A fast and selective two-photon phosphorescent probe for the imaging of nitric oxide in mitochondria

Biomaterials

Volumn 58, Issue , 2015, Pages 72-81

  Chen, Xiang ^a   Sun, Lingli ^a   Chen, Yu ^a   Cheng, Xiaolin ^a   Wu, Weijun ^a   Ji, Liangnian ^a   Chao, Hui ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

Iridium complex; Mitochondria; Nitric oxide; Two photon probe; Zebrafish

Indexed keywords

MITOCHONDRIA; NITRIC OXIDE; PHOSPHORESCENCE; PHOTONS; PROBES;

BEHAVIOR ANALYSIS; HIGH SPECIFICITY; IRIDIUM COMPLEX; LOW CYTOTOXICITIES; MULTICELLULAR SPHEROID; TRACKING PROBES; TWO-PHOTON PROBES; ZEBRAFISH;

IRIDIUM COMPOUNDS;

1,10 PHENANTHROLINE; IRIDIUM COMPLEX; NITRIC OXIDE; 1,10-PHENANTHROLINE-5,6-DIAMINE; DIAMINE; IRIDIUM; MOLECULAR PROBE; PHENANTHROLINE DERIVATIVE;

ADHERENT CELL; ANIMAL EXPERIMENT; ARTICLE; BEHAVIORAL SCIENCE; CYTOTOXICITY; HUMAN; HUMAN CELL; IMAGING; LIGHT ABSORPTION; MITOCHONDRION; MOLECULAR PROBE; MULTICELLULAR SPHEROID; NONHUMAN; PHOSPHORESCENCE; PHOTON; PRIORITY JOURNAL; SYNTHESIS; ZEBRA FISH; ANIMAL; CELL ADHESION; CHEMISTRY; CONFOCAL MICROSCOPY; DEVICES; HELA CELL LINE; LUMINESCENCE; MASS SPECTROMETRY; METABOLISM; TUMOR CELL CULTURE;

DANIO RERIO; VASCONCELLEA CANDICANS;

ANIMALS; CELL ADHESION; DIAMINES; HELA CELLS; HUMANS; IRIDIUM; LUMINESCENCE; MASS SPECTROMETRY; MICROSCOPY, CONFOCAL; MITOCHONDRIA; MOLECULAR PROBES; NITRIC OXIDE; PHENANTHROLINES; PHOTONS; SPHEROIDS, CELLULAR; TUMOR CELLS, CULTURED; ZEBRAFISH;

EID: 84929257469     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2015.04.012     Document Type: Article

References (62)

1. Kharitonov S.A., Yates D., Robbins R.A., Logan-Sinclair R., Shinebourne E.A., Barnes P.J. Increased nitric oxide in exhaled air of asthmatic patients. Lancet 1994, 343:133-135.
2. Vane J.R., Mitchell J.A., Appleton I., Tomlinson A., Bishop-Bailey D., Croxtall J., et al. Inducible isoforms of cyclooxygenase and nitric-oxide synthase in inflammation. Proc Natl Acad Sci U S A 1994, 91:2046-2050.
3. Eiserich J.P., Hristova M., Cross C.E., Jones A.D., Freeman B.A., Halliwell B., et al. Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 1998, 391:393-397.
4. Dinerman J.L., Lowenstein C.J., Snyder S.H. Molecular mechanisms of nitric oxide regulation. Potential relevance to cardiovascular disease. Circ Res 1993, 73:217-222.
5. Yetik-Anacak G., Catravas J.D. Nitric oxide and the endothelium: history and impact on cardiovascular disease. Vasc Pharmacol 2006, 45:268-276.
6. Cooke J.P., Dzau V.J. Nitric oxide synthase: role in the genesis of vascular disease. Annu Rev Med 1997, 28:489-509.
7. Koprowski H., Zheng Y.M., Heber-Katz E., Fraser N., Rorke L., Fu Z.F., et al. In vivo expression of inducible nitric oxide synthase in experimentally induced neurologic diseases. Proc Natl Acad Sci U S A 1993, 90:3024-3027.
8. Liberatore G.T., Jackson-Lewis V., Vukosavic S., Mandir A.S., Vila M., McAuliffe W.G., et al. Inducible nitric oxide synthase stimulates dopaminergic neurodegeneration in the MPTP model of Parkinson disease. Nat Med 1999, 5:1403-1409.
9. Law A., Gauthier S., Quirion R. Say NO to Alzheimer's disease: the putative links between nitric oxide and dementia of the Alzheimer's type. Brain Res Rev 2001, 35:73-96.
10. Cobbs C.S., Brenman J.E., Aldape K.D., Bredt D.S., Israel M.A. Expression of nitric oxide synthase in human central nervous system tumors. Cancer Res 1995, 55:727-730.
11. Thomsen L.L., Lawton F.G., Knowles R.G., Beesley J.E., Riveros-Moreno V., Moncada S. Nitric oxide synthase activity in human gynecological cancer. Cancer Res 1994, 54:1352-1354.
12. Xu W., Liu L.Z., Loizidou M., Ahmed M., Charles I.G. The role of nitric oxide in cancer. Cell Res 2002, 12:311-320.
13. Wilson K.T., Fu S., Ramanujam K.S., Meltzer S.J. Increased expression of inducible nitric oxide synthase and cyclooxygenase-2 in Barrett's esophagus and associated adenocarcinomas. Cancer Res 1998, 58:2929-2934.
14. Wink D.A., Kasprzak K.S., Maragos C.M., Elespuru R.K., Misra M., Dunams T.M., et al. DNA deaminating ability and genotoxicity of nitric oxide and its progenitors. Science 1991, 254:1001-1003.
15. Marletta M.A. Nitric oxide synthase: aspects concerning structure and catalysis. Cell 1994, 78:927-930.
16. Nisoli E., Clementi E., Paolucci C., Cozzi V., Tonello C., Sciorati C., et al. Mitochondrial biogenesis in mammals: the role of endogenous nitric oxide. Science 2003, 299:896-899.
17. Ghafourifar P., Richter C. Nitric oxide synthase activity in mitochondria. FEBS Lett 1997, 418:291-296.
18. López-Figueroa M.O., Caamaño C., Morano M.I., Rønn L.C., Akil H., Watson S.J. Direct evidence of nitric oxide presence within mitochondria. Biochem Biophys Res Commun 2000, 272:129-133.
19. Lacza Z., Pankotai E., Csordás A., Gero D., Kiss L., Horváth E.M., et al. Mitochondrial NO and reactive nitrogen species production: does mtNOS exist. Nitric Oxide 2006, 14:162-168.
20. van der Vliet A., Eiserich J.P., Halliwell B., Cross C.E. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity. J Biol Chem 1997, 272:7617-7625.
21. Darley-Usmar V., Halliwell B. Blood radicals: reactive nitrogen species, reactive oxygen species, transition metal ions, and the vascular system. Pharm Res 1996, 13:649-662.
22. Landmesser U., Dikalov S., Price S.R., McCann L., Fukai T., Holland S.M., et al. Oxidation of tetrahydrobiopterin leads to uncoupling of endothelial cell nitric oxide synthase in hypertension. J Clin Invest 2003, 111:1201-1209.
23. 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.
24. Zhang R., Ye Z., Wang G., Zhang W., Yuan J. Development of a ruthenium(II) complex based luminescent probe for imaging nitric oxide production in living cells. Chem Eur J 2010, 16:6884-6891.
25. Chen Y., Guo W., Ye Z., Wang G., Yuan J. A europium(III) cHeLate as an efficient time-gated luminescent probe for nitric oxide. Chem Commun 2011, 47:6266-6268.
26. Zhang W., Zhang J., Zhang H., Cao L., Zhang R., Ye Z., et al. Development and application of a ruthenium(II) complex-based photoluminescent and electrochemiluminescent dual-signaling probe for nitric oxide. Talanta 2013, 116:354-360.
27. Kumar P., Kalita A., Mondal B. Nitric oxide sensors based on copper(II) complexes of N-donor ligands. Inorg Chim Acta 2013, 404:88-96.
28. Lim M.H., Lippard S.J. Metal-based turn-on fluorescent probes for sensing nitric oxide. Acc Chem Res 2007, 40:41-51.
29. Dong X., Heo C.H., Chen S., Kim H.M., Liu Z. Quinoline-based two-photon fluorescent probe for nitric oxide in live cells and tissues. Anal Chem 2014, 86:308-311.
30. Zhang H.X., Chen J.B., Guo X.F., Wang H., Zhang H.S. Highly sensitive low-background fluorescent probes for imaging of nitric oxide in cells and tissues. Anal Chem 2014, 86:3115-3123.
31. Shiue T.W., Chen Y.H., Wu C.M., Singh G., Chen H.Y., Hung C.H., et al. Nitric oxide turn-on fluorescent probe based on deamination of aromatic primary monoamines. Inorg Chem 2012, 51:5400-5408.
32. Uppu R.M. Synthesis of peroxynitrite using isoamyl nitrite and hydrogen peroxide in a homogeneous solvent system. Anal Biochem 2006, 354:165-168.
33. Halliwell B., Gutteridge J.M.C. Oxygen free radicals and iron in relation to biology and medicine: some problems and concepts. Arch Biochem Biophys 1986, 246:501-514.
34. Sprouse S., King K.A., Spellane P.J., Watts R.J. Photophysical effects of metal-carbon.sigma. bonds in ortho-metalated complexes of iridium(III) and rhodium(III). J Am Chem Soc 1984, 106:6647-6653.
35. Bolger J., Gourdon A., Ishow E., Launay J.P. Mononuclear and binuclear tetrapyrido[3,2-a:2',3'-c:3″,2″-h:2‴,3‴-j]phenazine (tpphz) ruthenium and osmium Complexes. Inorg Chem 1996, 35:2937-2944.
36. Wang D.Z., Li J.R., Li L., Bu X.H. CoL(SO)·4HO and MnL· 2HO (L = 1,10-phenanthroline-4,5-triazolate): synthesis, crystal structures and hydrogen-bonded networks. J Chem Crystallogr 2008, 38:931-936.
37. Crosby G.A., Demas J.N. Measurement of photoluminescence quantum yields. Review. J Phys Chem 1971, 75:991-1024.
38. 2+): solvent effects. J Am Chem Soc 1983, 105:5583-5590.
39. Xu C., Webb W.W. Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J Opt Soc Am B 1996, 13:481-491.
40. Albota M.A., Xu C., Webb W.W. Two-photon fluorescence excitation crosssections of biomolecularprobes from 690 to 960 nm. Appl Opt 1998, 37:7352-7356.
41. Makarov N.S., Drobizhev M., Rebane A. Two-photon absorption standards in the 550-1600 nm excitation wavelength range. Opt Express 2008, 16:4029-4047.
42. Mosmann T.R. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983, 65:55-63.
43. Qian C., Wang J.Q., Song C.L., Wang L.L., Ji L.N., Chao H. The induction of mitochondria-mediated apoptosis in cancer cells by ruthenium(ii) asymmetric complexes. Metallomics 2013, 5:844-854.
44. Coneski P.N., Schoenfisch M.H. Nitric oxide release: part III. Measurement and reporting. Chem Soc Rev 2012, 41:3753-3758.
45. Kim K.Y., Farley R.T., Schanze K.S. An iridium(III) complex that exhibits dual mechanism nonlinear absorption. J Phys Chem B 2006, 110:17302-17304.
46. Ho M.L., Lin M.H., Chen Y.T., Sheu H.S. Iridium(III) complexes in discs for two-photon excitation applications. Chem Phys Lett 2011, 509:162-168.
47. 3. J Am Chem Soc 2006, 128:10990-10991.
48. Edkins R.M., Bettington S.L., Goeta A.E., Beeby A. Two-photon spectroscopy of cyclometalated iridium complexes. Dalton Trans 2011, 40:12765-12770.
49. Sekiguchi Y., Yamashita T., Vacha M. Effect of ligands in two-photon excited luminescence of organometallic iridium complexes. J Lumin 2008, 128:848-850.
50. Natrajan L.S., Toulmin A., Chew A., Magennis S.W. Two-photon luminescence from polar bis-terpyridyl-stilbene derivatives of Ir(III) and Ru(II). Dalton Trans 2010, 39:10837-10846.
51. Ho C.L., Wong K.L., Kong H.K., Ho Y.M., Chan C.T.L., Kwok W.M., et al. A strong two-photon induced phosphorescent golgi-specific in vitro marker based on a heteroleptic iridium complex. Chem Commun 2012, 48:2525-2527.
52. Xu W.J., Liu S.J., Zhao X., Zhao N., Liu Z.Q., Xu H., et al. Synthesis, one- and two-photon photophysical and excited-state properties, and sensing application of a new phosphorescent dinuclearcationic iridium(III) complex. Chem Eur J 2012, 19:621-629.
53. Groessl M., Zava O., Dyson P.J. Cellular uptake and subcellular distribution of ruthenium-based metallodrugs under clinical investigation versus cisplatin. Metallomics 2011, 3:591-599.
54. Verchot-Lubicz J., Goldstein R.E. Cytoplasmic streaming enables the distribution of molecules and vesicles in large plant cells. Protoplasma 2010, 240:99-107.
55. Zhu B., Gao C., Zhao Y., Liu C., Li Y., Wei Q., et al. A 4-hydroxynaphthalimide-derived ratiometric fluorescent chemodosimeter for imaging palladium in living cells. Chem Commun 2011, 47:8656-8658.
56. Ma S., Fang D.C., Ning B., Li M., He L., Gong B. The rational design of a highly sensitive and selective fluorogenic probe for detecting nitric oxide. Chem Commun 2014, 50:6475-6478.
57. Ball K.A., Castello P.R., Poyton R.O. Low intensity light stimulates nitrite-dependent nitric oxide synthesis but not oxygen consumption by cytochrome c oxidase: implications for phototherapy. J Photochem Photobiol B 2011, 102:182-191.
58. Mitchell U.H., Mack G.L. Low-level laser treatment with near-infrared light increases venous nitric oxide levels acutely: a single-blind, randomized clinical trial of efficacy. Am J Phys Med Rehabil 2013, 92:151-156.
59. Lane N. Cell biology: power games. Nature 2006, 443:901-903.
60. Karu T.I., Pyatibrat L.V., Afanasyeva N.I. Cellular effects of low power laser therapy can be mediated by nitric oxide. Lasers Surg Med 2005, 36:307-314.
61. Lipovsky A., Oron U., Gedanken A., Lubart R. Low-level visible light (LLVL) irradiation promotes proliferation of mesenchymal stem cells. Lasers Med Sci 2013, 28:1113-1117.
62. Ozel R.E., Alkasir R.S., Ray K., Wallace K.N., Andreescu S. Comparative evaluation of intestinal nitric oxide in embryonic zebrafish exposed to metal oxide nanoparticles. Small 2013, 24:4250-4261.