Functionalized Carbon Quantum Dots with Dopamine for Tyrosinase Activity Monitoring and Inhibitor Screening: In Vitro and Intracellular Investigation

ACS Applied Materials and Interfaces

Volumn 7, Issue 42, 2015, Pages 23564-23574

  Chai, Lujing ^a   Zhou, Jin ^b   Feng, Hui ^a   Tang, Cong ^a   Huang, Yuanyuan ^a   Qian, Zhaosheng ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

carbon quantum dots; fluorometric assay; inhibitor screening; intracellular imaging; tyrosinase

Indexed keywords

AMINES; BIOCOMPATIBILITY; DIAGNOSIS; FLUORESCENCE; FUNCTIONAL MATERIALS; NANOCRYSTALS; NEUROPHYSIOLOGY; QUENCHING;

CARBON QUANTUM DOTS; FLUOROMETRIC ASSAY; INHIBITOR SCREENINGS; INTRACELLULAR IMAGING; TYROSINASE;

SEMICONDUCTOR QUANTUM DOTS;

CARBON; DOPAMINE; MONOPHENOL MONOOXYGENASE; QUANTUM DOT;

ANTAGONISTS AND INHIBITORS; CHEMISTRY; ELECTRON TRANSPORT; FLUORESCENCE; GENETIC PROCEDURES; ISOLATION AND PURIFICATION; OXIDATION REDUCTION REACTION;

BIOSENSING TECHNIQUES; CARBON; DOPAMINE; ELECTRON TRANSPORT; FLUORESCENCE; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; QUANTUM DOTS;

EID: 84946031282     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b06711     Document Type: Article

References (49)

1. Seo, S.-Y.; Sharma, V. K.; Sharma, N. Mushroom Tyrosinase: Recent Prospects J. Agric. Food Chem. 2003, 51, 2837-2853 10.1021/jf020826f
2. Lin, J. Y.; Fisher, D. E. Melanocyte Biology and Skin Pigmentation Nature 2007, 445, 843-850 10.1038/nature05660
3. Slominski, A.; Tobin, D. J.; Shibahara, S.; Wortsman, J. Melanin Pigmentation in Mammalian Skin and Its Hormonal Regulation Physiol. Rev. 2004, 84, 1155-1228 10.1152/physrev.00044.2003
4. Angeletti, C.; Khomitch, V.; Halaban, R.; Rimm, D. L. Novel Tryamide-Based Tyrosinase Assay for the Detection of Melanoma Cells in Cytological Preparations Diagn. Cytopathol. 2004, 31, 33-37 10.1002/dc.20051
5. Baharav, E.; Merimski, O.; Shoenfeld, Y.; Zigelman, R.; Gilbrud, B.; Yecheskel, G.; Youinou, P.; Fishman, P. Tyrosinase As an Autoantigen in Patients with Vitiligo Clin. Exp. Immunol. 1996, 105, 84-88 10.1046/j.1365-2249.1996.d01-727.x
6. Friedman, M. Food Browning and Its Prevention: an Overview J. Agric. Food Chem. 1996, 44, 631-653 10.1021/jf950394r
7. Boyer, R. F. Spectrophotometric Assay of Polyphenoloxidase Activity. A special Project in Enzyme Characterization J. Chem. Educ. 1977, 54, 585-586 10.1021/ed054p585
8. Park, Y.-D.; Lee, J.-R.; Park, K.-H.; Hahn, H.-S.; Hahn, M.-J.; Yang, J.-M. A New Continuous Spectrophotometric Assay Method for DOPA Oxidase Activity of Tyrosinase J. Protein Chem. 2003, 22, 473-480 10.1023/B:JOPC.0000005463.21302.cd
9. Kong, F. J.; Liu, H. F.; Dong, J.; Qian, W. P. Growth-Sensitive Gold Nanoshells Precursor Nanocomposites for the Detection of L-DOPA and Tyrosinase Activity Biosens. Bioelectron. 2011, 26, 1902-1907 10.1016/j.bios.2010.03.029
10. Li, S.; Mao, L. Y.; Tian, Y. P.; Wang, J.; Zhou, N. D. Spectrophotometric Detection of Tyrosinase Activity Based on Boronic Acid-Functionalized Gold Nanoparticles Analyst 2012, 137, 823-825 10.1039/c2an16085d
11. Yildiz, H. B.; Freeman, R.; Gill, R.; Willner, I. Electrochemcial, Photoelctrochemical, and Piezoelectric Analysis of Tyrosinase Activity by Functionalized Nanoparticles Anal. Chem. 2008, 80, 2811-2816 10.1021/ac702401v
12. Feng, X. L.; Feng, F. D.; Yu, M. H.; He, F.; Xu, Q. L.; Tang, H. W.; Wang, S.; Li, Y. L.; Zhu, D. B. Synthesis of a New Water-Soluble Oligo(phenylenevinylenen) Containing a Tyrosine Moiety for Tyrosinase Activity Detection Org. Lett. 2008, 10, 5369-5372 10.1021/ol802210s
13. Li, X. H.; Shi, W.; Chen, S. M.; Jia, J.; Ma, H. M.; Wolfbeis, O. S. A Near-infrared Fluorescent Probe for Monitoring Tyrosinase Activity Chem. Commun. 2010, 46, 2560-2562 10.1039/c001225d
14. Yan, S. Y.; Huang, R.; Wang, C. C.; Zhou, Y. M.; Wang, J. Q.; Fu, B. S.; Weng, X. C.; Zhou, X. A Two-photon Fluorescent Probe for Intracellular Detection of Tyrosinase Activity Chem.-Asian J. 2012, 7, 2782-2785 10.1002/asia.201200762
15. Wang, C. C.; Yan, S. Y.; Huang, R.; Feng, S.; Fu, B. S.; Weng, X. C.; Zhou, X. A Turn-on Fluorescent Probe for Detection of Tyrosinase Activity Analyst 2013, 138, 2825-2828 10.1039/c3an00272a
16. Gill, R.; Freeman, R.; Xu, J.-P.; Willner, I.; Winograd, S.; Shweky, I.; Banin, U. Probing Biocatalytic Transfromations with CdSe-ZnS QDs J. Am. Chem. Soc. 2006, 128, 15376-15377 10.1021/ja066636t
17. Zhu, X. L.; Hu, J.; Zhao, Z. H.; Sun, M. J.; Chi, X. Q.; Wang, X. M.; Gao, J. H. Kinetic and Sensitivie Analysis of Tyrosinase Activity Using Electron Transfer Complexes: in Vitro and Intracellular Study Small 2015, 11, 862-879 10.1002/smll.201401595
18. Liu, X. Q.; Wang, F. A.; Niazov-Elkan, A.; Guo, W. W.; Willner, I. Probing Biocatalytic Transformations with Luminescent DNA/Silver Nanoclusters Nano Lett. 2013, 13, 309-314 10.1021/nl304283c
19. Teng, Y.; Jia, X. F.; Li, J.; Wang, E. K. Ratiometric Fluorescence Detection of Tyrosinase Activity and Dopamine Using Thiolate-protected Gold Nanoclusters Anal. Chem. 2015, 87, 4897-4902 10.1021/acs.analchem.5b00468
20. Baker, S. N.; Baker, G. A. Luminescent Carbon Nanodots: Emergent Nanolights Angew. Chem., Int. Ed. 2010, 49, 6726-6744 10.1002/anie.200906623
21. Shen, J. H.; Zhu, Y. H.; Yang, X. L.; Li, C. Z. Graphene Qauntum Dots: Emergent Nanolighs for Bioimaging, Sensors, Catalysis and Photovoltaic Devices Chem. Commun. 2012, 48, 3686-3699 10.1039/c2cc00110a
22. Zhao, A. D.; Chen, Z. W.; Zhao, C. Q.; Gao, N.; Ren, J. S.; Qu, X. G. Recent Advances in Bioapplications of C-dots Carbon 2015, 85, 309-327 10.1016/j.carbon.2014.12.045
23. Zheng, X. T.; Ananthanarayanan, A.; Luo, K. Q.; Chen, P. Glowing Graphene Quantum Dots and Carbon Dots: Properties, Syntheses, and Biological Applications Small 2015, 11, 1620-1636 10.1002/smll.201402648
24. Lim, S. Y.; Shen, W.; Gao, Z. Q. Carbon Quantum Dots and Their Applications Chem. Soc. Rev. 2015, 44, 362-381 10.1039/C4CS00269E
25. Qian, Z. S.; Shan, X. Y.; Chai, L. J.; Ma, J. J.; Chen, J. R.; Feng, H. A Universal Fluorescence Sensing Strategy Based on Biocompatible Graphene Quantum Dots and Graphen Oxide for the Detection of DNA Nanoscale 2014, 6, 5671-5674 10.1039/c3nr06583a
26. Qian, Z. S.; Shan, X. Y.; Chai, L. J.; Ma, J. J.; Chen, J. R.; Feng, H. DNA Nanosensor Based on Biocompatible Graphene Quantum Dots and Carbon Nanotubes Biosens. Bioelectron. 2014, 60, 64-70 10.1016/j.bios.2014.04.006
27. Qian, Z. S.; Shan, X. Y.; Chai, L. J.; Chen, J. R.; Feng, H. Simultaneous Detection of Multiple DNA Targets by Integrating Dual-color Graphene Quantum Dots Nanoprobes and Carbon Nanotubes Chem.-Eur. J. 2014, 20, 16065-16069 10.1002/chem.201404730
28. Noh, E.-H.; Ko, H. Y.; Lee, C. H.; Jeong, M.-S.; Chang, Y. W.; Kim, S. Carbon Nanodot-Based Self-delivering MicorRNA Sensor to Visualize MicroRNA124a Expression During Neurogenesis J. Mater. Chem. B 2013, 1, 4438-4445 10.1039/c3tb20710b
29. Li, X.; Zhu, S. J.; Xu, B.; Ma, K.; Zhang, J. H.; Yang, B.; Tian, W. J. Self-assembled Graphene Quantum Dots Induced by Cytochrome c: A Novel Biosensor for Trypsin with Remarkable Fluorescence Enhancement Nanoscale 2013, 5, 7776-7779 10.1039/c3nr00006k
30. Qian, Z. S.; Shan, X. Y.; Chai, L. J.; Chen, J. R.; Feng, H. Dual-colored Graphene Quantum Dots-labeled Nanoprobes/graphene oxide: Functional Carbon Materials for Respective and Simultaneous Detection of DNA and Thrombin Nanotechnology 2014, 25, 415501 10.1088/0957-4484/25/41/415501
31. Liu, S. Y.; Zhao, N.; Cheng, Z.; Liu, H. G. Amino-functionalized Green Fluorescent Carbon Dots as Surface Energy Transfer Biosensors for Hyaluronidase Nanoscale 2015, 7, 6836-6842 10.1039/C5NR00070J
32. Qian, Z. S.; Chai, L. J.; Huang, Y. Y.; Tang, C.; Shen, J. J.; Chen, J. R.; Feng, H. A Real-time Fluorescent Assay for the Detection of Alkaline Phosphatase Activity Based on Carbon Quantum Dots Biosens. Bioelectron. 2015, 68, 675-680 10.1016/j.bios.2015.01.068
33. Qian, Z. S.; Chai, L. J.; Tang, C.; Huang, Y. Y.; Chen, J. R.; Feng, H. Carbon Quantum Dots-based Recyclabe Real-time Fluorescence Assay for Alkaline Phosphatase with Adenosine Triphosphate as Substrate Anal. Chem. 2015, 87, 2966-2973 10.1021/ac504519b
34. Medintz, I. L.; Stewart, M. H.; Trammell, S. A.; Susumu, K.; Delehanty, J. B.; Mei, B. C.; Melinger, J. S.; Blanco-Canosa, J. B.; Dawson, P. E.; Mattoussi, H. Quantum-dot/dopamine Bioconjugates Function as Redox Coupled Assemblies for in Vitro and Intracellular pH Sensing Nat. Mater. 2010, 9, 676-684 10.1038/nmat2811
35. Ji, X.; Palui, G.; Avellini, T.; Na, H. B.; Yi, C. Y.; Knappenberger, K. L., Jr.; Mattoussi, H. On the pH-dependent Quenching of Quantum Dot Photoluminescence by Redox Active Dopamine J. Am. Chem. Soc. 2012, 134, 6006-6017 10.1021/ja300724x
36. Ma, W.; Liu, H.-T.; Long, Y.-T. Monitoring Dopamine Quinone-induced Dopaminergic Neurotoxicity Using Dopamine Functionalized Quantum Dots ACS Appl. Mater. Interfaces 2015, 7, 14352-14358 10.1021/acsami.5b03044
37. Ma, W.; Liu, H.-T.; He, X.-P.; Zang, Y.; Li, J.; Chen, G.-R.; Tian, H.; Long, Y.-T. Target-Specific Imaging of Transmembrance Receptors Using Quinonyl Glycosides Functionalized Quantum Dots Anal. Chem. 2014, 86, 5502-5507 10.1021/ac501463u
38. Ma, W.; Long, Y.-T. Quinone/Hydroquinone-functionalized Biointerfaces for Biological Applications from Macro- to Nano-scale Chem. Soc. Rev. 2014, 43, 30-41 10.1039/C3CS60174A
39. Ma, W.; Qin, L.-X.; Liu, F.-T.; Gu, Z.; Wang, J.; Pan, Z. G.; James, T. D.; Long, Y.-T. Ubiquinone-quantum Dot Bioconjugates for in Vitro and Intracellular Complex I Sensing Sci. Rep. 2013, 3, 1537 10.1038/srep01537
40. ·- Sensing Chem. Commun. 2011, 47, 8539-8541 10.1039/c1cc13160e
41. Qin, L.-X.; Ma, W.; Li, D.-W.; Li, Y.; Chen, X. Y.; Kraatz, H.-B.; James, T. D.; Long, Y.-T. Coenzyme Functionalized CdTe/ZnS Quantum Dots for Reactive Oxygen Species (ROS) Imaging Chem.-Eur. J. 2011, 17, 5262-5271 10.1002/chem.201003749
42. Funayama, M.; Arakawa, H.; Yamamoto, R.; Nishino, T.; Shin, T.; Murao, S. Effects of α- and β-arbutin on Activity of Tyrosinase from Mushroom and Mouse Melanoma Biosci., Biotechnol., Biochem. 1995, 59, 143-144 10.1271/bbb.59.143
43. Jin, Y. H.; Lee, S. J.; Chung, M. H.; Park, J. H.; Park, Y. I.; Cho, T. H.; Lee, S. K. Aloesin and Arbutin Inhibit Tyrosinase Activity in a Synergistic Manner via a Different Action Mechanism Arch. Pharmacal Res. 1999, 22, 232-236 10.1007/BF02976355
44. Sugimoto, K.; Nishimura, T.; Nomura, K.; Sugimoto, K.; Kuriki, T. Syntheses of Arbutin-α-glycosides and a Comparison of Their Inhibitory Effects with Those of α-arbutin and Arbutin on Human Tyrosinase Chem. Pharm. Bull. 2003, 51, 798-801 10.1248/cpb.51.798
45. Gauillard, F.; Richardforget, F.; Nicolas, J. New Spetrophotometric Assay for Polyphenol Oxidase Activity Anal. Biochem. 1993, 215, 59-65 10.1006/abio.1993.1554
46. Baron, R.; Zayats, M.; Willner, I. Dopamine-, L-DOPA-, Adrenaline-, and Noradrenaline-induced Growth of Au Nanoparticles: Assays for the Detection of Neurotransmitters and of Tyrosinase Activity Anal. Chem. 2005, 77, 1566-1571 10.1021/ac048691v
47. White, R.; Hu, F. Characteristics of Tyrosinase in B16 Melanoma J. Invest. Dermatol. 1977, 68, 272-276 10.1111/1523-1747.ep12494214
48. Chai, L. J.; Zhou, J.; Feng, H.; Lin, J. J.; Qian, Z. S. A Reversible Fluorescence Nanoswitch Based Carbon Quantum Dots Nanoassembly for Detection of Pyrophosphate Ion Sens. Actuators, B 2015, 220, 138-145 10.1016/j.snb.2015.05.070
49. Tafani, M.; Cohn, J. A.; Karpinich, N. O.; Rothman, R. J.; Russo, M. A.; Farber, J. L. Regulation of Intracellular pH Mediates Bax Activation in HeLa cells Treated with Staurosporine or Tumor Necrosis Factor-α J. Biol. Chem. 2002, 277, 49569-49576 10.1074/jbc.M208915200