectively. Glucose oxidase and horse radish peroxidase were encapsulated into vesicles to fabricate artificial cells, which mimicked the cell metabolism function. Amplex red was converted into resorufin via enzyme cascade reactions. The synthesized phospholipid analogues could provide new building blocks for artificial cells.
- Click chemistry,
- Artificial cells,
- Calcein,
- Melittin,
- Enzyme cascade reaction
1. [1]
  WANG H, ZHU X, TSARKOVA L, PICH A, MÖLLER M. ACS Nano, 2011, 5(5):3937-3942.
2. [2]
  LI M, HARBRON R L, WEAVER J V M, BINKS B P, MANN S. Nat. Chem., 2013, 5(6):529-536.
3. [3]
  LI M, HUANG X, MANN S. Small, 2014, 10(16):3291-3298.
4. [4]
  MORIGAKI K, WALDE P. Curr. Opin. Colloid Interface Sci., 2007, 12(2):75-80.
5. [5]
  MANSY S S, SZOSTAK J W. Proc. Natl. Acad. Sci. U. S. A., 2008, 105(36):13351-13355.
6. [6]
  HANCZYC M M, FUJIKAWA S M, SZOSTAK J W. Science, 2003, 302(5645):618-622.
7. [7]
  DISCHER D E, AHMED F. Annu. Rev. Biomed. Eng., 2006, 8(1):323-341.
8. [8]
  MAI Y, EISENBERG A. Chem. Soc. Rev., 2012, 41(18):5969-5985.
9. [9]
  DISCHER B M, WON Y Y, EGE D S, LEE J C M, BATES F S, DISCHER D E, HAMMER D A. Science, 1999, 284(5417):1143-1146.
10. [10]
  GHELLAB S E, LI Q C, FUHS T, BI H M, HAN X J. Colloids Surf., B, 2017, 160:697-703.
11. [11]
  LI Q C, WANG X J, MA S H, ZHANG Y, HAN X J. Colloids Surf., B, 2016, 147:368-375.
12. [12]
  ZHU C, LI Q, DONG M, HAN X. Anal. Chem., 2018, 90(24):14363-14367.
13. [13]
  LI C, LI Q, WANG Z, HAN X. Anal. Chem., 2020, 92(8):6060-6064.
14. [14]
  WANG X, DU H, WANG Z, MU W, HAN X J. Adv. Mater., 2021, 33(6):e2002635.
15. [15]
  ZHANG Y M, ROCK C O. Nat. Rev. Microbiol., 2008, 6(3):222-233.
16. [16]
  YAO J, ROCK C O. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids, 2013, 1831(3):495-502.
17. [17]
  BREA R J, COLE C M, DEVARAJ N K. Angew. Chem. Int. Ed., 2014, 53(51):14102-14105.
18. [18]
  BUDIN I, DEVARAJ N K. J. Am. Chem. Soc., 2012, 134(2):751-753.
19. [19]
  BHATTACHARYA A, BREA R J, NIEDERHOLTMEYER H, DEVARAJ N K. Nat. Commun., 2019, 10(1):300.
20. [20]
  PODOLSKY K A, DEVARAJ N K. Nat. Rev. Chem., 2021, 5(10):676-694.
21. [21]
  KONETSKI D, BARANEK A, MAVILA S, ZHANG X, BOWMAN C N. Soft Matter, 2018, 14(37):7645-7652.
22. [22]
  TAKAKURA K, TOYOTA T, SUGAWARA T. J. Am. Chem. Soc., 2003, 125(27):8134-8140.
23. [23]
  MATSUO M, HIRATA Y, KURIHARA K, TOYOTA T, MIURA T, SUZUKI K, SUGAWARA T. Micromachines, 2020, 11(6):606.
24. [24]
  BREA R J, COLE C M, LYDA B R, YE L, PROSSER R S, SUNAHARA R K, DEVARAJ N K. J. Am. Chem. Soc., 2017, 139(10):3607-3610.
25. [25]
  AHOU A, MARTIGNAGO D, ALABDALLAH O, TAVAZZA R, STANO P, MACONE A, PIVATO M, MASI A, RAMBLA J L, VERA-SIRERA F, ANGELINI R, FEDERICO R, TAVLADORAKI P. J. Exp. Bot., 2014, 65(6):1585-1603.
26. [26]
  ZHANG Y, CHEN Y, YANG X, HE X, LI M, LIU S, WANG K, LIU J, MANN S. J. Am. Chem. Soc., 2021, 143(7):2866- 2874.
27. [27]
  ELBAUM-GARFINKLE S, KIM Y, SZCZEPANIAK K, CHEN C C H, ECKMANN C R, MYONG S, BRANGWYNNE C P. Proc. Natl. Acad. Sci. U. S. A., 2015, 112(23):7189-7194.
28. [28]
  DENG N N, YELLESWARAPU M, HUCK W T S. J. Am. Chem. Soc., 2016, 138(24):7584-7591.
29. [29]
  SONG L, HOBAUGH M R, SHUSTAK C, CHELEY S, BAYLEY H, GOUAUX J E. Science, 1996, 274(5294):1859-1865.
30. [30]
  NOIREAUX V, LIBCHABER A. Proc. Natl. Acad. Sci. U. S. A., 2015, 101(51):17669-17674.
31. [31]
  LI Q, HAN X. iScience, 2018, 8:138-147.
32. [32]
  LI S, WANG X, MU W, HAN X. Anal. Chem., 2019, 91(10):6859-6864.
33. [33]
  WANG X, TIAN L, DU H, LI M, MU W, DRINKWATER B W, HAN X, MANN S. Chem. Sci., 2019, 10(41):9446-9453.
34. [34]
  YANG B, LI S, MU W, WANG Z, HAN X. Small, 2022:e2201305.
1. [1]
  Shuyu Liu , Xiaomin Sun , Bohan Song , Gaofeng Zeng , Bingbing Du , Chongshen Guo , Cong Wang , Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113
2. [2]
  Lilong Gao , Yuhao Zhai , Dongdong Zhang , Linjun Huang , Kunyan Sui . Exploration of Thiol-Ene Click Polymerization in Polymer Chemistry Experiment Teaching. University Chemistry, 2025, 40(4): 87-93. doi: 10.12461/PKU.DXHX202405143
3. [3]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
4. [4]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
5. [5]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
6. [6]
  Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
7. [7]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
8. [8]
  Weicheng Feng , Jingcheng Yu , Yilan Yang , Yige Guo , Geng Zou , Xiaoju Liu , Zhou Chen , Kun Dong , Yuefeng Song , Guoxiong Wang , Xinhe Bao . Regulating the High Entropy Component of Double Perovskite for High-Temperature Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(6): 2306013-0. doi: 10.3866/PKU.WHXB202306013
9. [9]
  Yuyang Xu , Ruying Yang , Yanzhe Zhang , Yandong Liu , Keyi Li , Zehui Wei . Research Progress of Aflatoxins Removal by Modern Optical Methods. University Chemistry, 2024, 39(11): 174-181. doi: 10.12461/PKU.DXHX202402064
10. [10]
  Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235
11. [11]
  Yang Li , Jiachen Li , Daidi Fan . 二硫化钼纳米片的制备及其纳米酶性能探究——介绍一个大学化学综合实验. University Chemistry, 2025, 40(8): 233-240. doi: 10.12461/PKU.DXHX202410016
12. [12]
  Cun WANG , Shaohan XU , Yuqian ZHANG , Yaoyao ZHANG , Tao GONG , Rong WEN , Yuhang LIAO , Yanrong REN . Terbium complex electrochemiluminescent emitters: Synthesis and application in the detection of epinephrine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1351-1360. doi: 10.11862/CJIC.20240427
13. [13]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
14. [14]
  Zongyuan Chen , ChunSheng Shi , Yiwen Li , Ganlin Zu , Qiang Jin , Haishan Wang , Fujun Wang , Dekun Yan , Zhijun Guo , Wangsuo Wu . Measurement of Uranium Isotopes in Environmental Water Samples by Alpha-Spectroscopy: Design of an Undergraduate Radiochemistry Experiment. University Chemistry, 2025, 40(4): 353-358. doi: 10.12461/PKU.DXHX202406103
15. [15]
  Huicheng Yang , Qianhong Sun . Practice of Ideological and Political Education in Organic Chemistry Laboratory Courses under the OBE Framework: A Case Study of Berberine Extraction. University Chemistry, 2025, 40(5): 276-282. doi: 10.12461/PKU.DXHX202410091
16. [16]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
17. [17]
  Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016
18. [18]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
19. [19]
  Yang Lv , Yingping Jia , Yanhua Li , Hexiang Zhong , Xinping Wang . Integrating the Ideological Elements with the “Chemical Reaction Heat” Teaching. University Chemistry, 2024, 39(11): 44-51. doi: 10.12461/PKU.DXHX202402059
20. [20]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(4030)
HTML views(126)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142