Self-assembled near-infrared dye nanoparticles as a selective protein sensor by activation of a dormant fluorophore

Journal of the American Chemical Society

Volumn 136, Issue 38, 2014, Pages 13233-13239

  Anees, Palapuravan ^a   Sreejith, Sivaramapanicker ^a   Ajayaghosh, Ayyappanpillai ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BLOOD; BODY FLUIDS; DIAGNOSIS; DYES; FLUORESCENCE; FLUOROPHORES; INFRARED DEVICES; METAL NANOPARTICLES; MOLECULES; NANOPARTICLES;

CLINICAL DIAGNOSTICS; DETECTION AND QUANTIFICATIONS; FLUORESCENT NANOPARTICLES; GREEN FLUORESCENCE; HUMAN SERUM ALBUMINS; MOLECULAR FLUOROPHORES; NONCOVALENT BINDING; POLYMERIC NANOPARTICLES;

PROTEINS;

BROMELAIN; CYSTEINE; DITHIOTHREITOL; FLUORESCENT DYE; GLUTATHIONE; GLUTATHIONE REDUCTASE; HEMOGLOBIN; HOMOCYSTEINE; HUMAN SERUM ALBUMIN; MERCAPTAMINE; MERCAPTOETHANOL; NANOPARTICLE; SQUARAINE; THIOGLYCOLIC ACID; THIOL; UNCLASSIFIED DRUG; CYCLOBUTANE DERIVATIVE; PHENOL DERIVATIVE; SERUM ALBUMIN; THIOL DERIVATIVE;

ABSORPTION; ARTICLE; BLOOD SAMPLING; COMPLEX FORMATION; CONJUGATION; COVALENT BOND; HIGH TEMPERATURE; HUMAN; HUMAN TISSUE; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR SENSOR; NEAR INFRARED SPECTROSCOPY; NORMAL HUMAN; PARTICLE SIZE; PH; STATIC ELECTRICITY; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED RADIATION; SPECTROFLUOROMETRY;

CYCLOBUTANES; FLUORESCENT DYES; HUMANS; INFRARED RAYS; MODELS, MOLECULAR; NANOPARTICLES; PHENOLS; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; SULFHYDRYL COMPOUNDS;

EID: 84921037012     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja503850b     Document Type: Article

References (90)

1. (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
2. Molecular Self-Assembly: Advances and Applications; Dequan, A. L., Ed.; Pan Stanford Publishing Pte Ltd.: Singapore, 2012.
3. (c) Whitesides, G. M.; Grzybowski, B. Science 2002, 295, 2418.
4. (d) Kinbara, K.; Aida, T. Chem. Rev. 2005, 105, 1377.
5. (e) Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644.
6. (f) Aida, T.; Meijer, E. W.; Stupp, S. I. Science 2012, 335, 813.
7. (g) Busseron, E.; Ruff, Y.; Moulin, E.; Giuseppone, N. Nanoscale 2013, 5, 7098.
8. (h) Babu, S. S.; Praveen, V. K.; Ajayaghosh, A. Chem. Rev. 2014, 114, 1973.
9. (i) Zhang, S. Nat. Biotechnol. 2007, 2, 318.
10. (j) Boekhoven, J.; Stupp, S. I. Adv. Mater. 2014, 26, 1642.
11. (k) Zhai, D.; Xu, W.; Zhang, L.; Chang, Y. T. Chem. Soc. Rev. 2014, 43, 2402.
12. Kartha, K. K.; Babu, S. S.; Srinivasan, S.; Ajayaghosh, A. J. Am. Chem. Soc. 2012, 134, 4834.
13. (a) Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620.
14. (b) Noble, J.; Porter, R.; Horgan, A. Chem. Soc. Rev. 2011, 40, 1547.
15. (b) Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973.
16. (d) Vendrell, M.; Zhai, D.; Er, J. C.; Chang, Y. T. Chem. Rev. 2012, 112, 4391.
17. (e) Saha, K.; Agasti, S. S.; Kim, C.; Li, X.; Rotello, V. M. Chem. Rev. 2012, 112, 2739.
18. (f) Mizakami, S.; Hori, Y.; Kikuchi, K. Acc. Chem. Res. 2014, 47, 247.
19. (a) Oh, K. J.; Cash, K. J.; Plaxco, K. W. J. Am. Chem. Soc. 2006, 128, 14018.
20. (b) Thurley, S.; Roglin, L.; Seitz, O. J. Am. Chem. Soc. 2007, 129, 12693.
21. (a) Wang, B.; Yu, C. Angew. Chem., Int. Ed. 2010, 49, 1485.
22. (b) Tang, D.; Liao, D.; Zhu, Q.; Wang, F.; Jiao, H.; Zhang, Y.; Yu, C. Chem. Commun. 2011, 47, 5485.
23. (c) Shi, H.; He, X. X.; Wang, K. M.; Wu, X.; Ye, X. S.; Guo, Q. P.; Tan, W. H.; Qing, Z. H.; Yang, X. H.; Zhou, B. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 3900.
24. Sakabe, M.; Asanuma, D.; Kamiya, M.; Iwatate, R. J.; Hanaoka, K.; Terai, T.; Nagano, T.; Urano, Y. J. Am. Chem. Soc. 2013, 135, 409.
25. (a) Xing, B.; Khanamiryan, A.; Rao, J. H. J. Am. Chem. Soc. 2005, 127, 4158.
26. (b) Shults, M. D.; Imperiali, B. J. Am. Chem. Soc. 2003, 125, 14248.
27. (c) Zhuang, Y. D.; Chiang, P. Y.; Wang, C. W.; Tan, K. T. Angew. Chem., Int. Ed. 2007, 46, 4097.
28. (a) Suzuki, Y.; Yokoyama, K. J. Am. Chem. Soc. 2005, 127, 17799.
29. (b) Yuan, C. X.; Tao, X. T.; Wang, L.; Yang, J. X.; Jiang, M. H. J. Phys. Chem. C 2009, 113, 6809.
30. (c) Ojha, B.; Das, G. Chem. Commun. 2010, 46, 2079.
31. (d) Wang, X.; Wang, X.; Wang, Y.; Guo, Z. Chem. Commun. 2011, 47, 8127.
32. (e) Wang, J.; Liu, H. B.; Park, S.; Kim, S. Y.; Joo, T.; Ha, C. S. RSC Adv. 2012, 2, 4242.
33. (f) Li, H.; Liu, F.; Han, J.; Cai, M.; Sun, S.; Fan, J.; Songa, F.; Peng, X. J. Mater. Chem. B 2013, 1, 693.
34. (g) Peng, L.; Wei, R.; Li, K.; Zhou, Z.; Song, P.; Tong, A. Analyst 2013, 138, 2068.
35. (a) Azagarsamy, M. A.; Sokkalingam, P.; Thayumanavan, S. J. Am. Chem. Soc. 2009, 131, 14184.
36. (b) Yesilyurt, V.; Ramireddy, R.; Azagarsamy, M. A.; Thayumanavan, S. Chem.-Eur. J. 2012, 18, 223.
37. (a) Guo, J.; Zhuang, J.; Wang, F.; Raghupathi, K. R.; Thayumanavan, S. J. Am. Chem. Soc. 2014, 136, 2220.
38. (b) Torres, D. A.; Garzoni, M.; Subrahmanyam, A. V.; Pavan, G. V.; Thayumanavan, S. J. Am. Chem. Soc. 2014, 136, 5385.
39. (a) Takaoka, Y.; Sakamoto, T.; Tsukiji, S.; Narazaki, M.; Matsuda, T.; Tochio, H.; Shirakawa, M.; Hamachi, I. Nat. Chem. 2009, 1, 557.
40. (b) Tsukiji, S.; Miyagawa, M.; Takaoka, Y.; Tamura, T.; Hamachi, I. Nat. Chem. Biol. 2009, 5, 341.
41. (c) Mizusawa, K.; Ishida, Y.; Takaoka, Y.; Miyagawa, M.; Tsukiji, S.; Hamachi, I. J. Am. Chem. Soc. 2010, 132, 7291.
42. (a) Mizusawa, K.; Takaoka, Y.; Hamachi, I. J. Am. Chem. Soc. 2012, 134, 13386.
43. (b) Takaoka, Y.; Ojida, A.; Hamachi, I. Angew. Chem., Int. Ed. 2013, 52, 4088.
44. (c) Hayashi, T.; Hamachi, I. Acc. Chem. Res. 2012, 45, 1460.
45. (a) Miranda, O. R.; You, C. C.; Phillips, R.; Kim, I. B.; Ghosh, P. S.; Bunz, U. H. F.; Rotello, V. M. J. Am. Chem. Soc. 2007, 129, 9856.
46. (b) You, C. C.; Miranda, O. R.; Gider, B.; Ghosh, P. S.; Kim, I. B.; Erdogan, B.; Krovi, S. A.; Bunz, U. H. F.; Rotello, V. M. Nat. Nanotechnol. 2007, 2, 318.
47. (c) De, M.; Rana, S.; Akpinar, H.; Miranda, O. R.; Arvizo, R. R.; Bunz, U. H. F.; Rotello, V. M. Nat. Chem. 2009, 1, 461.
48. (d) Rana, S.; Singla, A. K.; Bajaj, A.; Elci, S. G.; Miranda, O. R.; Mout, R.; Yan, B.; Jirik, F. R.; Rotello, V. M. ACS Nano 2012, 6, 8233.
49. (a) Zhang, Y. Z.; Zhou, B.; Zhang, X. P.; Huang, P.; Li, C. H.; Liu, Y. J. Hazard. Mater. 2009, 163, 1345.
50. (b) Ding, F.; Li, N.; Han, B. Y.; Liu, F.; Zhang, L.; Sun, Y. Dyes Pigm. 2009, 83, 249.
51. (a) Zhu, J.; Li, J. J.; Zhao, J. W. Sens. Actuators, B 2009, 138, 9.
52. (b) Wang, J.; Zhang, Y. Y.; Guo, Y.; Zhang, L.; Xu, R.; Xing, Z. Q.; Wang, S. X.; Zhang, X. D. Dyes Pigm. 2009, 80, 271.
53. (c) Wen, J. H.; Geng, Z. R.; Yin, Y. X.; Wang, Z. L. Dalton Trans. 2011, 40, 9737.
54. (a) Chen, X.; Zhou, Y.; Peng, X.; Yoon, J. Chem. Soc. Rev. 2010, 39, 2120.
55. (b) Zhou, Y.; Yoon, J. Chem. Soc. Rev. 2012, 41, 52.
56. (c) Jung, H. S.; Chen, X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2013, 42, 6019.
57. (a) Yin, C.; Huo, F.; Zhang, J.; Martínez-Mánãz, R.; Yang, Y.; Lv, H.; Li, S. Chem. Soc. Rev. 2013, 42, 6032.
58. (b) Lee, M. H.; Yang, Z.; Lim, C. W.; Lee, Y. H.; Sun, D.; Kang, C.; Kim, J. S. Chem. Rev. 2013, 113, 5071.
59. (c) Yang, Y.; Zhao, Q.; Feng, W.; Li, F. Chem. Rev. 2013, 113, 192.
60. (a) Ajayaghosh, A. Acc. Chem. Res. 2005, 38, 449.
61. (b) Sreejith, S.; Carol, P.; Chithra, P.; Ajayaghosh, A. J. Mater. Chem. 2008, 18, 264.
62. (c) Beverina, L.; Salice, P. Eur. J. Org. Chem. 2010, 1207.
63. (a) Gassensmith, J. J.; Arunkumar, E.; Barr, L.; Baumes, J. M.; DiVittorio, K. M.; Johnson, J. R.; Noll, B. C.; Smith, B. D. J. Am. Chem. Soc. 2007, 129, 15054.
64. (b) Ajayaghosh, A.; Arunkumar, E.; Daub, J. Angew. Chem., Int. Ed. 2002, 41, 1766.
65. (c) Basheer, M. C.; Alex, S.; Thomas, K. G.; Suresh, C. H.; Das, S. Tetrahedron 2006, 62, 605.
66. (d) Ros-Lis, J. V.; Martinez-Manez, R.; Rurack, K.; Sancenon, F.; Soto, J.; Spieles, M. Inorg. Chem. 2004, 43, 5183.
67. (e) Gassensmith, J. J.; Matthys, S.; Lee, J. J.; Wojcik, A.; Kamat, P. V.; Smith, B. D. Chem.-Eur. J. 2010, 16, 2916.
68. (a) Ros-Lis, J. V.; Garcia, B.; Jimenez, D.; Martinez-Manez, R.; Sancenon, F.; Soto, J.; Gonzalvo, F.; Valldecabres, M. C. J. Am. Chem. Soc. 2004, 126, 4064.
69. (b) Hewage, H. S.; Anslyn, E. V. J. Am. Chem. Soc. 2009, 131, 13099.
70. (c) Sreejith, S.; Divya, K. P.; Ajayaghosh, A. Angew. Chem., Int. Ed. 2008, 47, 7883.
71. (a) Suzuki, Y.; Yokoyama, K. Angew. Chem., Int. Ed. 2007, 46, 4097.
72. (b) Jisha, V. S.; Arun, K. T.; Hariharan, M.; Ramaiah, D. J. Am. Chem. Soc. 2006, 128, 6024.
73. (c) Jisha, V. S.; Arun, K. T.; Hariharan, M.; Ramaiah, D. J. Phys. Chem. B 2010, 114, 5912.
74. (d) Xu, Y. Q.; Li, Z. Y.; Malkovskiy, A.; Sun, S. G.; Pang, Y. J. Phys. Chem. B 2010, 114, 8574.
75. (a) Escobedo, J. O.; Rusin, O.; Lim, S.; Strongin, R. M. Curr. Opin. Chem. Biol. 2010, 14, 64.
76. (b) Sreejith, S.; Ma, X.; Zhao, Y. L. J. Am. Chem. Soc. 2012, 134, 17346.
77. (c) Baumes, J. M.; Gassensmith, J. J.; Giblin, J.; Lee, J. J.; White, A. G.; Culligan, W. J.; Leevy, W. M.; Kuno, M.; Smith, B. D. Nat. Chem. 2010, 2, 1025.
78. (a) Zhang, Y.; Yue, X.; Kim, B.; Yao, S.; Bondar, M. V.; Belfield, K. D. ACS Appl. Mater. Interfaces 2013, 5, 8710.
79. (b) Ahn, H. Y.; Yao, S.; Wang, X.; Belfield, K. D. ACS Appl. Mater. Interfaces 2012, 4, 2847.
80. Gao, F.-P.; Lin, Y.-X.; Li, L.-L.; Liu, Y.; Mayerhöffer, U.; Spenst, P.; Su, J.-G.; Li, J.-Y.; Würthner, F.; Wang, H. Biomaterials 2014, 35, 1004.
81. (a) Chen, H. J.; Law, K. Y.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7257.
82. (b) Arunkumar, E.; Forbes, C. C.; Noll, B. C.; Smith, B. D. J. Am. Chem. Soc. 2005, 127, 3288.
83. Azagarsamy, M. A.; Yesilyurt, V.; Thayumanavan, S. J. Am. Chem. Soc. 2010, 132, 4550.
84. (a) Carter, D. C.; He, X. M. Science 1990, 249, 302.
85. (b) He, X. M.; Carter, D. C. Nature 1992, 358, 209.
86. (a) Keil, D.; Hartmann, H. Dyes Pigm. 2001, 49, 161.
87. (b) Selms, R. C. D.; Fox, C. J.; Riodan, R. C. Tetrahedron Lett. 1970, 11, 781.
88. (a) Eldo, J.; Arunkumar, E.; Ajayaghosh, A. Tetrahedron Lett. 2000, 41, 6241.
89. (b) Eldo, J.; Ajayaghosh, A. Org. Lett. 2001, 3, 2595.
90. Sedkak, J.; Lindasay, R. H. Anal. Biochem. 1968, 25, 192.