Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles
- Corresponding author: Bo Song, songbo@suda.edu.cn
Citation: Xiao-Cheng Wang, Shi-Xin Zhou, Lan Ding, Yu-Han Zhao, Shen-Xi Min, Bin Dong, Bo Song. Controllable Emission via Tuning the Size of Fluorescent Nano-probes Formed by Polymeric Amphiphiles[J]. Chinese Journal of Polymer Science, ;2019, 37(8): 767-773. doi: 10.1007/s10118-019-2256-6
Jin, W. J.; Costa-Fernández, J. M.; Pereiro, R.; Sanz-Medel, A. Surface-modified CdSe quantum dots as luminescent probes for cyanide determination. Anal. Chim. Acta. 2004, 522, 1-8.
doi: 10.1016/j.aca.2004.06.057
Gao, X.; Yang, L.; Petros, J. A.; Marshall, F. F.; Simons, J. W.; Nie, S. In vivo molecular and cellular imaging with quantum dots. Curr. Opin. Biotechnol. 2005, 16, 63-72.
doi: 10.1016/j.copbio.2004.11.003
Zrazhevskiy, P.; Sena, M.; Gao, X. Designing multifunctional quantum dots for bioimaging, detection, and drug delivery. Chem. Soc. Rev. 2010, 39, 4326-4354.
doi: 10.1039/b915139g
Dubertret, B.; Skourides, P.; Norris, D. J.; Noireaux, V.; Brivanlou, A. H.; Libchaber, A. In vivo imaging of quantum dots encapsulated in phospholipid micelles. Science 2002, 298, 1759.
doi: 10.1126/science.1077194
Fernández-Suárez, M.; Ting, A. Y. Fluorescent probes for super-resolution imaging in living cells. Nat. Rev. Mol. Cell Biol. 2008, 9, 929-943.
doi: 10.1038/nrm2531
Zhang, J.; Campbell, R. E.; Ting, A. Y.; Tsien, R. Y. Creating new fluorescent probes for cell biology. Nat. Rev. Mol. Cell Biol. 2002, 3, 906-918.
doi: 10.1038/nrm976
Iino, R.; Koyama, I.; Kusumi, A. Single molecule imaging of green fluorescent proteins in living cells: E-cadherin forms oligomers on the free cell surface. Biophys. J. 2001, 80, 2667-2677.
doi: 10.1016/S0006-3495(01)76236-4
Nagai, T.; Ibata, K.; Park, E. S.; Kubota, M.; Mikoshiba, K.; Miyawaki, A. A variant of yellow fluorescent protein with fast and efficient maturation for cell-biological applications. Nat. Biotechnol. 2002, 20, 87-90.
doi: 10.1038/nbt0102-87
Yang, Z.; Cao, J.; He, Y.; Yang, J. H.; Kim, T.; Peng, X.; Kim, J. S. Macro-/micro-environment-sensitive chemosensing and biological imaging. Chem. Soc. Rev. 2014, 43, 4563-4601.
doi: 10.1039/C4CS00051J
Wu, C.; Hansen, S. J.; Hou, Q.; Yu, J.; Zeigler, M.; Jin, Y.; Burnham, D. R.; McNeill, J. D.; Olson, J. M.; Chiu, D. T. Design of highly emissive polymer dot bioconjugates for in vivo tumor targeting. Angew. Chem. Int. Ed. 2011, 123, 3492-3496.
doi: 10.1002/ange.201007461
Tao, Z.; Hong, G.; Shinji, C.; Chen, C.; Diao, S.; Antaris, A. L.; Zhang, B.; Zou, Y.; Dai, H. Biological imaging using nanoparticles of small organic molecules with fluorescence emission at wavelengths longer than 1000 nm. Angew. Chem. Int. Ed. 2013, 125, 13240-13244.
doi: 10.1002/ange.201307346
Ding, D.; Goh, C. C.; Feng, G.; Zhao, Z.; Liu, J.; Liu, R.; Tomczak, N.; Geng, J.; Tang, B. Z.; Ng, L. G., Liu, B. Ultrabright organic dots with aggregation-induced emission characteristics for real-time two-photon intravital vasculature imaging. Adv. Mater. 2013, 25, 6083-6088.
doi: 10.1002/adma.201301938
Liu, L. J.; Liu, W.; Ji, G.; Wu, Z. Y.; Xu, B.; Qian, J.; Tian, W. J. NIR emission nanoparticles based on FRET composed of AIE luminogens and NIR dyes for two-photon fluorescence imaging. Chinese J. Polym. Sci. 2019, 37, 401-408.
doi: 10.1007/s10118-019-2206-3
Zhang, X.; Zhang, X.; Wang, S.; Liu, M.; Tao, L.; Wei, Y. Surfactant modification of aggregation-induced emission material as biocompatible nanoparticles: Facile preparation and cell imaging. Nanoscale. 2013, 5, 147-150.
doi: 10.1039/C2NR32698A
Wu, X.; Sun, S.; Wang, Y.; Zhu, J.; Jiang, K.; Leng, Y.; Shu, Q.; Lin, H. A fluorescent carbon-dots-based mitochondria-targetable nanoprobe for peroxynitrite sensing in living cells. Biosens. Bioelectron. 2017, 90, 501-507.
doi: 10.1016/j.bios.2016.10.060
Tang, L.; Wu, T.; Tang, Z. W.; Xiao, J. Y.; Zhuo, R. X.; Shi, B.; Liu, C. J. Water-soluble photoluminescent fullerene capped mesoporous silica for pH-responsive drug delivery and bioimaging. Nanotechnology. 2016, 27, 315104.
doi: 10.1088/0957-4484/27/31/315104
Larson, D. R.; Zipfel, W. R.; Williams, R. M.; Clark, S. W.; Bruchez, M. P.; Wise, F. W.; Webb, W. W. Water-soluble quantum dots for multiphoton fluorescence imaging in vivo. Science. 2003, 300, 1434-1436.
doi: 10.1126/science.1083780
Michalet, X.; Pinaud, F. F.; Bentolila, L. A.; Tsay, J. M.; Doose, S.; Li, J. J.; Sundaresan, G.; Wu, A. M.; Gambhir, S. S.; Weiss, S. Quantum dots for live cells, in vivo imaging, and diagnostics. Science. 2005, 307, 538.
doi: 10.1126/science.1104274
Li, K.; Liu, B. Polymer-encapsulated organic nanoparticles for fluorescence and photoacoustic imaging. Chem. Soc. Rev. 2014, 43, 6570-6597.
doi: 10.1039/C4CS00014E
Feng, G.; Mao, D.; Liu, J.; Goh, C. C.; Ng, L. G.; Kong, D.; Tang, B. Z.; Liu, B. Polymeric nanorods with aggregation-induced emission characteristics for enhanced cancer targeting and imaging. Nanoscale. 2018, 10, 5869-5874.
doi: 10.1039/C7NR09196F
Zhang, X.; Wang, K.; Liu, M.; Zhang, X.; Tao, L.; Chen, Y.; Wei, Y. Polymeric AIE-based nanoprobes for biomedical applications: recent advances and perspectives. Nanoscale. 2015, 7, 11486-11508.
doi: 10.1039/C5NR01444A
Zhan, R.; Pan, Y.; Manghnani, P. N.; Liu, B. AIE Polymers: Synthesis, properties, and biological applications. Macromol. Biosci. 2017, 17, 1600433.
doi: 10.1002/mabi.v17.5
Ma, C.; Xie, G.; Zhang, X.; Yang, L.; Li, Y.; Liu, H.; Wang, K.; Wei, Y. Biocompatible fluorescent polymers from PEGylation of an aggregation-induced emission dye. Dyes Pigments 2017, 139, 672-680.
doi: 10.1016/j.dyepig.2016.12.070
Zhou, D.; Zhang, G.; Yu, Q.; Gan, Z. Folic acid modified polymeric micelles for intravesical instilled chemotherapy. Chinese J. Polym. Sci. 2018, 36, 479-487.
doi: 10.1007/s10118-018-2009-y
He, J.; Chen, H.; Guo, Y.; Wang, L.; Zhu, L.; Karahan, H. E.; Chen, Y. Polycondensation of a perylene bisimide derivative and l-malic acid as water-soluble conjugates for fluorescent labeling of live mammalian cells. Polymers. 2018, 10, 559.
doi: 10.3390/polym10050559
Wang, K.; Zhang, X.; Zhang, X.; Ma, C.; Li, Z.; Huang, Z.; Zhang, Q.; Wei, Y. Preparation of emissive glucose-containing polymer nanoparticles and their cell imaging applications. Polym. Chem. 2015, 6, 4455-4461.
doi: 10.1039/C5PY00378D
Huang, Z.; Zhang, X.; Zhang, X.; Wang, S.; Yang, B.; Wang, K.; Yuan, J.; Tao, L.; Wei, Y. Synthesis of amphiphilic fluorescent copolymers with smart pH sensitivity via RAFT polymerization and their application in cell imaging. Polym. Bull. 2017, 74, 4525-4536.
doi: 10.1007/s00289-017-1969-3
Hua, Z.; Wilks, T. R.; Keogh, R.; Herwig, G.; Stavros, V. G.; O’Reilly, R. K. Entrapment and rigidification of adenine by a photo-cross-linked thymine network leads to fluorescent polymer nanoparticles. Chem. Mater. 2018, 30, 1408-1416.
doi: 10.1021/acs.chemmater.7b05206
Yang, H. M.; Park, C. W.; Park, S.; Kim, J. D. Cross-linked magnetic nanoparticles with a biocompatible amide bond for cancer-targeted dual optical/magnetic resonance imaging. Colloids Surf., B 2018, 161, 183-191.
doi: 10.1016/j.colsurfb.2017.10.049
Zhang, X.; Zhang, X.; Yang, B.; Liu, M.; Liu, W.; Chen, Y.; Wei, Y. Fabrication of aggregation induced emission dye-based fluorescent organic nanoparticles via emulsion polymerization and their cell imaging applications. Polym. Chem. 2014, 5, 399-404.
doi: 10.1039/C3PY00984J
Shen, X.; Shi, Y.; Peng, B.; Li, K.; Xiang, J.; Zhang, G.; Liu, Z.; Chen, Y.; Zhang, D. Fluorescent polymeric micelles with tetraphenylethylene moieties and their application for the selective detection of glucose. Macromol. Biosci. 2012, 12, 1583-1590.
doi: 10.1002/mabi.v12.11
Lim, C. K.; Kim, S.; Kwon, I. C.; Ahn, C. H.; Park, S. Y. Dye-condensed biopolymeric hybrids: Chromophoric aggregation and self-assembly toward fluorescent bionanoparticles for near infrared bioimaging. Chem. Mater. 2009, 21, 5819-5825.
doi: 10.1021/cm902379x
Lu, H.; Su, F.; Mei, Q.; Zhou, X.; Tian, Y.; Tian, W.; Johnson, R. H.; Meldrum, D. R. A series of poly[N-(2-hydroxypropyl)methacrylamide] copolymers with anthracene-derived fluorophores showing aggregation-induced emission properties for bioimaging. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 890-899.
doi: 10.1002/pola.v50.5
Zhang, X.; Zhang, X.; Yang, B.; Hui, J.; Liu, M.; Chi, Z.; Liu, S.; Xu, J.; Wei, Y. Facile preparation and cell imaging applications of fluorescent organic nanoparticles that combine AIE dye and ring-opening polymerization. Polym. Chem. 2014, 5, 318-322.
doi: 10.1039/C3PY01143G
Zhang, X.; Zhang, X.; Yang, B.; Hui, J.; Liu, M.; Liu, W.; Chen, Y.; Wei, Y. PEGylation and cell imaging applications of AIE based fluorescent organic nanoparticles via ring-opening reaction. Polym. Chem. 2014, 5, 689-693.
doi: 10.1039/C3PY01272G
Chithrani, B. D.; Chan, W. C. W. Elucidating the mechanism of cellular uptake and removal of protein-coated gold nanoparticles of different sizes and shapes. Nano Lett. 2007, 7, 1542-1550.
doi: 10.1021/nl070363y
Barua, S.; Yoo, J. W.; Kolhar, P.; Wakankar, A.; Gokarn, Y. R.; Mitragotri, S. Particle shape enhances specificity of antibody-displaying nanoparticles. Proc. Nat. Acad. Sci. 2013, 110, 3270.
doi: 10.1073/pnas.1216893110
Salata, O. V. Applications of nanoparticles in biology and medicine. J. Nanobiotechnology. 2004, 2, 3.
doi: 10.1186/1477-3155-2-3
Albanese, A.; Tang, P. S.; Chan, W. C. W. The effect of nanoparticle size, shape, and surface chemistry on biological systems. Annu. Rev. Biomed. Eng. 2012, 14, 1-16.
doi: 10.1146/annurev-bioeng-071811-150124
Ding, L.; Zhou, S.; Li, D.; Wu, C.; Xing, Y.; Song, B. A facile method to incorporate tetraphenylethylene into polymeric amphiphiles: High emissive nanoparticles for cell-imaging. Dyes Pigments 2019, 160, 711-716.
doi: 10.1016/j.dyepig.2018.08.063
Gauthier, M. A.; Gibson, M. I.; Klok, H. A. Synthesis of functional polymers by post-polymerization modification. Angew. Chem. Int. Ed. 2009, 48, 48-58.
doi: 10.1002/anie.200801951
Günay, K. A.; Theato, P.; Klok, H. A. Standing on the shoulders of Hermann Staudinger: Post-polymerization modification from past to present. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 1-28.
doi: 10.1002/pola.26333
Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Aggregation-induced emission. Chem. Soc. Rev. 2011, 40, 5361-5388.
doi: 10.1039/c1cs15113d
Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Aggregation-induced emission: Together we shine, united we soar! Chem. Rev. 2015, 115, 11718-11940.
doi: 10.1021/acs.chemrev.5b00263
Zhao, Y.; Wu, Y.; Yan, G.; Zhang, K. Aggregation-induced emission block copolymers based on ring-opening metathesis polymerization. RSC Adv. 2014, 4, 51194-51200.
doi: 10.1039/C4RA08191A
Chaochao Wei , Ru Wang , Zhongkai Wu , Qiyue Luo , Ziling Jiang , Liang Ming , Jie Yang , Liping Wang , Chuang Yu . Revealing the size effect of FeS2 on solid-state battery performances at different operating temperatures. Chinese Chemical Letters, 2024, 35(6): 108717-. doi: 10.1016/j.cclet.2023.108717
Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
Jia-Mei Qin , Xue Li , Wei Lang , Fu-Hao Zhang , Qian-Yong Cao . An AIEgen nano-assembly for simultaneous detection of ATP and H2S. Chinese Chemical Letters, 2024, 35(6): 108925-. doi: 10.1016/j.cclet.2023.108925
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
Xiaoxiao Huang , Zhi-Long He , Yangpeng Chen , Lei Li , Zhenyu Yang , Chunyang Zhai , Mingshan Zhu . Novel P-doping-tuned Pd nanoflowers/S,N-GQDs photo-electrocatalyst for high-efficient ethylene glycol oxidation. Chinese Chemical Letters, 2024, 35(6): 109271-. doi: 10.1016/j.cclet.2023.109271
Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
Jianqiu Li , Yi Zhang , Songen Liu , Jie Niu , Rong Zhang , Yong Chen , Yu Liu . Cucurbit[8]uril-based non-covalent heterodimer realized NIR cell imaging through topological transformation from nanowire to nanorod. Chinese Chemical Letters, 2024, 35(10): 109645-. doi: 10.1016/j.cclet.2024.109645
Tiantian Man , Fulin Zhu , Yaqi Huang , Yuhao Piao , Yan Su , Shengyuan Deng , Ying Wan . Mobile mini-fluorimeter for antibiotic aptasensing based on surface-plasmonic effect of burlike nanogolds enhanced by digitized imaging diagnosis. Chinese Chemical Letters, 2024, 35(5): 109036-. doi: 10.1016/j.cclet.2023.109036
Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
Mengjuan Sun , Muye Zhou , Yifang Xiao , Hailei Tang , Jinhua Chen , Ruitao Zhang , Chunjiayu Li , Qi Ya , Qian Chen , Jiasheng Tu , Qiyue Wang , Chunmeng Sun . Reversibly size-switchable polyion complex micelles for antiangiogenic cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109110-. doi: 10.1016/j.cclet.2023.109110
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