Citation: LIU Ren-Yong, ZHANG Zhong-Ping. Click-Functionalized Fluorescent Nanoprobes with Folate Receptor-Targeting Ability for Cancer Cell Imaging[J]. Chinese Journal of Analytical Chemistry, ;2017, 45(12): 1956-1962. doi: 10.11895/j.issn.0253-3820.171125 shu

Click-Functionalized Fluorescent Nanoprobes with Folate Receptor-Targeting Ability for Cancer Cell Imaging

LIU Ren-Yong ^1,2 ,
ZHANG Zhong-Ping ^1,3,,

1.
Institute of Intelligent Machines, Chinese Academy of Sciences, Hefei 230031, China
2.
Department of Chemistry, University of Science and Technology of China, Hefei 230026, China
3.
School of Chemistry and Chemical Engineering, Anhui University, Hefei 230601, China

Corresponding author: ZHANG Zhong-Ping, zpzhang@iim.ac.cn
Received Date: 24 July 2017
Accepted Date: 22 August 2017

Fund Project: This work was supported by the National Natural Science Foundation of China (Nos. 61205152, 21335006)the National Natural Science Foundation of China 61205152the National Natural Science Foundation of China 21335006

Figures(6)

Folate receptor (FR)-targeted fluorescent nanoprobes (RSiNPs-Folate) were constructed by modifying Rubpy-doped silica nanoparticles (RSiNPs) with folic acid (FA) based on click chemistry coupling method, which was successfully used for cancer cell imaging. Firstly, RSiNPs were prepared by Stöber method and modified with azide groups through the hydrolysis of silane coupling agents (Az-PTES), then propargyl folate were conjugated onto the nanoparticle surfaces via click reaction. It was demonstrated that the FA-functionalized nanoprobes were successfully prepared by monitoring the characteristic peak of the azide group at 2105 cm^-1 before and after coupling. In the condition of physiological pH, the nanoprobes exhibited strong red emission at 601 nm when excited at the 458 nm excitation wavelength. The cell imaging results showed that RSiNPs-Folate could effectively target FR-positive HeLa cells, while no obvious fluorescence was observed for FR-negative A549 cells. The receptor-mediated imaging mechanism was confirmed by free FA competition experiments. More importantly, HeLa cells could be selectively recognized and imaged in the mixing cell system. Compared with the carbodiimide conjugation protocols, the click-functionalized nanoprobes had many advantages such as simple synthesis procedures, mild reaction conditions and high yields, which could be potentially used for fluorescent labeling and imaging of different cancer cells.
- Fluorescent silica nanoprobes,
- Click chemistry,
- Surface functionalization,
- Folate receptors,
- Cancer cells,
- Targeted imaging
1. [1]
  Coney L R, Tomassetti A, Carayannopoulos L, Frasca V, Kamen B A, Colnaghi M I, Zurawski V R Jr. Cancer Res., 1991, 51(22):6125-6132
2. [2]
  Masafumi T, Naomi T, Takahiro M. Chem. Lett., 2017, 46(7):944-946 doi: 10.1246/cl.170198
3. [3]
  Wu X X, Luo L Q, Yang S G, Ma, X H, Li Y L, Dong C, Tian Y C, Zhang L E, Shen Z Y, Wu A G. ACS Appl. Mater. Interfaces, 2015, 7(18):9965-9971 doi: 10.1021/acsami.5b02276
4. [4]
  Oseledchyk A, Andreou C, Wall M A, Kircher M F. ACS Nano, 2017, 11(2):1488-1497 doi: 10.1021/acsnano.6b06796
5. [5]
  Parker N, Turk M J, Westrick E, Lewis J D, Low P S, Leamon C P. Anal. Biochem., 2005, 338(2):284-293 doi: 10.1016/j.ab.2004.12.026
6. [6]
  Ross T L, Honer M, Müller C, Groehn V, Schibli R, Ametamey S M. J. Nucl. Med., 2010, 51(11):1756-1762 doi: 10.2967/jnumed.110.079756
7. [7]
  Lei K P, Sun M T, Du L B, Zhang X J, Yu H, Wang S H, Hayat T W, Alsaedi A. Talanta, 2017, 170:314-321 doi: 10.1016/j.talanta.2017.04.004
8. [8]
  Xu S Y, Huang S, He Q, Wang L Y. TrAC-Trends Anal. Chem., 2015, 66:72-79 doi: 10.1016/j.trac.2014.11.014
9. [9]
  LIAO Xiao-Yan, LIANG Shu-Cai, LIU Yu-Ping, ZHANG Jing-Ya, YAN Guo-Ping. Chinese J. Anal. Chem., 2017, 45(5):747-753. doi: 10.11895/j.issn.0253-3820.160757
10. [10]
  Feng D, Song Y C, Shi W, Li X H, Ma H M. Anal. Chem., 2013, 85(13):6530-6535 doi: 10.1021/ac401377n
11. [11]
  Zhou S, Huo D Q, Hou C J, Yang M, Fa H B, Xia C, Chen M. Anal. Methods, 2015, 7(22):9649-9654 doi: 10.1039/C5AY01760B
12. [12]
  Li H C, Cheng Y Q, Liu Y, Chen B. Talanta, 2016, 158:118-124 doi: 10.1016/j.talanta.2016.05.038
13. [13]
  Liu Q L, Xu S H, Niu C X, Li M F, He D C, Lu Z L, Ma L, Na N, Huang F, Jiang H, Ouyang J. Biosens. Bioelectron., 2015, 64:119-125 doi: 10.1016/j.bios.2014.08.052
14. [14]
  Yang X J, Xiao Q Q, Niu C X, Jin N, Ouyang J, Xiao X Y, He D C. J. Mater. Chem. B, 2013, 1(21):2757-2763 doi: 10.1039/c3tb00575e
15. [15]
  Wang X H, Morales A R, Urakami T, Zhang L F, Bondar M V, Komatsu M, Belfield K D. Bioconjugate Chem., 2011, 22(7):1438-1450 doi: 10.1021/bc2002506
16. [16]
  Peng J F, Wang K M, Tan W H, He X X, He C M, Wu P, Liu F. Talanta, 2007, 71(2):833-840 doi: 10.1016/j.talanta.2006.05.064
17. [17]
  CHEN Min-Yan, CHEN Ze-Zhong, WANG Wei, ZHU Lian, TANG Hong-Wu, PANG Dai-Wen. Chinese J. Anal. Chem., 2014, 42(3):326-331.
18. [18]
  Gole A, Murphy C J. Langmuir, 2008, 24(1):266-272 doi: 10.1021/la7026303
19. [19]
  AN Wei, ZHANG Hua-Cheng, SUN Tao, LI Xiang-Jun, HAO Ai-You. Chinese J. Org. Chem., 2011, 31(3):275-285.
20. [20]
  Schieber C, Bestetti A, Lim J P, Ryan A D, Nguyen T L, Eldridge R, White A R, Gleeson P A, Donnelly P S, Williams S J, Mulvaney P. Angew. Chem. Int. Ed., 2012, 51(42):10523-10527 doi: 10.1002/anie.201202876
21. [21]
  White M A, Johnson J A, Koberstein J T, Turro N J. J. Am. Chem. Soc., 2006, 128(35):11356-11357 doi: 10.1021/ja064041s
22. [22]
  Zhang Y F, Li B X, Xu C L. Analyst, 2010, 135(7):1579-1584 doi: 10.1039/c0an00056f
23. [23]
  Zhou Y, Wang S X, Zhang K, Jiang X Y. Angew. Chem. Int. Ed., 2008, 47(39):7454-7456 doi: 10.1002/anie.v47:39
24. [24]
  Hayashi K, Moriya M, Sakamoto W, Yogo T. Chem. Mater., 2009, 21(7):1318-1325 doi: 10.1021/cm803113e
25. [25]
  De P, Gondi S R, Sumerlin B S. Biomacromolecules, 2008, 9(3):1064-1070 doi: 10.1021/bm701255v
26. [26]
  Santra S, Kaittanis C, Grimm J, Perez J M. Small, 2009, 5(16):1862-1868 doi: 10.1002/smll.v5:16
27. [27]
  Ortega-Muñoz M, Lopez-Jaramillo J, Hernandez-Mateo F, Santoyo-Gonzaleza F. Adv. Synth. Catal., 2006, 348(16-17):2410-2420 doi: 10.1002/(ISSN)1615-4169
28. [28]
  Rossi L M, Shi L F, Quan F H, Rosenzweig Z. Langmuir, 2005, 21(10):4277-4280 doi: 10.1021/la0504098
29. [29]
  Santra S, Zhang P, Wang K M, Tapec R, Tan W H. Anal. Chem., 2001, 73(20):4988-4993 doi: 10.1021/ac010406+
30. [30]
  Ranjan R, Brittain W J. Macromol. Rapid Commun., 2008, 29(12-13):1104-1110
1. [1]
  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
2. [2]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
3. [3]
  Ruifeng CHEN , Chao XU , Jianting JIANG , Tianshe YANG . Gold nanorod/zinc oxide/mesoporous silica nanoplatform: A triple-modal platform for synergistic anticancer therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2272-2282. doi: 10.11862/CJIC.20250117
4. [4]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
5. [5]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
6. [6]
  Tiejin Chen , Xiaokuang Xue , Jian Li , Minhui Cui , Yongliang Hao , Mianqi Xue , Haihua Xiao , Jiechao Ge , Pengfei Wang . Membrane-anchoring nanoengineered carbon dots as a pyroptosis amplifier for robust tumor photodynamic-immunotherapy. Acta Physico-Chimica Sinica, 2025, 41(10): 100113-0. doi: 10.1016/j.actphy.2025.100113
7. [7]
  Xue Wu , Yupeng Liu , Bingzhe Wang , Lingyun Li , Zhenjian Li , Qingcheng Wang , Quansheng Cheng , Guichuan Xing , Songnan Qu . Rationally assembling different surface functionalized carbon dots for enhanced near-infrared tumor photothermal therapy. Acta Physico-Chimica Sinica, 2025, 41(9): 100109-0. doi: 10.1016/j.actphy.2025.100109
8. [8]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
9. [9]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
10. [10]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
11. [11]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
12. [12]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . Core cyanation of benzo[a]phenazine acceptor enables 19.04% binary organic solar cells with green solvent compatibility. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
13. [13]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
14. [14]
  Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO^- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
15. [15]
  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
16. [16]
  Shiyang He , Dandan Chu , Zhixin Pang , Yuhang Du , Jiayi Wang , Yuhong Chen , Yumeng Su , Jianhua Qin , Xiangrong Pan , Zhan Zhou , Jingguo Li , Lufang Ma , Chaoliang Tan . Pt Single-Atom-Functionalized 2D Al-TCPP MOF Nanosheets for Enhanced Photodynamic Antimicrobial Therapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-0. doi: 10.1016/j.actphy.2025.100046
17. [17]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
18. [18]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
19. [19]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
20. [20]
  Qiuyu Ming , Huijun Jiang , Zhihao Zhang . A Sightseeing Tour of Folic Acid Processing Plant. University Chemistry, 2024, 39(9): 11-15. doi: 10.12461/PKU.DXHX202404092

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(991)
HTML views(150)

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