Christopher Foote's discovery of the role of singlet oxygen [ 1O2 (1Δg)] in photosensitized oxidation reactions

Accounts of Chemical Research

Volumn 39, Issue 11, 2006, Pages 797-804

  Greer, Alexander ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SINGLET OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HISTORY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

HISTORY, 20TH CENTURY; HISTORY, 21ST CENTURY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMISTRY; SINGLET OXYGEN;

EID: 33845478539     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050191g     Document Type: Article

References (103)

1. (a) Adam, W. The Singlet Oxygen Story. Chem. Unserer Zeit 1981, 15, 190-196.
2. (b) Ranby, B. The History of Singlet Oxygen. An Introduction. Kern. Tidskr. 1981, 93, 36-37.
3. Benchmark Papers in Organic Chemistry, Vol. 5: Singlet Molecular Oxygen; Schaap, A. P., Ed.: Halsted Press: Stroudsburg, PA, 1976.
4. Foote, C. S. An Ancient Problem. CHEMTECH 1976, 6, 612-613.
5. Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press, Inc.: New York, 1979.
6. 2; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 1.
7. Foote, C. S.; Wexler, S. Olefin Oxidations with Excited Singlet Molecular Oxygen. J. Am. Chem. Soc. 1964, 86, 3879-3880.
8. Foote, C. S.; Wexler, S. Singlet Oxygen. A Probable Intermediate in Photosensitized Autoxidations. J. Am. Chem. Soc. 1964, 86, 3880-3881.
9. Foote, C. S. Photosensitized Oxygenations and the Role of Singlet Oxygen. Acc. Chem. Res. 1968, 1, 104-110.
10. Lewis, G. N. The Magnetochemical Theory. Chem. Rev. 1924, 1, 231-248.
11. Mulliken, R. S. Interpretation of the Atmospheric Oxygen Bands: Electronic Levels of the Oxygen Molecule. Nature 1928, 122, 505-505.
12. Mulliken, R. S. The Interpretation of Band Spectra: Part III. Electron Quantum Numbers and States of Molecules and Their Atoms. Rev. Mod. Phys. 1932, 4, 54-56.
13. Kautsky, H.; de Bruijn, H. The Explanation of the Inhibition of Photoluminescence of Fluorescent Systems by Oxygen: The Formation of Active, Diffusing Oxygen Molecules by Sensitization. Naturwissenschaften 1931, 19, 1043-1043.
14. Kautsky, H.; de Bruijn, H.; Neuwirth, R.; Baumeister, W. Energy Transfers at Surfaces. VII. Photosensitized Oxidation Mediated by a Reactive, Metastable State of the Oxygen Molecule. Ber. 1933, 66B, 1588-1600.
15. Kautsky, H.; Hirsch, A.; Flesch, W. Energy Transformations on Boundary Surfaces. VIII. The Significance of the Metastable State in Photosensitized Oxidations. Ber. 1935, 68B, 152-162.
16. Gaffron, H. The Mechanism of Oxygen Activation by Illuminated Dyes. II. Photooxidation in the Near Infrared. Ber. 1935, 68B, 1409-1411.
17. Gaffron, H. Metastable Oxygen and Carbon Dioxide Assimilation. Biochem. Z. 1936, 287, 130-139.
18. Terenin, A. N. The Nature of the Photochemical Action in Sensitized Oxygen Oxidation Reactions and Hydroperoxide Breakdown Reactions. Akad. Nauk S.S.S.R. 1955, 85-91.
19. Kautsky, H. Reciprocal Action between Sensitizers and Oxygen in Light. Biochem. Z. 1937, 291, 271-284.
20. Kautsky, H. Quenching of Luminescence by Oxygen. Trans. Faraday Soc. 1939, 35, 216-219.
21. 2; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 1, pp 1-12.
22. (b) Levine, I. N. Quantum Chemistry, 5th ed.; Prentice Hall: Upper Saddle River, NJ, 2000; pp 402-407.
23. Warburg, O.; Christian, W. The Yellow Oxidation Enzyme. Biochem. Z. 1933, 258, 496-498.
24. Warburg, O.; Christian, W. Pyridine, the Hydrogen-Transferring Component of the Fermentation Enzymes. (Pyridine Nucleotide). Biochem. Z. 1936, 287, 291-328.
25. A good historical account of biological oxidation, including Warburg's work, is the following: Molecules and Life. Historical Essays on the Interplay of Chemistry and Biology; Fruton, J. S., Ed.; Wiley-Interscience: New York, 1972. There is no mention of Kautsky's work in this book.
26. Schönberg, v. A. Notiz über die Photochemische Bildung von Biradikalen Liebigs Ann. Chem. 1935, 518, 299-302.
27. Schenck, G. O. Photosensitized Reactions with Molecular Oxygen. Naturwissenschaften 1948, 35, 28-29.
28. 2. Rosenberg, J. L.; Shombert, D. J. The Reaction of Oxygen with Electronically Excited Acriflavine. J. Am. Chem. Soc. 1960, 82, 3257-3260.
29. Blum, H. F. Physiological Effects of Sunlight on Man. Physiol. Rev. 1945, 25, 483-530.
30. Bowen, E. J. Photochemistry of Anthracene. II. The Photooxidation of Anthracenes in Solution. Discuss. Faraday Soc. 1953, 14, 143-146.
31. Livingston, R. S. Chemical Changes Produced by Radiation. Conf. Biol. Antioxid., Trans. 1950, 5, 17-40.
32. Gollnick, K.; Schenck, G. O. Mechanism and Stereoselectivity of Photosensitized Oxygen Transfer Reactions. Pure Appl. Chem. 1964, 9, 507-525. The formation of the hydroperoxide is stereospecific, where the new C-O bond bears a cis relationship to the C-H bond that is broken.
33. Nickon, A.; Bagli, J. F. Photosensitized Oxygenation of Mono-olefins. J. Am. Chem. Soc. 1959, 81, 6330-6330.
34. Khan, A. U.; Kasha, M. Red Chemiluminescence of Molecular Oxygen in Aqueous Solution. J. Chem. Phys. 1963, 39, 2105-2106.
35. Khan, A. U.; Kasha, M. Rotational Structure in the Chemiluminescence Spectrum of Molecular Oxygen in Aqueous Systems. Nature 1964, 204, 241-243.
36. Khan, A. U.; Kasha, M. Chemiluminescence Arising from Simultaneous Transitions in Pairs of Singlet Oxygen Molecules. J. Am. Chem. Soc. 1970, 92, 3293-3300.
37. Arnold, S. J.; Ogryzlo, E. A.; Witzke, H. Some New Emission Bands of Molecular Oxygen. J. Chem. Phys. 1964, 40, 1769-1770.
38. +). Discuss. Faraday Soc. 1964, 46-56.
39. Arnold, J. S.; Browne, R. J.; Ogryzlo, E. A. The Red Emission Bands of Molecular Oxygen. Photochem. Photobiol. 1965, 4, 963-969.
40. 2 in solution. (a) Krasnovskii, A. A., Jr. Photosensitized Luminescence of Singlet Oxygen in Solution. Biofizika 1976, 21, 748-749.
41. (b) Khan, A. U.; Kasha, M. Direct Spectroscopic Observation of Singlet Oxygen Emission at 1268 nm Excited by Sensitizing Dyes of Biological Interest in Liquid Solution. Proc. Nat. Acad. Sci. U.S.A. 1979, 76, 6047-6049.
42. (c) Hurst, J. R.; McDonald, J. D.; Schuster, G. B. Lifetime of Singlet Oxygen in Solution Directly Determined by Laser Spectroscopy. J. Am. Chem. Soc. 1982, 104, 2065-2067.
43. g) Luminescence in Solution Following Pulsed Laser Excitation. Solvent Deuterium Isotope Effects on the Lifetime of Singlet Oxygen. J. Am. Chem. Soc. 1982, 104, 2069-2070.
44. 1Δ Oxygen from a Phosphite-Ozone Complex. J. Am. Chem. Soc. 1968, 90, 4160-4161.
45. 1Δ Oxygen by Paramagnetic Resonance Spectroscopy. J. Am. Chem. Soc. 1969, 91, 1039-1040.
46. 1Δ Oxygen Produced by Gas-Phase Photosensitization with Naphthalene Derivatives. J. Am. Chem. Soc. 1969, 91, 1040-1041.
47. Wasserman, H. H.; Liberles, A. Formation of Epoxides in the Pyrrole and Furan Series by Photooxidation. J. Am. Chem. Soc. 1960, 82, 2086.
48. Schenck, G. O.; Foote, C. S. Über die Photosensibilisierte Autoxydation von Menthofuran Angew. Chem. 1958, 70, 505.
49. Foote, C. S.; Wexler, S.; Ando, W.; Higgins, R. Chemistry of Singlet Oxygen. IV. Oxygenations with Hypochlorite-Hydrogen Peroxide. J. Am. Chem. Soc. 1968, 90, 975-981.
50. Wolf, S.; Foote, C. S.; Rebek, J., Jr. Chemistry of Singlet Oxygen. 29. Three-Phase "Kautsky Test" for Singlet Oxygen. J. Am. Chem. Soc. 1978, 100, 7770-7771.
51. Other studies that are reminiscent of the Kautsky experiments include Midden, W. R.; Wang, S. Y. Singlet Oxygen Generation for Solution Kinetics: Clean and Simple. J. Am. Chem. Soc. 1983, 105, 4129-4135
52. and Eisenberg, W. C.; Taylor, K.; Murray, R. W. Gas-Phase Kinetics of the Reaction of Singlet Oxygen with Olefins at Atmospheric Pressure. J. Phys. Chem. 1986, 90, 1945-1948.
53. Corey, E. J.; Taylor, W. C. A Study of the Peroxidation of Organic Compounds by Externally Generated Singlet Oxygen Molecules. J. Am. Chem. Soc. 1964, 86, 3881-3882.
54. Foner, S. N.; Hudson, R. L. Metastable Oxygen Molecules Produced by Electrical Discharge. J. Chem. Phys. 1956, 25, 601-602.
55. Schenck, G. O. Mechanism of Formation of Singlet Oxygen in Photosensitized Oxygenation. Ann. N. Y. Acad. Sci. 1970, 171, 67-78.
56. Kopecky, K. R.; Reich, H. J. Reactivities in Photosensitized Olefin Oxidations. Can. J. Chem. 1965, 43, 2265-2270.
57. Foote, C. S.; Wexler, S.; Ando, W. Chemistry of Singlet Oxygen. III. Product Selectivity. Tetrahedron Lett. 1965, 46, 4111-4118.
58. Foote, C. S. in Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1976; pp 85-133.
59. Bartlett, P. D.; Mendenhall, G. D. Evidence for a Duality of Mechanism in the Oxidation Reactions of Triphenyl Phosphite Ozonide. J. Am. Chem. Soc. 1970, 92, 210-211.
60. Wasserman, H. H.; Scheffer, J. R. Singlet Oxygen Reactions from Photoperoxides. J. Am. Chem. Soc. 1967, 89, 3073-3075.
61. Stevens, B. Kinetics of Photoperoxidation in Solution. Acc. Chem. Res. 1973, 6, 90-96.
62. Wasserman, H. H.; Scheffer, J. R.; Cooper, J. C. Singlet Oxygen Reactions with 9,10-Diphenyl Peroxide J. Am. Chem. Soc. 1972, 94, 4991-4996.
63. Wasserman, H. H.; Larsen, D. L. Formation of 1, 4-Endoperoxides from the Dye-Sensitized Photooxygenation of Alkyl-naphthalenes. Chem. Commun. 1972, 253-254.
64. Saito, I.; Matsuura, T.; Inoue, K. Formation of Superoxide Ion from Singlet Oxygen. On the Use of a Water Soluble Singlet Oxygen Source. J. Am. Chem. Soc. 1981, 103, 188-190.
65. Di Mascio, P.; Sies, H. Quantification of Singlet Oxygen Generated by Thermolysis of 3,3′-(1,4-Naphthylene)dipropionate Endoperoxide. Monomol and Dimol Photoemission and the Effects of 1,4-Diazabicyclo[2.2.2]octane. J. Am. Chem. Soc. 1989, 111, 2909-2914.
66. Wasserman, H. H.; Yoo, J. U.; DeSimone, R. W. Singlet Oxygen Reactions from the Adducts of Ozone with Heterocycle Substrates. J. Am. Chem. Soc. 1995, 117, 9772-9773.
67. Aubry, J.-M.; Bouttemy, S. Preparative Oxidation of Organic Compounds in Microemulsions with Singlet Oxygen Generated Chemically by the Sodium Molybdate/Hydrogen Peroxide System. J. Am. Chem. Soc. 1997, 119, 5286-5294.
68. 2; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 2-4.
69. 60-69
70. Foote, C. S.; Denny, R. W. Chemistry of Singlet Oxygen. XIII. Solvent Effects on the Reaction with Olefins. J. Am. Chem. Soc. 1971, 93, 5168-5171.
71. Manring, L. E.; Kanner, R. C.; Foote, C. S. Chemistry of Singlet Oxygen. 43. Quenching by Conjugated Olefins. J. Am. Chem. Soc. 1983, 105, 4707-4710.
72. Liang, J. J.; Gu, C. L.; Kacher, M. L.; Foote, C. S. Chemistry of Singlet Oxygen. 45. Mechanism of the Photooxidation of Sulfides. J. Am. Chem. Soc. 1983, 105, 4717-4721.
73. Jensen, F.; Foote, C. S. Chemistry of Singlet Oxygen. 48. Isolation and Characterization of the Primary Photoproducts from Photooxidation of Catechols. Photochem. Photobiol. 1983, 46, 325-330.
74. Orfanopoulos, M.; Foote, C. S. Intermediate in the Ene Reaction of Singlet Oxygen with 1,4-Diphenyl-cis-2-butene and 2-Butene. J. Am. Chem. Soc. 1988, 110, 6583-6584.
75. O'Shea, K. E.; Foote, C. S. Chemistry of Singlet Oxygen. 51. Zwitterionic Intermediates from 2,4-Hexadienes. J. Am. Chem. Soc. 1988, 110, 7167-7170.
76. Selke, M.; Foote, C. S. Reactions of Organometallic Complexes with Singlet Oxygen. Photooxidation of Vaska's Complex. J. Am. Chem. Soc. 1993, 115, 1166-1167.
77. Nahm, K.; Li, Y.; Evanseck, J. D.; Houk, K. N.; Foote, C. S. Structures and Energies of Intermediates in the Reactions of Singlet Oxygen with Organic Phosphines and Sulfides. J. Am. Chem. Soc. 1993, 115, 4879-4884.
78. 60). J. Phys. Chem. 1991, 95, 11-12.
79. Singleton, D. A.; Szymanski, M. J.; Meyer, M. P.; Leach, A. G.; Kuwata, K. T.; Chen, J. S.; Greer, A.; Foote, C. S.; Houk, K. N. Mechanism of Ene Reactions of Singlet Oxygen. A Two-Step No-Intermediate Mechanism. J. Am. Chem. Soc. 2003, 125, 1319-1328.
80. Singleton, D. A.; Hang, C.; Szymanski, M. J.; Greenwald, E. E. A New Form of Kinetic Isotope Effect. Dynamic Effects on Isotopic Selectivity and Regioselectivity. J. Am. Chem. Soc. 2003, 125, 1176-1177.
81. Doubleday: C.; Suhrada, C. P.; Houk, K. N. Dynamics of the Degenerate Rearrangement of Bicyclo[3.1.0]hex-2-ene. J. Am. Chem. Soc. 2006, 128, 90-94.
82. Carpenter, B. K. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley: Hoboken, NJ, 2004; pp 925-960.
83. Stratton, S. P.; Liebler, D. C. Determination of Singlet Oxygen-Specific versus Radical-Mediated Lipid Peroxidation in Photosensitized Oxidation of Lipid Bilayers: Effect of β-Carotene and α-Tocopherol. Biochemistry 1997, 36, 12911-12920. See also refs 74-78.
84. Thomas, M. J.; Shirley, P. S.; Hedrick, C. C.; DeChatelet, L. R. Role of Free Radical Processes in Stimulated Human Polymorphonuclear Leukocytes. Biochemistry 1986, 25, 8042-8048.
85. Schafer, F. Q.; Buettner, G. R. Singlet Oxygen Toxicity Is Cell Line-Dependent: A Study of Lipid Peroxidation in Nine Leukemia Cell Lines. Photochem. Photobiol. 1999, 70, 858-867.
86. Girotti, A. W. Photosenstitized Oxidation of Mmebrane Lipids: Reaction Pathways, Cytotoxic Effects, and Cytoprotective Mechanisms. J. Photochem. Photobiol., B 2001, 63, 103-113.
87. Niziolek, M.; Korytowski, W.; Girotti, A. W. Self-Sensitized Photodegradation of Membrane-Bound Protoporphyrin Mediated by Chain Lipid Peroxidation: Inhibition by Nitric Oxide with Sustained Singlet Oxygen Damage. Photochem. Photobiol. 2005, 81, 299-305.
88. Nelson, M. J.; Seitz, S. P. The Mechanism of Lipoxygenases. In Active Oxygen in Biochemistry; Valentine, J. S., Foote, C. S., Greenberg, A., Liebman, J. L., Eds.; Blackie Academic and Professional: New York, 1995; Vol. 3, pp 276-312.
89. Foote, C. S. Photooxidation of Biological Model Compounds. Oxygen Oxy-Radicals Chem. Biol. 1981, 425-440.
90. Hickerson, R. P.; Prat, F.; Muller, J. G.; Foote, C. S.; Burrows, C. J. Sequence and Stacking Dependence of 8-Oxoguanine Oxidation: Comparison of One-Electron vs Singlet Oxygen Mechanisms. J. Am. Chem. Soc. 1999, 121, 9423-9428.
91. 60. J. Am. Chem. Soc. 1999, 121, 464-465.
92. McCallum, J. E. B.; Kuniyoshi, C. Y.; Foote, C. S. Characterization of 5-Hydroxy-8-oxo-7,8-dihydroguanosine in the Photosensitized Oxidation of 8-Oxo-7,8-dihydroguanosine and Its Rearrangement to Spiroiminodihydantoin. J. Am. Chem. Soc. 2004, 126, 16777-16782.
93. Kwon, B. M.; Foote, C. S.; Khan, S. I. Photooxygenation of Ascorbic Acid Derivatives and Model Compounds. J. Am. Chem. Soc. 1989, 111, 1854-1860.
94. Foote, C. S.; Ching, T.-Y. Chemistry of Singlet Oxygen. XXI. Kinetics of Bilirubin Photooxygenation. J. Am. Chem. Soc. 1975, 97, 6209-6214.
95. Pryor, W. A.; Houk, K. N.; Foote, C. S.; Fukuto, J. M.; Ignarro, L. J.; Squadrito, G.; Davies, K. J. A. Free Radical Biology and Medicine: It's a Gas Man! Am. J. Physiol. Regul. Integr. Comp. Physiol. 2006, 291, R491-R511.
96. 2 in single cells. Snyder, J. W.; Skovsen, E.; Lambert, J. D. C.; Ogilby, P. R. Subcellular, Time-Resolved Studies of Singlet Oxygen in Single Cells. J. Am. Chem. Soc. 2005, 127, 14558-14559.
97. 2; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; pp 85-144.
98. Porphyrin Photosensitization; Kessel, D., Dougherty, T. J., Eds.: Plenum Press: London, U.K., 1983.
99. Foote, C. S. Photooxidation and Toxicity. Mol. Basis Environ. Toxic. 1980, 37-50.
100. Daub, M. E.; Hangarter, R. P. Light-Induced Production of Singlet Oxygen and Superoxide by the Fungal Toxin, Cercosporin. Plant Physiol. 1983, 73, 855-857.
101. Youngman, R. J.; Schieberle, P.; Schnabl, H.; Grosch, W.; Elstner, E. F. The Photodynamic Generation of Singlet Molecular Oxygen by the Fungal Phytotoxin, Cercosporin. Photobiochem. Photobiophys. 1983, 6, 109-119.
102. Trevithick-Sutton, C. C.; Chin, K. K.; Contos, S. D. Lens α-Crystallin and Hypericin: A Photophysical Mechanism Explains Observed Lens Damage. Photochem. Photobiol. 2004, 80, 444-449.
103. Flors, C.; Nonell, S. Light and Singlet Oxygen in Plant Defense Against Pathogens: Phototoxic Phenalenone Phytoalexins. Acc. Chem. Res. 2006, 39, 293-300.