Metal-based turn-on fluorescent probes for sensing nitric oxide

Accounts of Chemical Research

Volumn 40, Issue 1, 2007, Pages 41-51

  Lim, Mi Hee ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; METAL; NITRIC OXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

FLUORESCENT DYES; METALS; MODELS, MOLECULAR; NITRIC OXIDE;

EID: 33846432398     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar950149t     Document Type: Article

References (36)

1. Murad, F. Discovery of Some of the Biological Effects of Nitric Oxide and Its Role in Cell Signaling. Angew. Chem., Int. Ed. 1999, 38, 1856-1868.
2. Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Nitric Oxide: Physiology, Pathophysiology, and Pharmacology. Pharmacol. Rev. 1991, 43, 109-142.
3. Conner, E. M.; Grisham, M. B. Nitric Oxide: Biochemistry, Physiology, and Pathophysiology. Methods Enzymol. 1995, 7, 3-13.
4. Lancaster, J. R., Jr. A Tutorial on the Diffusibility and Reactivity of Free Nitric Oxide. Nitric Oxide: Biol. Chem. 1997, 1, 18-30.
5. Wood, J.; Garthwaite, J. Models of the Diffusional Spread of Nitric Oxide: Implications for Neural Nitric Oxide Signalling and Its Pharmacological Properties. Neuropharmacology 1994, 33, 1235-1244.
6. Nagano, T.; Yoshimura, T. Bioimaging of Nitric Oxide. Chem. Rev. 2002, 102, 1235-1269 and references cited therein.
7. Hilderbrand, S. A.; Lim, M. H.; Lippard, S. J. In Topics in Fluorescence Spectroscopy, Geddes, C. O., Lakowicz, J. R., Eds.; Springer, 2005; pp 163-188 and references cited therein.
8. Hampl, V.; Walters, C. L.; Archer, S. L. In Methods in Nitric Oxide Research; Feelisch, M., Stamler, J. S., Eds.; John Wiley & Sons: New York, 1996; pp 309-318.
9. Malinski, T.; Mesaros, S.; Tomboulian, P. Nitric Oxide Measurement Using Electrochemical Methods. Methods Enzymol. 1996, 268, 58-69.
10. Katayama, Y.; Takahashi, S.; Maeda, M. Design, Synthesis and Characterization of a Novel Fluorescent Probe for Nitric Oxide (Nitrogen Monoxide). Anal. Chim. Acta 1998, 365, 159-167.
11. Soh, N.; Katayama, Y.; Maeda, M. A Fluorescent Probe for Monitoring Nitric Oxide Production Using a Novel Detection Concept. Analyst 2001, 126, 564-566.
12. Bergonzi, R.; Fabbrizzi, L.; Licchelli, M.; Mangano, C. Molecular Switches of Fluorescence Operating through Metal Centred Redox Couples. Coord. Chem. Rev. 1988, 170, 31-46.
13. Lim, M. H.; Lippard, S. J. Fluorescence-Based Nitric Oxide Detection by Ruthenium Porphyrin Fluorophore Complexes. Inorg. Chem. 2004, 43, 6366-6370.
14. Hilderbrand, S. A.; Lim, M. H.; Lippard, S. J. Dirhodium Tetracarboxylate Scaffolds as Reversible Fluorescence-Based Nitric Oxide Sensors. J. Am. Chem. Soc. 2004, 126, 4972-4978.
15. Ford; P. C.; Lorkovic, I. M. Mechanistic Aspects of the Reactions of Nitric Oxide with Transition-Metal Complexes. Chem. Rev. 2002, 102, 993-1017 and references cited therein.
16. Lim, M. H.; Lippard, S. J. Copper Complexes for Fluorescence-Based NO Detection in Aqueous Solution. J. Am. Chem. Soc. 2005, 127, 12170-12171.
17. Smith, R. C.; Tennyson, A. G.; Lim, M. H.; Lippard, S. J. Conjugated Polymer-Based Fluorescence Turn-On Sensor for Nitric Oxide. Org. Lett. 2005, 7, 3573-3575.
18. Franz, K. J.; Singh, N.; Spingler, B.; Lippard, S. J. Aminotroponiminates as Ligands for Potential Metal-Based Nitric Oxide Sensors. Inorg. Chem. 2000, 39, 4081-4092.
19. Hilderbrand, S. A.; Lippard, S. J. Nitric Oxide Reactivity of Fluorophore Coordinated Carboxylate-Bridged Diiron(II) and Dicobalt(II) Complexes. Inorg. Chem. 2004, 43, 5294-5301.
20. Lee, J.; Chen, L.; West, A. H.; Richter-Addo, G. B. Interactions of Organic Nitroso Compounds with Metals. Chem. Rev. 2002, 102, 1019-1065.
21. Tsuge, K.; DeRosa, F.; Lim, M. D.; Ford, P. C. Intramolecular Reductive Nitrosylation: Reaction of Nitric Oxide and a Copper(II) Complex of a Cyclam Derivative with Pendant Luminescent Chromophores. J. Am. Chem. Soc. 2004, 126, 6564-6565.
22. Lim, M. H.; Xu, D.; Lippard, S. J. Visualization of Nitric Oxide in Living Cells by a Copper-Based Fluorescent Probe. Nat. Chem. Biol. 2006, 2, 375-380.
23. Fluorescence studies of metal complexes described in this Account were performed in the presence of excess (mM) NO. The concentrations of NO in vivo (picomolar to micromolar) are generally much lower.
24. Franz, K. J.; Doerrer, L. H.; Spingler, B.; Lippard, S. J. Pentacoordinate Cobalt(III) Thiolate and Nitrosyl Tropocoronand Compounds. Inorg. Chem. 2001, 40, 3774-3780.
25. 2-Coordinated Palladium(II) Complex: Role of the Intra-and Intermolecular Aromatic-Ring Stacking Interaction. Inorg. Chem. 1899, 38, 1719-1724.
26. Lee, D.; Hung, P.-L.; Spingler, B.; Lippard, S. J. Sterically Hindered Carboxylate Ligands Support Water-Bridged Dimetallic Centers that Model Features of Metallohydrolase Active Sites. Inorg. Chem. 2002, 41, 521-531.
27. Lim, M. H.; Kuang, C.; Lippard, S. J. Nitric Oxide-Induced Fluorescence Enhancement by Displacement of Dansylated Ligands from Cobalt. ChemBioChem 2006, web release date: June 21, 2006, DOI: 10.1002/cbic. 200600042.
28. Hilderbrand, S. A.; Lippard, S. J. Cobalt Chemistry with Mixed Aminotroponiminate Salicylaldiminate Ligands: Synthesis, Characterization, and Nitric Oxide Reactivity. Inorg. Chem. 2004, 43, 4674-4682.
29. Soh, N.; Imato, T.; Kawamura, K.; Maeda, M.; Katayama, Y. Ratiometric Direct Detection of Nitric Oxide Based on a Novel Signal-Switching Mechanism. Chem. Commun. 2002, 2650-2651.
30. Yoon, S.; Lippard, S. J. Synthesis, Characterization, and Dioxygen Reactivity of Tetracarboxylate-Bridged Diiron(II) Complexes with Coordinated Substrates. Inorg. Chem. 2003, 42, 8606-8608.
31. Miranda, K. M.; Bu, X.; Lorkovic, I.; Ford, P. C. Synthesis and Structural Characterization of Several Ruthenium Porphyrin Nitrosyl Complexes. Inorg. Chem. 1997, 36, 4838-4848.
32. Kadish, K. M.; Adamian, V. A.; Van Caemelbecke, E.; Tan, Z.; Tagliatesta, P.; Bianco, P.; Boschi, T.; Yi, G.-B.; Khan, M. A.; Richter-Addo, G. B. Synthesis, Characterization, and Electrochemistry of Ruthenium Porphyrins Containing a Nitrosyl Axial Ligand. Inorg. Chem. 1996, 35, 1343-1348.
33. Boyar, E. B.; Robinson, S. D. Rhodium(II) Carboxylates. Coord. Chem. Rev. 1983, 50, 109-208.
34. Johnson, S. A.; Hunt, H. R.; Neumann, H. M. Preparation and Properties of Anhydrous Rhodium(II) Acetate and Some Adducts Thereof. Inorg. Chem. 1963, 2, 960-962.
35. Lim, M. H.; Lippard, S. J. Unpublished results, 2005.
36. Lim, M. H.; Wong, B. A.; Pitcock, W. H.; Mokshagundam, D.; Baik, M.-H.; Lippard, S. J. Direct Nitric Oxide Detection In Aqueous Solution by Copper(II) Fluorescein Complexes. J. Am. Chem. Soc. 2006, in press.