The effect of nitro substitution on the photochemistry of benzyl benozhydroxamate: Photoinduced release of benzohydroxamic acid

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 227, Issue 1, 2012, Pages 1-10

  Grither, Whitney R ^a   Korang, James ^a   Sauer, Jacob P ^a   Sherman, Matthew P ^a   Vanegas, Pamela L ^a   Zhang, Miao ^a   McCulla, Ryan D ^a  

^a Saint Louis University   (United States)

Author keywords

Hydroxamate; Nitrobenzyl; Nitrosyl hydride; Nitroxyl; Photolabile protecting group; Wavelength dependent

Indexed keywords

EID: 83555168130     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2011.10.005     Document Type: Article

References (58)

1. W. Flores-Santana, C. Switzer, L.A. Ridnour, D. Basudhar, D. Mancardi, S. Donzelli, D.D. Thomas, K.M. Miranda, J.M. Fukuto, and D.A. Wink Arch. Pharm. Res. 32 2009 1139 1153
2. N. Paolocci, M. Jackson, B. Lopez, K. Miranda, C. Tocchetti, D. Wink, A. Hobbs, and J. Fukuto Pharmacol. Therapeut. 113 2007 442 458
3. J.M. Fukuto, M.D. Bartberger, A.S. Dutton, N. Paolocci, D.A. Wink, and K.N. Houk Chem. Res. Toxicol. 18 2005 790 801
4. D.A. Wink, K.M. Miranda, T. Katori, D. Mancardi, D.D. Thomas, L. Ridnour, M.G. Espey, M. Feelisch, C.A. Colton, J.M. Fukuto, P. Pagliaro, D.A. Kass, and N. Paolocci Am. J. Physiol. Heart Circ. Physiol. 285 2003 H2264 H2276
5. K.M. Miranda, N. Paolocci, T. Katori, D.D. Thomas, E. Ford, M.D. Bartberger, M.G. Espey, D.A. Kass, M. Feelisch, J.M. Fukuto, and D.A. Wink Proc. Natl. Acad. Sci. U. S. A. 100 2003 9196 9201
6. E.G. DeMaster, B. Redfern, and H.T. Nagasawa Biochem. Pharmacol. 55 1998 2007 2015
7. H.T. Nagasawa, E.G. DeMaster, B. Redfern, F.N. Shirota, and D.J. Goon J. Med. Chem. 33 1990 3120 3122
8. N. Paolocci, T. Katori, H. Champion, M. St John, K. Miranda, J. Fukuto, D. Wink, and D. Kass Proc. Natl. Acad. Sci. U. S. A. 100 2003 5537 5542
9. P. Pagliaro, D. Mancardi, R. Rastaldo, C. Penna, D. Gattullo, K.M. Miranda, M. Feelisch, D.A. Wink, D.A. Kass, and N. Paolocci Free Radic. Biol. Med. 34 2003 33 43
10. C.G. Tocchetti, W. Wang, J.P. Froehlich, S. Huke, M.A. Aon, G.M. Wilson, G. Di Benedetto, B. O'Rourke, W.D. Gao, D.A. Wink, J.P. Toscano, M. Zaccolo, D.M. Bers, H.H. Valdivia, H. Cheng, D.A. Kass, and N. Paolocci Circ. Res. 100 2007 96 104
11. J.M. Fukuto, K. Chiang, R. Hszieh, P. Wong, and G. Chaudhuri J. Pharmacol. Exp. Ther. 263 1992 546 551
12. E. Bermejo, D.A. Sáenz, F. Alberto, R.E. Rosenstein, S.E. Bari, and M.A. Lazzari Thromb. Haemost. 94 2005 578 584
13. A. Ellis, C.G. Li, and M.J. Rand Br. J. Pharmacol. 129 2000 315 322
14. W. Kim, Y. Choi, P. Rayudu, P. Das, W. Asaad, D. Arnelle, J. Stamler, and S. Lipton Neuron 24 1999 461 469
15. B. Lopez, D. Wink, and J. Fukuto Arch. Biochem. Biophys. 465 2007 430 436
16. M. Doyle, S. Mahapatro, R. Broene, and J. Guy J. Am. Chem. Soc. 110 1988 593 599
17. S. Maraj, S. Khan, X. Cui, R. Cammack, C. Joannou, and M. Hughes Analyst 120 1995 699 703
18. H. Ohshima, I. Gilibert, and F. Bianchini Free Radic. Biol. Med. 26 1999 1305 1313
19. F. Kohout, and F. Lampe J. Am. Chem. Soc. 87 1965 5795 5796
20. V. Shafirovich, and S.V. Lymar Proc. Natl. Acad. Sci. U. S. A. 99 2002 7340 7345
21. K.M. Miranda, H.T. Nagasawa, and J. Toscano Curr. Top. Med. Chem. 5 2005 649 664
22. Y. Adachi, H. Nakagawa, K. Matsuo, T. Suzuki, and N. Miyata Chem. Commun. 2008 5149 5151
23. A.D. Cohen, B.B. Zeng, S.B. King, and J.P. Toscano J. Am. Chem. Soc. 125 2003 1444 1445
24. G. Mayer, and A. Heckel Angew. Chem. Int. Ed. 45 2006 4900 4921
25. R.S. Givens, P.G. Conrad, A.L. Yousef, and J. Leel CRC Handbook of Organic Photochemistry and Photobiology second ed. 2004 CRC Press Boca Raton (Chapter 69)
26. C. Walling, and A.N. Naglieri J. Am. Chem. Soc. 82 1960 1820 1825
27. T. Sakurai, S. Yamada, and H. Inoue Chem. Lett. 1983 4975 4978
28. T. Sakurai, H. Yamamoto, S. Yamada, and H. Inoue Bull. Chem. Soc. Jpn. 58 1985 1174 1181
29. B. Hosangadi, P. Chhaya, M. Nimbalkar, and N. Patel Tetrahedron 43 1987 5375 5380
30. E. Lipczynska-Kochany Chem. Rev. 91 1991 477 491
31. J.E. Johnson, M. Arfan, R. Hodzi, L.R. Caswell, and S. Rasmussen Photochem. Photobiol. 51 1990 139 144
32. R. White, K. Oppliger, and J. Johnson J. Photochem. Photobiol. A 101 1996 197 200
33. M.M. Aly, A.M. Fahmy, F.F. Abdellatif, and M.Z.A. Badr Bull. Pol. Acad. Sci., Chem. 35 1987 47 52
34. Y. Il'ichev, M. Schworer, and J. Wirz J. Am. Chem. Soc. 126 2004 4581 4595
35. A. Blanc, and C.G. Bochet J. Org. Chem. 67 2002 5567 5577
36. C. Bochet Angew. Chem. Int. Ed. 40 2001 2071 2073
37. A. Blanc, and C.G. Bochet Org. Lett. 9 2007 2649 2651
38. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09 2009 Gaussian, Inc. Wallingford, CT
39. R. Stratmann, G. Scuseria, and M. Frisch J. Chem. Phys. 109 1998 8218 8224
40. G.A. Zhurko, and D.A. Zhurko ChemCraft 2007 Pilmus Inc. Milpatas, CA
41. W.L.P. Armarego, and D.D. Perrin Purification of Laboratory Chemicals 1998 Pergamon Press Inc. Elmsford, NY
42. O. Miyata, T. Koizumi, H. Asai, R. Iba, and T. Naito Tetrahedron 60 2004 3893 3914
43. A.S. Singha, and B.N. Misra Indian J. Chem. 21B 1982 361 363
44. A. Gissot, A. Volonterio, and M. Zanda J. Org. Chem. 70 2005 6925 6928
45. O. Brady, and F. Peakin J. Chem. Soc. 1930 226 229
46. P. Mamalis, J. Green, and D. Mchale J. Chem. Soc. 1960 229 238
47. N.J. Bunce, J. LaMarre, and S.P. Vaish Photochem. Photobiol. 39 1984 531 533
48. M. Schworer, and J. Wirz Helv. Chim. Acta 84 2001 1441 1458
49. R. Yip, Y. Wen, D. Gravel, R. Giasson, and D. Sharma J. Phys. Chem. 95 1991 6078 6081
50. D. Gravel, R. Giasson, D. Blanchet, R. Yip, and D. Sharma Can. J. Chem. 69 1991 1193 1200
51. R. Yip, D. Sharma, R. Giasson, and D. Gravel J. Phys. Chem. 89 1985 5328 5330
52. R. Yip, D. Sharma, R. Giasson, and D. Gravel J. Phys. Chem. 88 1984 5770 5772
53. L. Hviid, J.W. Verhoeven, A.M. Brouwer, M.N. Paddon-Row, and J. Yang Photochem. Photobiol. Sci. 3 2004 246 251
54. D.E. Falvey, and C. Sundararajan Photochem. Photobiol. Sci. 3 2004 831 838
55. N. Turro, V. Ramamurthy, W. Cherry, and W. Farneth Chem. Rev. 78 1978 125 145
56. S.L. Murov, I. Carmichael, and G.L. Hug Handbook of Photochemistry second ed. 1993 Marcel Dekker Inc. New York, NY
57. R. Finnegan, and D. Knutson J. Am. Chem. Soc. 90 1968 1670 1671
58. N. Turro Modern Molecular Photochemistry 1991 University Science Books Sausalito, CA (Chapter 6)