Coumarin-based fluorescent probes for dual recognition of copper(II) and iron(III) ions and their application in bio-imaging

Sensors (Switzerland)

Volumn 14, Issue 1, 2014, Pages 1358-1371

  García Beltrán, Olimpo ^a,b   Cassels, Bruce K ^a   Pérez, Claudio ^a   Mena, Natalia ^a   Núñez, Marco T ^a   Martínez, Natalia P ^c   Pavez, Paulina ^c   Aliaga, Margarita E ^c  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD DE IBAGUÉ   (Colombia)

^c PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Bio imaging; Coumarin based probes; Fluorescence sensors; Turn off probes

Indexed keywords

COPPER; FLUORESCENCE; METAL IONS; PROBES;

3 ,4-DIHYDROXYBENZALDEHYDE; BIO-IMAGING; EPIFLUORESCENCE MICROSCOPY; FLUORESCENCE SENSORS; FLUORESCENT PROBES; HUMAN NEUROBLASTOMA; HYDROLYSIS REACTION; TURN OFFS;

IRON COMPOUNDS;

EID: 84892575344     PISSN: 14248220     EISSN: None     Source Type: Journal    
DOI: 10.3390/s140101358     Document Type: Article

References (35)

1. Lakowicz, J.R. Topics in Fluorescence Spectroscopy: Probe Design and Chemical Sensing; Plenum Press: New York, NY, USA, 1994; Volume 4, pp. 21-68.
2. De Silva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 1997, 97, 1515-1566.
3. Demchenko, A.P. Introduction to Fluorescence Sensing, 1st ed.; Springer: Heidelberg, Germany, 2008; pp. 1-6.
4. Chen, X.; Sun, M.; Ma, H.M. Progress in spectroscopic probes with cleavable active bonds. Curr. Org. Chem. 2006, 10, 477-489.
5. Li, X.; Gao, X.; Shi, W.; Ma, H. Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. Chem. Rev. 2013, doi:10.1021/cr300508p.
6. Linder, M.C. Biochemistry of Copper; Plenum Press: New York, NY, USA, 1991; pp. 73-134.
7. Ponka, P. Cellular iron metabolism. Kidney Int. 1999, 55, S2-S11.
8. Wood, R.J.; Ronnenberg, A.G. Iron. In Modern Nutrition in Health and Disease, 10th ed.; Shils, M.E., Shike, M., Ross, A.C., Caballero, B., Cousins, R.J., Eds.; Lippincott Williams & Wilkins: Philadelphia, PA, USA, 2006; pp. 248-270.
9. Atkins, P.; Overton, T.; Rourke, J.; Weller, M.; Armstrong, F. Inorganic Chemistry, 4th ed.; Prentice Hall: Oxford, UK, 2006; p. 712.
10. 2+ and pyrophosphate anion. Macromolecules 2010, 43, 739-744.
11. Que, E.L.; Domaille, D.W.; Chang, C.J. Metals in neurobiology: Probing their chemistry and biology with molecular imaging. Chem. Rev. 2008, 108, 1517-1549.
12. Luo, W.; Ma, Y.M.; Quinn, P.J.; Hider, R.C.; Liu, Z.D. Design, synthesis and properties of novel iron(III)-specific fluorescent probes. J. Pharm. Pharmacol. 2004, 56, 529-536.
13. 3+ in water. Inorg. Chem. Comm. 2009, 12, 116-118.
14. Chen, X.; Pradhan, T.; Wang, F.; Kim, J.S.; Yoon, J. Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. Chem. Rev. 2012, 112, 1910-1956.
15. 2+ in aqueous solution and living cells. Anal. Chem. 2009, 81, 7022-7030.
16. 2+ sensing chemodosimeter for fast and selective detection. Org. Biomol. Chem. 2012, 10, 3104-3109.
17. 2+-promoted hydrolysis of lactone moiety in coumarin. Chem. Commun. 2010, 46, 3363-3365.
18. 2+ ions. Chem. Commun. 2009, 45, 4838-4840.
19. Lee, M.H.; Giap, T.V.; Kim, S.H.; Lee, Y.H.; Kang, C.; Kim, J.S. A novel strategy to selectively detect Fe(III) in aqueous media driven by hydrolysis of a rhodamine 6G Schiff base. Chem. Commun. 2010, 46, 1407-1409.
20. Lim, N.C.; Pavlova, S.V.; Bruckner, C. Squaramide hydroxamate-based chemidosimeter responding to iron(iii) with a fluorescence intensity increase. Inorg. Chem. 2009, 48, 1173-1182.
21. Benesi, H.A.; Hildebrand, J.H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 1949, 71, 2703-2707.
22. 2+. Eur. J. Med. Chem. 2013, 67, 60-63.
23. Brouwer, A.M. Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report). Pure Appl. Chem. 2011, 83, 2213-2228.
24. Hohenstein, E.G.; Chill, S.T.; Sherrill, C.D. Assessment of the performance of the M05-2X and M06-2X exchange-correlation functionals for noncovalent interactions in biomolecules. J. Chem. Theory Comput. 2008, 4, 1996-2000.
25. Mena, N.; Bulteau A.L.; Salazar J.; Hirsch E.C.; Núñez M.T. Effect of mitochondrial complex I inhibition on Fe-S cluster protein activity. Biochem. Biophys. Res. Commun. 2011, 409, 241246.
26. 2+. Tetrahedron Lett. 2012, 53, 5280-5283.
27. Li, H.-Y.; Gao, S.; Xi, Z. A colorimetric and "turn-on" fluorescent chemosensor for Zn(II) based on coumarin Schiff-base derivative. Inorg. Chem. Commun. 2009, 12, 300-303.
28. 2+-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells. J. Am. Chem. Soc. 2009, 131, 2008-2012.
29. Jung, H.S.; Han, J.H.; Habata, Y.; Kang, C.; Kim, J.S. An iminocoumarin-Cu(II) ensemble-based chemodosimeter toward thiols. Chem. Commun. 2011, 47, 5142-5144.
30. Chen, Z.; Wang, L.; Zou, G.; Tang, J.; Cai, X.; Teng, M.; Chen, L. Highly selective fluorescence turn-on chemosensor based on naphthalimide derivatives for detection of copper(II) ions. Spectrochim Acta A Mol. Biomol. Spectrosc. 2013, 105, 57-61.
31. Reed, A.E.; Curtiss, L.A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88, 899-926.
32. Larson, J.W.; McMahon, T.B. Gas-phase bihalide and pseudobihalide ions. An ion cyclotron resonance determination of hydrogen bond energies in XHY-species (X, Y = F, Cl, Br, CN). Inorg. Chem. 1984, 23, 2029-2033.
33. Emsley, J. Very strong hydrogen bonding. Chem. Soc. Rev. 1980, 9, 91-124.
34. Horobin, R.W.; Rashid-Doubell, F.; Pediani, J.D.; Milligan, G. Predicting small molecule fluorescent probe localization in living cells using QSAR modeling. 1. Overview and models for probes of structure, properties and function in single cells. Biotech. Histochem. 2013, 88, 440-460.
35. Anderegg, G. Critical survey of stability constants of NTA complexes. Pure Appl. Chem. 1982, 54, 2693-2758.