Mechanism of action studies of lomaiviticin A and the monomeric lomaiviticin aglycon. Selective and potent activity toward DNA double-strand break repair-deficient cell lines

Journal of the American Chemical Society

Volumn 137, Issue 17, 2015, Pages 5741-5747

  Colis, Laureen C ^a   Hegan, Denise C ^b   Kaneko, Miho ^a   Glazer, Peter M ^b   Herzon, Seth B ^a  

^a YALE UNIVERSITY   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CELL DEATH; CELLS; CYTOLOGY; DISEASES; ENZYME ACTIVITY; FREE RADICALS; MOBILE SECURITY; PROTEINS; REPAIR;

ATAXIA-TELANGIECTASIA MUTATED; CHRONIC MYELOGENOUS LEUKEMIA; DNA DOUBLE STRAND BREAKS; DNA-DEPENDENT PROTEIN KINASE; HOMOLOGOUS RECOMBINATION; NONHOMOLOGOUS END JOINING; P53 BINDING PROTEIN 1 (53BP1); PHOSPHATASE AND TENSIN HOMOLOGUES;

DNA;

CYTOTOXIC AGENT; DNA DEPENDENT PROTEIN KINASE; LOMAIVITICIN A; MK 7 206; PROTEIN P53; UNCLASSIFIED DRUG; BRCA2 PROTEIN; FLUORENE DERIVATIVE; MONOLOMAIVITICIN AGLYCON; PHOSPHATIDYLINOSITOL 3,4,5 TRISPHOSPHATE 3 PHOSPHATASE; PTEN PROTEIN, HUMAN;

ANIMAL CELL; APOPTOSIS; ARTICLE; ATAXIA TELANGIECTASIA; BREAST CANCER; CANCER GROWTH; CELL LINE; DNA END JOINING REPAIR; DNA REPAIR; DNA SUPERCOILING; DOUBLE STRANDED DNA BREAK; DRUG MECHANISM; DRUG POTENCY; DRUG RESPONSE; DRUG SCREENING; HOMOLOGOUS RECOMBINATION; HUMAN; HUMAN CELL; K562 CELL LINE; LC50; NONHUMAN; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; CRICETULUS; DEFICIENCY; DRUG EFFECTS; KINETICS; STRUCTURE ACTIVITY RELATION;

ANIMALS; APOPTOSIS; BRCA2 PROTEIN; CELL LINE; CRICETULUS; DNA BREAKS, DOUBLE-STRANDED; DNA REPAIR; FLUORENES; HUMANS; K562 CELLS; KINETICS; MOLECULAR STRUCTURE; PTEN PHOSPHOHYDROLASE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84928962994     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja513117p     Document Type: Article

References (50)

1. Reed, E. Clin. Cancer Res. 2010, 16, 4511
2. Curtin, N. J. Nat. Rev. Cancer 2012, 12, 801
3. Hosoya, N.; Miyagawa, K. Cancer Sci. 2014, 105, 370
4. Kaelin, W. G., Jr. Nat. Rev. Cancer 2005, 5, 689
5. Hartman, J. L.; Garvik, B.; Hartwell, L. Science 2001, 291, 1001
6. He, H.; Ding, W. D.; Bernan, V. S.; Richardson, A. D.; Ireland, C. M.; Greenstein, M.; Ellestad, G. A.; Carter, G. T. J. Am. Chem. Soc. 2001, 123, 5362
7. Woo, C. M.; Beizer, N. E.; Janso, J. E.; Herzon, S. B. J. Am. Chem. Soc. 2012, 134, 15285
8. Colis, L. C.; Woo, C. M.; Hegan, D. C.; Li, Z.; Glazer, P. M.; Herzon, S. B. Nat. Chem. 2014, 6, 504
9. Brandsma, I.; van Gent, D. Genome Integr 2012, 3, 9
10. Chowdhury, D.; Choi, Y. E.; Brault, M. E. Nat. Rev. Mol. Cell Biol. 2013, 14, 181
11. Aparicio, T.; Baer, R.; Gautier, J. DNA Repair 2014, 19, 169
12. Gould, S. J. Chem. Rev. 1997, 97, 2499
13. Marco-Contelles, J.; Molina, M. T. Curr. Org. Chem. 2003, 7, 1433
14. Arya, D. P. Top. Heterocycl. Chem. 2006, 2, 129
15. Nawrat, C. C.; Moody, C. J. Nat. Prod. Rep. 2011, 28, 1426
16. Herzon, S. B. The Kinamycins. In Total Synthesis of Natural Products. At the Frontiers of Organic Chemistry; Li, J. J.; Corey, E. J., Eds.; Springer-Verlag: Berlin, 2012.
17. Herzon, S. B.; Woo, C. M. Nat. Prod. Rep. 2012, 29, 87
18. Ito, S.; Matsuya, T.; Omura, S.; Otani, M.; Nakagawa, A. J. Antibiot. 1970, 23, 315
19. Hata, T.; Omura, S.; Iwai, Y.; Nakagawa, A.; Otani, M. J. Antibiot. 1971, 24, 353
20. Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A.; Watanabe, T. Chem. Pharm. Bull. 1971, 19, 2428
21. Furusaki, A.; Matsui, M.; Watanabe, T.; Omura, S.; Nakagawa, A.; Hata, T. Isr. J. Chem. 1972, 10, 173
22. Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A.; Watanabe, T. Chem. Pharm. Bull. 1973, 21, 931
23. Woo, C. M.; Ranjan, N.; Arya, D. P.; Herzon, S. B. Angew. Chem., Int. Ed. 2014, 53, 9325
24. Roy, R.; Chun, J.; Powell, S. N. Nat. Rev. Cancer 2012, 12, 68
25. Bassi, C.; Ho, J.; Srikumar, T.; Dowling, R. J. O.; Gorrini, C.; Miller, S. J.; Mak, T. W.; Neel, B. G.; Raught, B.; Stambolic, V. Science 2013, 341, 395
26. Hopkins, B. D.; Hodakoski, C.; Barrows, D.; Mense, S. M.; Parsons, R. E. Trends Biochem. Sci. 2014, 39, 183
27. Collins, A. Mol. Biotechnol. 2004, 26, 249
28. Olive, P. L.; Banath, J. P. Nat. Protoc. 2006, 1, 23
29. Schultz, L. B.; Chehab, N. H.; Malikzay, A.; Halazonetis, T. D. J. Cell Biol. 2000, 151, 1381
30. Anderson, L.; Henderson, C.; Adachi, Y. Mol. Cell. Biol. 2001, 21, 1719
31. Rappold, I.; Iwabuchi, K.; Date, T.; Chen, J. J. Cell Biol. 2001, 153, 613
32. Kastan, M. B.; Lim, D. S. Nat. Rev. Mol. Cell Biol. 2000, 1, 179
33. Bakkenist, C. J.; Kastan, M. B. Nature 2003, 421, 499
34. Rogakou, E. P.; Pilch, D. R.; Orr, A. H.; Ivanova, V. S.; Bonner, W. M. J. Biol. Chem. 1998, 273, 5858
35. Pilch, D. R.; Sedelnikova, O. A.; Redon, C.; Celeste, A.; Nussenzweig, A.; Bonner, W. M. Biochem. Cell Biol. 2003, 81, 123
36. Bonner, W. M.; Redon, C. E.; Dickey, J. S.; Nakamura, A. J.; Sedelnikova, O. A.; Solier, S.; Pommier, Y. Nat. Rev. Cancer 2008, 8, 957
37. Muslimovic, A.; Ismail, I. H.; Gao, Y.; Hammarsten, O. Nat. Protoc. 2008, 3, 1187
38. Podhorecka, M.; Skladanowski, A.; Bozko, P. J. Nucleic Acids 2010, 1
39. Stiff, T.; ODriscoll, M.; Rief, N.; Iwabuchi, K.; Lobrich, M.; Jeggo, P. A. Cancer Res. 2004, 64, 2390
40. Ward, I. M.; Chen, J. J. Biol. Chem. 2001, 276, 47759
41. Nunez, M. I.; Villalobos, M.; Olea, N.; Valenzuela, M. T.; Pedraza, V.; McMillan, T. J.; Ruiz de Almodovar, J. M. Br. J. Cancer 1995, 71, 311
42. DiBiase, S. J.; Zeng, Z. C.; Chen, R.; Hyslop, T.; Curran, W. J., Jr.; Iliakis, G. Cancer Res. 2000, 60, 1245
43. Mukherjee, B.; Kessinger, C.; Kobayashi, J.; Chen, B. P.; Chen, D. J.; Chatterjee, A.; Burma, S. DNA Repair 2006, 5, 575
44. Hickson, I.; Zhao, Y.; Richardson, C. J.; Green, S. J.; Martin, N. M. B.; Orr, A. I.; Reaper, P. M.; Jackson, S. P.; Curtin, N. J.; Smith, G. C. M. Cancer Res. 2004, 64, 9152
45. Sarkaria, J. N.; Busby, E. C.; Tibbetts, R. S.; Roos, P.; Taya, Y.; Karnitz, L. M.; Abraham, R. T. Cancer Res. 1999, 59, 4375
46. Leahy, J. J. J.; Golding, B. T.; Griffin, R. J.; Hardcastle, I. R.; Richardson, C.; Rigoreau, L.; Smith, G. C. M. Bioorg. Med. Chem. Lett. 2004, 14, 6083
47. Zhao, Y.; Thomas, H. D.; Batey, M. A.; Cowell, I. G.; Richardson, C. J.; Griffin, R. J.; Calvert, A. H.; Newell, D. R.; Smith, G. C.; Curtin, N. J. Cancer Res. 2006, 66, 5354
48. Aziz, K.; Nowsheen, S.; Pantelias, G.; Iliakis, G.; Gorgoulis, V. G.; Georgakilas, A. G. Pharmacol. Ther. 2012, 133, 334
49. Mahaney, B. L.; Meek, K.; Lees-Miller, S. P. Biochem. J. 2009, 417, 639
50. Lobrich, M.; Shibata, A.; Beucher, A.; Fisher, A.; Ensminger, M.; Goodarzi, A. A.; Barton, O.; Jeggo, P. A. Cell Cycle 2010, 9, 662