Silicon Quantum Dot-Based Fluorescence Turn-On Metal Ion Sensors in Live Cells

ACS Applied Materials and Interfaces

Volumn 8, Issue 36, 2016, Pages 23953-23962

  Dhenadhayalan, Namasivayam ^a,b   Lee, Hsin Lung ^a,b   Yadav, Kanchan ^a,b   Lin, King Chuen ^a,b   Lin, Yih Tyng ^c   Chang, A H H ^c  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b INSTITUTE OF ATOMIC AND MOLECULAR SCIENCES   (Taiwan)

^c NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

aza crown ether; bioimaging; metal ion; photoinduced electron transfer; sensors; silicon quantum dots

Indexed keywords

CALCIUM; CROWN ETHERS; ELECTRON TRANSITIONS; ELECTRONS; ETHERS; FLUORESCENCE; LIGANDS; MANGANESE; METAL IONS; NANOCRYSTALS; NEGATIVE IONS; SEMICONDUCTOR QUANTUM DOTS; SENSORS; SILICON;

AZA-CROWN-ETHER; BIO-IMAGING; ELECTRON-HOLE RECOMBINATION; FLUORESCENCE SUPPRESSION; MULTIPLE SENSOR SYSTEMS; PHOTO-INDUCED ELECTRON TRANSFER; SELECTIVITY AND SENSITIVITY; SILICON QUANTUM DOTS;

METALS;

CROWN ETHER; ION; METAL; QUANTUM DOT; SILICON;

CELL SURVIVAL;

CELL SURVIVAL; CROWN ETHERS; IONS; METALS; QUANTUM DOTS; SILICON;

EID: 84987738953     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.6b07789     Document Type: Article

References (70)

1. Silvi, S.; Credi, A. Luminescent Sensors Based on Quantum Dot-Molecule Conjugates Chem. Soc. Rev. 2015, 44, 4275-4289 10.1039/C4CS00400K
2. Frasco, M. F.; Chaniotakis, N. Semiconductor Quantum Dots in Chemical Sensors and Biosensors Sensors 2009, 9, 7266-7286 10.3390/s90907266
3. Freeman, R.; Willner, I. Optical Molecular Sensing with Semiconductor Quantum Dots (QDs) Chem. Soc. Rev. 2012, 41, 4067-4085 10.1039/c2cs15357b
4. Tyrakowski, C. M.; Snee, P. T. A Primer on the Synthesis, Water-Solubilization, and Functionalization of Quantum Dots, Their Use as Biological Sensing Agents, and Present Status Phys. Chem. Chem. Phys. 2014, 16, 837-855 10.1039/C3CP53502A
5. Wu, P.; Zhao, T.; Wang, S.; Hou, X. Semiconductor Quantum Dots-Based Metal Ion Probes Nanoscale 2014, 6, 43-64 10.1039/C3NR04628A
6. Wegner, K. D.; Hildebrandt, N. Quantum Dots: Bright and Versatile In Vitro and In Vivo Fluorescence Imaging Biosensors Chem. Soc. Rev. 2015, 44, 4792-4834 10.1039/C4CS00532E
7. Tu, C.-C.; Chen, K.-P.; Yang, T.-A.; Chou, M.-Y.; Lin, L. Y.; Li, Y.-K. Silicon Quantum Dot Nanoparticles with Antifouling Coatings for Immunostaining on Live Cancer Cells ACS Appl. Mater. Interfaces 2016, 8, 13714-13723 10.1021/acsami.6b02318
8. Gu, L.; Hall, D. J.; Qin, Z. T.; Anglin, E.; Joo, J.; Mooney, D. J.; Howell, S. B.; Sailor, M. J. In Vivo Time-Gated Fluorescence Imaging with Biodegradable Luminescent Porous Silicon Nanoparticles Nat. Commun. 2013, 4, 2326 10.1038/ncomms3326
9. Wu, S.; Zhong, Y.; Zhou, Y.; Song, B.; Chu, B.; Ji, X.; Wu, Y.; Su, Y.; He, Y. Biomimetic Preparation and Dual-Color Bioimaging of Fluorescent Silicon Nanoparticles J. Am. Chem. Soc. 2015, 137, 14726-14732 10.1021/jacs.5b08685
10. McVey, B. F. P.; Tilley, R. D. Solution Synthesis, Optical Properties, and Bioimaging Applications of Silicon Nanocrystals Acc. Chem. Res. 2014, 47, 3045-3051 10.1021/ar500215v
11. Cheng, X. Y.; Lowe, S. B.; Reece, P. J.; Gooding, J. J. Colloidal Silicon Quantum Dots: From Preparation to the Modification of Self-Assembled Monolayers (SAMs) for Bio-Applications Chem. Soc. Rev. 2014, 43, 2680-2700 10.1039/c3cs60353a
12. Zhong, Y.; Sun, X.; Wang, S.; Peng, F.; Bao, F.; Su, Y.; Li, Y.; Lee, S.-T.; He, Y. Facile, Large-Quantity Synthesis of Stable, Tunable-Color Silicon Nanoparticles and Their Application for Long-Term Cellular Imaging ACS Nano 2015, 9, 5958-5967 10.1021/acsnano.5b00683
13. Liu, J.; Erogbogbo, F.; Yong, K. T.; Ye, L.; Liu, J.; Hu, R.; Chen, H.; Hu, Y.; Yang, Y.; Yang, J.; Roy, I.; Karker, N. A.; Swihart, M. T.; Prasad, P. N. Assessing Clinical Prospects of Silicon Quantum Dots: Studies in Mice and Monkeys ACS Nano 2013, 7, 7303-7310 10.1021/nn4029234
14. Ji, X. Y.; Peng, F.; Zhong, Y. L.; Su, Y. Y.; Jiang, X. X.; Song, C. X.; Yang, L.; Chu, B. B.; Lee, S. T.; He, Y. Highly Fluorescent, Photostable, and Ultrasmall Silicon Drug Nanocarriers for Long-Term Tumor Cell Tracking and In-Vivo Cancer Therapy Adv. Mater. 2015, 27, 1029-1034 10.1002/adma.201403848
15. Peng, F.; Su, Y. Y.; Zhong, Y. L.; Fan, C. H.; Lee, S. T.; He, Y. Silicon Nanomaterials Platform for Bioimaging, Biosensing, and Cancer Therapy Acc. Chem. Res. 2014, 47, 612-623 10.1021/ar400221g
16. Erogbogbo, F.; Yong, K. T.; Roy, I.; Hu, R.; Law, W. C.; Zhao, W. W.; Ding, H.; Wu, F.; Kumar, R.; Swihart, M. T.; Prasad, P. N. In Vivo Targeted Cancer Imaging, Sentinel Lymph Node Mapping and Multi-channel Imaging with Biocompatible Silicon Nanocrystals ACS Nano 2011, 5, 413-423 10.1021/nn1018945
17. Rosso-Vasic, M.; Spruijt, E.; Popovic, Z.; Overgaag, K.; van Lagen, B.; Grandidier, B.; Vanmaekelbergh, D.; Dominguez-Gutierrez, D.; De Cola, L.; Zuilhof, H. Amine-Terminated Silicon Nanoparticles: Synthesis, Optical Properties and Their Use in Bioimaging J. Mater. Chem. 2009, 19, 5926-5933 10.1039/b902671a
18. Valeur, B.; Leray, I. Design Principles of Fluorescent Molecular Sensors for Cation Recognition Coord. Chem. Rev. 2000, 205, 3-40 10.1016/S0010-8545(00)00246-0
19. Wu, J.; Liu, W.; Ge, J.; Zhang, H.; Wang, P. New Sensing Mechanisms for Design of Fluorescent Chemosensors Emerging in Recent Years Chem. Soc. Rev. 2011, 40, 3483-3495 10.1039/c0cs00224k
20. Kim, J. S.; Quang, D. T. Calixarene-Derived Fluorescent Probes Chem. Rev. 2007, 107, 3780-3799 10.1021/cr068046j
21. 2+ Chem. Soc. Rev. 2010, 39, 1996-2006 10.1039/b916287a
22. Martinez-Manez, R.; Sancenon, F. Fluorogenic and Chromogenic Chemosensors and Reagents for Anions Chem. Rev. 2003, 103, 4419-4476 10.1021/cr010421e
23. Englich, F. V.; Foo, T. C.; Richardson, A. C.; Ebendorff-Heidepriem, H.; Sumby, C. J.; Monro, T. M. Photoinduced Electron Transfer Based Ion Sensing within an Optical Fiber Sensors 2011, 11, 9560-9572 10.3390/s111009560
24. Bergonzi, R.; Fabbrizzi, L.; Licchelli, M.; Mangano, C. Molecular Switches of Fluorescence Operating Through Metal Centred Redox Couples Coord. Chem. Rev. 1998, 170, 31-46 10.1016/S0010-8545(98)00069-1
25. Kulatilleke, C. P.; de Silva, S. A.; Eliav, Y. A Coumarin Based Fluorescent Photoinduced Electron Transfer Cation Sensor Polyhedron 2006, 25, 2593-2596 10.1016/j.poly.2006.03.020
26. Ushakov, E. N.; Alfimov, M. V.; Gromov, S. P. Crown Ether-Based Optical Molecular Sensors and Photocontrolled Ionophores Makrogeterotsikly 2010, 3, 189-200 10.6060/mhc2010.4.189
27. Singh, N.; Mulrooney, R. C.; Kaur, N.; Callan, J. F. Fluorescent Recognition of Potassium and Calcium Ions Using Functionalised CdSe/ZnS Quantum Dots J. Fluoresc. 2009, 19, 777-782 10.1007/s10895-009-0474-y
28. 3+ Fluorescence Turn-On Sensors and for Aggregation Induced Emissions J. Mater. Chem. A 2013, 1, 1310-1318 10.1039/C2TA00574C
29. Bianchi, A.; Delgado-Pinar, E.; Garcia-Espana, E.; Giorgi, C.; Pina, F. Highlights of Metal Ion-Based Photochemical Switches Coord. Chem. Rev. 2014, 260, 156-215 10.1016/j.ccr.2013.09.023
30. Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M. New Fluorescent Chemosensors for Metal Ions in Solution Coord. Chem. Rev. 2012, 256, 170-192 10.1016/j.ccr.2011.09.010
31. 2+ Ions by Schiff Base Chemosensor: Effect of Diamine Structural Rigidity and Solvent RSC Adv. 2014, 4, 41565-41571 10.1039/C4RA05827E
32. + Ion RSC Adv. 2015, 5, 4926-4933 10.1039/C4RA10925B
33. He, H.; Mortellaro, M. A.; Leiner, M. J. P.; Fraatz, R. J.; Tusa, J. K. A Fluorescent Sensor with High Selectivity and Sensitivity for Potassium in Water J. Am. Chem. Soc. 2003, 125, 1468-1469 10.1021/ja0284761
34. 3+ Based on Rhodamine B and a 4, 13-Diaza-18-Crown 6-Ether Conjugate RSC Adv. 2014, 4, 2563-2567 10.1039/C3RA46237D
35. III-amplified Fluorescence J. Am. Chem. Soc. 2005, 127, 13522-13529 10.1021/ja050652t
36. Lochman, L.; Svec, J.; Roh, J.; Novakova, V. The Role of the Size of Aza-Crown Recognition Moiety in Azaphthalocyanine Fluorescence Sensors for Alkali and Alkaline Earth Metal Cations Dyes Pigm. 2015, 121, 178-187 10.1016/j.dyepig.2015.05.020
37. Bakthavatsalam, S.; Sarkar, A.; Rakshit, A.; Jain, S.; Kumar, A.; Datta, A. Tuning Macrocycles to Design 'Turn-On' Fluorescence Probes for Manganese (II) Sensing in Live Cells Chem. Commun. 2015, 51, 2605-2608 10.1039/C4CC09542A
38. 2O Chem. Commun. 2006, 263-265 10.1039/B512677K
39. Han, C.; Li, H. Host-Molecule-Coated Quantum Dots as Fluorescent Sensors Anal. Bioanal. Chem. 2010, 397, 1437-1444 10.1007/s00216-009-3361-0
40. Banerjee, S.; Kar, S.; Santra, S. A Simple Strategy for Quantum Dot Assisted Selective Detection of Cadmium Ions Chem. Commun. 2008, 3037-3039 10.1039/b803166e
41. Ruedas-Rama, M. J.; Hall, E. A. H. Azamacrocycle Activated Quantum Dot for Zinc Ion Detection Anal. Chem. 2008, 80, 8260-8268 10.1021/ac801396y
42. Lin, S.-Y.; Chen, C.-H.; Lin, M.-C.; Hsu, H.-F. A Cooperative Effect of Bifunctionalized Nanoparticles on Recognition: Sensing Alkali Ions by Crown and Carboxylate Moieties in Aqueous Media Anal. Chem. 2005, 77, 4821-4828 10.1021/ac050443r
43. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652 10.1063/1.464913
44. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789 10.1103/PhysRevB.37.785
45. Hay, P. J.; Wadt, W. R. Ab Initio Effective Core Potentials for Molecular Calculations. Potentials for K to Au Including the Outermost Core Orbitals J. Chem. Phys. 1985, 82, 299-310 10.1063/1.448975
46. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.,: Wallingford, CT, 2009.
47. Jin, H.; Nam, J.; Park, J.; Jung, S.; Im, K.; Hur, J.; Park, J.-J.; Kim, J.-M.; Kim, S. Strong Polyelectrolyte Quantum Dot Surface for Stable Bioconjugation and Layer-By-Layer Assembly Applications Chem. Commun. 2011, 47, 1758-1760 10.1039/C0CC04524A
48. Shiohara, A.; Prabakar, S.; Faramus, A.; Hsu, C.-Y.; Lai, P.-S.; Northcote, P. T.; Tilley, R. D. Sized Controlled Synthesis, Purification, and Cell Studies with Silicon Quantum Dots Nanoscale 2011, 3, 3364-3370 10.1039/c1nr10458f
49. Rosso-Vasic, M.; Spruijt, E.; van Lagen, B.; De Cola, L.; Zuilhof, H. Alkyl-Functionalized Oxide-Free Silicon Nanoparticles: Synthesis and Optical Properties Small 2008, 4, 1835-1841 10.1002/smll.200800066
50. Warner, J. H.; Rubinsztein-Dunlop, H.; Tilley, R. D. Surface Morphology Dependent Photoluminescence from Colloidal Silicon Nanocrystals J. Phys. Chem. B 2005, 109, 19064-19067 10.1021/jp054565z
51. Warner, J. H.; Hoshino, A.; Yamamoto, K.; Tilley, R. D. Water Soluble Photoluminescent Silicon Quantum Dots Angew. Chem., Int. Ed. 2005, 44, 4550-4554 10.1002/anie.200501256
52. Dhenadhayalan, N.; Lin, K.-C. Chemically Induced Fluorescence Switching of Carbon-Dots and Its Multiple Logic Gate Implementation Sci. Rep. 2015, 5, 10012 10.1038/srep10012
53. Mao, X.; Su, H.; Tian, D.; Li, H.; Yang, R. Bipyrene-Functionalized Graphene as a "Turn-On" Fluorescence Sensor for Manganese (II) Ions in Living cells ACS Appl. Mater. Interfaces 2013, 5, 592-597 10.1021/am3026807
54. 3+ Sens. Actuators, B 2014, 201, 535-544 10.1016/j.snb.2014.05.035
55. Kim, K. B.; Park, G. J.; Kim, H.; Song, E. J.; Bae, J. M.; Kim, C. A Novel Colorimetric Chemosensor for Multiple Target Ions in Aqueous Solution: Simultaneous Detection of Mn(II) and Fe(II) Inorg. Chem. Commun. 2014, 46, 237-240 10.1016/j.inoche.2014.06.009
56. 2+ Based on Bis(N-salicylidene)ethylenediamine in Pure Aqueous Solution Chem. Lett. 2011, 40, 1082-1084 10.1246/cl.2011.1082
57. 2+ Ions by Simple Schiff Base Chemosensor Spectrochim. Acta, Part A 2015, 136, 1658-1665 10.1016/j.saa.2014.10.061
58. Ma, S.-Y.; Yeh, Y.-C. One-Step Synthesis of Water-Soluble Fluorescent Copper Nanoparticles for Label-Free Detection of Manganese Ions Anal. Methods 2015, 7, 6475-6478 10.1039/C5AY01567G
59. Lee, S. A.; Lee, J. J.; You, G. R.; Choi, Y. W.; Kim, C. Distinction Between Mn(III) and Mn(II) by Using a Colorimetric Chemosensor in Aqueous Solution RSC Adv. 2015, 5, 95618-95630 10.1039/C5RA20396A
60. Adhikari, S.; Ghosh, A.; Sahana, A.; Guria, S.; Das, D. Tailoring Ligand Environment toward Development of Colorimetric and Fluorescence Indicator for Biological Mn(II) Imaging Anal. Chem. 2016, 88, 1106-1110 10.1021/acs.analchem.5b03551
61. 2+ Based on Supramolecular Silver Nanoparticle Clusters New J. Chem. 2014, 38, 2237-2240 10.1039/c3nj01593a
62. 2+ Ions by a Calix[4]Arene Diamide Derivative Tetrahedron Lett. 2007, 48, 5397-5400 10.1016/j.tetlet.2007.06.010
63. 2+: Crystallographic Evidence, DFT Calculation and Its Use for Quantitative Determination of Magnesium in Drinking Water Dalton Trans. 2015, 44, 2755-2762 10.1039/C4DT03068K
64. Liu, S.; Wang, H.; Cheng, Z.; Liu, H. Hexametaphosphate-Capped Quantum Dots as Fluorescent Probes for Detection of Calcium Ion and Fluoride Sens. Actuators, B 2016, 232, 306-312 10.1016/j.snb.2016.03.077
65. Lin, C.-F.; Liu, Y.-H.; Lai, C.-C.; Peng, S.-M.; Chiu, S.-H. An Extremely Stable Host-Guest Complex That Functions as a Fluorescence Probe for Calcium Ions Chem.-Eur. J. 2006, 12, 4594-4599 10.1002/chem.200600090
66. Hurtado, P.; Hortal, A. R.; Gamez, F.; Hamad, S.; Martinez-Haya, B. Gas-Phase Complexes of Cyclic and Linear Polyethers with Alkali Cations Phys. Chem. Chem. Phys. 2010, 12, 13752-13758 10.1039/c0cp00595a
67. Izatt, R. M.; Christensen, J. J., Eds.; Syntheric Multidenrate Macrocyclic Compounds; Academic Press: New York, 1978.
68. Maleknia, S.; Brodbelt, J. Cavity-Size-Dependent Dissociation of Crown Ether/ Ammonium Ion Complexes in the Gas Phase J. Am. Chem. Soc. 1993, 115, 2837-2843 10.1021/ja00060a034
69. Gaft, M.; Reisfeld, R.; Panczer, G. Modern Luminescence Spectroscopy of Minerals and Materials; Springer: New York, 2015.
70. 2+ Bound to a Soluble β-Galactoside Binding Hepatic Lectin FEBS Lett. 1995, 368, 285-288 10.1016/0014-5793(95)00673-W