Live-fibroblast IR imaging of a cytoprotective photoCORM activated with visible light

Journal of Medicinal Chemistry

Volumn 56, Issue 17, 2013, Pages 6719-6731

  Zobi, Fabio ^a   Quaroni, Luca ^b   Santoro, Giuseppe ^a   Zlateva, Theodora ^c   Blacque, Olivier ^a   Sarafimov, Blagoj ^b   Schaub, Marcus C ^a   Bogdanova, Anna Yu ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b PAUL SCHERRER INSTITUTE   (Switzerland)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ACTININ; CARBON MONOXIDE; CYANOCOBALAMIN; INTEGRIN; MYOGLOBIN; PAXILLIN; PHALLOIDIN; TALIN; VINCULIN;

ACTIN FILAMENT; ADHERENT CELL; ANIMAL CELL; AQUEOUS SOLUTION; ARTICLE; ATOMIC ABSORPTION; CELL PROLIFERATION; CELL PROTECTION; CELLULAR DISTRIBUTION; CHROMATOPHORE; CONFORMATION; CONJUGATION; CONTROLLED STUDY; CYTOSOLIC FRACTION; CYTOTOXICITY; ELECTROMAGNETIC RADIATION; FIBROBLAST; FIBROBLAST CULTURE; FOCAL ADHESION; HYDROGEN BOND; HYPOXIA; INFRARED RADIATION; INFRARED SPECTROSCOPY; INTERNALIZATION; LIGHT; LONG TERM EXPOSURE; MOUSE; NONHUMAN; PHENOTYPE; PHOTOLYSIS; SIGNAL NOISE RATIO; SYNCHROTRON; VASCULARIZATION; WATER VAPOR;

3T3 CELLS; ANIMALS; CARBON MONOXIDE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOPROTECTION; FIBROBLASTS; LIGHT; MICE; MODELS, MOLECULAR; SPECTROPHOTOMETRY, ATOMIC; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84884221752     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400527k     Document Type: Article

References (60)

1. Wu, L. Y.; Wang, R. Carbon monoxide: Endogenous production, physiological functions, and pharmacological applications Pharmacol. Rev. 2005, 57, 585-630
2. Motterlini, R.; Otterbein, L. E. The therapeutic potential of carbon monoxide Nat. Rev. Drug Discovery 2010, 9, 728-742
3. Mann, B. E. Carbon monoxide: an essential signalling molecule Top. Organomet. Chem. 2010, 32, 247-285
4. Vummaleti, S. V. C.; Branduardi, D.; Masetti, M.; De Vivo, M.; Motterlini, R.; Cavalli, A. Theoretical insights into the mechanism of carbon monoxide (CO) release from CO-releasing molecules Chem.-Eur. J. 2012, 18, 9267-9275
5. Crook, S. H.; Mann, B. E.; Meijer, A. J. H. M.; Adams, H.; Sawle, P.; Scapens, D.; Motterlini, R. [Mn(CO)(4){S2CNMe(CH2CO2H)}], a new water-soluble CO-releasing molecule Dalton Trans. 2011, 40, 4230-4235
6. Hewison, L.; Crook, S. H.; Mann, B. E.; Meijer, A. J. H. M.; Adams, H.; Sawle, P.; Motterlini, R. A. New types of CO-releasing molecules (CO-RMs), based on iron dithiocarbamate complexes and [Fe(CO)(3)I(S2COEt)] Organometallics 2012, 31, 5823-5834
7. Zobi, F.; Blacque, O.; Jacobs, R. A.; Schaub, M. C.; Bogdanova, A. Y. 17 e(-) rhenium dicarbonyl CO-releasing molecules on a cobalamin scaffold for biological application Dalton Trans. 2012, 41, 370-378
8. Atkin, A. J.; Fairlamb, I. J. S.; Ward, J. S.; Lynam, J. M. CO release from norbornadiene iron(0) tricarbonyl complexes: importance of ligand dissociation Organometallics 2012, 31, 5894-5902
9. Zhang, W. Q.; Atkin, A. J.; Fairlamb, I. J. S.; Whitwood, A. C.; Lynam, J. M. Synthesis and reactivity of molybdenum complexes containing functionalized alkynyl ligands: a photochemically activated CO-releasing molecule (photoCO-RM) Organometallics 2011, 30, 4643-4654
10. Zhang, W. Q.; Atkin, A. J.; Thatcher, R. J.; Whitwood, A. C.; Fairlamb, I. J. S.; Lynam, J. M. Diversity and design of metal-based carbon monoxide-releasing molecules (CO-RMs) in aqueous systems: revealing the essential trends Dalton Trans. 2009, 4351-4358
11. Atkin, A. J.; Williams, S.; Sawle, P.; Motterlini, R.; Lynam, J. M.; Fairlamb, I. J. S. μ(2)-Alkyne dicobalt(0)hexacarbonyl complexes as carbon monoxide-releasing molecules (CO-RMs): probing the release mechanism Dalton Trans. 2009, 3653-3656
12. Fairlamb, I. J. S.; Lynam, J. M.; Moulton, B. E.; Taylor, I. E.; Duhme-Klair, A. K.; Sawle, P.; Motterlini, R. η(1)-2-Pyrone metal carbonyl complexes as CO-releasing molecules (CO-RMs): a delicate balance between stability and CO liberation Dalton Trans. 2007, 3603-3605
13. Romanski, S.; Kraus, B.; Guttentag, M.; Schlundt, W.; Rucker, H.; Adler, A.; Neudorfl, J.-M.; Alberto, R.; Amslinger, S.; Schmalz, H.-G. Acyloxybutadiene tricarbonyl iron complexes as enzyme-triggered CO-releasing molecules (ET-CORMs): a structure-activity relationship study Dalton Trans. 2012, 41, 13862-13875
14. Romanski, S.; Kraus, B.; Schatzschneider, U.; Neudorfl, J. M.; Amslinger, S.; Schmalz, H. G. Acyloxybutadiene-iron tricarbonyl complexes as enzyme-triggered CO-releasing molecules (ET-CORMs) Angew. Chem., Int. Ed. 2011, 50, 2392-2396
15. Rimmer, R. D.; Pierri, A. E.; Ford, P. C. Photochemically activated carbon monoxide release for biological targets. Toward developing air-stable photoCORMs labilized by visible light Coord. Chem. Rev. 2012, 256, 1509-1519
16. Rimmer, R. D.; Richter, H.; Ford, P. C. A photochemical precursor for carbon monoxide release in aerated aqueous media Inorg. Chem. 2010, 49, 1180-1185
17. Schatzschneider, U. PhotoCORMs: light-triggered release of carbon monoxide from the coordination sphere of transition metal complexes for biological applications Inorg. Chim. Acta 2011, 374, 19-23
18. Desmard, M.; Davidge, K. S.; Bouvet, O.; Morin, D.; Roux, D.; Foresti, R.; Ricard, J. D.; Denamur, E.; Poole, R. K.; Montravers, P.; Motterlini, R.; Boczkowski, J. A carbon monoxide-releasing molecule (CORM-3) exerts bactericidal activity against Pseudomonas aeruginosa and improves survival in an animal model of bacteraemia FASEB J. 2009, 23, 1023-1031
19. McLean, S.; Mann, B. E.; Poole, R. K. Sulfite species enhance carbon monoxide release from CO-releasing molecules: Implications for the deoxymyoglobin assay of activity Anal. Biochem. 2012, 427, 36-40
20. Smith, H.; Mann, B. E.; Motterlini, R.; Poole, R. K. The carbon monoxide-releasing molecule, CORM-3 (Ru(CO)(3)Cl(glycinate)), targets respiration and oxidases in Campylobacter jejuni, generating hydrogen peroxide IUBMB Life 2011, 63, 363-371
21. Davidge, K. S.; Sanguinetti, G.; Yee, C. H.; Cox, A. G.; McLeod, C. W.; Monk, C. E.; Mann, B. E.; Motterlini, R.; Poole, R. K. Carbon monoxide-releasing antibacterial molecules target respiration and global transcriptional regulators J. Biol. Chem. 2009, 284, 4516-4524
22. Wilson, J. L.; Jesse, H. E.; Hughes, B. M.; Lund, V.; Naylor, K.; Davidge, K. S.; Cook, G. M.; Mann, B. E.; Poole, R. K. Ru(CO)3Cl(glycinate) (CORM-3): a CO-releasing molecule with broad-spectrum antimicrobial and photosensitive activities against respiration and cation transport in Escherichia coli Antioxid. Redox Signaling 2013, 19, 497-509
23. Zobi, F.; Blacque, O. Reactivity of 17 e- complex [ReII(Br)4(CO)(2)](2-) with bridging aromatic ligands. Characterization and CO-releasing properties Dalton Trans. 2011, 40, 4994-5001
24. Zobi, F.; Degonda, A. CO-releasing properties of cis-trans-[Re-II(CO)(2) Br2L2](n) complexes Nucl. Med. Biol. 2010, 37, 712-712
25. Zobi, F.; Degonda, A.; Schaub, M. C.; Bogdanova, A. Y. CO releasing properties and cytoprotective effect of cis-trans-[Re-II(CO)(2)Br2L2](n) complexes Inorg. Chem. 2010, 49, 7313-7322
26. Moreira, E. S.; Brasch, N. E.; Yun, J. Vitamin B-12 protects against superoxide-induced cell injury in human aortic endothelial cells Free Radical Biol. Med. 2011, 51, 876-883
27. Hygum, K.; Lildballe, D. L.; Greibe, E. H.; Morkbak, A. L.; Poulsen, S. S.; Sorensen, B. S.; Petersen, T. E.; Nexo, E. Mouse transcobalamin has features resembling both human transcobalamin and haptocorrin PLoS One 2011, 6, e20638
28. Wuerges, J.; Garau, G.; Geremia, S.; Fedosov, S. N.; Petersen, T. E.; Randaccio, L. Structural basis for mammalian vitamin B-12 transport by transcobalamin Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4386-4391
29. Vortherms, A. R.; Kahkoska, A. R.; Rabideau, A. E.; Zubieta, J.; Andersen, L. L.; Madsen, M.; Doyle, R. P. A water soluble vitamin B-12-Re(I) fluorescent conjugate for cell uptake screens: use in the confirmation of cubilin in the lung cancer line A549 Chem. Commun. 2011, 47, 9792-9794
30. Kunze, S.; Zobi, T.; Kurz, P.; Spingler, B.; Alberto, R. Vitamin B12 as a ligand for technetium and rhenium complexes Angew. Chem., Int. Ed. 2004, 43, 5025-5029
31. Mundwiler, S.; Spingler, B.; Kurz, P.; Kunze, S.; Alberto, R. Cyanide-bridged vitamin B-12-cisplatin conjugates Chem.-Eur. J. 2005, 11, 4089-4095
32. Ruiz-Sanchez, P.; Mundwiler, S.; Medina-Molner, A.; Spingler, B.; Alberto, R. Iodination of cisplatin adduct of Vitamin B-12 [{B-12}-CN-{cis- PtCl(NH3)(2)}](+) J. Organomet. Chem. 2007, 692, 1358-1362
33. Zobi, F.; Kromer, L.; Spingler, B.; Alberto, R. Synthesis and reactivity of the 17 e(-) complex [(ReBr4)-Br-II(CO)(2)](2-): a convenient entry into rhenium(II) chemistry Inorg. Chem. 2009, 48, 8965-8970
34. Günzler, H.; Gremlich, H.-U. IR Spectroscopy; Wiley-VCH: Hoboken, NJ, 2002.
35. Miller, L. M.; Carr, G. L.; Williams, G. P.; Chance, M. R. Synchrotron infrared microspectroscopy as a means of studying chemical composition at a cellular level Biophys. J. 1997, 72, TU445-TU445
36. Matthaeus, C.; Bird, B.; Miljkovic, M.; Chernenko, T.; Romeo, M.; Diem, M. Infrared and Raman Microscopy in Cell Biology. In Biophysical Tools for Biologists; Correia, J. J.; Detrich, H., III, Eds.; Elsevier: New York, 2008; Vol. 2, In Vivo Techniques, pp 275-308.
37. Carr, G. L. Resolution limits for infrared microspectroscopy explored with synchrotron radiation Rev. Sci. Instrum. 2001, 72, 1613-1619
38. Quaroni, L.; Zlateva, T. Infrared spectromicroscopy of biochemistry in functional single cells Analyst 2011, 136, 3219-3232
39. Holman, H. Y. N.; Bechtel, H. A.; Hao, Z.; Martin, M. C. Synchrotron IR spectromicroscopy: chemistry of living cells Anal. Chem. 2011, 82, 8757-8765
40. Quaroni, L.; Zlateva, T.; Normand, E. Detection of weak absorption changes from molecular events in time-resolved FT-IR spectromicroscopy measurements of single functional cells Anal. Chem. 2011, 83, 7371-7380
41. Noda, I. Generalized two-dimensional correlation spectroscopy Front. Mol. Spectrosc. 2009, 367-381
42. Massaro, S.; Zlateva, T.; Torre, V.; Quaroni, L. Detection of molecular processes in the intact retina by ATR-FTIR spectromicroscopy Anal. Bioanal. Chem. 2008, 390, 317-322
43. Quaroni, L.; Normand, E. Two-Dimensional Correlation Spectroscopy Analysis for the Recovery of Weak Bands from Time-Resolved Infrared Spectra of Single Cells. In Wirms 2009: 5th International Workshop on Infrared Microscopy and Spectroscopy with Accelerator Based Sources; American Institue of Physics: College Park, MD, 2010; Vol. 1214, pp 66-68.
44. Ye, X. D.; Fels, D.; Tovmasyan, A.; Aird, K. M.; Dedeugd, C.; Allensworth, J. L.; Kos, I.; Park, W.; Spasojevic, I.; Devi, G. R.; Dewhirst, M. W.; Leong, K. W.; Batinic-Haberle, I. Cytotoxic effects of Mn(III) N-alkylpyridylporphyrins in the presence of cellular reductant ascorbate Free Radical Res. 2011, 45, 1289-1306
45. Woo, E. S.; Lazo, J. S. Nucleocytoplasmic functionality of metallothionein Cancer Res. 1997, 57, 4236-4241
46. Meister, K.; Niesel, J.; Schatzschneider, U.; Metzler-Nolte, N.; Schmidt, D. A.; Havenith, M. Label-free imaging of metal-carbonyl complexes in live cells by Raman microspectroscopy Angew. Chem., Int. Ed. 2010, 49, 3310-3312
47. Policar, C.; Waern, J. B.; Plamont, M. A.; Clede, S.; Mayet, C.; Prazeres, R.; Ortega, J. M.; Vessieres, A.; Dazzi, A. Subcellular IR imaging of a metal-carbonyl moiety using photothermally induced resonance Angew. Chem., Int. Ed. 2011, 50, 860-864
48. Jamin, N.; Miller, L.; Moncuit, J.; Fridman, W.-H.; Dumas, P.; Teillaud, J.-L. Chemical heterogeneity in cell death: combined synchrotron IR and fluorescence microscopy studies of single apoptotic and necrotic cells Biopolymers 2003, 72, 366-373
49. Nielsen, M. J.; Rasmussen, M. R.; Andersen, C. B. F.; Nexo, E.; Moestrup, S. K. Vitamin B-12 transport from food to the body's cells-a sophisticated, multistep pathway Nat. Rev. Gastroenterol. Hepatol. 2012, 9, 345-354
50. Vicente-Manzanares, M.; Ma, X. F.; Adelstein, R. S.; Horwitz, A. R. Non-muscle myosin II takes centre stage in cell adhesion and migration Nat. Rev. Mol. Cell Biol. 2009, 10, 778-790
51. Hinz, B. The myofibroblast: Paradigm for a mechanically active cell J. Biomech. 2010, 43, 146-155
52. Schmid-Brunclik, N.; Burgi-Taboada, C.; Antoniou, X.; Gassmann, M.; Ogunshola, O. O. Astrocyte responses to injury: VEGF simultaneously modulates cell death and proliferation Am. J. Physiol. Reg. Integr. Comp. Physiol. 2008, 295, R864-R873
53. Iyengar, S. S.; Frisch, M. J. Effect of time-dependent basis functions and their superposition error on atom-centered density matrix propagation (ADMP): connections to wavelet theory of multiresolution analysis J. Chem. Phys. 2004, 121, 5061-5070
54. Becke, A. D. Density functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648-5652
55. Hay, P. J.; Wadt, W. R. Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg J. Chem. Phys. 1985, 82, 270-283
56. Hay, P. J.; Wadt, W. R. Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals J. Chem. Phys. 1985, 82, 299-310
57. Wadt, W. R.; Hay, P. J. Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi J. Chem. Phys. 1985, 82, 284-298
58. Dapprich, S.; Komaromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. A new ONIOM implementation in Gaussian98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives J. Mol. Struct. (Theochem) 1999, 462, 1-21
59. Vreven, T.; Byun, K. S.; Komaromi, I.; Dapprich, S.; Montgomery, J. A.; Morokuma, K.; Frisch, M. J. Combining quantum mechanics methods with molecular mechanics methods in ONIOM J. Chem. Theory Comput. 2006, 2, 815-826
60. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. UFF, a full periodic-table force-field for molecular mechanics and molecular-dynamics simulations J. Am. Chem. Soc. 1992, 114, 10024-10035