Bromoacetophenone-based photonucleases: Photoinduced cleavage of DNA by 4′-bromoacetophenone-pyrrolecarboxamide conjugates

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2117-2120

  Wender, Paul A ^a   Jeon, Raok ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b ALLERGAN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4' BROMOACETOPHENONE PYRROLECARBOXAMINE; 4'-BROMOACETOPHENONE-PYRROLECARBOXAMINE; ACETOPHENONE DERIVATIVE; DNA; PHENACYL BROMIDE; PYRROLE DERIVATIVE; SCAVENGER;

ARTICLE; AUTORADIOGRAPHY; CHEMISTRY; LIGHT; PHOTOCHEMISTRY; POLYACRYLAMIDE GEL ELECTROPHORESIS; RADIATION EXPOSURE; SYNTHESIS;

ACETOPHENONES; AUTORADIOGRAPHY; DNA; ELECTROPHORESIS, POLYACRYLAMIDE GEL; FREE RADICAL SCAVENGERS; LIGHT; PHOTOCHEMISTRY; PYRROLES;

EID: 0033619839     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9903279     Document Type: Article

References (55)

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7. For examples and lead references on nucleic acid cleaving agents, see: Nucleic Acid Targeted Drug Design; Propst, C. L., Perun, T. J., Eds.; Dekker: New York, 1992. Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI Press: London, 1992; Vol. 1, pp 217-243. Armitage, B. Chem. Rev. 1998, 98, 1171-1200. Gasper, S. M.; Armitage, B.; Shui, X. Q.; Hu, G. G.; Yu, C. J.; Schuster, G. B.; Williams, L. D. J. Am. Chem. Soc. 1998, 120, 12402-12409. Ciftan, S. A.; Thorp, H. H. J. Am. Chem. Soc. 1998, 120, 9995-10000. Kelley, S. O.; Barton, J. K. Science 1999, 283, 375-381. Kino, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 7373-7374.
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11. For recent reviews, see: Enediyne Antibiotics As Antitumor Agents: Border, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. H. Tetrahedron 1996, 52, 6453-6518. Doyle, T. W.; Kadow, J. F. Tetrahedron Symposia-In - Print Number 53; Oxford, 1994; Vol. 50, pp 1311-1538. Wang, K. K. Chem. Rev. 1996, 96, 207. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
12. For recent reviews, see: Enediyne Antibiotics As Antitumor Agents: Border, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. H. Tetrahedron 1996, 52, 6453-6518. Doyle, T. W.; Kadow, J. F. Tetrahedron Symposia-In - Print Number 53; Oxford, 1994; Vol. 50, pp 1311-1538. Wang, K. K. Chem. Rev. 1996, 96, 207. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
13. For recent reviews, see: Enediyne Antibiotics As Antitumor Agents: Border, D. B., Doyle, T. W., Eds.; Marcel-Dekker: New York, 1995. Maier, M. E. Synlett 1995, 13-26. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. H. Tetrahedron 1996, 52, 6453-6518. Doyle, T. W.; Kadow, J. F. Tetrahedron Symposia-In - Print Number 53; Oxford, 1994; Vol. 50, pp 1311-1538. Wang, K. K. Chem. Rev. 1996, 96, 207. Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
14. (a) For representative studies from our laboratory, see: Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863. Wender P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311. Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C; Suffert, J. Tetrahedron Lett. 1988, 29, 909.
15. (a) For representative studies from our laboratory, see: Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863. Wender P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311. Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C; Suffert, J. Tetrahedron Lett. 1988, 29, 909.
16. (a) For representative studies from our laboratory, see: Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863. Wender P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311. Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C; Suffert, J. Tetrahedron Lett. 1988, 29, 909.
17. (a) For representative studies from our laboratory, see: Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863. Wender P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311. Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C; Suffert, J. Tetrahedron Lett. 1988, 29, 909.
18. (a) For representative studies from our laboratory, see: Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863. Wender P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311. Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C; Suffert, J. Tetrahedron Lett. 1988, 29, 909.
19. (a) For representative studies from our laboratory, see: Wender, P. A.; Beckham, S.; O'Leary, J. G. Synthesis 1994, 1278. Wender, P. A.; Tebbe, M. J. Tetrahedron 1994, 50, 1419. Wender, P. A.; Zercher, C. K.; Beckham, S.; Haubold, E. J. Org. Chem. 1993, 58, 5867. Wender, P. A.; Tebbe, M. J. Tetrahedron Lett. 1991, 32, 4863. Wender P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311. Wender, P. A.; Harmata, M.; Jeffrey, D.; Mukai, C; Suffert, J. Tetrahedron Lett. 1988, 29, 909.
20. (b) Studies from other laboratories are cited in ref 2 and include contributions from the groups of Brückner, Clive, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. Recent representative examples and further lead references include the following: Myers, A. G.; Liang, J.; Hammond, M.; Harrington, P. M.; Wu, Y.; Kuo, E. Y. J. Am. Chem. Soc. 1998, 120, 5319-5320. Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1998, 120, 10332-10349. Churcher, I.; Hallett, D.; Magnus, P. J. Am. Chem. Soc. 1998, 120, 10350-10358. Suenaga, H.; Nakashima, K.; Mizuno, T.; Takeuchi, M.; Hamachi, I.; Shinkai, S. J. Chem. Soc., Perkin Trans, 1 1998, 1263-1268.
21. (b) Studies from other laboratories are cited in ref 2 and include contributions from the groups of Brückner, Clive, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. Recent representative examples and further lead references include the following: Myers, A. G.; Liang, J.; Hammond, M.; Harrington, P. M.; Wu, Y.; Kuo, E. Y. J. Am. Chem. Soc. 1998, 120, 5319-5320. Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1998, 120, 10332-10349. Churcher, I.; Hallett, D.; Magnus, P. J. Am. Chem. Soc. 1998, 120, 10350-10358. Suenaga, H.; Nakashima, K.; Mizuno, T.; Takeuchi, M.; Hamachi, I.; Shinkai, S. J. Chem. Soc., Perkin Trans, 1 1998, 1263-1268.
22. (b) Studies from other laboratories are cited in ref 2 and include contributions from the groups of Brückner, Clive, Danishefsky, Doyle, Grierson, Hirama, Isobe, Kadow, Kende, Krause, Krebs, Magnus, Maier, Myers, Nicolaou, Nuss, Saito, Schreiber, Semmelhack, Suffert, Takahashi, and Terashima. Recent representative examples and further lead references include the following: Myers, A. G.; Liang, J.; Hammond, M.; Harrington, P. M.; Wu, Y.; Kuo, E. Y. J. Am. Chem. Soc. 1998, 120, 5319-5320. Clive, D. L. J.; Bo, Y.; Tao, Y.; Daigneault, S.; Wu, Y.-J.; Meignan, G. J. Am. Chem. Soc. 1998, 120, 10332-10349. Churcher, I.; Hallett, D.; Magnus, P. J. Am. Chem. Soc. 1998, 120, 10350-10358. Suenaga, H.; Nakashima, K.; Mizuno, T.; Takeuchi, M.; Hamachi, I.; Shinkai, S. J. Chem. Soc., Perkin Trans, 1 1998, 1263-1268.
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43. For lead references, see: Bouziane, M.; Ketterle, C.; Helissey, P.; Herfeld, P.; Le Bret, M.; Giorgi-Renault, S.; AuClair, C. Biochemistry 1995, 34, 14051-14058. Boutorine, A. S.; Brault, D.; Takasugi, M.; Delgado, O. Hélène. C. J. Am. Chem. Soc. 1996, 118, 9469-9476. Nakamura, E.; Tokuyama, H.; Yamago, S.; Shiraki, T.; Sugiura, Y. Bull. Chem. Soc. Jpn. 1996, 69, 2143-2151. Frier, C.; Mouscadet, J. F.; Decout, J. L.; Auclair, C.; Fontecave, M. Chem. Commun. 1998, 2457-2458. Bailly, C.; Chaires, J. B. Bioconjugate Chem. 1998, 9, 513-538. Ninomiya, K.; Sugiyama, T.; Kuroda, R. Nucleic Acids Symp. Ser. 1998, 39, 231-232. Hashimoto, S.; Nakamura, Y. Chem. Phann. Bull. 1998. 46, 1941-1943. Herman, D. M.; Turner, J. M.; Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1999. 121, 1121-1129.
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47. For lead references, see: Bouziane, M.; Ketterle, C.; Helissey, P.; Herfeld, P.; Le Bret, M.; Giorgi-Renault, S.; AuClair, C. Biochemistry 1995, 34, 14051-14058. Boutorine, A. S.; Brault, D.; Takasugi, M.; Delgado, O. Hélène. C. J. Am. Chem. Soc. 1996, 118, 9469-9476. Nakamura, E.; Tokuyama, H.; Yamago, S.; Shiraki, T.; Sugiura, Y. Bull. Chem. Soc. Jpn. 1996, 69, 2143-2151. Frier, C.; Mouscadet, J. F.; Decout, J. L.; Auclair, C.; Fontecave, M. Chem. Commun. 1998, 2457-2458. Bailly, C.; Chaires, J. B. Bioconjugate Chem. 1998, 9, 513-538. Ninomiya, K.; Sugiyama, T.; Kuroda, R. Nucleic Acids Symp. Ser. 1998, 39, 231-232. Hashimoto, S.; Nakamura, Y. Chem. Phann. Bull. 1998. 46, 1941-1943. Herman, D. M.; Turner, J. M.; Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1999. 121, 1121-1129.
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