Controlled photochemical release of nitric oxide from O2- substituted diazeniumdiolates

Free Radical Biology and Medicine

Volumn 37, Issue 6, 2004, Pages 745-752

  Pavlos, Christopher M ^a   Xu, Hua ^a   Toscano, John P ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

Caged compounds; Diazeniumdiolate; Free radicals; Nitric oxide; Photosensitive precursors; Phototriggers

Indexed keywords

ALCOHOL; ALDEHYDE; AMINE; BENZYL DERIVATIVE; NAPHTHYL GROUP; NITRIC OXIDE DONOR; NITRO DERIVATIVE; NITROSO DERIVATIVE; NITROUS OXIDE; PRODRUG;

ACIDIFICATION; ANGIOGENESIS; APOPTOSIS; CANCER CELL; CELL KILLING; CELL PROLIFERATION; DECOMPOSITION; DEPROTECTION REACTION; DIMERIZATION; DISSOCIATION; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; HUMAN; LEARNING; LONG TERM DEPRESSION; LONG TERM POTENTIATION; LOW TEMPERATURE; MEMORY; NEUROPHYSIOLOGY; NONHUMAN; PH MEASUREMENT; PHOTOCHEMISTRY; PHOTODEGRADATION; PRIORITY JOURNAL; PROTON TRANSPORT; REVIEW; ROOM TEMPERATURE; SUBSTITUTION REACTION; TEMPERATURE DEPENDENCE; THROMBOCYTE AGGREGATION;

ANIMALS; AZO COMPOUNDS; DRUG DELIVERY SYSTEMS; DRUG DESIGN; HUMANS; MODELS, CHEMICAL; NITRIC OXIDE; NITROBENZENES; OXYGEN; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; PRODRUGS;

EID: 4043096884     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.06.010     Document Type: Review

References (74)

1. Hrabie J.A., Keefer L.K. Chemistry of the nitric oxide-releasing diazeniumdiolate ("nitrosohydroxylamine") functional group and its oxygen-substituted derivatives. Chem. Rev. 102:2002;1135-1154
2. Drago R.S., Karstetter B.R. The reactions of nitrogen(II) oxide with various primary and secondary amines. J. Am. Chem. Soc. 83:1960;1819-1822
3. Drago R.S., Paulik F.E. The reaction of nitrogen(II) oxide with diethylamine. J. Am. Chem. Soc. 82:1960;96-98
4. Drago R.S., Ragsdale R.O., Eyman D.P. A mechanism for the reaction of diethylamine with nitric oxide. J. Am. Chem. Soc. 83:1961;4337-4339
5. Longhi R., Ragsdale R.O., Drago R.S. Reactions of nitrogen(II) oxide with miscellaneous Lewis bases. Inorg. Chem. 1:1962;768-770
6. Dutton A.S., Fukuto J.M., Houk K.N. The mechanism of NO formation from the decomposition of dialkylamino diazeniumdiolates: density functional theory and CBS-QB3 predictions. Inorg. Chem. 43:2004;1039-1045
7. Keefer L.K. Progress toward clinical application of the nitric oxide-releasing diazeniumdiolates. Annu. Rev. Pharmacol. Toxicol. 43:2003;585-607
8. Saavedra J.E., Fitzhugh A.L., Keefer L.K. Diazeniumdiolates (formerly NONOates) in cardiovascular research and potential clinical applications. Nitric Oxide Cardiovasc. Syst. 2000;431-446
9. Mooradian D.L., Hutsell T.C., Keefer L.K. Nitric oxide (NO) donor molecules: effect of NO release rate on vascular smooth muscle cell proliferation in vitro. J. Cardiovasc. Pharmacol. 25:1995;674-678
10. - group. J. Med. Chem. 39:1996;1148-1156
11. Mowery K.A., Schoenfisch M.H., Meyerhoff M.E., Saavedra J.E., Keefer L.K. Polymeric diazeniumdiolates for fabricating thromboresistant electrochemical sensors via nitric oxide release. Polym. Mater. Sci. Eng. 79:1998;33-34
12. Mowery K.A., Schoenfisch M.H., Saavedra J.E., Keefer L.K., Meyerhoff M.E. Preparation and characterization of hydrophobic polymeric films that are thromboresistant via nitric oxide release. Biomaterials. 21:1999;9-21
13. Schoenfisch M.H., Mowery K.A., Rader M.V., Baliga N., Wahr J.A., Meyerhoff M.E. Improving the thromboresistivity of chemical sensors via nitric oxide release: fabrication and in vivo evaluation of NO-releasing oxygen-sensing catheters. Anal. Chem. 72:2000;1119-1126
14. Kaul S., Cercek B., Rengstrom J., Xu X.-P., Molloy M.D., Dimayuga P., Parikh A.K., Fishbein M.C., Nilsson J., Rajavashisth T.B., Shah P.K. Polymeric-based perivascular delivery of a nitric oxide donor inhibits intimal thickening after balloon denudation arterial injury: role of nuclear factor-kappaB. J. Am. Coll. Cardiol. 35:2000;493-501
15. Zhang H.P., Annich G.M., Miskulin J., Stankiewicz K., Osterholzer K., Merz S.I., Bartlett R.H., Meyerhoff M.E. Nitric oxide-releasing fumed silica particles: synthesis, characterization, and biomedical application. J. Am. Chem. Soc. 125:2003;5015-5024
16. Batchelor M.M., Reoma S.L., Fleser P.S., Nuthakki V.K., Callahan R.E., Shanley C.J., Politis J.K., Elmore J., Merz S.I., Meyerhoff M.E. More lipophilic dialkyldiamine-based diazeniumdiolates: synthesis, characterization, and application in preparing thromboresistant nitric oxide release polymeric coatings. J. Med. Chem. 46:2003;5153-5161
17. -: O-functionalization chemistry. J. Org. Chem. 57:1992;6134-6138
18. Saavedra J.E., Billiar T.R., Williams D.L., Kim Y.-M., Watkins S.C., Keefer L.K. Targeting nitric oxide (NO) delivery in vivo. Design of a liver-selective NO donor prodrug that blocks tumor necrosis factor-α- induced apoptosis and toxicity in the liver. J. Med. Chem. 40:1997;1947-1954
19. Tang X., Xian M., Trikha M., Honn K.V., Wang P.G. Synthesis of peptide-diazeniumdiolate conjugates: towards enzyme activated antitumor agents. Tetrahedron Lett. 42:2001;2625-2629
20. McCray J.A., Trentham D.R. Properties and uses of photoreactive caged compounds. Annu. Rev. Biophys. Biophys. Chem. 18:1989;239-270
21. Adams S.R., Tsien R.Y. Controlling cell chemistry with caged compounds. Annu. Rev. Physiol. 55:1993;755-784
22. Givens R.S., Kueper L.W. III Photochemistry of phosphate esters. Chem. Rev. 93:1993;55-66
23. Zacharias D.A., Baird G.S., Tsien R.Y. Recent advances in technology for measuring and manipulating cell signals. Curr. Opin. Neurobiol. 10:2000;416-421
24. Bochet C.G. Photolabile protecting groups and linkers. J. Chem. Soc. Perkin Trans. 1:2002;125-142
25. Pelliccioli A.P., Wirz J. Photoremovable protecting groups: reaction mechanisms and applications. Photochem. Photobiol. Sci. 1:2002;441-458
26. Givens R.S., Conrad P.G. II, Yousef A.L., Lee J.-I. Photoremovable protecting groups. Horspool W., Lenci F. CRC handbook of organic photochemistry and photobiology. 2nd ed.:2004;69/61-69/46 CRC Press, Boca Raton (FL)
27. Hoshino M., Laverman L., Ford P.C. Nitric oxide complexes of metalloporphyrins: an overview of some mechanistic studies. Coord. Chem. Rev. 187:1999;75-102
28. De Leo M., Ford P.C. Reversible photolabilization of NO from chromium(III)-coordinated nitrite: a new strategy for nitric oxide delivery. J. Am. Chem. Soc. 121:1999;1980-1981
29. Works C.F., Jocher C.J., Bart G.D., Bu X., Ford P.C. Photochemical nitric oxide precursors: synthesis, photochemistry, and ligand substitution kinetics of ruthenium salen nitrosyl and ruthenium salophen nitrosyl complexes. Inorg. Chem. 41:2002;3728-3739
30. Namiki S., Arai T., Fujimori K. High-performance caged nitric oxide: a new molecular design, synthesis, and photochemical reaction. J. Am. Chem. Soc. 119:1997;3840-3841
31. Namiki S., Kaneda F., Ikegami M., Arai T., Fujimori K., Asada S., Hama H., Kasuya Y., Goto K. Bis-n-nitroso-caged nitric oxides: photochemistry and biological performance test by rat aorta vasorelaxation. Bioorg. Med. Chem. 7:1999;1695-1702
32. Yoshida M., Ikegami M., Namiki S., Arai T., Fujimori K. Triplet sensitized laser flash photolysis of BNN3, caged nitric oxide. Chem. Lett. 2000;730-731
33. Fukuhara K., Kurihara M., Miyata N. Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene. J. Am. Chem. Soc. 123:2001;8662-8666
34. Patra A.K., Afshar R., Olmstead M.M., Mascharak P.K. The first non-heme iron(III) complex with a ligated carboxamido group that exhibits photolability of a bound NO ligand. Angew. Chem. Int. Ed. Engl. 41:2002;2512-2515
35. Hwang K.-J., Kim S.K., Shim S.C. Photochemical generation of nitric oxide from 3,4-bis-2′-chlorophenylfuroxan. Chem. Lett. 1998;859-860
36. Cabail M.Z., Lace P.J., Uselding J., Pacheco A.A. Kinetic studies of the photoinitiated NO-releasing reactions of N,N′-bis-(carboxymethyl)-N, N′-dinitroso-1,4-phenylenediamine. J. Photochem. Photobiol. A. 152:2002;109-121
37. 2-. Inorg. Chem. 38:1999;2947-2952
38. 2. Proc. Natl. Acad. Sci. USA. 98:2001;355-360
39. Wink D.A., Vodovotz Y., Laval J., Laval F., Dewhirst M.W., Mitchell J.B. The multifaceted roles of nitric oxide in cancer. Carcinogenesis. 19:1998;711-721
40. Wink D.A., Vodovotz Y., Cook J.A., Krishna M.C., Kim S., Coffin D., DeGraff W., Deluca A.M., Liebmann J., Mitchell J.B. The role of nitric oxide chemistry in cancer treatment. Biochemistry (Moscow). 63:1998;802-809
41. Mitchell J.B., Cook J.A., Stein W., Coffin D., Espey M.G., Miranda K.M., Wink D.A. Is there a role for nitric oxide in cancer treatment? Radiat. Res. 2:2000;618-621
42. Hofseth L.J., Hussain S.P., Wogan G.N., Harris C.C. Nitric oxide in cancer and chemoprevention. Free Radic. Biol. Med. 34:2003;955-968
43. Howard-Flanders P. Effect of nitric oxide on the radiosensitivity of bacteria. Nature. 180:1957;1191-1192
44. Mitchell J.B., Wink D.A., DeGraff W., Gamson J., Keefer L.K., Krishna M.C. Hypoxic mammalian cell radiosensitization by nitric oxide. Cancer Res. 53:1993;5845-5848
45. Barth A., Hauser K., Maentele W., Corrie J.E.T., Trentham D.R. Photochemical release of ATP from "caged ATP" studied by time-resolved infrared spectroscopy. J. Am. Chem. Soc. 117:1995;10311-10316
46. Il'ichev Y.V., Wirz J. Rearrangements of 2-nitrobenzyl compounds.1. Potential energy surface of 2-nitrotoluene and its isomers explored with ab initio and density functional theory methods. J. Phys. Chem. A. 104:2000;7856-7870
47. Cheng Q., Steinmetz M.G., Jayaraman V. Photolysis of γ-(α- carboxy-2-nitrobenzyl)-L-glutamic acid investigated in the microsecond time scale by time-resolved FTIR. J. Am. Chem. Soc. 124:2002;7676-7677
48. Il'ichev Y.V., Schwoerer M.A., Wirz J. Photochemical reaction mechanisms of 2-nitrobenzyl compounds: methyl ethers and caged ATP. J. Am. Chem. Soc. 126:2004;4581-4595
49. Corrie J.E.T., Barth A., Munasinghe V.R.N., Trentham D.R., Hutter M.C. Photolytic cleavage of 1-(2-nitrophenyl)ethyl ethers involves two parallel pathways and product release is rate-limited by decomposition of a common hemiacetal intermediate. J. Am. Chem. Soc. 123:2003;1636-1644
50. Makings L.R., Tsien R.Y. Caged nitric oxide: stable organic molecules from which nitric oxide can be photoreleased. J. Biol. Chem. 269:1994;6282-6285
51. 2+ transients. Neuron. 15:1995;407-415
52. Lev-Ram V., Nebyelul Z., Ellisman M.H., Huang P.L., Tsien R.Y. Absence of cerebellar long-term depression in mice lacking neuronal nitric oxide synthase. Learn. Memory. 4:1997;169-177
53. 2+ in the induction of cerebellar long-term depression. Neuron. 18:1997;1025-1038
54. Arancio O., Kiebler M., Lee C.J., Lev-Ram V., Tsien R.Y., Kandel E.R., Hawkins R.D. Nitric oxide acts directly in the presynaptic neuron to produce long-term potentiation in cultured hippocampal neurons. Cell. 87:1996;1025-1035
55. Arancio O., Lev-Ram V., Tsien R.Y., Kandel E.R., Hawkins R.D. Nitric oxide acts as a retrograde messenger during long-term potentiation in cultured hippocampal neurons. J. Physiol. 90:1997;321-322
56. Lev-Ram V., Wong S.T., Storm D.R., Tsien R.Y. A new form of cerebellar long-term potentiation is postsynaptic and depends on nitric oxide but not cAMP. Proc. Natl. Acad. Sci. USA. 99:2002;8389-8393
57. Srinivasan A., Kebede N., Saavedra J.E., Nikolaitchik A.V., Brady D.A., Yourd E., Davies K.M., Keefer L.K., Toscano J.P. Chemistry of the diazeniumdiolates. 3. Photoreactivity. J. Am. Chem. Soc. 123:2001;5465-5472
58. 2-benzyl-substituted diazeniumdiolates. J. Am. Chem. Soc. 124:2002;9806-9811
59. Zimmerman H.E. The meta effect in organic photochemistry: mechanistic and exploratory organic photochemistry. J. Am. Chem. Soc. 117:1995;8988-8991
60. Pincock J.A. Photochemistry of arylmethyl esters in nucleophilic solvents: radical pair and ion pair intermediates. Acc. Chem. Res. 30:1997;43-49
61. Zimmerman H.E. Meta-ortho effect in organic photochemistry: mechanistic and exploratory organic photochemistry. J. Phys. Chem. A. 102:1998;5616-5621
62. Zimmerman H.E., Somasekhara S. Mechanistic organic photochemistry. III. Excited state solvolyses. J. Am. Chem. Soc. 85:1963;992-997
63. Barltrop J.A., Schofield P. Organic photochemistry. II. Some photosensitive protecting groups. J. Chem. Soc. 1965;4758-4765
64. Chamberlin J.W. Use of the 3,5-dimethoxybenzyloxycarbonyl group as a photosensitive n-protecting group. J. Org. Chem. 31:1966;1658-1660
65. Bartok W., Lucchesi P.J., Snider N.S. Protolytic dissociation of electronically excited organic acids. J. Am. Chem. Soc. 84:1962;1842-1844
66. Tolbert L.M., Solntsev K.M. Excited-state proton transfer: from constrained systems to "super" photoacids to superfast proton transfer. Acc. Chem. Res. 35:2002;19-27
67. Pavlos C.M., Cohen A.D., D'Sa R.A., Sunoj R.B., Wasylenko W.A., Kapur P., Relyea H.A., Kumar N.A., Toscano J.P. Photochemistry of 1-(N,N-diethylamino) diazen-1-ium-1,2-diolate: an experimental and computational investigation. J. Am. Chem. Soc. 125:2003;14934-14940
68. 2-naphthylallyl-substituted diazeniumdiolates. J. Am. Chem. Soc. 124:2002;12640-12641
69. Givens R.S., Matuszewski B., Neywick C.V. Mechanistic and synthetic studies in organic photochemistry. XII. Photodecarboxylation of esters: photolysis of α- and β-naphthalenemethyl derivatives. J. Am. Chem. Soc. 96:1974;5547-5552
70. DeCosta D.P., Pincock J.A. Photochemistry of substituted 1-naphthylmethyl esters of phenylacetic and 3-phenylpropanoic acid: radical pairs, ion pairs, and Marcus electron transfer. J. Am. Chem. Soc. 115:1993;2180-2190
71. Rao G.V., Reddy M.J.R., Srinivas K., Reddy M.J.R., Bushan K.M., Rao V.J. Ionic photodissociation in arylallyl acetates. Photochem. Photobiol. 76:2002;29-34
72. Seiler P., Wirz J. Photohydrolysis of eight isomeric trifluoromethylnaphthols. Tetrahedron Lett. 12:1971;1683-1686
73. Shizuka H. Excited-state proton-transfer reactions and proton-induced quenching of aromatic compounds. Acc. Chem. Res. 18:1985;141-147
74. Agmon N., Rettig W., Groth C. Electronic determinants of photoacidity in cyanonaphthols. J. Am. Chem. Soc. 124:2002;1089-1096