

FOLLOWUS
a.Chimie ParisTech, PSL University Paris, CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France
b.Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China
min-hui.li@chimieparistech.psl.eu
Received:01 November 2018,
Revised:2018-11-28,
Accepted:03 December 2018,
Online First:21 January 2019,
Published:2019-04
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Citation: Chen, H.; Li, M. H. Recent progress in fluorescent vesicles with aggregation-induced emission. Chinese J. Polym. Sci. 2019, 37, 352–371
Hui Chen, Min-Hui Li. Recent Progress in Fluorescent Vesicles with Aggregation-induced Emission[J]. Chinese Journal of Polymer Science, 2019, 37(4): 352-371.
Citation: Chen, H.; Li, M. H. Recent progress in fluorescent vesicles with aggregation-induced emission. Chinese J. Polym. Sci. 2019, 37, 352–371 DOI: 10.1007/s10118-019-2204-5.
Hui Chen, Min-Hui Li. Recent Progress in Fluorescent Vesicles with Aggregation-induced Emission[J]. Chinese Journal of Polymer Science, 2019, 37(4): 352-371. DOI: 10.1007/s10118-019-2204-5.
Fluorescent vesicles have recently attracted increasing attention because of their potential applications in bioimaging
diagnostics
and theranostics
for example
in vivo
study of the delivery and the distribution of active substances. However
fluorescent vesicles containing conventional organic dyes often suffer from the problem of aggregation-caused quenching (ACQ) of fluorescence. Fluorescent vesicles working with aggregation-induced emission (AIE) offer an extraordinary tool to tackle the ACQ issue
showing advantages such as high emission efficiency
superior photophysical stability
low background interference
and high sensitivity. AIE fluorescent vesicles represent a new type of fluorescent and functional nanomaterials. In this review
we summarize the recent advances in the development of AIE fluorescent vesicles. The review is organized according to the chemical structures and architectures of the amphiphilic molecules that constitute the AIE vesicles
i.e.
small-molecule amphiphiles
amphiphilic polymers
and amphiphilic supramolecules and supramacromolecules. The studies on the applications of these AIE vesicles as stimuli-responsive vesicles
fluorescence-guided drug release carriers
cell imaging tools
and fluorescent materials based on fluorescence resonance energy transfer (FRET) are also discussed.
Hocine, S.; Li, M. H . Thermoresponsive self-assembled polymer colloids in water . Soft Matter , 2013 . 9 5839 - 5861 . DOI: 10.1039/c3sm50428j http://doi.org/10.1039/c3sm50428j .
Blanazs, A.; Armes, S. P.; Ryan, A. J . Self-assembled block copolymer aggregates: From micelles to vesicles and their biological applications . Macromol. Rapid Commun. , 2009 . 30 267 - 77 . DOI: 10.1002/marc.v30:4/5 http://doi.org/10.1002/marc.v30:4/5 .
Karami, Z.; Hamidi, M . Cubosomes: Remarkable drug delivery potential . Drug Discov. Today , 2016 . 21 789 - 801 . DOI: 10.1016/j.drudis.2016.01.004 http://doi.org/10.1016/j.drudis.2016.01.004 .
Percec, V.; Wilson, D. A.; Leowanawat, P.; Wilson, C. J.; Hughes, A. D.; Kaucher, M. S.; Hammer, D. A.; Levine, D. H.; Kim, A. J.; Bates, F. S.; Davis, K. P.; Lodge, T. P.; Klein, M. L.; DeVane, R. H.; Aqad, E.; Rosen, B. M.; Argintaru, A. O.; Sienkowska, M. J.; Rissanen, K.; Nummelin, S.; Ropponen, J . Self-assembly of Janus dendrimers into uniform dendrimersomes and other complex architectures . Science , 2010 . 328 1009 - 1014 . DOI: 10.1126/science.1185547 http://doi.org/10.1126/science.1185547 .
Lombardo, D.; Kiselev, M. A.; Magazù, S.; Calandra, P . Amphiphiles self-Assembly: Basic concepts and future perspectives of supramolecular approaches . Adv. Cond. Matter Phys. , 2015 . 2015 1 - 22 . .
Discher, D. E.; Ahmed, F . Polymersomes . Annu. Rev. Biomed. Eng. , 2006 . 8 323 - 341 . DOI: 10.1146/annurev.bioeng.8.061505.095838 http://doi.org/10.1146/annurev.bioeng.8.061505.095838 .
Ahmed, F.; Pakunlu, R. I.; Brannan, A.; Bates, F.; Minko, T.; Discher, D. E . Biodegradable polymersomes loaded with both paclitaxel and doxorubicin permeate and shrink tumors, inducing apoptosis in proportion to accumulated drug . J. Control. Release , 2006 . 116 150 - 158 . DOI: 10.1016/j.jconrel.2006.07.012 http://doi.org/10.1016/j.jconrel.2006.07.012 .
Eloy, J. O.; Claro de Souza, M.; Petrilli, R.; Barcellos, J. P. A.; Lee, R. J.; Marchetti, J. M . Liposomes as carriers of hydrophilic small molecule drugs: Strategies to enhance encapsulation and delivery . Colloids Surf. B , 2014 . 123 345 - 363 . DOI: 10.1016/j.colsurfb.2014.09.029 http://doi.org/10.1016/j.colsurfb.2014.09.029 .
Antonietti, M.; Förster, S . Vesicles and liposomes: A self-assembly principle beyond lipids . Adv. Mater. , 2003 . 15 1323 - 1333 . DOI: 10.1002/(ISSN)1521-4095 http://doi.org/10.1002/(ISSN)1521-4095 .
Broz, P.; Benito, S. M.; Saw, C.; Burger, P.; Heider, H.; Pfisterer, M.; Marsch, S.; Meier, W.; Hunziker, P . Cell targeting by a generic receptor-targeted polymer nanocontainer platform . J. Control. Release , 2005 . 102 475 - 488 . DOI: 10.1016/j.jconrel.2004.10.014 http://doi.org/10.1016/j.jconrel.2004.10.014 .
Lin, Y. S.; Lee, M. Y.; Yang, C. H.; Huang, K. S . Active targeted drug delivery for microbes using nano-carriers . Curr. Top. Med. Chem. , 2015 . 15 1525 - 1531 . DOI: 10.2174/1568026615666150414123157 http://doi.org/10.2174/1568026615666150414123157 .
De Oliveira, H.; Thevenot, J.; Lecommandoux, S . Smart polymersomes for therapy and diagnosis: Fast progress toward multifunctional biomimetic nanomedicines . Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. , 2012 . 4 525 - 546 . DOI: 10.1002/wnan.1183 http://doi.org/10.1002/wnan.1183 .
Deng, Y.; Ling, J.; Li, M. H . Physical stimuli-responsive liposomes and polymersomes as drug delivery vehicles based on phase transitions in the membrane . Nanoscale , 2018 . 10 6781 - 6800 . DOI: 10.1039/C8NR00923F http://doi.org/10.1039/C8NR00923F .
Li, M. H.; Keller, P . Stimuli-responsive polymer vesicles . Soft Matter , 2009 . 5 927 - 937 . DOI: 10.1039/b815725a http://doi.org/10.1039/b815725a .
Mabrouk, E.; Cuvelier, D.; Brochard-Wyart, F.; Nassoy, P.; Li, M. H . Bursting of sensitive polymersomes induced by curling . Proc. Natl. Acad. Sci , 2009 . 106 7294 - 7298 . DOI: 10.1073/pnas.0813157106 http://doi.org/10.1073/pnas.0813157106 .
Meng, F. H.; Zhong, Z. Y.; Feijen, J . Stimuli-responsive polymersomes for programmed drug delivery . Biomacromolecules , 2009 . 10 197 - 209 . DOI: 10.1021/bm801127d http://doi.org/10.1021/bm801127d .
Du, J.; O'Reilly, R. K . Advances and challenges in smart and functional polymer vesicles . Soft Matter , 2009 . 3544 - 3561 . .
Smart, T.; Lomas, H.; Massignani, M.; Flores-Merino, M. V.; Perez, L. R.; Battaglia, G . Block copolymer nanostructures . Nano Today , 2008 . 3 38 - 46 . DOI: 10.1016/S1748-0132(08)70043-4 http://doi.org/10.1016/S1748-0132(08)70043-4 .
Discher, B. M.; Bermudez, H.; Hammer, D. A.; Discher, D. E.; Won, Y. Y.; Bates, F. S. . Cross-linked polymersome membranes: Vesicles with broadly adjustable properties . J. Phys. Chem. B , 2002 . 106 2848 - 2854 . DOI: 10.1021/jp011958z http://doi.org/10.1021/jp011958z .
Kikuchi, K . Design, synthesis and biological application of chemical probes for bio-imaging . Chem. Soc. Rev. , 2010 . 39 2048 - 2053 . DOI: 10.1039/b819316a http://doi.org/10.1039/b819316a .
Haugland, R. P. in The molecular probes handbook: A guide to fluorescent probes and labeling technologies . Life Technologies: Carlsbad, CA, 2010 .
Liang, J.; Tang, B. Z.; Liu, B . Specific light-up bioprobes based on AIEgen conjugates . Chem. Soc. Rev. , 2015 . 44 2798 - 2811 . DOI: 10.1039/C4CS00444B http://doi.org/10.1039/C4CS00444B .
Zhang, X.; Zhang, X.; Tao, L.; Chi, Z.; Xu, J.; Wei, Y . Aggregation induced emission-based fluorescent nanoparticles: Fabrication methodologies and biomedical applications . J. Mater. Chem. B , 2014 . 2 4398 - 4414 . .
Yan, L.; Zhang, Y.; Xu, B.; Tian, W . Fluorescent nanoparticles based on AIE fluorogens for bioimaging . Nanoscale , 2016 . 8 2471 - 2487 . DOI: 10.1039/C5NR05051K http://doi.org/10.1039/C5NR05051K .
Li, K.; Liu, B . Polymer-encapsulated organic nanoparticles for fluorescence and photoacoustic imaging . Chem. Soc. Rev. , 2014 . 43 6570 - 6597 . DOI: 10.1039/C4CS00014E http://doi.org/10.1039/C4CS00014E .
Chen, M.; Yin, M . Design and development of fluorescent nanostructures for bioimaging . Prog. Polym. Sci. , 2014 . 39 365 - 395 . DOI: 10.1016/j.progpolymsci.2013.11.001 http://doi.org/10.1016/j.progpolymsci.2013.11.001 .
Ghoroghchian, P. P.; Frail, P. R.; Susumu, K.; Blessington, D.; Brannan, A. K.; Bates, F. S.; Chance, B.; Hammer, D. A.; Therien, M. J . Near-infrared-emissive polymersomes: Self-assembled soft matter for in vivo optical imaging . Proc. Natl. Acad. Sci. , 2005 . 102 2922 - 2927 . DOI: 10.1073/pnas.0409394102 http://doi.org/10.1073/pnas.0409394102 .
Kamat, N. P.; Liao, Z.; Moses, L. E.; Rawson, J.; Therien, M. J.; Dmochowski, I. J.; Hammer, D. A . Sensing membrane stress with near IR-emissive porphyrins . Proc. Natl. Acad. Sci. , 2011 . 108 13984 - 13989 . DOI: 10.1073/pnas.1102125108 http://doi.org/10.1073/pnas.1102125108 .
Duncan, T. V.; Ghoroghchian, P. P.; Rubtsov, I. V.; Hammer, D. A.; Therien, M. J . Ultrafast excited-state dynamics of nanoscale near-infrared emissive polymersomes . J. Am. Chem. Soc. , 2008 . 130 9773 - 9784 . DOI: 10.1021/ja711497w http://doi.org/10.1021/ja711497w .
Christian, N. A.; Benencia, F.; Milone, M. C.; Li, G.; Frail, P. R.; Therien, M. J.; Coukos, G.; Hammer, D. A . In vivo dendritic cell tracking using fluorescence lifetime imaging and near-infrared-emissive polymersomes . Mol. Imaging Biol. , 2009 . 11 167 - 177 . DOI: 10.1007/s11307-008-0184-x http://doi.org/10.1007/s11307-008-0184-x .
Birks, J. B. in Photophysics of aromatic molecules . Wiley, New York, 1970 .
Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z . Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole . Chem. Commun. , 2001 . 0 1740 - 1741 . .
Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z . Aggregation-induced emission: Together we shine, united we soar! . Chem. Rev. , 2015 . 115 11718 - 11940 . .
Mei, J.; Hong, Y.; Lam, J. W. Y.; Qin, A.; Tang, Y.; Tang, B. Z . Aggregation-induced emission: The whole is more brilliant than the parts . Adv. Mater. , 2014 . 26 5429 - 5479 . DOI: 10.1002/adma.201401356 http://doi.org/10.1002/adma.201401356 .
Ding, D.; Li, K.; Liu, B.; Tang, B. Z . Bioprobes based on AIE fluorogens . Acc. Chem. Res. , 2013 . 46 2441 - 2453 . DOI: 10.1021/ar3003464 http://doi.org/10.1021/ar3003464 .
Huang, J.; Yu, Y.; Wang, L.; Wang, X.; Gu, Z.; Zhang, S . Tetraphenylethylene-induced cross-linked vesicles with tunable luminescence and controllable stability . ACS Appl. Mater. Interfaces , 2017 . 9 29030 - 29037 . DOI: 10.1021/acsami.7b06954 http://doi.org/10.1021/acsami.7b06954 .
Nonappa; Maitra, U . Unlocking the potential of bile acids in synthesis, supramolecular/materials chemistry and nanoscience . Org. Biomol. Chem. , 2008 . 6 657 - 669 . DOI: 10.1039/b714475j http://doi.org/10.1039/b714475j .
Zhang, M.; Yin, X.; Tian, T.; Liang, Y.; Li, W.; Lan, Y.; Li, J.; Zhou, M.; Ju, Y.; Li, G . AIE-induced fluorescent vesicles containing amphiphilic binding pockets and the FRET triggered by host-guest chemistry . Chem. Commun. , 2015 . 51 10210 - 10213 . DOI: 10.1039/C5CC02377G http://doi.org/10.1039/C5CC02377G .
Dan, N., in Nanostructures for drug delivery, core-shell drug carriers: Liposomes, polymersomes, and niosomes . Elsevier, 2017 , pp 63−105.
Wang, X.; Yang, Y.; Zhuang, Y.; Gao, P.; Yang, F.; Shen, H.; Guo, H.; Wu, D . Fabrication of pH-responsive nanoparticles with an AIE feature for imaging intracellular drug delivery . Biomacromolecules , 2016 . 17 2920 - 2929 . DOI: 10.1021/acs.biomac.6b00744 http://doi.org/10.1021/acs.biomac.6b00744 .
Wang, X.; Yang, Y.; Zuo, Y.; Yang, F.; Shen, H.; Wu, D . Facile creation of FRET systems from a pH-responsive AIE fluorescent vesicle . Chem. Commun. , 2016 . 52 5320 - 5323 . DOI: 10.1039/C6CC01706A http://doi.org/10.1039/C6CC01706A .
Wang, X.; Yang, Y.; Yang, F.; Shen, H.; Wu, D . pH-triggered decomposition of polymeric fluorescent vesicles to induce growth of tetraphenylethylene nanoparticles for long-term live cell imaging . Polymer , 2017 . 118 75 - 84 . DOI: 10.1016/j.polymer.2017.04.064 http://doi.org/10.1016/j.polymer.2017.04.064 .
Li, G.; Du, F.; Wang, H.; Bai, R . Synthesis and self-assembly of carbazole-based amphiphilic triblock copolymers with aggregation-induced emission enhancement . React. Funct. Polym. , 2014 . 75 75 - 80 . DOI: 10.1016/j.reactfunctpolym.2013.12.007 http://doi.org/10.1016/j.reactfunctpolym.2013.12.007 .
Ma, C. P.; Chi, Z. G.; Zhou, X.; Zhang, Y.; Liu, S. W.; Xu, J. R . AIE vesicles consisting of tetraphenylethylene-based amphiphilic diblock copolymer with a poly( N -isopropylacrylamide) sequence . J. Control. Release , 2013 . 172 e95 .
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 http://doi.org/10.1039/C4RA08191A .
Zhao, Y.; Zhu, W.; Ren, L.; Zhang, K . Aggregation-induced emission polymer nanoparticles with pH-responsive fluorescence . Polym. Chem. , 2016 . 7 5386 - 5395 . DOI: 10.1039/C6PY01009A http://doi.org/10.1039/C6PY01009A .
Zhang, N.; Chen, H.; Fan, Y.; Zhou, L.; Trepout, S.; Guo, J.; Li, M. H . Fluorescent polymersomes with aggregation-induced emission . ACS Nano , 2018 . 12 4025 - 4035 . DOI: 10.1021/acsnano.8b01755 http://doi.org/10.1021/acsnano.8b01755 .
Liu, Q.; Xia, Q.; Wang, S.; Li, B. S.; Tang, B. Z . In situ visualizable self-assembly, aggregation-induced emission and circularly polarized luminescence of tetraphenylethene and alanine-based chiral polytriazole . J. Mater. Chem. C , 2018 . 6 4807 - 4816 . DOI: 10.1039/C8TC00838H http://doi.org/10.1039/C8TC00838H .
Wang, C.; Wang, Z. Q.; Zhang, X . Amphiphilic building blocks for self-assembly: From amphiphiles to supra-amphiphiles . Acc. Chem. Res. , 2012 . 45 608 - 618 . DOI: 10.1021/ar200226d http://doi.org/10.1021/ar200226d .
Zhang, X.; Wang, C . Supramolecular amphiphiles . Chem. Soc. Rev. , 2011 . 40 94 - 101 . DOI: 10.1039/B919678C http://doi.org/10.1039/B919678C .
Chen, L. J.; Ren, Y. Y.; Wu, N. W.; Sun, B.; Ma, J. Q.; Zhang, L.; Tan, H.; Liu, M.; Li, X.; Yang, H. B . Hierarchical self-assembly of discrete organoplatinum(II) metallacycles with polysaccharide via electrostatic interactions and their application for heparin detection . J. Am. Chem. Soc. , 2015 . 137 11725 - 11735 . DOI: 10.1021/jacs.5b06565 http://doi.org/10.1021/jacs.5b06565 .
Zheng, W.; Yang, G.; Jiang, S. T.; Shao, N.; Yin, G. Q.; Xu, L.; Li, X.; Chen, G.; Yang, H. B . A tetraphenylethylene (TPE)-based supra-amphiphilic organoplatinum(II) metallacycle and its self-assembly behaviour . Mater. Chem. Front. , 2017 . 1 1823 - 1828 . DOI: 10.1039/C7QM00107J http://doi.org/10.1039/C7QM00107J .
Zhang, C. W.; Ou, B.; Jiang, S. T.; Yin, G. Q.; Chen, L. J.; Xu, L.; Li, X.; Yang, H. B . Cross-linked AIE supramolecular polymer gels with multiple stimuli-responsive behaviours constructed by hierarchical self-assembly . Polym. Chem. , 2018 . 9 2021 - 2030 . DOI: 10.1039/C8PY00226F http://doi.org/10.1039/C8PY00226F .
Chi, X.; Zhang, H.; Vargas-Zuniga, G. I.; Peters, G. M.; Sessler, J. L . A Dual-responsive bola-type supra-amphiphile constructed from a water-soluble calix[4] pyrrole and a tetraphenylethene-containing pyridine bis- N -oxide . J. Am. Chem. Soc. , 2016 . 138 5829 - 5832 . DOI: 10.1021/jacs.6b03159 http://doi.org/10.1021/jacs.6b03159 .
Li, J.; Shi, K.; Drechsler, M.; Tang, B. Z.; Huang, J.; Yan, Y . A supramolecular fluorescent vesicle based on a coordinating aggregation induced emission amphiphile: Insight into the role of electrical charge in cancer cell division . Chem. Commun. , 2016 . 52 12466 - 12469 . DOI: 10.1039/C6CC06432A http://doi.org/10.1039/C6CC06432A .
Li, J.; Liu, K.; Chen, H.; Li, R.; Drechsler, M.; Bai, F.; Huang, J.; Tang, B. Z.; Yan, Y . Functional built-in template directed siliceous fluorescent supramolecular vesicles as diagnostics . ACS Appl. Mater. Interfaces , 2017 . 9 21706 - 21714 . DOI: 10.1021/acsami.7b06306 http://doi.org/10.1021/acsami.7b06306 .
Li, J.; Liu, K.; Han, Y.; Tang, B. Z.; Huang, J.; Yan, Y . Fabrication of propeller-shaped supra-amphiphile for construction of enzyme-responsive fluorescent vesicles . ACS Appl. Mater. Interfaces , 2016 . 8 27987 - 27995 . DOI: 10.1021/acsami.6b08620 http://doi.org/10.1021/acsami.6b08620 .
Wei, Y.; Wang, L.; Huang, J.; Zhao, J.; Yan, Y . Multifunctional metallo-organic vesicles displaying aggregation-Induced emission: Two-photon cell-Imaging, drug delivery, and specific detection of zinc ion . ACS Appl. Nano Mater. , 2018 . 1 1819 - 1827 . DOI: 10.1021/acsanm.8b00226 http://doi.org/10.1021/acsanm.8b00226 .
Kong, Q.; Zhuang, W.; Li, G.; Jiang, Q.; Wang, Y . Cation-anion interaction-directed formation of functional vesicles and their biological application for nucleus-specific imaging . New J. Chem. , 2018 . 42 9187 - 9192 . DOI: 10.1039/C8NJ01503A http://doi.org/10.1039/C8NJ01503A .
He, L.; Liu, X.; Liang, J.; Cong, Y.; Weng, Z.; Bu, W . Fluorescence responsive conjugated poly(tetraphenylethene) and its morphological transition from micelle to vesicle . Chem. Commun. , 2015 . 51 7148 - 7151 . DOI: 10.1039/C5CC00934K http://doi.org/10.1039/C5CC00934K .
Ji, X. F.; Li, Y.; Wang, H.; Zhao, R.; Tang, G. P.; Huang, F. H . Facile construction of fluorescent polymeric aggregates with various morphologies by self-assembly of supramolecular amphiphilic graft copolymers . Polym. Chem. , 2015 . 6 5021 - 5025 . DOI: 10.1039/C5PY00801H http://doi.org/10.1039/C5PY00801H .
Shen, J.; Pang, J.; Xu, G.; Xin, X.; Yang, Y.; Luan, X.; Yuan, S . Smart stimuli-responsive fluorescent vesicular sensor based on inclusion complexation of cyclodextrins with Tyloxapol . RSC Adv. , 2016 . 6 11683 - 11690 . DOI: 10.1039/C5RA26464B http://doi.org/10.1039/C5RA26464B .
Shen, J.; Wang, Z.; Sun, D.; Xia, C.; Yuan, S.; Sun, P.; Xin, X . pH-responsive nanovesicles with enhanced emission co-assembled by Ag(I) nanoclusters and polyethyleneimine as a superior sensor for Al 3+ . ACS Appl. Mater. Interfaces , 2018 . 10 3955 - 3963 . DOI: 10.1021/acsami.7b16316 http://doi.org/10.1021/acsami.7b16316 .
Zhang, X.; Rehm, S.; Safont-Sempere, M. M.; Würthner, F . Vesicular perylene dye nanocapsules as supramolecular fluorescent pH sensor systems . Nat. Chem. , 2009 . 1 623 - 629 . DOI: 10.1038/nchem.368 http://doi.org/10.1038/nchem.368 .
Sapsford, K. E.; Berti, L.; Medintz, I. L . Fluorescence resonance energy transfer: Concepts, applications and advances . Minerva. Biotecnol. , 2004 . 16 247 - 273 . .
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