A novel coumarin fluorescent sensor to probe polarity around biomolecules

Journal of Biomedical Nanotechnology

Volumn 5, Issue 6, 2009, Pages 722-729

  Signore, Giovanni ^a   Nifosì, Riccardo ^a   Albertazzi, Lorenzo ^b   Bizzarri, Ranieri ^a,b  

^a INFM   (Italy)

^b SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

Coumarin; Fluorescent biosensor; Molecular binding process; Polarity sensitive probe; Solvatochromism

Indexed keywords

BEFORE AND AFTER; BIOCHEMICAL PROCESS; BOVINE SERUM ALBUMINS; CELL TARGETING; ELECTRON-RICH; FLUORESCENCE SIGNALS; FLUORESCENT SENSORS; FUNCTIONALIZED NANOPARTICLES; MOLECULAR BINDING; NANOPARTICLE COATINGS; POLARITY-SENSITIVE PROBE; SENSITIVE PROBE; SOLVATOCHROMIC; SOLVATOCHROMIC PROPERTIES; SOLVATOCHROMISMS; STATISTICALLY SIGNIFICANT DIFFERENCE; STREPTAVIDIN; SUB-CELLULAR; SULFONYL CHLORIDES;

BIOSENSORS; BODY FLUIDS; CHLORINE COMPOUNDS; NANOPARTICLES; PROBES;

FLUOROPHORES;

ALBUMIN; BIOTIN; COUMARIN; NANOCOATING; NANOPARTICLE; STREPTAVIDIN; SULFONIC ACID DERIVATIVE;

ALBUMIN BLOOD LEVEL; ARTICLE; BIOSENSOR; CONTROLLED STUDY; ELECTRON; FLUORESCENCE; NANOPROBE; POLARIZATION; SIGNAL TRANSDUCTION; SPECTROSCOPY;

BIOPOLYMERS; BIOSENSING TECHNIQUES; COUMARINS; ELECTROCHEMISTRY; EQUIPMENT DESIGN; EQUIPMENT FAILURE ANALYSIS; MOLECULAR PROBE TECHNIQUES; SPECTROMETRY, FLUORESCENCE; STATIC ELECTRICITY;

EID: 76749107083     PISSN: 15507033     EISSN: 15507041     Source Type: Journal    
DOI: 10.1166/jbn.2009.1089     Document Type: Article

References (32)

1. H. R. Petty, Fluorescence microscopy: Established and emerging methods, experimental strategies, and applications in immunology. Microsc. Res. Tech. 70, 687 (2007).
2. C. Roeckerl, M. Poetzl, F. Zhang, W. J. Parak, and G. U. Nienhaus, A quantitative fluorescence study of protein monolayer formation on colloidal nanoparticles. Nat. Nanotech 4, 577 (2009).
3. T. Cedervall, I. Lynch, S. Lindman, T. Berggård, E. Thulin, H. Nilsson, K. A. Dawson, and S. Linse, Understanding the nanoparticle-protein corona using methods to quantify exchange rates and affinities of proteins for nanoparticles. Pro. Natl. Acad. Sci. U.S.A 104, 2050 (2007).
4. L. Lynch, A. Salvati, and K. A. Dawson, What does the cell see? Nat. Nanotech. 4, 546 (2009).
5. J. A. Prescher and C. R. Bertozzi, Chemistry in living systems. Nat. Chem. Biol. 1, 13 (2005).
6. A. Toutchkine, V. Kraynov, and K. Hahn, Solvent-sensitive dyes to report protein conformational changes in living cells. J. Am. Chem. Soc. 125, 4132 (2003).
7. R. M. Christie, K. M. Morgan, and M. S. Islam, Molecular design and synthesis of N-arylsulfonated coumarin fluorescent dyes and their application to textiles. Dyes Pigm. 76, 741 (2008).
8. 3+ based on hydrolysis of bis(coumarinyl) schiff base. Eur. J. Org. Chem. 73, 2689 (2008).
9. 2+ ions with an ICT fluorescent sensor molecule: Remarkable emission spectra shift and unique selectivity. J. Org. Chem. 71, 4308 (2006).
10. M.-T. Lee, C.-K. Yen, W.-P. Yang, H.-H. Chen, C.-H. Liao, C.-H. Tsai, and C. H. Chen, Efficient green coumarin dopants for organic light-emitting devices. Org. Lett. 6, 1241 (2004).
11. H. Turki, S. Abid, S. Fery-Forgues, and R. El Gharbi, Optical properties of new fluorescent iminocoumarins: Part 1. Dyes Pigm. 73, 311 (2007).
12. R. M. Christie and C.-H. Lui, Studies of fluorescent dyes: Part 2. An investigation of the synthesis and electronic spectral properties of substituted 3-(20-benzimidazolyl)coumarins. Dyes Pigm. 47, 79 (2000).
13. A. Elangovan, J.-H. Lin, S.-W. Yang, H.-Y. Hsu, and T.-I. Ho, Synthesis and electrogenerated chemiluminescence of donor-substituted phenylethynylcoumarins. J. Org. Chem. 69, 8086 (2004).
14. W. R. Webb and J. E. T. Corrie, Fluorescent coumarin-labeled nucleotides to measure ADP release from actomyosin. Biophys. J. 81, 1562 (2001).
15. R. Katritzky, J. Cusido, and T. Narindoshvili, Monosaccharide-based water-soluble fluorescent tags. Bioconjugate Chem. 19, 1471 (2008).
16. M. S. Dillingham, K. L. Tibbles, J. L. Hunter, J. C Bell, S. C. Kowalczykowski, and M. R. Webb, Fluorescent single-stranded DNA binding protein as a probe for sensitive, real-time assays of helicase activity. Biophys. J. 95, 3330 (2008).
17. M.-P. Brun, L. Bischoff, and C. Garbay, A very short route to enantiomerically pure coumarin-bearing fluorescent amino acids. Angew. Chem. Int. Ed. 43, 3432 (2004).
18. K. Komatsu, Y. Urano, H. Kojima, and T. Nagano, Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc. J. Am. Chem. Soc. 129, 13447 (2007).
19. P. Suppan and N. Ghoneim, Solvatochromism, The Royal Society of Chemistry, ISBN 0-85404-419-1, Thomas Graham House, Science Park, Milton Road, Cambridge, UK (1997).
20. G. Signore, R. Nifosl, L. Albertazzi, B. Storti, and R. Bizzarri, Polarity-sensitive coumarins tailored to live cell imaging. J. Am. Chem. Soc., submitted.
21. B. Xu, J. Yang, X. Jiang, Y. Wang, H. Sun, and J. Yin, Ground and excited states calculations of 7-phenylamino-substituted coumarins. J. Mol. Struct. 917, 15 (2009).
22. J. Preat, D. Jacquemin, and E. A. Perpete, Theoretical investigations of the UV spectra of coumarin derivatives. Chem. Phys. Lett. 415, 20 (2005).
23. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03; (revision C.02); Gaussian, Inc.: Pittsburgh, PA (2003).
24. S. M. Moghimi, Chemical camouflage of nanospheres with a poorly reactive surface: Towards development of stealth and target-specific nanocarriers. BBA-Molecular Cell Research 1590, 131 (2002).
25. W. Liu, M. Howarth, A. B. Greytak, Y. Zheng, D. G. Nocera, A. Y. Ting, and M. G. Bawendi, Compact biocompatible quantum dots functionalized for cellular imaging. J. Am. Chem. Soc. 130, 1274 (2008).
26. M. L. F. Ruano, K. Nag, A. Worthman, C. Casals, J. Pérez-Gil, and K. M. W. Keough, Differential partitioning of pulmonary surfactant protein SP-A into regions of monolayers of dipalmitoylphosphati-dylcholine and dipalmitoylphosphatidylcholine/dipalmitoylphospha-tidylglycerol. Biophys. J. 74, 1101 (1998).
27. K. Satpati, M. Kumbhakar, S. Nath, and H. Pal, Photophysical properties of coumarin-7 dye: Role of twisted intramolecular charge transfer state in high polarity protic solvents. Photochem. Photobiol. 85, 119 (2009).
28. A. Barik, S. Nath, and H. Pal, Effect of solvent polarity on the photophysical properties of coumarin-1 dye. J. Chem. Phys. 119, 10202 (2003).
29. P. Dahiya, M. Kumbhakar, T. Mukherjee, and H. Pal, Effect of protic solvents on twisted intramolecular charge transfer state formation in coumarin-152 and coumarin-481 dyes. Chem. Phys. Lett. 414, 148 (2005).
30. S. Senthilkumar, S. Nath, and H. Pal, Photophysical properties of coumarin-30 dye in aprotic and protic solvents of varying polarities. Photochem. Photobiol. 80, 104 (2004).
31. A. K. Satpati, S. Senthilkumar, M. Kumbhakar, S. Nath, D. K. Maity, and H. PaI, Investigations of the solvent polarity effect on the photophysical properties of coumarin-7 dye. Photochem. Photobiol. 81, 270 (2005).
32. P. Nalbant, L. Hodgson, V. Kraynov, A. Toutchkine, and K. M. Hahn, Activation of endogenous Cdc42 visualized in living cells. Science 305, 1615 (2004).