A cell apoptosis probe based on fluorogen with aggregation induced emission characteristics

ACS Applied Materials and Interfaces

Volumn 7, Issue 8, 2015, Pages 4875-4882

  Hu, Qinglian ^a   Gao, Meng ^b   Feng, Guangxue ^a   Chen, Xiaodong ^c   Liu, Bin ^a,b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

^c NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

aggregation induced emission; cell apoptosis; lipid droplet; zinc coordination

Indexed keywords

CELL DEATH; DROPS; ZINC;

AGGREGATION-INDUCED EMISSIONS; APOPTOTIC CELLS; CELL APOPTOSIS; HIGH AFFINITY; LATE STAGE; LIPID DROPLETS; PROBE-BASED;

PROBES;

BIS-DIPICOLYLAMINE-ZINC(II); FLUORESCENT DYE; HYDROGEN PEROXIDE; LIPOSOME; ORGANOMETALLIC COMPOUND; PICOLINIC ACID DERIVATIVE;

APOPTOSIS; CHEMISTRY; CONFOCAL MICROSCOPY; DRUG EFFECTS; HELA CELL LINE; HEPG2 CELL LINE; HUMAN; METABOLISM;

APOPTOSIS; FLUORESCENT DYES; HELA CELLS; HEP G2 CELLS; HUMANS; HYDROGEN PEROXIDE; LIPOSOMES; MICROSCOPY, CONFOCAL; ORGANOMETALLIC COMPOUNDS; PICOLINIC ACIDS;

EID: 84924263538     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am508838z     Document Type: Article

References (41)

1. Stavridi, F.; Karapanagiotou, E. M.; Syrigos, K. N. Targeted Therapeutic Approaches for Hormone-Refractory Prostate Cancer Cancer Treat. Rev. 2010, 36, 122-130
2. Brindle, K. New Approaches for Imaging Tumour Responses to Treatment Nat. Rev. Cancer 2008, 8, 94-107
3. Lee, B. W.; Olin, M. R.; Johnson, G. L.; Griffin, R. J. In Vitro and in Vivo Apoptosis Detection Using Membrane Permeant Fluorescent-Labeled Inhibitors of Caspases Methods Mol. Biol. 2008, 414, 109-135
4. 18F]-Labeled Isatin Sulfonamide Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 16375-16380
5. Wu, Y.; Xing, D.; Luo, S.; Tang, Y.; Chen, Q. Detection of Caspase-3 Activation in Single Cells by Fluorescence Resonance Energy Transfer During Photodynamic Therapy Induced Apoptosis Cancer Lett. 2006, 235, 239-247
6. Eldadah, B. A.; Yakovlev, A. G.; Faden, A. I. A New Approach for the Electrophoretic Detection of Apoptosis Nucleic Acids Res. 1996, 24, 4092-4093
7. Walker, P. R.; Leblanc, J.; Smith, B.; Pandey, S.; Sikorska, M. Detection of DNA Fragmentation and Endonucleases in Apoptosis Methods 1999, 17, 329-338
8. White, M. K.; Cinti, C. A Morphologic Approach to Detect Apoptosis Based on Electron Microscopy Methods Mol. Biol. 2004, 285, 105-111
9. Schlegel, R. A.; Williamson, P. Phosphatidylserine, a Death Knell Cell Death Differ. 2001, 8, 551-63
10. Plasier, B.; Lloyd, D. R.; Paul, G. C.; Thomas, C. R.; Al-Rubeai, M. Automatic Image Analysis for Quantification of Apoptosis in Animal Cell Culture by Annexin-V Affinity Assay J. Immunol. Methods 1999, 229, 81-95
11. Jung, K. H.; Lee, J. H.; Park, J. W.; Paik, J. Y.; Quach, C. H.; Lee, E. J.; Lee, K. H. Annexin V Imaging Detects Diabetes-Accelerated Apoptosis and Monitors the Efficacy of Benfotiamine Treatment in Ischemic Limbs of Mice Mol. Imaging 2014, 13, 1-7
12. Williamson, P.; van den Eijnde, S.; Schlegel, R. A. Phosphatidylserine Exposure and Phagocytosis of Apoptotic Cells Methods Cell Biol. 2001, 66, 339-364
13. Koulov, A. V.; Stucker, K. A.; Lakshmi, C.; Robinson, J. P.; Smith, B. D. Detection of Apoptotic Cells Using a Synthetic Fluorescent Sensor for Membrane Surfaces That Contain Phosphatidylserine Cell Death Differ. 2003, 10, 1357-1359
14. Kwong, J. M.; Hoang, C.; Dukes, R. T.; Yee, R. W.; Gray, B. D.; Pak, K. Y.; Caprioli, J. Bis(zinc-dipicolylamine), Zn-DPA, a New Marker for Apoptosis Invest. Ophthalmol. Visual Sci. 2014, 55, 4913-4921
15. Hanshaw, R. G.; Lakshmi, C.; Lambert, T. N.; Johnson, J. R.; Smith, B. D. Fluorescent Detection of Apoptotic Cells by Using Zinc Coordination Complexes with a Selective Affinity for Membrane Surfaces Enriched with Phosphatidylserine ChemBioChem 2005, 6, 2214-2220
16. ONeil, E. J.; Jiang, H.; Smith, B. D. Effect of Bridging Anions on the Structure and Stability of Phenoxide Bridged Zinc Dipicolylamine Coordination Complexes Supramol. Chem. 2013, 25, 315-322
17. Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Bioprobes Based on AIE Fluorogens Acc. Chem. Res. 2013, 46, 2441-2453
18. Shi, H.; Kwok, R. T.; Liu, J.; Xing, B.; Tang, B. Z.; Liu, B. Real-Time Monitoring of Cell Apoptosis and Drug Screening Using Fluorescent Light-Up Probe with Aggregation-Induced Emission Characteristics J. Am. Chem. Soc. 2012, 134, 17972-17981
19. Zhao, J.; Yang, D.; Zhao, Y.; Yang, X. J.; Wang, Y. Y.; Wu, B. Anion-Coordination-Induced Turn-On Fluorescence of an Oligourea-Functionalized Tetraphenylethene in a Wide Concentration Range Angew. Chem., Int. Ed. 2014, 53, 6632-6636
20. Liu, M.; Zhang, X.; Yang, B.; Liu, L.; Deng, F.; Wei, Y. Polylysine Crosslinked AIE Dye Based Fluorescent Organic Nanoparticles for Biological Imaging Applications Macromol. Biosci. 2014, 14, 1260-1267
21. Yuan, Y.; Kwok, R. T.; Tang, B. Z.; Liu, B. Targeted Theranostic Platinum(IV) Prodrug with a Built-in Aggregation-Induced Emission Light-Up Apoptosis Sensor for Noninvasive Early Evaluation of its Therapeutic Responses in Situ J. Am. Chem. Soc. 2014, 136, 2546-2554
22. Hu, F.; Huang, Y.; Zhang, G.; Zhao, R.; Yang, H.; Zhang, D. Targeted Bioimaging and Photodynamic Therapy of Cancer Cells with an Activatable Red Fluorescent Bioprobe Anal. Chem. 2014, 86, 7987-7995
23. Li, C.; Wu, T.; Hong, C.; Zhang, G.; Liu, S. A General Strategy to Construct Fluorogenic Probes from Charge-Generation Polymers (CGPs) and AIE-Active Fluorogens Through Triggered Complexation Angew. Chem., Int. Ed. 2012, 51, 455-459
24. Li, K.; Liu, B. Polymer-Encapsulated Organic Nanoparticles for Fluorescence and Photoacoustic Imaging Chem. Soc. Rev. 2014, 43, 6570-6597
25. Zhang, X.; Zhang, X.; Yang, B.; Yang, Y.; Wei, Y. Renewable Itaconic Acid Based Cross-Linked Fluorescent Polymeric Nanoparticles for Cell Imaging Polym. Chem. 2014, 5885-5889
26. Li, H.; Zhang, X.; Yang, B.; Yang, Y.; Huang, Z.; Wei, Y. Zwitterionic Red Fluorescent Polymeric Nanoparticles for Cell Imaging Macromol. Biosci. 2014, 14, 1361-1367
27. Hong, Y.; Lam, J. W.; Tang, B. Z. Aggregation-Induced Emission Chem. Soc. Rev. 2011, 40, 5361-5388
28. Gao, M.; Sim, C. K.; Leung, C. W.; Hu, Q.; Feng, G.; Xu, F.; Tang, B. Z.; Liu, B. A Fluorescent Light-Up Probe with AIE Characteristics for Specific Mitochondrial Imaging to Identify Differentiating Brown Adipose Cells Chem. Commun. (Cambridge, U.K.) 2014, 50, 8312-8315
29. Song, Z.; Kwok, R. T.; Zhao, E.; He, Z.; Hong, Y.; Lam, J. W.; Liu, B.; Tang, B. Z. A Ratiometric Fluorescent Probe Based on ESIPT and AIE Processes for Alkaline Phosphatase Activity Assay and Visualization in Living Cells ACS Appl. Mater. Interfaces 2014, 6, 17245-17254
30. Tang, W.; Xiang, Y.; Tong, A. Salicylaldehyde Azines as Fluorophores of Aggregation-Induced Emission Enhancement Characteristics J. Org. Chem. 2009, 74, 2163-2166
31. 2+ in Aqueous Ethanol: A Ratiometric Approach Luminescence 2010, 25, 445-451
32. Li, K.; Wang, X.; Tong, A. A ′′Turn-On Fluorescent Chemosensor for Zinc Ion with Facile Synthesis and Application in Live Cell Imaging Anal. Chim. Acta 2013, 776, 69-73
33. 131I-Labeled Peptides as Caspase Substrates for Apoptosis Imaging J. Nucl. Med. 2005, 46, 1066-1074
34. 2+-Selective Cyanine-Based Probe and Its Use for Tracing Endogenous Zinc Ions in Cells and Organisms Nat. Protoc. 2014, 9, 1245-1254
35. Zhu, Z.; Xu, L.; Li, H.; Zhou, X.; Qin, J.; Yang, C. A Tetraphenylethene-Based Zinc Complex as a Sensitive DNA Probe by Coordination Interaction Chem. Commun. (Cambridge, U.K.) 2014, 50, 7060-7062
36. Wooding, F. B. Lipid Droplet Secretion by the Rabbit Harderian Gland J. Ultrastruct. Res. 1980, 71, 68-78
37. Krahmer, N.; Farese, R. V., Jr.; Walther, T. C. Balancing the Fat: Lipid Droplets and Human Disease EMBO Mol. Med. 2013, 5, 905-915
38. Przybytkowski, E.; Behrendt, M.; Dubois, D.; Maysinger, D. Nanoparticles Can Induce Changes in the Intracellular Metabolism of Lipids without Compromising Cellular Viability FEBS J. 2009, 276, 6204-6217
39. Yamanaka, K.; Urano, Y.; Takabe, W.; Saito, Y.; Noguchi, N. Induction of Apoptosis and Necroptosis by 24(S)-Hydroxycholesterol is Dependent on Activity of Acyl-CoA:Cholesterol Acyltransferase 1 Cell Death Dis. 2014, 5, e990-1-e990-9
40. Boren, J.; Brindle, K. M. Apoptosis-Induced Mitochondrial Dysfunction Causes Cytoplasmic Lipid Droplet Formation Cell Death Differ. 2012, 19, 1561-1570
41. Cort, A. D.; Mandolini, L.; Pasquini, C.; Schiaffino, L. A Novel Ditopic Zinc-Salophen Macrocycle: A Potential Two-Stationed Wheel for [2]-Pseudorotaxanes Org. Biomol. Chem. 2006, 4, 4543-4546