Boronic acid library for selective, reversible near-infrared fluorescence quenching of surfactant suspended single-walled carbon nanotubes in response to glucose

ACS Nano

Volumn 6, Issue 1, 2012, Pages 819-830

  Yum, Kyungsuk ^a   Ahn, Jin Ho ^a   McNicholas, Thomas P ^a   Barone, Paul W ^a   Mu, Bin ^a   Kim, Jong Ho ^a,b   Jain, Rishabh M ^a   Strano, Michael S ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

^b Hanyang University   (South Korea)

Author keywords

boronic acids; glucose; near infrared fluorescence; near infrared optical sensor; single walled carbon nanotubes

Indexed keywords

BORONATE; BORONIC ACID; DESIGN RULES; ELECTRON TRANSFER; ELECTRONWITHDRAWING; FLUORESCENCE MODULATION; GLUCOSE CONCENTRATION; HIGH-THROUGHPUT SCREENING; ION FORMATION; NANOTUBE SURFACE; NEAR INFRARED; NEAR-INFRARED FLUORESCENCE; PHOTO-INDUCED; PHYSIOLOGICAL RANGE; SINGLE-WALLED CARBON; SODIUM CHOLATE; WAVELENGTH RED SHIFT;

CARBON; EXCITED STATES; FLUORESCENCE; GLUCOSE; INFRARED DEVICES; PHYSIOLOGICAL MODELS; SENSORS; SURFACE ACTIVE AGENTS;

SINGLE-WALLED CARBON NANOTUBES (SWCN);

BORONIC ACID DERIVATIVE; CARBON NANOTUBE; GLUCOSE; SURFACTANT;

ARTICLE; CHEMISTRY; CRYSTALLIZATION; EQUIPMENT; EQUIPMENT DESIGN; GENETIC PROCEDURES; INSTRUMENTATION; METHODOLOGY; NEAR INFRARED SPECTROSCOPY; PARTICLE SIZE; SPECTROFLUOROMETRY; ULTRASTRUCTURE;

BIOSENSING TECHNIQUES; BORONIC ACIDS; CRYSTALLIZATION; EQUIPMENT DESIGN; EQUIPMENT FAILURE ANALYSIS; GLUCOSE; NANOTUBES, CARBON; PARTICLE SIZE; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, NEAR-INFRARED; SURFACE-ACTIVE AGENTS;

EID: 84856171023     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn204323f     Document Type: Article

References (32)

1. O'Connell, M. J.; Bachilo, S. M.; Huffman, C. B.; Moore, V. C.; Strano, M. S.; Haroz, E. H.; Rialon, K. L.; Boul, P. J.; Noon, W. H.; Kittrell, C. et al. Band Gap Fluorescence from Individual Single-Walled Carbon Nanotubes Science 2002, 297, 593-596
2. Bachilo, S. M.; Strano, M. S.; Kittrell, C.; Hauge, R. H.; Smalley, R. E.; Weisman, R. B. Structure-Assigned Optical Spectra of Single-Walled Carbon Nanotubes Science 2002, 298, 2361-2366
3. Strano, M. S.; Moore, V. C.; Miller, M. K.; Allen, M. J.; Haroz, E. H.; Kittrell, C.; Hauge, R. H.; Smalley, R. E. The Role of Surfactant Adsorption during Ultrasonication in the Dispersion of Single-Walled Carbon Nanotubes J. Nanosci. Nanotechnol. 2003, 3, 81-86
4. Barone, P. W.; Baik, S.; Heller, D. A.; Strano, M. S. Near-Infrared Optical Sensors Based on Single-Walled Carbon Nanotubes Nat. Mater. 2005, 4, 86-92
5. Kim, J.-H.; Heller, D. A.; Jin, H.; Barone, P. W.; Song, C.; Zhang, J.; Trudel, L. J.; Wogan, G. N.; Tannenbaum, S. R.; Strano, M. S. The Rational Design of Nitric Oxide Selectivity in Single-Walled Carbon Nanotube Near-Infrared Fluorescence Sensors for Biological Detection Nat. Chem. 2009, 1, 473-481
6. Walsh, A. G.; Vamivakas, A. N.; Yin, Y.; Cronin, S. B.; Ünlü, M. S.; Goldberg, B. B.; Swan, A. K. Screening of Excitons in Single, Suspended Carbon Nanotubes Nano Lett. 2007, 7, 1485-1488
7. Yoon, H.; Ahn, J.-H.; Barone, P. W.; Yum, K.; Sharma, R.; Boghossian, A. A.; Han, J.-H.; Strano, M. S. Periplasmic Binding Proteins as Optical Modulators of Single-Walled Carbon Nanotube Fluorescence: Amplifying a Nanoscale Actuator Angew. Chem., Int. Ed. 2011, 50, 1828-1831
8. Heller, D. A.; Pratt, G. W.; Zhang, J.; Nair, N.; Hansborough, A. J.; Boghossian, A. A.; Reuel, N. F.; Barone, P. W.; Strano, M. S. Peptide Secondary Structure Modulates Single-Walled Carbon Nanotube Fluorescence as a Chaperone Sensor for Nitroaromatics Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 8544-8549
9. Satishkumar, B. C.; Brown, L. O.; Gao, Y.; Wang, C.-C.; Wang, H.-L.; Doorn, S. K. Reversible Fluorescence Quenching in Carbon Nanotubes for Biomolecular Sensing Nat. Nanotechnol. 2007, 2, 560-564
10. Ahn, J.-H.; Kim, J.-H.; Reuel, N. F.; Barone, P. W.; Boghossian, A. A.; Zhang, J.; Yoon, H.; Chang, A. C.; Hilmer, A. J.; Strano, M. S. Label-Free, Single Protein Detection on a Near-Infrared Fluorescent Single-Walled Carbon Nanotube/Protein Microarray Fabricated by Cell-Free Synthesis Nano Lett. 2011, 11, 2743-2752
11. Cognet, L.; Tsyboulski, D. A.; Rocha, J.-D. R.; Doyle, C. D.; Tour, J. M.; Weisman, R. B. Stepwise Quenching of Exciton Fluorescence in Carbon Nanotubes by Single-Molecule Reactions Science 2007, 316, 1465-1468
12. Jin, H.; Heller, D. A.; Kim, J.-H.; Strano, M. S. Stochastic Analysis of Stepwise Fluorescence Quenching Reactions on Single-Walled Carbon Nanotubes: Single Molecule Sensors Nano Lett. 2008, 8, 4299-4304
13. Heller, D. A.; Jin, H.; Martinez, B. M.; Patel, D.; Miller, B. M.; Yeung, T.-K.; Jena, P. V.; Hobartner, C.; Ha, T.; Silverman, S. K. et al. Multimodal Optical Sensing and Analyte Specificity Using Single-Walled Carbon Nanotubes Nat. Nanotechnol. 2009, 4, 114-120
14. Heller, D. A.; Baik, S.; Eurell, T. E.; Strano, M. S. Single-Walled Carbon Nanotube Spectroscopy in Live Cells: Towards Long-Term Labels and Optical Sensors Adv. Mater. 2005, 17, 2793-2799
15. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Saccharide Sensing with Molecular Receptors Based on Boronic Acid Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922
16. Mader, H. S.; Wolfbeis, O. S. Boronic Acid Based Probes for Microdetermination of Saccharides and Glycosylated Biomolecules Microchim. Acta 2008, 162, 1-34
17. a Changes of Poly(aniline boronic acid) J. Am. Chem. Soc. 2002, 124, 12486-12493
18. James, T. D.; Samankumara Sandanayake, K. R. A.; Shinkai, S. Chiral Discrimination of Monosaccharides Using a Fluorescent Molecular Sensor Nature 1995, 374, 345-347
19. Takahashi, S.; Anzai, J.-i. Phenylboronic Acid Monolayer-Modified Electrodes Sensitive to Sugars Langmuir 2005, 21, 5102-5107
20. Ori, A.; Shinkai, S. Electrochemical Detection of Saccharides by the Redox Cycle of a Chiral Ferrocenylboronic Acid Derivative: A Novel Method for Sugar Sensing J. Chem. Soc., Chem. Commun. 1995, 1771-1772
21. Cordes, D. B.; Gamsey, S.; Singaram, B. Fluorescent Quantum Dots with Boronic Acid Substituted Viologens To Sense Glucose in Aqueous Solution Angew. Chem., Int. Ed. 2006, 45, 3829-3832
22. Fang, H.; Kaur, G.; Wang, B. Progress in Boronic Acid-Based Fluorescent Glucose Sensors J. Fluoresc. 2004, 14, 481-489
23. Edwards, N. Y.; Sager, T. W.; McDevitt, J. T.; Anslyn, E. V. Boronic Acid Based Peptidic Receptors for Pattern-Based Saccharide Sensing in Neutral Aqueous Media, an Application in Real-Life Samples J. Am. Chem. Soc. 2007, 129, 13575-13583
24. Pickup, J. C.; Hussain, F.; Evans, N. D.; Rolinski, O. J.; Birch, D. J. S. Fluorescence-Based Glucose Sensors Biosens. Bioelectron. 2005, 20, 2555-2565
25. Kondepati, V.; Heise, H. Recent Progress in Analytical Instrumentation for Glycemic Control in Diabetic and Critically Ill Patients Anal. Bioanal. Chem. 2007, 388, 545-563
26. Heller, D. A.; Jeng, E. S.; Yeung, T.-K.; Martinez, B. M.; Moll, A. E.; Gastala, J. B.; Strano, M. S. Optical Detection of DNA Conformational Polymorphism on Single-Walled Carbon Nanotubes Science 2006, 311, 508-511
27. Choi, J. H.; Strano, M. S. Solvatochromism in Single-Walled Carbon Nanotubes Appl. Phys. Lett. 2007, 90, 223114
28. O'Connell, M. J.; Eibergen, E. E.; Doorn, S. K. Chiral Selectivity in the Charge-Transfer Bleaching of Single-Walled Carbon-Nanotube Spectra Nat. Mater. 2005, 4, 412-418
29. Zheng, M.; Diner, B. A. Solution Redox Chemistry of Carbon Nanotubes J. Am. Chem. Soc. 2004, 126, 15490-15494
30. Chen, L.; McBranch, D. W.; Wang, H.-L.; Helgeson, R.; Wudl, F.; Whitten, D. G. Highly Sensitive Biological and Chemical Sensors Based on Reversible Fluorescence Quenching in a Conjugated Polymer Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12287-12292
31. Wulff, G. Selective Binding to Polymers via Covalent Bonds. The Construction of Chiral Cavities as Specific Receptor Sites Pure Appl. Chem. 1982, 54, 2093-2102
32. Kim, K. T.; Cornelissen, J. J. L. M.; Nolte, R. J. M.; van Hest, J. C. M. Polymeric Monosaccharide Receptors Responsive at Neutral pH J. Am. Chem. Soc. 2009, 131, 13908-13909