Fluorescent organic nanoparticles with enhanced fluorescence by self-aggregation and their application to cellular imaging

ACS Applied Materials and Interfaces

Volumn 6, Issue 20, 2014, Pages 18337-18343

  Tang, Fu ^a   Wang, Chun ^a   Wang, Jinshan ^a   Wang, Xiaoyu ^a   Li, Lidong ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY BEIJING   (China)

Author keywords

cellular imaging; enhanced fluorescence; fluorescence; nanoparticle; quenching; self aggregation

Indexed keywords

ADENOSINETRIPHOSPHATE; BIOCOMPATIBILITY; NANOPARTICLES; QUENCHING;

AGGREGATIONINDUCED EMISSION ENHANCEMENT (AIEE); CELLULAR IMAGING; CONFOCAL LASER SCANNING MICROSCOPY; ENHANCED FLUORESCENCE; FLUORESCENCE ENHANCEMENT; FLUORESCENT NANOPARTICLES; NANOPARTICLE FORMATION; SELF AGGREGATION;

FLUORESCENCE;

FLUORESCENT DYE; NANOPARTICLE; ORGANIC COMPOUND;

CELL SURVIVAL; CHEMISTRY; ENDOCYTOSIS; HUMAN; MOLECULAR IMAGING; PROCEDURES; SPECTROFLUOROMETRY; SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE; ULTRASTRUCTURE;

CELL LINE, TUMOR; CELL SURVIVAL; ENDOCYTOSIS; FLUORESCENT DYES; HUMANS; MOLECULAR IMAGING; NANOPARTICLES; ORGANIC CHEMICALS; SPECTROMETRY, FLUORESCENCE; SPECTRUM ANALYSIS;

EID: 84908178873     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am505776a     Document Type: Article

References (42)

1. Xu, X.; Chen, S.; Li, L.; Yu, G.; Di, C.; Liu, Y. Photophysical Properties of Polyphenylphenyl Compounds in Aqueous Solutions and Application of Their Nanoparticles for Nucleobase Sensing J. Mater. Chem. 2008, 18, 2555-2561
2. Zheng, C.; Xu, X.; He, F.; Li, L.; Wu, B.; Yu, G.; Liu, Y. Preparation of High-Quality Organic Semiconductor Nanoparticle Films by Solvent-Evaporation-Induced Self-Assembly Langmuir 2010, 26, 16730-16736
3. Wang, J.; Xu, X.; Shi, L.; Li, L. Fluorescent Organic Nanoparticles Based on Branched Small Molecule: Preparation and Ion Detection in Lithium-Ion Battery ACS Appl. Mater. Interfaces 2013, 5, 3392-3400
4. Wang, X.; He, F.; Li, L.; Wang, H.; Yan, R.; Li, L. Conjugated Oligomer-based Fluorescent Nanoparticles as Functional Nanocarriers for Nucleic Acids Delivery ACS Appl. Mater. Interfaces 2013, 5, 5700-5708
5. Wang, F.; Han, M.-Y.; Mya, K. Y.; Wang, Y.; Lai, Y.-H. Aggregation-Driven Growth of Size-Tunable Organic Nanoparticles Using Electronically Altered Conjugated Polymers J. Am. Chem. Soc. 2005, 127, 10350-10355
6. Han, M.; Hara, M. Intense Fluorescence from Light-Driven Self-Assembled Aggregates of Nonionic Azobenzene Derivative J. Am. Chem. Soc. 2005, 127, 10951-10955
7. Xiao, D.; Xi, L.; Yang, W.; Fu, H.; Shuai, Z.; Fang, Y.; Yao, J. Size-Tunable Emission from 1,3-Diphenyl-5-(2-anthryl)-2-pyrazoline Nanoparticles J. Am. Chem. Soc. 2003, 125, 6740-6745
8. Zhu, L.; Yang, C.; Qin, J. An Aggregation-Induced Blue Shift of Emission and the Self-Assembly of Nanoparticles from a Novel Amphiphilic Oligofluorene Chem. Commun. 2008, 6303-6305
9. Vijayakumar, C.; Sugiyasu, K.; Takeuchi, M. Oligofluorene-based Electrophoretic Nanoparticles in Aqueous Medium as a Donor Scaffold for Fluorescence Resonance Energy Transfer and White-Light Emission Chem. Sci. 2011, 2, 291-294
10. Koizumi, Y.; Seki, S.; Tsukuda, S.; Sakamoto, S.; Tagawa, S. Self-Condensed Nanoparticles of Oligofluorenes with Water-Soluble Side Chains J. Am. Chem. Soc. 2006, 128, 9036-9037
11. Petkau, K.; Kaeser, A.; Fischer, I.; Brunsveld, L.; Schenning, A. P. H. J. Pre- and Postfunctionalized Self-Assembled π-Conjugated Fluorescent Organic Nanoparticles for Dual Targeting J. Am. Chem. Soc. 2011, 133, 17063-17071
12. Tseng, K.-P.; Fang, F.-C.; Shyue, J.-J.; Wong, K.-T.; Raffy, G.; Guerzo, A. D.; Bassani, D. M. Spontaneous Generation of Highly Emissive RGB Organic Nanospheres Angew. Chem., Int. Ed. 2011, 50, 7032-7036
13. Palacios, R. E.; Fan, F.-R. F.; Grey, J. K.; Suk, J.; Bard, A. J.; Barbara, P. F. Charging and Discharging of Single Conjugated-Polymer Nanoparticles Nat. Mater. 2007, 6, 680-685
14. Feng, X.; Tang, Y.; Duan, X.; Liu, L.; Wang, S. Lipid-Modified Conjugated Polymer Nanoparticles for Cell Imaging and Transfection J. Mater. Chem. 2010, 20, 1312-1316
15. Li, K.; Liu, B. Polymer-Encapsulated Organic Nanoparticles for Fluorescence and Photoacoustic Imaging Chem. Soc. Rev. 2014, 43, 6570-6597
16. Yuan, H.; Liu, Z.; Liu, L.; Lv, F.; Wang, Y.; Wang, S. Cationic Conjugated Polymers for Discrimination of Microbial Pathogens Adv. Mater. 2014, 26, 4333-4338
17. Li, L.; Shen, X.; Xu, Q.-H.; Yao, S. Q. A Switchable Two-Photon Membrane Tracer Capable of Imaging Membrane-Associated Protein Tyrosine Phosphatase Activities Angew. Chem., Int. Ed. 2013, 52, 424-428
18. Feng, L.; Zhu, C.; Yuan, H.; Liu, L.; Lv, F.; Wang, S. Conjugated Polymer Nanoparticles: Preparation, Properties, Functionalization and Biological Applications Chem. Soc. Rev. 2013, 42, 6620-6633
19. Decher, G. Fuzzy Nanoassemblies: Toward Layered Polymeric Multicomposites Science 1997, 277, 1232-1237
20. Donath, E.; Sukhorukov, G. B.; Caruso, F.; Davis, S. A.; Möhwald, H. Novel Hollow Polymer Shells by Colloid-Templated Assembly of Polyelectrolytes Angew. Chem., Int. Ed. 1998, 37, 2201-2205
21. Sukhorukov, G. B.; Antipov, A. A.; Voigt, A.; Donath, E.; Möhwald, H. pH-Controlled Macromolecule Encapsulation in and Release from Polyelectrolyte Multilayer Nanocapsules Macromol. Rapid Commun. 2001, 22, 44-46
22. Skirtach, A. G.; Yashchenok, A. M.; Möhwald, H. Encapsulation, Release and Applications of LbL Polyelectrolyte Multilayer Capsules Chem. Commun. 2011, 47, 12736-12746
23. Li, G. L.; Möhwald, H.; Shchukin, D. G. Precipitation Polymerization for Fabrication of Complex Core-Shell Hybrid Particles and Hollow Structures Chem. Soc. Rev. 2013, 42, 3628-3646
24. Yan, Y.; Björnmalm, M.; Caruso, F. Assembly of Layer-by-Layer Particles and Their Interactions with Biological Systems Chem. Mater. 2014, 26, 452-460
25. Xing, C.; Xu, Q.; Tang, H.; Liu, L.; Wang, S. Conjugated Polymer/Porphyrin Complexes for Efficient Energy Transfer and Improving Light-Activated Antibacterial Activity J. Am. Chem. Soc. 2009, 131, 13117-13124
26. 2 Hybrid Fluorescent Nanoparticles for Application to Cellular Imaging Langmuir 2010, 26, 11774-11778
27. Tang, F.; Ma, N.; Wang, X.; He, F.; Li, L. Hybrid Conjugated Polymer-Ag@PNIPAM Fluorescent Nanoparticles with Metal-Enhanced Fluorescence J. Mater. Chem. 2011, 21, 16943-16948
28. Cui, Q.; He, F.; Wang, X.; Xia, B.; Li, L. Gold Nanoflower@Gelatin Core-Shell Nanoparticles Loaded with Conjugated Polymer Applied for Cellular Imaging ACS Appl. Mater. Interfaces 2013, 5, 213-219
29. Birks, J. B. Excimers and Exciplexs Nature 1967, 214, 1187-1190
30. Davis, R.; Kumar, N. S. S.; Abraham, S.; Suresh, C. H.; Rath, N. P.; Tamaoki, N.; Das, S. Molecular Packing and Solid-State Fluorescence of Alkoxy-Cyano Substituted Diphenylbutadienes: Structure of the Luminescent Aggregates J. Phys. Chem. C 2008, 112, 2137-2146
31. Hu, R.; Leung, N.-L.-C.; Tang, B.-Z. AIE Macromolecules: Syntheses, Structures and Functionalities Chem. Soc. Rev. 2014, 43, 4494-4562
32. Ding, D.; Li, K.; Liu, B.; Tang, B.-Z. Bioprobes Based on AIE Fluorogens Acc. Chem. Res. 2013, 46, 2441-2453
33. Hong, Y.; Lam, J.-W.-Y.; Tang, B.-Z. Aggregation-Induced Emission Chem. Soc. Rev. 2011, 40, 5361-5388
34. Zhao, Z.; Deng, C.; Chen, S.; Lam, J. W. Y.; Qin, W.; Lu, P.; Wang, Z.; Kwok, H. S.; Ma, Y.; Qiu, H.; Tang, B. Z. Full Emission Color Tuning in Luminogens Constructed from Tetraphenylethene, Benzo-2,1,3-thiadiazole and Thiophene Building Blocks Chem. Commun. 2011, 47, 8847-8849
35. Shi, J.; Wu, Y.; Sun, S.; Tong, B.; Zhi, J.; Dong, Y. Tunable Fluorescence Conjugated Copolymers Consisting of Tetraphenylethylene and Fluorene Units: From Aggregation-Induced Emission Enhancement to Dual-Channel Fluorescence Response J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 229-240
36. Aldred, M. P.; Li, C.; Zhang, G.-F.; Gong, W.-L.; Li, A. D. Q.; Dai, Y.; Ma, D.; Zhu, M.-Q. Fluorescence Quenching and Enhancement of Vitrifiable Oligofluorenes End-Capped with Tetraphenylethene J. Mater. Chem. 2012, 22, 7515-7528
37. Ananthakrishnan, S. J.; Varathan, E.; Ravindran, E.; Somanathan, N.; Subramanian, V.; Mandal, A. B.; Sudha, J. D.; Ramakrishnan, R. A Solution Processable Fluorene-Fluorenone Oligomer with Aggregation Induced Emission Enhancement Chem. Commun. 2013, 49, 10742-10744
38. Stork, M.; Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. Energy Transfer in Mixtures of Water-Soluble Oligomers: Effect of Charge, Aggregation, and Surfactant Complexation Adv. Mater. 2002, 14, 361-366
39. Duan, X.; Liu, L.; Feng, F.; Wang, S. Cationic Conjugated Polymers for Optical Detection of DNA Methylation, Lesions, and Single Nucleotide Polymorphisms Acc. Chem. Res. 2010, 43, 260-270
40. Zhou, J.; Chang, Z.; Jiang, Y.; He, B.; Du, M.; Lu, P.; Hong, Y.; Kwok, H. S.; Qin, A.; Qiu, H.; Zhao, Z.; Tang, B. Z. From Tetraphenylethene to Tetranaphthylethene: Structural Evolution in AIE Luminogen Continues Chem. Commun. 2013, 49, 2491-2493
41. An, B.-K.; Lee, D.-S.; Lee, J.-S.; Park, Y.-S.; Song, H.-S.; Park, S. Y. Strongly Fluorescent Organogel System Comprising Fibrillar Self-Assembly of a Trifluoromethyl-based Cyanostilbene Derivative J. Am. Chem. Soc. 2004, 126, 10232-10233
42. Wang, Z.; Chen, S.; Lam, J. W. Y.; Qin, W.; Kwok, R. T. K.; Xie, N.; Hu, Q.; Tang, B. Z. Long-Term Fluorescent Cellular Tracing by the Aggregates of AIE Bioconjugates J. Am. Chem. Soc. 2012, 135, 8238-8245