Fast-response and highly selective fluorescent probes for biological signaling molecule NO based on N-nitrosation of electron-rich aromatic secondary amines

Biomaterials

Volumn 78, Issue , 2016, Pages 11-19

  Miao, Junfeng ^a   Huo, Yingying ^a   Lv, Xin ^a   Li, Zhe ^a   Cao, Hualiang ^a   Shi, Heping ^a   Shi, Yawei ^a   Guo, Wei ^a  

^a SHANXI UNIVERSITY   (China)

Author keywords

Aromatic secondary amine; Bioimaging; Fluorescent probes; Nitric oxide; Nitrosation

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; ASCORBIC ACID; CHEMICAL REACTIONS; ENDOTHELIAL CELLS; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; MOLECULES; NITRIC OXIDE; SCAFFOLDS (BIOLOGY); WELL STIMULATION;

BIO-IMAGING; ELECTRON-RICH AROMATICS; FLUORESCENT PROBES; NITROSATION; OXYGEN GLUCOSE DEPRIVATION; PHYSIOLOGICAL PROCESS; REACTIVE OXYGEN SPECIES; SECONDARY AMINES;

PROBES;

AMINE; FLUORESCENT DYE; NITRIC OXIDE;

CHEMISTRY; ELECTRON; NITROSATION;

AMINES; ELECTRONS; FLUORESCENT DYES; NITRIC OXIDE; NITROSATION;

EID: 84949994339     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2015.11.011     Document Type: Article

References (64)

1. Snyder S.H. Nitric oxide: first in a new class of neurotransmitters. Science 1992, 257:494-496.
2. Jasid S., Simontacchi M.C., Bartoli G., Puntarulo S. Chloroplasts as a nitric oxide cellular source. Effect of reactive nitrogen species on chloroplastic lipids and proteins. Plant Physiol. 2006, 142:1246-1255.
3. Fukumura D., Kashiwagi S., Jain R.K. The role of nitric oxide in tumor progression. Nat. Rev. Cancer 2006, 6:521-534.
4. Taysi S., Uslu C., Akcay F., Sutbeyaz M.Y. Malondialdehyde and nitric oxide levels in the plasma of patients with advanced laryngeal cancer. Surg. Today 2003, 33:651-654.
5. Biro G.P. Adverse HBOC-endothelial dysfunction synergism: a possible contributor to adverse clinical outcomes. Curr. Drug Discov. Technol. 2012, 9:194-203.
6. Choi D.Y., Lee Y.J., Hong J.T., Lee H.J. Antioxidant properties of natural polyphenols and their therapeutic potentials for Alzheimer's disease. Brain Res. Bull. 2012, 87:144-153.
7. Kinsella J.P., Cutter G.R., Walsh W.F., Gerstmann D.R., Bose C.L., Hart C., Sekar K.C., Auten R.L., Bhutani V.K., Gerdes J.S., George T.N., Southgate W.M., Carriedo H., Couser R.J., Mammel M.C., Hall D.C., Pappagallo M., Sardesai S., Strain J.D., Baier M., Abman S.H. Early inhaled nitric oxide therapy in premature newborn with respiratory failure. N. Engl. J. Med. 2006, 355:354-364.
8. Wang P.G., Xian M., Tang X.P., Wu X.J., Wen Z., Cai T.W., Janczuk A.J. Nitric oxide donors: chemical activities and biological applications. Chem. Rev. 2002, 102:1091-1134.
9. Yuan L., Lin W., Zheng K., He L., Huang W. Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging. Chem. Soc. Rev. 2013, 42:622-661.
10. Yang Y., Zhao Q., Feng W., Li F. Luminescent chemodosimeters for bioimaging. Chem. Rev. 2013, 113:192-270.
11. Zhu H., Fan J., Wang B., Peng X. Fluorescent, MRI, and colorimetric chemical sensors for the first-row d-block metal ions. Chem. Soc. Rev. 2015, 44:4337-4366.
12. Lou Z., Li P., Han K. Redox-responsive fluorescent probes with different design strategies. Acc. Chem. Res. 2015, 48:1358-1368.
13. You L., Zha D., Anslyn E.V. Recent advances in supramolecular analytical chemistry using optical sensing. Chem. Rev. 2015, 115:7840-7892.
14. Yu F., Li P., Li G., Zhao G., Chu T., Han K. A near-IR reversible fluorescent probe modulated by selenium for monitoring peroxynitrite and imaging in living cells. J. Am. Chem. Soc. 2011, 133:11030-11033.
15. 2 oxidative stress cycles in living cells. Chem. Commun. 2013, 49:391-393.
16. Kojima H., Urano Y., Kikuchi K., Higuchi T., Hirata Y., Nagano T. Fluorescent indicators for imaging nitric oxide production. Angew. Chem. Int. Ed. 1999, 38:3209-3212.
17. Gabe Y., Urano Y., Kikuchi K., Kojima H., Nagano T. Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophores: rational design of potentially useful bioimaging fluorescence probe. J. Am. Chem. Soc. 2004, 126:3357-3367.
18. Sasaki E., Kojima H., Nishimatsu H., Urano Y., Kikuchi K., Hirata Y., Nagano T. Highly sensitive near-infrared fluorescent probes for nitric oxide and their application to isolated organs. J. Am. Chem. Soc. 2005, 127:3684-3685.
19. Yu H., Xiao Y., Jin L. A lysosome-targetable and two-photon fluorescent probe for monitoring endogenous and exogenous nitric oxide in living cells. J. Am. Chem. Soc. 2012, 134:17486-17489.
20. 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.
21. Huang C.-B., Huang J., Xu L. A highly selective fluorescent probe for fast detection of nitric oxide in aqueous solution. RSC Adv. 2015, 5:13307-13310.
22. Takakura H., Kojima R., Kamiya M., Kobayashi E., Komatsu T., Ueno T., Terai T., Hanaoka K., Nagano T., Urano Y. New class of bioluminogenic probe based on bioluminescent enzyme-induced electron transfer: BioLeT. J. Am. Chem. Soc. 2015, 137:4010-4013.
23. Lim M.H., Lippard S.J. Copper complexes for fluorescence-based NO detection in aqueous solution. J. Am. Chem. Soc. 2005, 127:12170-12171.
24. 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.
25. 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, 128:14364-14373.
26. Pluth M.D., McQuade L.E., Lippard S.J. Cell-trappable fluorescent probes for nitric oxide visualization in living cells. Org. Lett. 2010, 12:2318-2321.
27. McQuade L.E., Ma J., Lowe G., Ghatpande A., Gelperin A., Lippard S.J. Visualization of nitric oxide production in the mouse main olfactory bulb by a cell-trappable copper(II) fluorescent probe. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:8525-8530.
28. Johnson I., Spence M.T.Z. The Molecular Probes Handbook-a Guide to Fluorescent Probes and Labeling Technologies 2010, Life Technologies, Carlsbad, Calif, USA. eleventh ed.
29. Zhang X., Kim W.-S., Hatcher N., Potgieter K., Moroz L.L., Gillette R., Sweedler J.V. Interfering with nitric oxide measurements. J. Biol. Chem. 2002, 277:48472-48478.
30. Ye X., Rubakhin S.S., Sweedler J.V. Simultaneous nitric oxide and dehydroascorbic acid imaging by combining diaminofluoresceins and diaminorhodamines. J. Neurosci. Methods 2008, 168:373-382.
31. Wang T., Douglass E.F., Fitzgerald K.J., Spiegel D.A. A "turn-On" fluorescent sensor for methylglyoxal. J. Am. Chem. Soc. 2013, 135:12429-12433.
32. Yang Y., Seidlits S.K., Adams M.M., Lynch V.M., Schmidt C.E., Anslyn E.V., Shear J.B. A highly selective low-background fluorescent imaging agent for nitric oxide. J. Am. Soc. Chem. 2010, 132:13114-13116.
33. Shiue T.-W., Chen Y.-H., Wu C.-M., Singh G., Chen H.-Y., Hung C.-H., Liaw W.-F., Wang Y.-M. Nitric oxide turn-on fluorescent probe based on deamination of aromatic primary monoamines. Inorg. Chem. 2012, 51:5400-5408.
34. Beltrán A., Burguete M.I., Abánades D.R., Pérez-Sala D., Lius S.V., Galindo F. Turn-on fluorescent probes for nitric oxide sensing based on the ortho-hydroxyamino structure showing no interference with dehydroascorbic acid. Chem. Commun. 2014, 50:3579-3581.
35. Sun C., Shi W., Song Y., Chen W., Ma H. An unprecedented strategy for selective and sensitive fluorescence detection of nitric oxide based on its reaction with a selenide. Chem. Commun. 2011, 47:8638-8640.
36. Ma S., Fang D.-C., Ning B., Li M., He L., Gong B. Rational design of a highly sensitive and selective fluorogenic probe for detecting nitric oxide. Chem. Commun. 2014, 50:6475-6478.
37. Yu H., Zhang X., Xiao Y., Zou W., Wang L., Jin L. Targetable fluorescent probe for monitoring exogenous and endogenous NO in mitochondria of living cells. Anal. Chem. 2013, 85:7076-7084.
38. Yu H., Jin L., Dai Y., Li H., Xiao Y. From a BODIPY-rhodamine scaffold to a ratiometric fluorescent probe for nitric oxide. New J. Chem. 2013, 37:1688-1691.
39. Sun Y.-Q., Liu J., Zhang H., Huo Y., Lv X., Shi Y., Guo W. A mitochondria-targetable fluorescent probe for dual-channel NO imaging assisted by intracellular cysteine and glutathione. J. Am. Chem. Soc. 2014, 136:12520-12523.
40. Moncada S., Palmer R.M., Higgs E.A. Nitricoxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 1991, 43:109-142.
41. Marletta M.A. Nitric oxide synthase: aspects concerning structure and catalysis. Cell 1994, 78:927-930.
42. Förstermann U., Gath I., Schwarz P., Closs E.I., Kleinert H. Isoforms of nitric oxide synthase: Properties, cellular distribution and expressional control. Biochem. Pharmacol. 1995, 50:1321-1332.
43. Yu H., Zhang X., Xiao Y., Zou W., Wang L., Jin L. Targetable fluorescent probe for monitoring exogenous and endogenous NO in mitochondria of living cells. Anal. Chem. 2013, 85:7076-7084.
44. Uppu R.M., Pryor W.A. Synthesis of peroxynitrite in a two-phase system using isoamyl nitrite and hydrogen peroxide. Anal. Biochem. 1996, 236:242-249.
45. Nagano T., Takizawa H., Hirobe M. Reactions of nitric oxide with amines in the presence of dioxygen. Tetrahedron Lett. 1995, 36:8239-8242.
46. Nonoyama N., Oshima H., Shoda C., Suzuki H. The reaction of peroxynitrite with organic molecules bearing a biologically important functionality. The multiplicity of reaction modes as exemplified by hydroxylation, nitration, nitrosation, dealkylation, oxygenation, and oxidative dimerization and cleavage. Bull. Chem. Soc. Jpn. 2001, 74:2385-2395.
47. Sturzbecher M., Kissner R., Nauser T., Koppenol W.H. Homolysis of the peroxynitrite anion detected with permanganate. Inorg. Chem. 2007, 46:10655-10658.
48. Zheng H., Shang G.-Q., Yang S.-Y., Gao X., Xu J.-G. Fluorogenic and chromogenic rhodamine spirolactam based probe for nitric oxide by spiro ring opening reaction. Org. Lett. 2008, 10:2357-2360.
49. Setsukinai K., Urano Y., Kakinuma K., Majima H.J., Nagano T. Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species. J. Biol. Chem. 2003, 278:3170-3175.
50. Guo T., Cui L., Shen J., Wang R., Zhu W., Xu Y., Qian X. Dual-emission and large Stokes shift fluorescence probe for real-time discrimination of ROS/RNS and its imaging in living cells. Chem. Commun. 2013, 49:1862-1864.
51. Sun Z.-N., Liu F.-Q., Chen Y., Tam K.H., Yang D. A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid. Org. Lett. 2008, 10:2171-2174.
52. Hu J.J., Wong N.-K., Gu Q., Bai X., Ye S., Yang D. HKOCl-2 series of green BODIPY-based fluorescent probes for hypochlorous acid detection and imaging in live cells. Org. Lett. 2014, 16:3544-3547.
53. Palao E., Agarrabeitia A.R., Bañuelos-Prieto J., Lopez T.A., Lopez-Arbeloa I., Armesto D., Ortiz M.J. 8-Functionalization of alkyl-substituted-3,8-dimethyl BODIPYs by Knoevenagel condensation. Org. Lett. 2013, 15:4454-4457.
54. Seneviratne U., Godoy L.C., Wishnok J.S., Wogan G.N., Tannenbaum S.R. Mechanism-based triarylphosphine-ester probes for capture of endogenous RSNOs. J. Am. Chem. Soc. 2013, 135:7693-7704.
55. Lippert A.R., Van de Bittner G.C., Chang C.J. Boronate oxidation as a bioorthogonal reaction approach for studying the chemistry of hydrogen peroxide in living systems. Acc. Chem. Res. 2011, 44:793-804.
56. Masanta G., Lim C.S., Kim H.J., Han J.H., Kim H.M., Cho B.R. A mitochondrial-targeted two-photon probe for zinc ion. J. Am. Chem. Soc. 2011, 133:5698-5700.
57. Bogdan C. Nitric oxide and the immune response. Nat. Immunol. 2001, 2:907-916.
58. Prathapasinghe G.A., Siow Y.L., Xu Z., O K. Inhibition of cystathionine-β-synthase activity during renal ischemia-reperfusion: role of pH and nitric oxide. Am. J. Physiol. Ren. Physiol. 2008, 295:F912-F922.
59. Dugo L., Serraino I., Fulia F., De Sarro A., Caputi A.P., Cuzzocrea S. Effect of melatonin on cellular energy depletion mediated by peroxynitrite and poly (ADP-ribose) synthetase activation in an acute model of inflammation. J. Pineal. Res. 2001, 31:76-84.
60. Teixeira A., Morfim M.P., de Cordova C.A., Charão C.C., de Lima V.R., Creczynski T.B. Melatonin protects against pro-oxidant enzymes and reduces lipid peroxidation in distinct membranes induced by the hydroxyl and ascorbyl radicals and by peroxynitrite. J. Pineal. Res. 2003, 35:262-268.
61. Yin J., Liu Y.H., Xu Y.F., Zhang Y.J., Chen J.G., Shu B.H., Wang J.Z. Melatonin arrests peroxynitrite-induced tau hyperphosphorylation and the overactivation of protein kinases in rat brain. J. Pineal. Res. 2006, 41:124-129.
62. Golderg M.P., Choi D.W. Combined oxygen and glucose deprivation in cortical cell culture: calcium-dependent and calcium-independent mechanisms of neuronal injury. J. Neurosci. 1993, 13:3510-3524.
63. Shi H., Liu S., Miyake M., Liu K.J. Ebselen induced C6 Glioma cell death in oxygen and glucose deprivation. Chem. Res. Toxicol. 2006, 19:655-660.
64. Yang W., Will Thompson J., Wang Z., Wang L., Sheng H., Foster M.W. Analysis of oxygen/glucose-deprivation-induced changes in SUMO3 conjugation using SILAC-based quantitative proteomics. J. Proteome Res. 2012, 11:1108-1117.