Understanding the relationship between photolysis efficiency and metal binding using argencast photocages

Photochemistry and Photobiology

Volumn 88, Issue 4, 2012, Pages 844-850

  Mbatia, Hannah W ^a   Kennedy, Daniel P ^a   Burdette, Shawn C ^b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b Worcester Polytechnic Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; COORDINATION COMPOUND; COPPER; FLUORESCENT DYE; LIGAND; MERCURY; MESYLIC ACID DERIVATIVE; SILVER; SOLVENT; TRIFLUOROMETHANESULFONIC ACID TRIMETHYLSILYL ESTER; TRIMETHYLSILYL DERIVATIVE; WATER;

CHEMISTRY; CONFERENCE PAPER; KINETICS; PHOTOLYSIS; SPECTROSCOPY;

ANILINE COMPOUNDS; COORDINATION COMPLEXES; COPPER; FLUORESCENT DYES; KINETICS; LIGANDS; MERCURY; MESYLATES; PHOTOLYSIS; SILVER; SOLVENTS; SPECTRUM ANALYSIS; TRIMETHYLSILYL COMPOUNDS; WATER;

EID: 84863718861     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2012.01136.x     Document Type: Conference Paper

References (35)

1. Kaplan, J., B. Forbush, and, J. Hoffman, (1978) Rapid photolytic release of adenosine 5'-triphosphate from a protected analog: utilization by the sodium:potassium pump of human red blood cell ghosts. Biochemistry 17, 1929-1935.
2. Lee, H., D. R. Larson, and, D. S. Lawrence, (2009) Illuminating the chemistry of life: design, synthesis, and applications of "caged" and related photoresponsive compounds. ACS Chem. Biol. 4, 409-427.
3. Tsien, R. Y., and, R. S. Zucker, (1986) Control of cytoplasmic calcium with photolabile tetracarboxylate 2-nitrobenzhydrol chelators. Biophys. J. 50, 843-853.
4. Kennedy, D. P., C. Gwizdala, and, S. C. Burdette, (2009) Methods for preparing metal ion photocages: application to the synthesis of crowncast. Org. Lett. 11, 2587-2590.
5. 3+. Inorg. Chem. 49, 916-923.
6. Kennedy, D. P., D. C. Brown, and, S. C. Burdette, (2010) Probing nitrobenzhydrol uncaging mechanisms using FerriCast. Org. Lett. 12, 4486-4489.
7. Mbatia, H. W., D. P. Kennedy, C. E. Camire, C. D. Incarvito, and, S. C. Burdette, (2010) Buffering heavy metal ions with photoactive crowncast cages. Eur. J. Inorg. Chem. 2010, 5069-5078.
8. 2+. Chem. Commun., 6967-6969.
9. Peters, C., B. Munoz, F. J. Sepulveda, J. Urrutia, M. Quiroz, S. Luza, G. V. De Ferrari, L. G. Aguayo, and, C. Opazo, (2011) Biphasic effects of copper on neurotransmission in rat hippocampal neurons. J. Neurochem. 119, 78-88.
10. Florea, A., and, D. Buesselberg, (2006) Occurrence, use and potential toxic effects of metals and metal compounds. Biometals 19, 419-427.
11. Furno, F., K. Morley, B. Wong, B. Sharp, P. Arnold, S. Howdle, R. Bayston, P. Brown, P. Winship, and, H. Reid, (2004) Silver nanoparticles and polymeric medical devices: a new approach to prevention of infection? J. Antimicrob. Chemother. 54, 1019-1024.
12. Ishikawa, J., H. Sakamoto, T. Mizuno, and, M. Otomo, (1995) Hydrazones derived from dithiamonoaza and tetrathiamonoaza analogs of polyethers as silver ion selective ionophores: syntheses, proton-dissociation behaviors, and metal ion complexing properties in 1,4-dioxane-water acidic solution. Bull. Chem. Soc. Jpn. 68, 3071-3076.
13. Kienzle, F., (1980) The reaction of phthalaldehydes with 3-nitropropionates-a simple route to 3-nitro-2-naphthoic acids. Helv. Chim. Acta 63, 2364-2369.
14. ID Business Solutions Limited (2009) XLfit, 5.1.0.0. ID Business Solutions Limited, Guildford.
15. Dodani, S. C., Q. He, and, C. J. Chang, (2009) A turn-on fluorescent sensor for detecting nickel in living cells. J. Am. Chem. Soc. 131, 18020-18021.
16. Schwarze, T., H. Mueller, C. Dosche, T. Klamroth, W. Mickler, A. Kelling, H. Loehmannsroeben, P. Saalfrank, and, H. Holdt, (2007) Luminescence detection of open-shell transition-metal ions by photoinduced electron transfer controlled by internal charge transfer of a receptor. Angew. Chem. Int. Ed. 46, 1671-1674.
17. Zeng, L., E. W. Miller, A. Pralle, E. Y. Isacoff, and, C. J. Chang, (2006) A selective turn-on fluorescent sensor for imaging copper in living cells. J. Am. Chem. Soc. 128, 10-11.
18. Yang, L., R. McRae, M. M. Henary, R. Patel, B. Lai, S. Vogt, and, C. J. Fahrni, (2005) Imaging of the intracellular topography of copper with a fluorescent sensor and by synchrotron X-ray fluorescence microscopy. Proc. Natl Acad. Sci. USA 102, 11179-11184.
19. Ishikawa, J., H. Sakamoto, S. Nakao, and, H. Wada, (1999) Silver ion selective fluoroionophores based on anthracene-linked polythiazaalkane or polythiaalkane derivatives. J. Org. Chem. 64, 1913-1921.
20. 2+ in living cells. Chem. Eur. J. 16, 919-930.
21. + in aqueous solution. Dalton Trans. 39, 1316-1320.
22. Yoon, S., E. W. Miller, Q. He, P. H. Do, and, C. J. Chang, (2007) A bright and specific fluorescent sensor for mercury in water, cells, and tissue. Angew. Chem. Int. Ed. 46, 6658-6661.
23. Yuan, M., Y. Li, J. Li, C. Li, X. Liu, J. Lv, J. Xu, H. Liu, S. Wang, and, D. Zhu, (2007) A colorimetric and fluorometric dual-modal assay for mercury ion by a molecule. Org. Lett. 9, 2313-2316.
24. Coskun, A., and, E. Akkaya, (2005) Ion sensing coupled to resonance energy transfer: a highly selective and sensitive ratiometric fluorescent chemosensor for Ag(I) by a modular approach. J. Am. Chem. Soc. 127, 10464-10465.
25. Wang, H., L. Xue, and, H. Jiang, (2011) Ratiometric fluorescent sensor for silver ion and its resultant complex for iodide anion in aqueous solution. Org. Lett. 13, 3844-3847.
26. Miller, E. W., L. Zeng, D. W. Domaille, and, C. J. Chang, (2006) Preparation and use of Coppersensor-1, a synthetic fluorophore for live-cell copper imaging. Nat. Protoc. 1, 824-827.
27. Domaille, D. W., E. L. Que, and, C. J. Chang, (2008) Synthetic fluorescent sensors for studying the cell biology of metals. Nat. Chem. Biol. 4, 168-175.
28. Dodani, S. C., S. C. Leary, P. A. Cobine, D. R. Winge, and, C. J. Chang, (2011) A targetable fluorescent sensor reveals that copper-deficient SCO1 and SCO2 patient cells prioritize mitochondrial copper homeostasis. J. Am. Chem. Soc. 133, 8606-8616.
29. Dodani, S. C., D. W. Domaille, C. I. Nam, E. W. Miller, L. A. Finney, S. Vogt, and, C. J. Chang, (2011) Calcium-dependent copper redistributions in neuronal cells revealed by a fluorescent copper sensor and X-ray fluorescence microscopy. Proc. Natl Acad. Sci. USA 108, 5980-5985.
30. Domaille, D. W., L. Zeng, and, C. J. Chang, (2010) Visualizing ascorbate-triggered release of labile copper within living cells using a ratiometric fluorescent sensor. J. Am. Chem. Soc. 132, 1194-1195.
31. Momotake, A., N. Lindegger, E. Niggli, R. Barsotti, and, G. Ellis-Davies, (2006) The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells. Nat. Methods 3, 35-40.
32. Lusic, H., R. Uprety, and, A. Deiters, (2010) Improved synthesis of the two-photon caging group 3-nitro-2-ethyldibenzofuran and its application to a caged thymidine phosphoramidite. Org. Lett. 12, 916-919.
33. Singh, A. K., and, P. K. Khade, (2002) Synthesis and photochemical properties of nitro-naphthyl chromophore and the corresponding immunoglobulin bioconjugate. Bioconjug. Chem. 13, 1286-1291.
34. Singh, A., and, P. Khade, (2005) 3-Nitro-2-naphthalenemethanol: a photocleavable protecting group for carboxylic acids. Tetrahedron 61, 10007-10012.
35. Singh, A. K., and, P. K. Khade, (2011) 7-Methoxy-3-nitro-2- naphthalenemethanol-a new phototrigger for caging applications. Tetrahedron Lett. 52, 4899-4902.