Exploiting endogenous cellular process to generate quinone methides in vivo

Current Organic Chemistry

Volumn 18, Issue 1, 2014, Pages 70-85

  Cao, Sheng ^a   Peng, Xiaohua ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

Arylboronates and arylboronic acids; Enzymatic oxidation; Enzymatic reduction; In vivo generation; Phenols; Quinone methides; Quinones; ROS induction

Indexed keywords

ANTIBIOTICS;

ARYLBORONATE AND ARYLBORONIC ACID; ARYLBORONATES; ARYLBORONIC ACIDS; CELLULAR PROCESS; ENZYMATIC OXIDATIONS; ENZYMATIC REDUCTION; IN VIVO GENERATION; IN-VIVO; QUINONE METHIDE; ROS INDUCTION;

ENZYME INHIBITION;

EID: 84892950629     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527281801140121123221     Document Type: Review

References (176)

1. Kim, D. H.; Shin, E. K.; Kim, Y. H.; Lee, B. W.; Jun, J. G.; Park, J. H.; Kim, J. K. Suppression of inflammatory responses by celastrol, a quinone methide triterpenoid isolated from Celastrus regelii. Eur J Clin Invest. 2009, 39, 819-827.
2. Lee, J. H.; Choi, K. J.; Seo, W. D.; Jang, S. Y.; Kim, M.; Lee, B. W.; Kim, J. Y.; Kang, S.; Park, K. H.; Lee, Y. S.; Bae, S. Enhancement of radiation sensitivity in lung cancer cells by celastrol is mediated by inhibition of Hsp90. Int J Mol Med. 2011, 27, 441-446.
3. Murayama, T.; Eizuru, Y.; Yamada, R.; Sadanari, H.; Matsubara, K.; Rukung, G.; Tolo, F. M.; Mungai, G. M.; Kofi-Tsekpo, M. Anticytomegalovirus activity of pristimerin, a triterpenoid quinone methide isolated from Maytenus heterophylla (Eckl. & Zeyh.). Antivir Chem Chemother. 2007, 18, 133-139.
4. Ulubelen, A.; Topçu, G.; Chai, H.-B.; Pezzuto, J. M. Cytotoxic Activity of Diterpenoids Isolated from Salvia hypargeia. Pharm. Biol. 1999, 37, 148-151.
5. Bajpai, V. K.; Kan, S. C. Antibacterial abietane-type diterpenoid, taxodone from Metasequoia glyptostroboides Miki ex Hu. J. Biosciences 2010, 35, 533-538.
6. Bode, H. B.; Zeeck, A. Structure and biosynthesis of kendomycin, a carboxylic ansa-compound from Streptomyces. J. Chem. Soc. Perkin Trans. 1 2000, 323-328.
7. Willis, N. J.; Bray, C. D. Quinone Methides in Natural Product Synthesis. Chem. Eur. J. 2012, 18, 9160-9173.
8. Padias, A. B.; Hall, H. K. Jr. Mechanism Studies of LCP Synthesis. Polymers 2011, 3, 833-845.
9. Pathak, T. P.; Gligorich, K. M.; Welm, B. E.; Sigman, M. S. Synthesis and Preliminary Biological Studies of 3-Substituted Indoles Accessed by a Palladium-Catalyzed Enantioselective Alkene Difunctionalization Reaction. J. Am. Chem. Soc. 2010, 132, 7870-7871.
10. Ralph, J.; Schatz, P. F.; Lu, F.; Kim, H.; Akiyama, T.; Nelsen, S. F. In Quinone Methides, S. Rokita, Eds., Wiley-Blackwell, Hoboken, NJ, Vol. 1, 2009.
11. Lenger, J.; Schröder, M.; Ennemann, E. C.; Müller, B.; Wong, C. H.; Noll, T.; Dierks, T.; Hanson, S. R.; Sewald, N. Evaluation of sulfatase-directed quinone methide traps for proteomics. Bioorg Med Chem. 2012, 20, 622-627.
12. Zhou, Q.; Turnbull, K. D. Quinone Methide Phosphodiester Alkylation under Aqueous Conditions. J. Org. Chem. 2001, 66, 7072-7077.
13. Wang, P.; Song, Y.; Zhang, L.; He, H.; Zhou, X. Quinone Methide Derivatives: Important Intermediates to DNA Alkylating and DNA Cross-linking Actions. Curr Med Chem. 2005, 12, 2893-2913.
14. Richter, S. N.; Maggi, S.; Mels, S. C.; Palumbo, M.; Freccero, M. Binol Quinone Methides as Bisalkylating and DNA Cross-Linking Agents. J. Am. Chem Soc. 2004, 126, 13973-13979.
15. Kumar, D.; Veldhuyzen, W. F.; Zhou, Q.; Rokita, S. E. Conjugation of a Hairpin Pyrrole-Imidazole Polyamide to a Quinone Methide for Control of DNA Cross-Linking. Bioconjug Chem. 2004, 15, 915-922.
16. Thompson, D.; Moldéus, P. Formation and reactivity of a quinone methide in biological systems. Adv. Exp. Med. Biol. 1991, 283, 589-596.
17. Wan, P.; Barker, B.; Diao, L.; Fischer, M.; Shi, Y.; Yang, C. Quinone methides: relevant intermediates in organic chemistry. Can. J. Chem. 1996, 74, 465-475.
18. Van De Water, R. W.; Pettus, T. R. R. O-Quinone methides: intermediates underdeveloped and underutilized in organic synthesis. Tetrahedron 2002, 58, 5367-5405.
19. Peng, X.; Gandhi, V. ROS-activated anticancer prodrugs: a new strategy for tumor-specific damage. Therapeutic Delivery 2012, 7, 823-833.
20. Berson, J. In The chemistry of the quinonoid compounds. Vol. 2, Part 1. Edited by S. Patai and Z. Rappoport. Wiley, Chichester. 1988. pp. 455-536.
21. Desimoni, G.; Tacconi, G. Heterodiene syntheses with i,-unsaturated carbonyl compounds. Chem. Rev. 1975, 75, 651-692.
22. Ferreira, S. B.; da Silva, F. d. C; Pinto, A. C.; Gonzaga, D. T. G.; Ferreira, V. F. Syntheses of chromenes and chromanes via o-quinone methide intermediates. J. Heterocyclic Chem. 2009, 46, 1080-1097.
23. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder reaction. Wiley, New York. 1990.
24. Chapman, O. L.; Engel, M. R.; Springeer, J. P.; Clardy, J. C. Total synthesis of carpanone. J. Am. Chem. Soc. 1971, 93, 6696-6698.
25. Matsumoto, M.; Kuroda, K. Transition metal(ii) schiff's base complexes catalyzed oxidation of trans-2-(1-propenyl)-4, 5-methylenedioxyphenol to carpanone by molecular oxygen. Tetrahedron Lett. 1981, 22, 4437-4440.
26. Marino, J. P.; Dax, S. L. An efficient desilylation method for the generation of o-quinone methides: application to the synthesis of (+)-and (-)-hexahydrocannabinol. J. Org. Chem. 1984, 49, 3671-3672.
27. Talley, J. J. Stereospecific intramolecular Diels-Alder reaction of an oquinone methide. J. Org. Chem. 1985, 50, 1695-1699.
28. Chambers, J. D.; Crawford, J.; Williams, H. W. R.; Dufresne, C.; Scheigetz, J.; Bernstein, M. A.; Lau, C. K. Reactions of 2-phenyl-4H-1, 3, 2-benzodioxaborin, a stable ortho-quinone methide precursor. Can. J. Chem. 1992, 70, 1717-1732.
29. Gtnisson, Y.; Qler, P. C.; Young, R. N. Total synthesis of (.)-thielocin A1): a novel inhibitor of phospholipase A2. J. Am. Chem. Soc. 1994, 116, 759-760.
30. Gtnisson, Y.; Young, Y. N. Practical total synthesis of a naturally occurring thielocin via the regioselective arylation of a cyclic boronate. Tetrahedron Lett. 1994, 35, 7747-7750.
31. Angle, S. R.; Louie, M. S.; Mattson, H. L.; Yang, W. Para-quinone methide initiated intramolecular electrophilic substitution reactions. Tetrahedron Lett. 1989, 30, 1193-1196.
32. Clive, D. L. J.; Fletcher, S. P.; Zhu, M. Formal radical cyclization onto benzene rings-a general method proceeding via cross-conjugated dienones. Chem. Commun. 2003, 4, 526-527.
33. Chaires, J. B.; Dattagupta, N.; Crothers, D. M. Studies on interaction of anthracycline antibiotics and deoxyribonucleic acid: equilibrium binding studies on the interaction of daunomycin with deoxyribonucleic acid. Biochemistry 1982, 21, 3933-3940.
34. Angle, S. R.; Yang, W. Synthesis and chemistry of a quinone methide model for anthracycline antitumor antibiotics. J. Am. Chem. Soc. 1990, 112, 4524-4528.
35. Angle, S. R.; Rainier, J. D.; Woytowicz, C. Synthesis and Chemistry of Quinone Methide Models for the Anthracycline Antitumor Antibiotics. J. Org. Chem. 1997, 62, 5884-5892.
36. Thompson, D. C.; Thompson, J. A.; Sugumaran, M.; Moldéus, P. Biological and toxicological consequences of quinone methide formation. Chem. Biol. Interact. 1993, 86, 129-162.
37. Wang, H.; Wahi, M. S.; Rokita, S. E. Immortalizing a Transient Electrophile for DNA Cross-linking. Angew. Chem. Int. Ed. 2008, 47, 1291-1293.
38. Freccero, M. Quinone methides as alkylating and cross-linking agents. Mini-Reviews in Organic Chemistry 2004, 1, 403-415.
39. Merijan, A.; Gardner, P. D.; Shoulders, B. A. The Structures of Substituted o-Quinone Methide Trimers. J. Org. Chem. 1963, 28, 2148-2149.
40. Starnes, W. H. Novel dimeric products from 10-methyleneanthrone. J. Org. Chem. 1970, 35, 1974-1978.
41. Boger, D. L.; Nishi, T.; Teegarden, B. R. p-Quinonemethide Analog of the CC-1065 and Duocarmycin Alkylation Subunits. J. Org. Chem. 1994, 59, 4943-4949.
42. Rabin, O.; Vigalok, A.; Milstein, D. Metal-Mediated Generation, Stabilization, and Controlled Release of a Biologically Relevant, Simple Para Quinone Methide: BHT-QM. J. Am. Chem. Soc. 1998, 120, 7119-7120.
43. Dufrasne, F.; Gelbcke, M.; Nève, J.; Kiss, R.; Kraus, J.-L. Quinone methides and their prodrugs: a subtle equilibrium between cancer promotion, prevention, and cure. Curr. Med. Chem. 2011, 18, 3995-4011.
44. Zanaletti, R.; Freccero, M. Synthesis, spectroscopic characterization and chemical reactions of stable o-QM on solid phase. Chem. Commun. 2002, 1908-1909.
45. Modica, E.; Zanalateei, R.; Freccero, M.; Mella, M. Alkylation of Amino Acids and Glutathione in Water by o-Quinone Methide. Reactivity and Selectivity. J. Org. Chem. 2001, 66, 41-52.
46. Bolton, J. L.; Turnipseed, S. B.; Thompson, J. A. Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models. Chem.-Biol. Interact. 1997, 107, 185-200.
47. Peter, M. G. Chemical modifications of biopolymers by quinones and quinone methides. Angew. Chem. Int. Ed. Engl. 1989, 28, 555-570.
48. Rokita, S. E.; Yang, J.; Pande, P.; Greenberg, W. A. Quinone methide alkylation of deoxycytidine. J. Org. Chem. 1997, 62, 3010-3012.
49. Pande, P.; Shearer, J.; Yang, J.; Greenberg, W. A.; Rokita, S. E. Alkylation of nucleic acids by a model quinone methide. J. Am. Chem. Soc. 1999, 121, 6773-6779.
50. Zhou, Q.; Turnbull, K. D. Phosphodiester alkylation with a quinone methide. J. Org. Chem. 1999, 64, 2847-2851.
51. Zhou, Q.; Turnbull, K. D. Trapping Phosphodiester-Quinone Methide Adducts through in Situ Lactonization. J. Org. Chem. 2000, 65, 2022-2029.
52. Brousmiche, D. W.; Wan, P. Photogeneration of quinone methide-type intermediates from pyridoxine and derivatives. J. Photochem. Photobiol. A: Chem. 2002, 149, 71-81.
53. Weinert, E. E.; Dondi, R.; Colloredo-Melz, S.; Frankenfield, K. N.; Mitchell, C. H.; Freccero, M.; Rokita, S. E. Substituents on Quinone Methides Strongly Modulate Formation and Stability of Their Nucleophilic Adducts. J. Am. Chem. Soc. 2006, 128, 11940-11947.
54. Diao, L.; Yang, C.; Wan, P. Quinone Methide Intermediates from the Photolysis of Hydroxybenzyl Alcohols in Aqueous Solution. J. Am. Chem. Soc. 1995, 117, 5369-5370.
55. Nakatani, K.; Higashida, N.; Saito, I. Highly efficient photochemical generation of o-Quinone methide from Mannich bases of phenol derivatives. Tetrahedron Lett. 1997, 38, 5005-5008.
56. Wang, P.; Liu, R.; Wu, X. Ma, H.; Cao, X.; Zhou, P.; Zhang, J.; Weng, X.; Zhang, X.; Qi, J.; Zhou, X.; Weng, L. A Potent, Water-Soluble and Photoinducible DNA Cross-Linking Agent. J. Am. Chem. Soc. 2003, 125, 1116-1117.
57. Bolon, D. A. O-quinone methides. II. Trapping with production of chromans. J. Org. Chem. 1970, 35, 3666-3670.
58. Angle, S. R.; Arnaiz, D. O.; Boyce, J. P.; Frutos, P. R.; Louie, M. S.; Mattson-Arnaiz, H. L.; Rainer, J. D.; Turnbull, K. D.; Yang, W. Formation of Carbon-Carbon Bonds via Quinone Methide-Initiated Cyclization Reactions. J. Org. Chem. 1994, 59, 6322-6337.
59. Cook, C. D.; Butler, L. C. Dimerization of the quinone methide, 2, 4-di-tertbutyl-6-ethylidene-2, 5-cyclohexadien-1-one. Possible Diels-Alder mechanism. J. Org. Chem. 1969, 34, 227-229.
60. Kasturi, T. R.; Jayaram, S. K.; Sattigeri, J. A.; Pragnacharyulu, P. V. P.; Row, T. N. G.; Renuka, K.; Venkatesan, K.; Begum, N. S.; Munirathinam, N. DDQ oxidation of bisnaphthols-structures of novel products Tetrahedron. Tetrahedron 1993, 49, 7145-7158.
61. Rosenau, T.; Habicher, W. D. Novel tocopherol compounds I. Bromination of tocopherol-reaction mechanism and synthetic applications. Tetrahedron 1995, 51, 7919-7926.
62. Moore, R. F.; Waters, W. W. Some products formed from phenolic inhibitors during the autoxidation of cumene. J. Chem. Soc. 1954, 243-246.
63. Dorrestijn, E.; Pugin, R.; Nogales, M. V. C.; Mulder, P. Thermal Decomposition of Chroman. Reactivity of o-Quinone Methide. J. Org. Chem. 1997, 62, 4804-4810.
64. Wojciechowski, K.; Dolatowska, K. Generation of ortho-quinone methides upon thermal extrusion of sulfur dioxide from benzosultones. Tetrahedron 2005, 61, 8419-8422.
65. Britt, P. F.; Buchanan, A. C.; Cooney, M. J.; Martineau, D. R. Flash Vacuum Pyrolysis of Methoxy-Substituted Lignin Model Compounds. J. Org. Chem. 2000, 65, 1376-1389.
66. Büyükidan, B.; Bilgic, S.; Bilgic, O. The syhtnesis of some chromans via oquinone methide intermediates. Synth. Commun. 2001, 31, 1263-1270.
67. Yato, M.; Ohwada, T.; Shudo, K. 4H-1, 2-Benzoxazines as novel precursors of o-benzoquinone methide. J. Am. Chem. Soc. 1990, 112, 5341-5342.
68. Merijan, A.; Gardner, P. D. Quinone Methides. Base-Catalyzed Condensation Reactions of Hydroxybenzyl Alcohols and Ethers. J. Org. Chem. 1965, 30, 3965-3967.
69. Chiang, Y.; Kresge, A. J.; Zhu, Y. Reactive intermediates. Some chemistry of quinone methides. Pure Appl. Chem. 2000, 72, 2299-2308.
70. Chiba, K.; Hirano, T.; Kitano, Y.; Tada, M. Montmorillonite-mediated hetero-Diels-Alder reaction of alkenes and o-quinomethanes generated in situ by dehydration of o-hydroxybenzyl alcohols. Chem. Commun. 1999, 8, 691-692.
71. Loubinoux, B.; Miazimbakana, J.; Gerardin, P. Reactivity of new precursors of quinone methides. Tetrahedron Lett. 1989, 30, 1939-1942.
72. Rokita, S. E.; Yang, J.; Pande, P.; Greenberg, W. A. Quinone Methide Alkylation of Deoxycytidine. J. Org. Chem. 1997, 62, 3010-3012.
73. Veldhuyzen, W. F., Lam, Y.-F.; Rokita, S. E. 2'-Deoxyguanosine Reacts with a Model Quinone Methide at Multiple Sites. Chem. Res. Toxicol. 2001, 14, 1345-1351.
74. Cao, S.; Christiansen, R; Peng, X. Substituents Effects on Oxidation-Induced Quinone Methides Formation from Their Arylboronic Ester Precursors. Chem. Eur. J. 2013, 19, 9050-9058.
75. Cao, S.; Wang, Y.; Peng, X. ROS-Inducible DNA Cross-linking Agent as a New Anticancer Prodrug Building Block. Chem. Eur. J. 2012, 18, 3850-3854.
76. Kuang, Y.; Balakrishnan, K.; Gandhi, V.; Peng. X. Hydrogen Peroxide Inducible DNA Cross-Linking Agents: Targeted Anticancer Prodrugs. J. Am. Chem. Soc. 2011, 133, 19278-19231.
77. Kemp, D. S.; Roberts, D. C. New protective groups for peptide synthesis-II the Dobz group boron-derived affinity protection with the pdihydroxyborylbenzyloxycarbonylamino function. Tetrahedron Lett. 1975, 16, 4629-4632.
78. Miller, E. W.; Albers, A. E.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. Boronate-Based Fluorescent Probes for Imaging Cellular Hydrogen Peroxide. J. Am. Chem. Soc. 2005, 127, 16652-16659.
79. Dickinson, B. C.; Chang, C. J. A Targetable Fluorescent Probe for Imaging Hydrogen Peroxide in the Mitochondria of Living Cells. J. Am. Chem. Soc. 2008, 130, 9638-9639.
80. Miller, E. W.; Tulyathan, O.; Isacoff, E. Y.; Chang, C. J. Molecular imaging of hydrogen peroxide produced for cell signaling. Nat. Chem. Biol. 2007, 3, 263-267.
81. Lo, L.-C.; Chu, C.-Y. Development of highly selective and sensitive probes for hydrogen peroxide. Chem. Commun. 2003, 21, 2728-2729.
82. Karton-Lifshin, N.; Segal, E.; Omer, L.; Portnoy, M.; Satchi-Fainaro, R.; Shabat, D. A Unique Paradigm for a Turn-ON Near-Infrared Cyanine-Based Probe: Noninvasive Intravital Optical Imaging of Hydrogen Peroxide. J. Am. Chem. Soc. 2011, 133, 10960-10965.
83. Major Jourden, J. L.; Cohen, S. M. Hydrogen peroxide activated matrix metalloproteinase inhibitors: A prodrug approach. Angew. Chem. Int. Ed. 2010, 49, 6795-6797.
84. Pettus, T. R. R.; Selenski, C.; Griesbeck, A. G. in: Science of Synthesis, 28, (Ed.: A. G. Griesbeck), Thieme, Stuttgart, New York, 2006, Chapter 12, 831-839.
85. Bamber, R. K. A general theory for the origin of growth stresses in reaction wood: how trees stay upright. IAWA Journal 2001, 22, 205-212.
86. Tomasz, M. Mitomycin C: small, fast and deadly (but very selective). Chem. Biol. 1995, 2, 575-579.
87. Leary, G. L. Quinone methides and the structure of lignin. Wood Sci. Technol. 1980, 14, 21-34.
88. Shevchenko, S. M.; Apushkinskii, A. G. Current questions concerning the theory of highly excited vibrational states. Russ. Chem. Rev. 1992, 61, 1-14.
89. Chang, F. R.; Hayashi, K.; Chen, I. H.; Liaw, C.-C.; Bastow, K. F.; Nakanishi, Y.; Nozaki, H.; Cragg, G. M.; Wu, Y.-C.; Lee, K.-H. Antitumor agents. 228. five new agarofurans, Reissantins A-E, and cytotoxic principles from Reissantia buchananii. J. Nat. Prod. 2003, 66, 1416-1420.
90. Salminen, A.; Lehtonen, M.; Paimela, T. Celastrol: Molecular Targets of Thunder God Vine, " Biochemical and Biophysical Research Communications. Biochem. Bioph. Res. Co. 2010, 394, 439-442.
91. Yang, H.; Chen, D.; Cui, Q. C.; Yuan, X.; Dou, Q. P. Celastrol, a triterpene extracted from the Chinese "Thunder of God Vine, " is a potent proteasome inhibitor and suppresses human prostate cancer growth in nude mice. Cancer Res. 2006, 66, 4758-4765.
92. Kupchan, S. M.; Karim, A.; Marcks, C. Tumor inhibitors. XXXIV. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum. J. Am. Chem. Soc. 1968, 90, 5923-5924.
93. Hanson, R. L.; Lardy, H. A.; Kupchan, S. M. Inhibition of Phosphofructokinase by Quinone Methide and α-Methylene Lactone Tumor Inhibitors. Science 1970, 68, 378-380.
94. Abou-Zeid, A. M. Review on Citrinin: Synthetic Methods, Molecular Biosynthesis and Effect of Plant Extracts. Br. Microbiol. Res. J. 2012, 2, 108-122.
95. Council of Agricultural Science and Technology. (2003). Mycotoxin: Risks in plant, animal, and human systems. Task force rep. No. 139. Ames, IA: CAST.
96. Kumar, M., Dwivedi, P., Sharma, A. K., Singh, N. D., & Patil, R. D. Ochratoxin A and citrinin nephrotoxicity in New Zealand white rabbits: An ultrastructural assessment. Mycopathologia 2007, 163, 21-30.
97. Aleo, M. D., Wyatt, R. D., & Schnellmann, R. G. The role of alteredmitochondrial function in citrinin-induced toxicity to rat renal proximal tubule suspensions. Toxicol. Appl. Pharmacol. 1991, 109, 455-463.
98. Clardy, J.; Walsh, C. Lessons from natural molecules. Nature 2004, 432, 829-837.
99. Bode, H. B.; Zeeck, A. Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces. J. Chem. Soc. Perkin Trans. 1 2000, 323-328.
100. Elnakady, Y. A.; Rohde, M.; Sasse, F.; Backes, C.; Keller, A.; Lenhof, H. P.; Weissman, K. J.; Müller, R. Evidence for the Mode of Action of the Highly Cytotoxic Streptomyces Polyketide Kendomycin. ChemBioChem 2007, 8, 1261-1272.
101. Jansen, R.; Gerth, K.; Steinmetz, H.; Reinecke, S.; Kessler, W.; Kirschning, A.; Müller, R. Elansolid-A3, a Unique p-Quinone Methide Antibiotic from Chitinophaga sancti. Chem. Eur. J. 2011, 17, 7739-7744.
102. Koymans, L.; Donné-Op Den Kelder, G. M.; Te Koppele, J. M.; Vermeulen, N. P. E. Generalized cytochrome P450-mediated oxidation and oxygenation reactions in aromatic substrates with activated N-H, O-H, C-H, or S-H substituents. Xenobiotica 1993, 23, 633-648.
103. Thompson, D. C.; Perera, K.; London, R. Quinone Methide Formation from Para Isomers of Methylphenol (Cresol), Ethylphenol, and Isopropylphenol: Relationship to Toxicity. Chem. Res. Toxicol. 1995, 8, 55-60.
104. Thompson, D. C.; Perera, K.; Krol, E. S.; Bolton, J. L. Quinone Methide Formation from Para Isomers of Methylphenol (Cresol), Ethylphenol, and Isopropylphenol: Relationship to Toxicity. Chem. Res. Toxicol. 1995, 8, 323-327.
105. Sànchez-Ferrer, A.; Rodríguez-López, J. N.; García-Cánovas, F. Tyrosinase: a comprehensive review of its mechanism. Biochim. Biophys. Acta. 1995, 1247, 1-11.
106. Krol, E. S.; Bolton, J. L. Oxidation of 4-alkylphenols and catechols by tyrosinase: ortho-substituents alter the mechanism of quinoid formation. Chem. Biol. Interact. 1997, 104, 11-27.
107. Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Multicopper Oxidases and Oxygenases. Chem. Rev. 1996, 96, 2563-2605.
108. Bao, W.; O'Malley, D. M.; Whetten, R.; Sederoff, R. R. A laccase associated with lignification in loblolly pine xylem. Science 1993, 260, 672-674.
109. Hatakka, A. Lignin-modifying enzymes from selected white-rot fungi: production and role in lignin degradation. FEMS Microbiol. Rev. 1994, 13, 125-135.
110. Harkin, J. M.; Obst, J. R. Syringaldazine, an Effective Reagent for Detecting Laccase and Peroxidase in Fungi. Experientia 1973, 29, 381-387.
111. Sugumaran, M.; Bolton, J. L. Laccase-and not tyrosinase-is the enzyme responsible for quinone methide production from 2, 6-dimethoxy-4-allyl phenol. Arch. Biochem. Biophys. 1998, 353, 207-212.
112. Thompson, D.; Norbeck, K.; Olsson, L. I.; Constantin-Teodosiu, D.; Van der zee, J.; Moldéus, P. Peroxidase-catalyzed oxidation of eugenol: formation of a cytotoxic metabolite(s). J. Biol. Chem. 1989, 264, 1016-1021.
113. IARC Monographs Eugenol, International Agency for Research on Cancer, Lyon, France, 1985, 36, 75-97.
114. Thompson, D. C.; Perera, K. Inhibition of Mitochondrial Respiration by a para-Quinone Methide. Biochem. Biophys. Res. Commun. 1995, 209, 6-11.
115. Thompson, D. C.; Constantin-Teodosiu, D.; Moldéus, P. Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes. Chem. Biol. Interact. 1991, 77, 137-147.
116. Babich, H.; Stern, A.; Borenfreund, E. Eugenol cytotoxicity evaluated with continuous cell lines. Toxicol. In Vitro 1993, 7, 105-109.
117. Hume, W. R. Effect of Eugenol on Constrictor Responses in Blood Vessels of the Rabbit Ear. J. Dent. Res. 1984, 62, 1013-1015.
118. Dewhirst, F. E. Structure-activity relationships for inhibition of prostaglandin cyclooxygenase by phenolic compounds. Prostaglandins 1980, 20, 209-222.
119. LaVoie, E. J.; Adams, J. D.; Reinhardt, J.; Rivenson, A.; Hoffman, D. Toxicity studies on clove cigarette smoke and constituents of clove: determination of the LD50 of eugenol by intratracheal instillation in rats and hamsters. Arch. Toxicol. 1986, 59, 78-81.
120. Thompson, D. C.; Barhoumi, R.; Burghardt, R. C. Comparative toxicity of eugenol and its quinone methide metabolite in cultured liver cells using kinetic fluorescence bioassays. Toxicol. Appl. Pharmacol. 1998, 149, 55-63.
121. Kohlroser, J.; Mathai, J.; Reichheld, J.; Banner, B. F.; Bonkovsky, H. L. Hepatotoxicity due to troglitazone: report of two cases and review of adverse events reported to the United States Food and Drug Administration. Am. J. Gastroenterol. 2000, 95, 272-276.
122. Kassahun, K.; Pearson, P. G.; Tang, W.; McIntosh, I.; Leung, K.; Elmore, C.; Dean, D.; Wang, R.; Doss, G.; Baillie, T. A. Studies on the Metabolism of Troglitazone to Reactive Intermediates in vitro and in vivo. Evidence for Novel Biotransformation Pathways Involving Quinone Methide Formation and Thiazolidinedione Ring Scission. Chem. Res. Toxicol. 2001, 14, 62-70.
123. Dehal, S. S.; Kupfer, D. Cytochrome P-450 3A and 2D6 Catalyze ortho Hydroxylation of 4-Hydroxytamoxifen and 3-Hydroxytamoxifen (Droloxifene) Yielding Tamoxifen Catechol: Involvement of Catechols in Covalent Binding to Hepatic Proteins. Drug Metab. Dispos. 1999, 27, 681-688.
124. Fan, P. W.; Bolton, J. L. Bioactivation of Tamoxifen to Metabolite E Quinone Methide: Reaction with Glutathione and DNA. Drug Metab. Dispos. 2001, 29, 891-896.
125. Hillard, E. A.; Vessières, A.; Thouin, L.; Jaouen, G.; Amatore, C. Ferrocene-Mediated Proton-Coupled Electron Transfer in a Series of Ferrocifen-Type Breast-Cancer Drug Candidates. Angew. Chem. Int. Ed. 2006, 45, 285-290.
126. Hamels, D.; Dansette, P. M.; Hillard, E. A.; Top, S.; Vessières, A.; Herson, P.; Jaouen, G.; Mansuy, D.; Ferrocenyl Quinone Methides as Strong Antiproliferative Agents: Formation by Metabolic and Chemical Oxidation of Ferrocenyl Phenols. Angew. Chem. Int. Ed. 2009, 48, 9124-9126.
127. Messina, P.; Labbé, E.; Buriez, O.; Hillard, E. A.; Vessières, A.; Hamels, D.; Top, S.; Jaouen, G.; Frapart, Y. M.; Mansuy, D.; Amatore, C. Deciphering the activation sequence of ferrociphenol anticancer drug candidates. Chem. Eur. J. 2012, 18, 6581-6587.
128. Gribkoff, V. K.; Starrett, J. E. Jr.; Dworetzky, S. I.; Hewawasam, P.; Boissard, C. G.; Cook, D. A.; Frantz, S. W.; Herman, K.; Hibbard, J. R.; Huston, K.; et al. Targeting acute ischemic stroke with a calcium-sensitive opener of maxi-K potassium channels. Nat Med. 2001, 7, 471-477.
129. Wen, B.; Chen, Y.; Fitch, W. L. Metabolic Activation of Nevirapine in Human Liver Microsomes: Dehydrogenation and Inactivation of Cytochrome P450 3A4. Drug Metab. Dispos. 2009, 37, 1557-1562.
130. Jin, H.; Shen, S.; Chen, X.; Zhong, D.; Zheng, J. CYP3A-mediated apoptosis of dauricine in cultured human bronchial epithelial cells and in lungs of CD-1 mice. Toxicol. Appl. Pharmacol. 2012, 261, 248-254.
131. Crampton, R. F.; Gray, T. J. B.; Grasso, P.; Parke, D. V. Long-term studies on chemically induced liver enlargement in the rat. II. Transient induction of microsomal enzymes leading to liver damage and nodular hyperplasia produced by safrole and Ponceau MX. Toxicology 1977, 7, 307-326.
132. Bolton, J. L.; Acay, N. M. Vukomanovic, V. Evidence That 4-Allyl-oquinones Spontaneously Rearrange to Their More Electrophilic Quinone Methides: Potential Bioactivation Mechanism for the Hepatocarcinogen Safrole. Chem. Res. Toxicol. 1994, 7, 443-450.
133. Gauthier, S.; Caron, B.; Cloutier, J.; Dory, Y. L.; Favre, A.; Larouche, D.; Mailhot, J.; Ouellet, C.; Schwerdtfeger, A.; Leblanc, G.; Martel, C.; Simard, J.; Mâerand, Y.; Bâelanger, A.; Labrie, C.; Labrie, F. (S)-(+)-4-[7-(2, 2-Dimethyl-1-oxopro-poxy)-4-methyl-2-[4-[2-(1-piperidinyl)-ethoxy]phenyl]-2H-1-benzo-pyran-3-yl]-phenyl 2, 2-Dimethylpropanoate (EM-800): α A Highly Potent, Specific, and Orally Active Nonsteroidal Antiestrogen. J. Med. Chem. 1997, 40, 2117-2122.
134. Liu, J.; Liu, H.; van Breemen, R. B.; Thatcher, G. R. J.; Bolton, J. L. Bioactivation of the Selective Estrogen Receptor Modulator Acolbifene to Quinone Methides. Chem. Res. Toxicol. 2005, 18, 174-182.
135. Clarkson, C.; Musonda, C. C.; Chibale, K.; Campbell, W. E.; Smith, P. Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity. Bioorg. Med. Chem. 2003, 11, 4417-4422.
136. Ncanana, S.; Baratto, L.; Roncaglia, L.; Riva, S.; Burton, S. G. Laccase-Mediated Oxidation of Totarol. Adv Synth Catal. 2007, 349, 1507-1513.
137. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol. Med. 1996, 20, 933-956.
138. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. Flavonoids as Antioxidants. J. Am. Chem. Soc. 1994, 116, 4846-4851.
139. Middleton, E.; Kandaswami, C. (1994) The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In The flavonoids. Advances in research since 1986 (Harborne, J. B., Ed.) pp 619-652, Chapman & Hall, London.
140. MacGregor, J. T.; Jurd, L. Mutagenicity of plant flavonoids: Structural requirements for mutagenic activity in Salmonella typhimurium. Mutat. Res. 1978, 54, 297-309.
141. Boersma, M. G.; Vervoort, J.; Szymusiak, H.; Lemanska, K.; Tyrakowska, B.; Cenas, N.; Segura-Aguilar, J.; Rietjens, I. M. Regioselectivity and Reversibility of the Glutathione Conjugation of Quercetin Quinone Methide. Chem. Res. Toxicol. 2000, 13, 185-191.
142. Awad, H. M.; Boersma, M. G.; Vervoort, J.; Rietjens, I. M. Peroxidasecatalyzed formation of quercetin quinine methide-glutathione adducts. Arch. Biochem. Biophys. 2000, 378, 224-233.
143. Wilson, W. R.; Hay, M. P. Targeting hypoxia in cancer therapy. Nat. Rev. Cancer 2011, 11, 393-410.
144. Pan, S.; Iracki, T.; Bachur, N. R. DNA alkylation by enzyme-activated mitomycin C. Mol. Pharmacol. 1986, 29, 622-628.
145. Fry, F. H.; Jacob, C. Sensor/Effector Drug Design with Potential Relevance to Cancer. Curr. Pharm. Design 2006, 12, 4479-4499.
146. Hashimoto, Y.; Shudo, K. Chemical modification of DNA with mutacarcinogens. III. Reductive alkylation of DNA with mitomycin C. Environ. Health Perspect. 1985, 62, 219-222.
147. Tomasz, M.; Lipman, R.; Chowdary, D.; Pawlak, J.; Verdine, J. L.; Nakanishi, K. Isolation and structure of a covalent cross-link adduct between mitomycin C and DNA. Science 1987, 235, 1204-1208.
148. Reddy, M. V.; Randerath, K. 32P-analysis of DNA adducts in somatic and reproductive tissues of rats treated with the anticancer antibiotic, mitomycin C. Mutat. Res. 1987, 179, 75-88.
149. Keyes, S. R.; Rockwell, S.; Sartorelli, A. C. Porfiromycin as a bioreductive alkylating agent with selective toxicity to hypoxic EMT6 tumor cells in vivo and in vitro. Cancer Res. 1985, 45, 3642-3645.
150. Seddon, B.; Kelland, L. R.; Workman, P. Bioreductive prodrugs for cancer therapy. Methods Mol. Med. 2004, 90, 515-542.
151. Fracasso, P. M.; Sartorelli, A. C. Cytotoxicity and DNA Lesions Produced by Mitomycin C and Porfiromycin in Hypoxic and Aerobic EMT6 and Chinese Hamster Ovary Cells. Cancer Res. 1986, 46, 3939-3944.
152. Maliepaard, M.; Wolfs, A.; Groot, S. E.; De Mol, N. J.; Janssen, L. H. M. Indoloquinone EO9: DNA interstrand cross-linking upon reduction by DTdiaphorase or xanthine oxidase. Br. J. Cancer 1995, 71, 836-839.
153. Phillips, R. M.; Loadman, P. M.; Cronin, B. P. Evaluation of a novel in vitro assay for assessing drug penetration into avascular regions of tumours. Br. J. Cnacer 1998, 77, 2112-2119.
154. Loadman, P. M.; Phillips, R. M.; Lim, L. E.; Bibby, M. C. Pharmacological properties of a new aziridinylbenzoquinone, RH1 (2, 5-diaziridinyl-3-(hydroxymethyl)-6-methyl-1, 4-benzoquinone), in mice-cytochrome b5 reductase in human tumour cells. Biochem. Pharmacol. 2000, 59, 831-837.
155. Abdella, B. R.; Fisher, J. A chemical perspective on the anthracycline antitumor antibiotics. Environ. Health Perspect. 1985, 64, 3-18.
156. Gaudiano, G.; Koch, T. H. Redox chemistry of anthracycline antitumor drugs and use of captodative radicals as tools for its elucidation and control. Chem. Res. Toxicol. 1991, 4, 2-16.
157. Moore, H. W.; Czerniak, R. Naturally occurring quinones as potential bioreductive alkylating agents. Med. Res. Rev. 1981, 1, 249-280.
158. Paul, A.; Hume, A.; Margaret, A.; Brimble, A.; Reynisson, J. The bioreductive alkylation of DNA by kalafungin. A theoretical investigation. Aust. J. Chem. 2012, 65, 402-408.
159. Siegel, D.; Reigan, P.; Ross, D. One-and Two-Electron-Mediated Reduction of Quinones: Enzymology and Toxicological Implications. in Advances in Bioactivation Research 2008, Volume IX, pp. 169-197 (Ed. A. Elfarra) (Springer, New York, NY).
160. Sharma, P.; Jha, A. B.; Dubey, R. S.; Pessarakli, M. Reactive Oxygen Species, Oxidative Damage, and Antioxidative Defense Mechanism in Plants under Stressful Conditions. Journal of Botany 2012, Article ID 217037, 26 pages.
161. Klotz, L-O. Oxidant-induced signaling: effects of peroxynitrite and singlet oxygen. Biol. Chem. 2002, 383, 443-456.
162. Mishra, S.; Jha, A. B.; Dubey, R. S. Arsenite treatment induces oxidative stress, upregulates antioxidant system, and causes phytochelatin synthesis in rice seedlings. Protoplasma 2011, 248, 565-577.
163. Kawanishi, S.; Hiraku, Y.; Pinlaor, S.; Ma, N. Oxidative and nitrative DNA damage in animals and patients with inflammatory diseases in relation to inflammation-related carcinogenesis. Biol. Chem. 2006, 365-372.
164. Pelicano, H.; Carney, D.; Huang, P. ROS stress in cancer cells and therapeutic implications. Drug Resist. Updates 2004, 7, 97-110.
165. Trachootham, D.; Alexandre, J.; Huang, P. Targeting cancer cells by ROSmediated mechanisms: a radical therapeutic approach? Nature Rev. 2009, 8, 579-591.
166. López-Lázaro M. Dual role of hydrogen peroxide in cancer: Possible relevance to cancer chemoprevention and therapy. Cancer Lett. 2007, 252, 1-8.
167. Lee, Y. J.; Shacter, E. Hydrogen peroxide inhibits activation, not activity, of cellular caspase-3 in vivo. Free Radic. Biol. Med. 2000, 29, 684-692.
168. Apopa, P. L.; He, X.; Ma, Q. Phosphorylation of Nrf2 in the transcription activation domain by casein kinase 2 (CK2) is critical for the nuclear translocation and transcription activation function of Nrf2 in IMR-32 neuroblastoma cells. J. Biochem. Mol. Toxicol. 2008, 22, 63-76.
169. Szatrowski, T. P.; Nathan, C. F. Production of large amounts of hydrogen peroxide by human tumor cells. Cancer Res. 1991, 51, 794-798.
170. Zieba, M.; Suwalski, M.; Kwiatkowska, S.; Piasecka, G.; Grzelewska-Rzymowska, I.; Stolarek, R.; Nowak, D. Comparison of hydrogen peroxide generation and the content of lipid peroxidation products in lung cancer tissue and pulmonary parenchyma. Respir. Med. 2000, 94, 800-805.
171. Lim, S. D.; Sun, C.; Lambeth, J. D.; Marshall, F.; Amin, M.; Chung, L.; Petros, J. A.; Arnold, R. S. Increased Nox1 and hydrogen peroxide in prostate cancer. Prostate 2005, 62, 200-207.
172. Hagen, H.; Marzenell, P.; Jentzsch, E.; Wenz, F.; Veldwijk, M. R.; Mokhir, A. Aminoferrocene-Based Prodrugs Activated by Reactive Oxygen Species. J. Med. Chem. 2012, 55, 924-934.
173. Hulsman, N.; Medema, J. P.; Bos, C.; Jongejan, A.; Leurs, R.; Smit, M. J.; de Esch, I. J. P.; Richel, D.; Wijtmans, M. Chemical Insights in the Concept of Hybrid Drugs: The Antitumor Effect of Nitric Oxide-Donating Aspirin Involves A Quinone Methide but Not Nitric Oxide nor Aspirin. J. Med. Chem. 2007, 50, 2424-2431.
174. Movsas, B.; Chapman, J. D.; Horwitz, E. M.; Pinover, W. H.; Greenberg, R. E.; Hanlon, A. L.; Iyer, R.; Hanks, G. E. Hypoxic regions exist in human prostate carcinoma. Urology 1999, 53, 11-18.
175. Evans, S. M.; Hahn, S.; Pook, D. R.; Jenkins, W. T.; Chalian, A. A.; Zhang, P.; Stevens, C.; Weber, R.; Weinstein, G.; Benjamin, I.; Mirza, N.; Morgan, M.; Rubin, S.; McKenna, W. G.; Lord, E. M.; Koch, C. J. Detection of Hypoxia in Human Squamous Cell Carcinoma by EF5 Binding. Cancer Res. 2000, 60, 2018-2024.
176. Brown, J. M. Evidence for acutely hypoxic cells in mouse tumours, and a possible mechanism of reoxygenation. Br. J. Radiol. 1979, 52, 650-656.