Quinone methides: Photochemical generation and its application in biomedicine

Current Organic Chemistry

Volumn 18, Issue 1, 2014, Pages 3-18

  Basarić, Nikola ^a   Mlinarić Majerski, Kata ^a   Kralj, Marijeta ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

DNA alkylating agents; DNA cross linking; Excited state intramolecular proton transfer (ESIPT); Photo deammination; Photodehydration; Quinone methides

Indexed keywords

BIOACTIVITY; EXCITED STATES; PHENOLS; PHOTOCHEMICAL REACTIONS; PROTON TRANSFER;

ALKYLATING AGENTS; CROSS LINKING; DNA ALKYLATING AGENT; DNA CROSS-LINKING; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; PHOTO-DEAMMINATION; PHOTOCHEMICAL GENERATION; PHOTODEHYDRATION; QUINONE METHIDE;

DNA;

EID: 84893021157     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527281801140121122330     Document Type: Review

References (136)

1. Rokita, S. E., Ed. Quinone Methides, John Wiley & Sons: Hoboken, 2009.
2. Li, V. S.; Kohn, H. Studies on the bonding specificity for mitomycin CDNA monoalkylation processes. J. Am. Chem. Soc., 1991, 113, 275-283.
3. Han, I.; Russell, D. J.; Kohn, H. Studies on the mechanism of mitomycin C(1) electrophilic transformations: structure-reactivity relationships. J. Org. Chem., 1992, 57, 1799-1807.
4. Tomasz, M.; Das, A.; Tang, K. S.; Ford, M. G. J.; Minnock, A.; Musser, S. M.; Waring, M. J. The Purine 2-Amino Group as the Critical Recognition Element for Sequence-Specific Alkylation and Cross-Linking of DNA by Mitomycin C. J. Am. Chem. Soc., 1998, 120, 11581-11593.
5. Engholm, M.; Koch, T. H. Coupling of the anthracycline antitumor drug menogaril to 2'-deoxyguanosine through reductive activation. J. Am. Chem. Soc., 1989, 111, 8291-8293.
6. Gaudiano, G.; Frigerio, M.; Bravo, P.; Koch, T. H. Intramolecular trapping of the quinone methide from reductive cleavage of daunomycin with oxygen and nitrogen nucleophiles. J. Am. Chem. Soc., 1990, 112, 6704-6709.
7. Angle S. R.; Yang, W. Nucleophilic addition of 2'-deoxynucleosides to the o-quinone methides 10-(acetyloxy)-and 10-methoxy-3, 4-dihydro-9(2H)-anthracenone. J. Org. Chem. 1992, 57, 1092-1097.
8. Angle, S. R.; Rainer, J. D.; Woytowicz, C. Synthesis and chemistry of quinone methide Models for the anthracycline antitumor antibiotics. J. Org. Chem., 1997, 62, 5884-5892.
9. Warpehoski, M. A.; Harper, D. E. Acid-Dependent electrophilicity of cyclopropylpyrroloindoles. Nature's masking strategy for a potent DNA alkylator. J. Am. Chem. Soc., 1994, 116, 7573-7580.
10. Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mésini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. Reversed and sandwiched analogs of duocarmycin SA: Establishment of the origin of the sequence-selective alkylation of DNA and new insights into the source of catalysis. J. Am. Chem. Soc., 1997, 119, 4987-4998.
11. Boger, D. L.; Santillán, A. Jr.; Searcey, M.; Jin, Q. Critical role of the linking amide in CC-1065 and the duocarmycins: Implications on the source of DNA alkylation catalysis. J. Am. Chem. Soc., 1998, 120, 11554-11557.
12. Toteva, M. M.; Moran, M.; Amyes, T. L.; Richard, J. P. Substituent effects on carbocation stability: The pKR for p-quinone methide. J. Am. Chem. Soc., 2003, 125, 8814-8819.
13. Bolon, D. A. o-Quinone methides. II. Trapping with production of chromans. J. Org. Chem. 1970, 35, 3666-3670.
14. Qiao, G. G.-H.; Lenghaus, K.; Solomon, D. H.; Reisinger, A.; Bytheway, I.; Wentrup, C. 4, 6-Dimethyl-o-quinone methide and 4, 6-dimethylbenzoxete. J. Org. Chem., 1998, 63, 9806-9811.
15. Dorrestijn, E.; Kranenburg, M.; Ciriano, M. V.; Mulder, P. The reactivity of o-hydroxybenzyl alcohol and derivatives in solution at elevated temperatures. J. Org. Chem., 1999, 64, 3012-3018.
16. 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.
17. 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.
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. Pathak, T. P.; Sigman, M. S. Applications of ortho-quinone methide intermediates in catalysis and asymmetric synthesis. J. Org. Chem., 2011, 76, 9210-9215.
20. Lukeman, M. Photochemical generation and characterization of quinone methides. In: Quinone Methides; Rokita, S. E., Ed.; John Wiley & Sons: Hoboken, 2009; pp 1-31.
21. Lukeman, M.; Wan, P. Photochemistry of hydroxyarenes. In: Handbook of organic photochemistry and photobiology; Horspool, W.; Lenci, F., Eds; CRC Press: Boca Raton, 2004; pp. 39. 1-39. 19.
22. Wan, P.; Brousmiche, D. W.; Chen, C. Z.; Cole, J.; Lukeman, M.; Xu, M., Quinone methide intermediates in organic photochemistry. Pure Appl. Chem., 2001, 73, 529-534.
23. Wan, P.; Barker, B.; Diao, L.; Fisher, M.; Shi, Y.; Yang, C. Quinone methides: relevant intermediates in organic chemistry. Can. J. Chem. 1996, 74, 465-475.
24. Chapman, O. L.; McIntosh, C. L. Photochemical decarbonylation of unsaturated lactones and carbonates. J. Chem. Soc. D: Chem. Commun., 1971, 383-384.
25. Oude-Alink, B. A. M.; Chan, A. W. K.; Gutsche, C. D. Photolysis of 2-keto-2, 3-dihydrobenzofurans, o-hydroxystyrenes and 1-(o-hydroxyphenyl)-1, 5-hexadienes. J. Org. Chem., 1973, 38, 1993-2001.
26. Padwa, A.; Dehm, D.; Oine, T.; Lee, G. A. Photochemical transformations of small ring heterocyclic compounds. LXII. Competitive keto-enolate photochemistry in the 3-phenylcoumaran-2-one system. J. Am. Chem. Soc., 1975, 97, 1837-1845.
27. Padwa, A.; Lee, G. A. Photochemical transformations of 2, 2-disubstituted chromenes. J. Chem. Soc. Chem. Commun., 1972, 795-796.
28. Wang, P.; Hu, H.; Wang, Y. Novel Photolabile Protecting Group for Carbonyl Compounds. Org. Lett., 2007, 9, 1533-1535.
29. Yang, H.; Mu, F.; Wang, P. Oxidation with a photolabile carbonyl protecting group. J. Org. Chem., 2011, 76, 8955-8961.
30. Kim, J.-H.; Huang, F.; Ly, M.; Linhardt, R. J. Stereoselective synthesis of a C-linked neuraminic acid disaccharide: Potential building block for the synthesis of C-analogues of polysialic acids. J. Org. Chem. 2008, 73, 9497-9500.
31. Wang, P.; Wang, Y.; Hu, H.; Spencer, C.; Liang, X.; Pan, L. Sequential removal of photolabile protecting groups for carbonyls with controlled wavelength. J. Org. Chem., 2008, 73, 6152-6157.
32. Seiler, P.; Wirz, J. The photohydrolysis of eight isomeric trifluoromethylnaphthols. Tetrahedron Lett., 1971, 12, 1683-1686.
33. Seiler, P.; Wirz, J. Struktur und photochemische Reaktivität: Photohydrolyse von Trifluormethylsubstituierten Phenolen und Naphtholen. Helv. Chim. Acta, 1972, 55, 2693-2712.
34. Omura, K.; Matsuura, T. Photoinduced reactions-L: Photolysis of halogenophenols in aqueous alkali and in aqueous cyanide. Tetrahedron, 1971, 27, 3101-3109.
35. Guyon, C.; Boule, P.; Lemaire, J. Photochimie et environnement. III-formation d'acide cyclopentadienique par irradiation du chloro-2 phenol en solution aqueuse basique. Tetrahedron Lett., 1982, 23, 1581-1584.
36. Boule, C.; Richard, C.; David-Oudjehani, K.; Grabner, G. Photochemical behaviour of halophenols in aqueous solution. Proc. Indian Acad. Sci. Chem. Sci., 1997, 109, 509-519.
37. Grabner, G.; Richard, C.; Kohler, G. Formation and Reactivity of 4-Oxocyclohexa-2, 5-dienylidene in the Photolysis of 4-Chlorophenol in Aqueous Solution at Ambient Temperature. J. Am. Chem. Soc., 1994, 116, 11470-11480.
38. Gomberg, M., On triphenylmethyl. XXIII. Tautomerism of the hydroxytriphenyl carbinols. J. Am. Chem. Soc., 1913, 35, 1035-1042.
39. Lewis, T. W.; Curtin, D. Y.; Paul, I. C. Thermal, photochemical, and photonucleated thermal dehydration of p-hydroxytriarylmethanols in solids. (3, 5-Dimethyl-4-hydroxyphenyl)diphenylmethanol and (3, 5-dibromo-4-hydroxyphenyl)diphenylmethanol. X-ray crystal structures of (4-hydroxyphenyl)diphenylmethanol and its 3, 5-dimethyl derivative. J. Am. Chem. Soc., 1979, 101, 5717-5725.
40. Hamai, S.; Kokubun, H. Photochromism of o-hydroxytriphenylcarbinol. Z. Phys. Chem., 1974, 88, 211-214.
41. Hamai, S.; Kokubun, H. Thermal decay of the colored form in photochromism of 2-hydroxy-4-methoxytriphenylmethanol in n-hexane. Bull. Chem. Soc. Jpn., 1974, 47, 2085-2088.
42. Wan, P.; Chak, B. Structure-reactivity studies and catalytic effects in the photosolvolysis of methoxy-substituted benzyl alcohols. J. Chem. Soc. Perkin Trans 2, 1986, 1751-1756.
43. Baker, B.; Diao, L.; Wan, P. Intramolecular [4+2] cycloaddition of a photogenerated o-quinone methide in aqueous solution. J. Photochem. Photobiol. A. Chem., 1997, 104, 91-96.
44. 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.
45. Diao, L.; Wan, P. Chemistry of photogenerated phenyl-substituted o-, m-, and p-quinone methides from phenol derivatives in aqueous solution. Can. J. Chem., 2008, 86, 105-118.
46. Basari, N.; Sabi, I.; MlinariMajerski, K.; Wan, P. Photochemical Formation and Chemistry of long-lived adamantylidene-quinone methides and 2-adamantyl cations. J. Org. Chem., 2010, 75, 102-116.
47. Shi, Y.; Wan, P. Solvolysis and ring closure of quinone methides photogenerated from biaryl systems. Can. J. Chem., 2005, 83, 1306-1323.
48. Brousmiche, D.; Xu, M.; Lukeman, M.; Wan, P. Photohydration and photosolvolysis of biphenyl alkenes and alcohols via biphenyl quinone methidetype intermediates and diarylmethyl carbocations. J. Am. Chem. Soc., 2003, 125, 12961-12970.
49. Xu, M.; Lukeman, M.; Wan, P. Photogeneration and chemistry of biphenyl quinone methides from hydroxybiphenyl methanols. Photochem. Photobiol., 2006, 82, 50-56.
50. Basari, N.; Cindro, N.; Bobinac, D.; MlinariMajerski, K.; Uzelac, L.; Kralj, M.; Wan, P. Sterically congested quinone methides in photodehydration reactions of 4-hydroxybiphenyl derivatives and investigation of their antiproliferative activity. Photochem. Photobiol. Sci, 2011, 10, 1910-1925.
51. Xu, M.; Chen, C. Z.; Wan, P. Intramolecular charge transfer in photoexcited hydroxyterphenyls: Evidence for formation of terphenyl quinone methides in aqueous solution. J. Photochem. Photobiol. A: Chem., 2008, 198, 26-33.
52. Lukeman, M.; Veale, D.; Wan, P.; Munasinghe, V. R.; Corrie, J. E. T. Photogeneration of 1, 5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution. Can. J. Chem., 2004, 82, 240-253.
53. Arumugam, S.; Popik, V. V. Photochemical generation and the reactivity of o-naphthoquinone methides in aqueous solutions. J. Am. Chem. Soc., 2009, 131, 11892-11899.
54. Doria, F.; Richter, S. N.; Nadai, M.; Colloredo-Mels, S.; Mella, M.; Palumbo, M.; Freccero, M. BINOLamino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents. J. Med. Chem., 2007, 50, 6570-6579.
55. Richter, S. N.; Maggi, S.; Colloredo Mels, S.; Palumbo, M., Freccero, M. Binol quinone methides as bisalkylating and DNA cross-linking agents. J. Am. Chem. Soc., 2004, 126, 13973-13979.
56. Kulikov, A.; Arumugam, S.; Popik, V. V. Photolabile protection of alcohols, phenols, and carboxylic acids with 3-hydroxy-2-naphthalenemethanol. J. Org. Chem., 2008, 73, 7611-7615.
57. Kostikov, A. P.; Popik, V. V. Photolabile protection of 1, 2-and 1, 3-diols with salicylaldehyde derivatives. Org. Lett., 2008, 10, 5277-5280.
58. Kostikov, A. P.; Malashikhina, N.; Popik, V. V. Caging of carbonyl compounds as photolabile (2, 5-dihydroxyphenyl)ethylene glycol acetals. J. Org. Chem., 2009, 74, 1802-1804.
59. Kostikov, A. P.; Popik, V. V. 2, 5-Dihydroxybenzyl and (1, 4-dihydroxy-2-naphthyl)methyl, novel reductively armed photocages for the hydroxyl moiety. J. Org. Chem., 2007, 72, 9190-9194.
60. Arumugam, S.; Popik, V. V. Dual reactivity of hydroxy-and methoxy-substituted o-quinone methides in aqueous solutions: hydration versus tautomerization. J. Org. Chem., 2010, 75, 7338-7346.
61. Chiang, Y.; Kresge, A. J.; Zhu, Y. Kinetics and mechanisms of hydration of o-quinone methides in aqueous solution. J. Am. Chem. Soc., 2000, 122, 9854-9855.
62. Chiang, Y.; Kresge, A. J.; Zhu, Y. Flash photolytic generation of ortho-quinone methide in aqueous solution and study of its chemistry in that medium. J. Am. Chem. Soc., 2001, 123, 8089-8094.
63. Chiang, Y.; Kresge, A. J.; Zhu, Y. Flash photolytic generation of o-quinone-phenylmethide and o-quinone-(p-anisyl)methide in aqueous solution and investigation of their reactions in that medium. Saturation of acid-catalyzed hydration. J. Am. Chem. Soc., 2002, 124, 717-722.
64. Chiang, Y.; Kresge, A. J.; Zhu, Y. Flash photolytic generation and study of pquinone methide in aqueous solution. An estimate of rate and equilibrium constants for heterolysis of the carbonbromine bond in p-hydroxybenzyl bromide. J. Am. Chem. Soc., 2002, 124, 6349-6356.
65. 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.
66. Modica, E.; Zanaletti, R.; Freccero, M.; Mella, M. Alkylation of amino acids and glutathione in qater by o-quinone methide. Reactivity and selectivity. J. Org. Chem., 2001, 66, 41-52.
67. Wang, P.; Liu, R.; Wu, X.; Ma, H.; Cao, X.; Zhou, P.; Zhang, J.; Weng, X.; Zhang, X.-L.; Qi, J.; Zhou, X.; Weng, L. A potent, water-soluble and photoinducible DNA cross-linking agent. J. Am. Chem. Soc., 2003, 125, 1116-1117.
68. Verga, D.; Richter, S. N.; Palumbo, M.; Gandolfi, R.; Freccero, M. Bipyridyl ligands as photoactivatable mono-and bis-alkylating agents capable of DNA cross-linking. Org. Biomol. Chem., 2007, 5, 233-235.
69. Verga, D.; Nadai, M.; Doria, F.; Percivalle, C.; Di Antonio, M.; Palumbo, M.; Richter, S. N.; Freccero, M. Photogeneration and reactivity of naphthoquinone methides as purine selective DNA alkylating agents. J. Am. Chem. Soc., 2010, 132, 14625-14637.
70. Percivalle, C.; La Rosa, A.; Verga, D.; Doria, F.; Mella, M.; Palumbo, M.; Di Antonio, M.; Freccero, M. Quinone methide generation via photoinduced electron transfer. J. Org. Chem., 2011, 76, 3096-3106.
71. Di Antonio, M.; Doria, F.; Richter, S. N.; Bertipaglia, C.; Mella, M.; Sissi, C.; Palumbo, M.; Freccero, M. Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents. J. Am. Chem. Soc., 2009, 131, 13132-13141.
72. Rommel, E.; Wirz, J. The photoenol tautomer of 5-methyl-1, 4-naphthoquinone. Helv. Chim. Acta, 1977, 60, 38-42.
73. Kang, H.; Rokita, S. E. Site-specific and photo-induced alkylation of DNA by a dimethylanthraquinone-oligodeoxynucleotide conjugate. Nucl. Acid. Res., 1996, 24, 3896-3902.
74. Givens, R. S.; Heger, D.; Hellrung, B.; Kamdzhilov, Y.; Mac, M.; Conrad, P. G.; Cope, E.; Lee, J. I.; Mata-Segrada, J. F.; Cshowen, R. L.; Wirz, J. The photo-Favorskii reaction of p-hydroxyphenacyl compounds is initiated by water-assisted, adiabatic extrusion of a triplet biradical. J. Am. Chem. Soc., 2008, 130, 3307-3309.
75. Xu, M.; Lukeman, M.; Wan, P. Photodecarboxylation of benzoyl-substituted biphenylacetic acids and photo-retro-Aldol reaction of related compounds in aqueous solution. Acid and base catalysis of reaction. J. Photochem. Photobiol. A: Chem., 2009, 204, 52-62.
76. An, H.-Y.; Kwok, W. M.; Ma, C.; Guan, X.; Kan, J. T. W.; Toy, P. H.; Phillips, D. L. Photophysics and photodeprotection reactions of p-methoxyphenacyl phototriggers: An ultrafast and nanosecond time-resolved spectroscopic and density functional theory study. J. Org. Chem., 2010, 75, 5837-5851.
77. Klíová,.; ebej, P.; Olomek, T.; Hellrung, B.; Slavíek, P.; Klán, P.; Heger, D.; Wirz, J. Adiabatic triplet state tautomerization of phydroxyacetophenone in aqueous solution. J. Phys. Chem. A, 2012, 116, 2935-2944.
78. Kalnderopoulos, P.; Yates, K. Intramolecular proton transfer in photohydration reactions. J. Am. Chem. Soc., 1986, 108, 6290-6295.
79. Foster, K. L.; Baker, S.; Brousmiche, D. W.; Wan, P. o-Quinone methide formation from excited state intramolecular proton transfer (ESIPT) in an ohydroxystyrene. J. Photochem. Photobiol. A: Chem., 1999, 129, 157-163.
80. Fischer, M.; Wan, P. m-Quinone methides from m-hydroxy-1, 1-diaryl alkenes via excited-state (formal) intramolecular proton transfer mediated by a water trimer. J. Am. Chem. Soc., 1998, 120, 2680-2681.
81. Fischer, M.; Wan, P. Nonlinear solvent water effects in the excited-state (formal) intramolecular proton transfer (ESIPT) in m-hydroxy-1, 1-diaryl alkenes: Efficient formation of m-quinone methides. J. Am. Chem. Soc., 1999, 121, 4555-4562.
82. Zimmermann, H. E. The meta effect in organic photochemistry: Mechanistic and exploratory organic photochemistry. J. Am. Chem. Soc., 1995, 117, 8988-8991.
83. Murohoshi, T.; Kaneda, K.; Ikegami, M.; Arai, T. Photoisomerization and isomer-specific addition of water in hydroxystilbenes. Photochem. Photobiol. Sci., 2003, 2, 1247-1249.
84. Lukeman, M.; Wan, P. Excited state intramolecular proton transfer (ESIPT) in2-phenylphenol: an example of proton transfer to a carbon of an aromaticring. Chem. Commun., 2001, 1004-1005.
85. Lukeman, M.; Wan, P. A new type of excited-state intramolecular proton transfer: Proton transfer from phenol OH to a carbon atom of an aromatic ring observed for 2-phenylphenol. J. Am. Chem. Soc., 2002, 124, 9458-9464.
86. Lukeman, M.; Wan, P. Excited-state intramolecular proton transfer in ohydroxybiaryls: A new route to dihydroaromatic compounds. J. Am. Chem. Soc., 2003, 125, 1164-1165.
87. Webb, S. P.; Philips, L. A.; Yeh, S. W.; Tolbert, L. M.; Clark, J. H. Picosecond kinetics of the excited-state, proton-transfer reaction of 1-naphthol in water. J. Phys. Chem., 1986, 90, 5154-5164.
88. Flegel, M.; Lukeman, M.; Wan, P. Photochemistry of 1, 1bi-2-naphthol (BINOL)-ESIPT is responsible for photoracemization and photocyclization. Can. J. Chem., 2008, 86, 161-169.
89. Kumar, M.; Wan, P. Direct and water-mediated excited state intramolecular proton transfer (ESIPT) from phenol OH to carbon atoms of extended orthosubstituted biaryl systems. Photochem. Photobiol. Sci., 2008, 7, 1544-1554.
90. Lukeman, M.; Burns, M.-D.; Wan, P. Excited state intramolecular proton transfer in 1-hydroxypyrene. Can. J. Chem., 2011, 89, 433-440.
91. Basari, N.; Doli, N.; Ivković, J.; Wang, Y. H.; Malić, P.; Wan, P. Very efficient generation of quinone methides through excited state intramolecular proton transfer to a carbon atom. Chem. Eur. J., 2012, 18, 10617-10623.
92. Flegel, M.; Lukeman, M.; Huck, L.; Wan, P. Photoaddition of water and alcohols to the anthracene moiety of 9-(2'-hydroxyphenyl)anthracene via formal excited state intramolecular proton transfer. J. Am. Chem. Soc., 2004, 126, 7890-7897.
93. Basarić, N.; Wan, P. Competing excited state intramolecular proton transfer pathways from phenol to anthracene moieties. J. Org. Chem., 2006, 71, 2677-2686.
94. Wang, Y.-H.; Wan, P. Excited state intramolecular proton transfer (ESIPT) in dihydroxyphenyl anthracenes. Photochem. Photobiol. Sci., 2011, 10, 1934-1944.
95. Isaks, M.; Yates, K.; Kalanderopoulos, P. Photohydration via intramolecular proton transfer to carbon in electronically excited states. J. Am. Chem. Soc., 1984, 106, 2728-2730.
96. Doria, F.; Percivalle, C.; Freccero, M. Vinylidene-quinone methides, photochemical generation and silicon effect on reactivity. J. Org. Chem., 2012, 77, 3615-3619.
97. Frecero, M. Quinone mMethides as alkylating and cross-linking agents. Mini Rev. Org. Chem., 2004, 1, 403-415.
98. 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.
99. McCracken, P. G.; Bolton, J. L.; Thatcher, G. R. J. Covalent modification of proteins and peptides by the quinone methide from 2-tert-butyl-4, 6-dimethylphenol: Selectivity and reactivity with respect to competitive hydration. J. Org. Chem., 1997, 62, 1820-1825.
100. 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.
101. McDonald, I. A.; Nyce, P. L.; Jung, M. J.; Sabol, J. S. Syntheses of DL-2-fluoromethy-p-tyrosine and DL-2-difluoromethyl-p-tyrosine as potential inhibitors of tyrosine hydroxylase. Tetrahedron Lett., 1991, 32, 887-890.
102. Wang, Q.; Dechert, U.; Jirik, F.; Withers, S. G. Suicide Inactivation of human prostatic acid phosphatase and a phosphotyrosine phosphatase. Biochem. Biophys. Res. Commun., 1994, 200, 577-583.
103. Myers, J. K.; Cohen, J. D., Widlanski, T. S., Substituent effects on the mechanism-based inactivation of prostatic acid phosphatase. J. Am. Chem. Soc., 1995, 117, 11049-11054.
104. Storwell, J. K., Widlanski, T. S.; Kutaleladze, T. G.; Raines, R. T. Mechanismbased inactivation of ribonuclease A. J. Org. Chem., 1995, 60, 6930-6936.
105. Chung, S.-K.; Lee J. W.; Shim, N. Y.; Kwon, T. W. p-Quinone methides as geometric analogues of quinolone carboxylate antibacterials. Bioorg. Med. Chem. Lett., 1996, 6, 1309-1312.
106. Cabaret, D.; Adediran, S. A.; Gonzalez, M. J. G.; Pratt, R. F.; Wakselman, M. Synthesis and reactivity with lactamases of "penicillin-like" cyclic depsipeptides. J. Org. Chem., 1999, 64, 713-720.
107. Jiang, J.; Zeng, D.; Li, S. Photogenerated quinone methides as protein affinity labeling reagents. ChemBioChem, 2009, 10, 635-638.
108. Arumugam, S.; Popik, V. V. Patterned surface derivatization using Diels-Alder photoclick reaction. J. Am. Chem. Soc., 2011, 133, 15730-15736.
109. Arumugam, S.; Popik, V. V. Attach, remove, or replace: Reversible surface functionalization using thiol-quinone methide photoclick chemistry. J. Am. Chem. Soc., 2012, 134, 8408-8411.
110. Zhou, Q. Turnbull, K. D. Phosphodiester alkylation with a quinone methide. J. Org. Chem., 1999, 64, 2847-2851.
111. Zhou, Q.; Turnbull, K. D. Trapping phosphodiester-quinone methide adducts through in situ lactonization. J. Org. Chem., 2000, 65, 2022-2029.
112. Zhou, Q.; Turnbull, K. D. Quinone methide phosphodiester alkylations under aqueous conditions. J. Org. Chem., 2001, 66, 7072-7077.
113. Bakke, B. A.; McIntosh, M. C.; Turnbull, K. D. Improved alkylation and product stability in phosphotriester formation through quinone methide reactions with dialkyl phosphates. J. Org. Chem., 2005, 70, 4338-4345.
114. Zeng, Q.; Rokita, S. E. Tandem quinone methide generation for crosslinking DNA. J. Org. Chem., 1996, 61, 9080-9081.
115. Rokita, S. E.; Yang, J.; Pande, P.; Greenberg, W. A. Quinone methide alkylation of deoxycytidine. J. Org. Chem., 1997, 62, 3010-3012.
116. Veldhuyzen, W. F.; Shallop, A. J.; Jones, R. A.; Rokita, S. E. Thermodynamic versus kinetic products of DNA alkylation as modeled by reaction of deoxyadenosine. J. Am. Chem. Soc., 2001, 123, 11126-11132.
117. 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.
118. Weinert, E. E.; Frankenfield, K. N.; Rokita, S. E. Time-dependent evolution of adducts formed between deoxynucleosides and a model quinone methide. Chem. Res. Toxicol., 2005, 18, 1364-1370.
119. Lewis, M. A.; Yoerg, D. G.; Bolton, J. L.; Thompson, J. A. Alkylation of 2'-deoxynucleosides and DNA by quinone methides derived from 2, 6-ditert-butyl-4-methylphenol. Chem. Res. Toxicol., 1996, 9, 1368-1374.
120. Zhou, Q.; Qu, Y.; Mangrum, J. B.; Wang, X. DNA alkylation with Nmethylquinolinium quinone methide to N2-dG adducts resulting in extensive stops in primer extension with DNA polymerases and subsequent suppression of GFP expression in A549 Cells. Chem. Res. Toxicol., 2011, 24, 402-411.
121. Freccero, M.; Gandolfi, R.; Sarzi-Amadè, M. Selectivity of purine alkylation by a quinone methide. Kinetic or thermodynamic control? J. Org. Chem., 2003, 68, 6411-6423.
122. Di Valentin, C.; Freccero, M.; Zanaletti, R.; Sarzi-Amadè, M. O-Quinone methide as alkylating agent of nitrogen, oxygen, and sulfur nucleophiles. The role of H-bonding and solvent effects on the reactivity through a DFT computational study. J. Am. Chem. Soc., 2001, 123, 8366-8377.
123. Freccero, M.; Di Valentin, C.; Sarzi-Amadè, M. Modeling H-bonding and solvent effects in the alkylation of pyrimidine bases by a prototype quinone methide: A DFT study. J. Am. Chem. Soc., 2003, 125, 3544-3553.
124. Zhou, Q.; Rokita, S. E. A general strategy for target-promoted alkylation in biological systems. Proc. Natl. Acad. Sci., 2003, 100, 15452-15457.
125. Wang, H.; Wahi, M. S.; Rokita, S. E. Immortalizing a transient electrophile for DNA cross-linking. Angew. Chem. Int. Ed., 2008, 47, 1291-1293.
126. Wang, H.; Rokita, S. E. Dynamic cross-linking is retained in duplex DNA after multiple exchange of strands. Angew. Chem. Int. Ed., 2010, 49, 5957-5960.
127. Rossiter, C. S.; Modica, E.; Kumar, D.; Rokita, S. E. Few constraints limit the design of quinone methide-oligonucleotide self-adducts for directing DNA alkylation. Chem. Commun., 2011, 47, 1476-1478.
128. Veldhuyzen, W. F.; Pande, P.; Rokita, S. E. A transient product of DNA alkylation can be stabilized by binding localization. J. Am. Chem. Soc., 2003, 125, 14005-14013.
129. 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.
130. Chatterjee, M.; Rokita, S. E. Inducible alkylation of DNA using an oligonucleotide-quinone conjugate. J. Am. Chem. Soc., 1990, 112, 6397-6399.
131. Chatterjee, M.; Rokita, S. E. The role of a quinone methide in the sequence specific alkylation of DNA. J. Am. Chem. Soc., 1994, 116, 1690-1697.
132. Weinder, M. F.; Millard, J. T.; Hopkins, P. B. Determination at single nucleotide resolution of the sequence specificity of DNA interstrand crosslinking agents in DNA fragments. J. Am. Chem. Soc., 1989, 111, 9270-9272.
133. Chiang, Y.; Kresge, A. J. Alkylation of guanosine and 2deoxyguanosine by o-quinone (p-anisyl)methide in aqueous solution. Org. Biomol. Chem., 2004, 2, 1090-1092.
134. Basarić, N.; Cindro, N.; Bobinac, D.; Uzelac, L.; MlinariMajerski, K.; Kralj, M.; Wan, P. Zwitterionic biphenyl quinone methides in photodehydration reactions of 3-hydroxybiphenyl derivatives: laser flash photolysis and antiproliferation study. Photochem. Photobiol. Sci., 2012, 11, 381-396.
135. Veljković, J.; Uzelac, L.; Molanov, K.; MlinariMajerski, K.; Kralj, M.; Wan, P.; Basarić, N. Sterically congested adamantylnaphthalene quinone methides. J. Org. Chem., 2012, 77, 4596-4610.
136. He, H.; Tian, T.; Wang, P.; Wu, L.; Xu, J.; Zhou, X.; Zhang, X.; Cao, X.; Wu, X. Porphyrin-DNA cross-linking agent hybrids: chemical synthesis and biological studies. Bioorg. Med. Chem. Lett., 2004, 14, 3013-3016.