Design and synthesis of 8-hydroxyquinoline-based radioprotective agents

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 15, 2014, Pages 3891-3905

  Ariyasu, Shinya ^a   Sawa, Akiko ^a   Morita, Akinori ^b   Hanaya, Kengo ^a   Hoshi, Misato ^a   Takahashi, Ippei ^c   Wang, Bing ^d   Aoki, Shin ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c HIROSHIMA UNIVERSITY   (Japan)

^d NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

Author keywords

8 Hydroxyquinoline; Mechanistic study; Radioprotector

Indexed keywords

5 N,N DIMETHYLAMINOSULFONYL 7 IODE 8 METHOXYIODEQUINALDINE; 5 N,N DIMETHYLAMINOSULFONYL 8 ETHOXY 7 IODEQUINALDINE; 5 N,N DIMETHYLAMINOSULFONYL 8 ETHOXYQUINALDINE; 5 N,N DIMETHYLAMINOSULFONYL 8 HYDROXY 7 IODEQUINALDINE; 5 N,N DIMETHYLAMINOSULFONYL 8 METHOXYQUINALDINE; 5,7 BIS(2 AMINOETHYLAMINOSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(AMINOSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(ETHYL 3 PROPANOATE 1 AMINOSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(HOMOPIPERAZINYLSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(METHYLAMINOSULFONYL) 8 HYDROXYQUINOLINE; 5,7 BIS(N METHYLAMINOSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(N METHYLAMINOSULFONYL) 8 HYDROXYQUINOLINE; 5,7 BIS(N N PROPYLAMINOSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(N,N DIETHYLAMINOSULFONYL) 8 HYDROXYQUINALDINE; 5,7 BIS(PIPERAZINYLSULFONYL) 8 HYDROXYQUINALDINE; 7 BROMO 5 N,N DIMETHYLAMINOSULFONYL 8 ETHOXYQUINALDINE; 7 BROMO 5 N,N DIMETHYLAMINOSULFONYL 8 HYDROXYQUINALDINE; 7 BROMO 5 N,N DIMETHYLAMINOSULFONYL 8 HYDROXYQUINOLINE; 7 BROMO 5 N,N DIMETHYLAMINOSULFONYL 8 METHANESULFONYLOXYQUINALDINE; 7 BROMO 5 N,N DIMETHYLAMINOSULFONYL 8 METHOXYQUINALDINE; 8 BENZENESULFONYLOXY 7 BROMO 5 N,N DIMETHYLAMINOSULFONYLQUINALDINE; 8 HYDROXY 5 N METHYLAMINOSULFONYLQUINALDINE; 8 HYDROXY 5 N METHYLAMINOSULFONYLQUINOLINE; 8 METHOXY 5 N METHYLAMINOSULFONYLQUINALDINE; 8 METHOXYQUINOLINE DERIVATIVE; 8 QUINOLINOL; BISPICEN; PROTEIN P53; RADIOPROTECTIVE AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZINC;

APOPTOSIS; ARTICLE; CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; GAMMA RADIATION; PROTEIN DENATURATION; RADIATION PROTECTION; SIGNAL TRANSDUCTION; CHEMISTRY; DRUG EFFECTS; GEL MOBILITY SHIFT ASSAY; HUMAN; METABOLISM; RADIATION RESPONSE; SYNTHESIS; TUMOR CELL LINE;

APOPTOSIS; CELL LINE, TUMOR; DRUG DESIGN; ELECTROPHORETIC MOBILITY SHIFT ASSAY; GAMMA RAYS; HUMANS; OXYQUINOLINE; RADIATION-PROTECTIVE AGENTS; TUMOR SUPPRESSOR PROTEIN P53; ZINC;

EID: 84905560125     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.06.017     Document Type: Article

References (48)

1. M. Sadeghi, M. Enferadi, and A. Shirazi J. Cancer Res. Ther. 6 2010 239
2. V.S. Kuntić, M.B. Stanković, Z.B. Vujić, J.S. Brborić, and S.M. Uskoković-Marković Chem. Biodiv. 10 2013 1791
3. K.H. Vousden, and C. Prives Cell 137 2009 413
4. S. Rashi-Elkeles, R. Elkon, S. Shavit, Y. Lerenthal, C. Linhart, A. Kupershtein, N. Amariglio, G. Rechavi, R. Shamir, and Y. Shiloh Mol. Oncol. 5 2011 336
5. P. Hainaut, and K.G. Wilman 25 Years of p53 Research 2005 Springer Netherlands
6. Y. Cho, S. Gorina, P.D. Jeffrey, and N.P. Pavletich Science 265 1994 346
7. P. Hainaut, and J. Milner Cancer Res. 53 1993 1739
8. G.W. Verhaegh, M.-O. Parat, M.-J. Richard, and P. Hainaut Mol. Carcinog. 21 1998 205
9. Z.A. Stewart, and J.A. Pietenpol Chem. Res. Toxicol. 14 2001 243
10. J. Duan, and L. Nilson Biochemistry 45 2006 7483
11. A.V. Gudkov, and E.A. Komarova Hum. Mol. Genet. 16 2007 R67
12. E. Kim, A. Giese, and W. Deppert Biochem. Pharm. 77 2009 11
13. R. Puca, L. Nardinocchi, M. Porru, A.J. Simon, G. Rechavi, C. Leonetti, D. Givol, and G. D'Orazi Cell Cycle 10 2011 1679
14. P.A.J. Muller, and K.H. Vousden Cancer Cell 25 2014 304
15. R.F. Johnson, and N.D. Perkins Trends Biochem. Sci. 37 2012 317
16. A. Berns Nature 443 2006 153
17. M.A. Christophorou, I. Ringshausen, A.J. Finch, L.B. Swigart, and G.I. Evan Nature 443 2006 214
18. Z. Wang, and Y. Sun Transl. Oncol. 3 2010 1
19. J. Yu, and J. Zhang Biochem. Biophys. Res. Commun. 331 2005 851
20. V.K. Singh, L.A. Beattie, and T.M. Seed J. Radiet. Res. 54 2013 973
21. A. Chatterjee Nutrients 5 2013 525
22. R.J. Ormsby, M.D. Lawrence, B.J. Blyth, K. Bexis, E. Bezak, J.S. Murley, D.J. Grdina, and P.J. Sykes Cell Biol. Toxicol. 30 2014 55
23. P.G. Komarov, E.A. Komarova, R.V. Kondratov, K. Christov-Tselkov, J.S. Coon, M.V. Chernov, and A.V. Gudkov Science 285 1999 1733
24. E.M. Abdelalim, and I. Tooyama Biochem. Biophys. Res. Commun. 420 2012 605
25. E. Strom, S. Sathe, P.G. Komarov, O.B. Chernova, I. Pavlovska, I. Shyshynova, D.A. Bosykh, L.G. Burdelya, R.M. Macklis, R. Skaliter, E.A. Komarova, and A.V. Gudkov Nat. Chem. Biol. 2 2006 474
26. A. Morita, J. Zhu, N. Suzuki, A. Enomoto, Y. Matsumoto, M. Tomita, T. Suzuki, K. Ohtomo, and Y. Hosoi Cell Death Differ. 13 2006 499
27. A. Morita, S. Yamamoto, B. Wang, K. Tanaka, N. Suzuki, S. Aoki, A. Ito, T. Nanao, S. Ohya, M. Yoshino, J. Zhu, A. Enomoto, Y. Matsumoto, O. Funatsu, Y. Hosoi, and M. Ikekita Cancer Res. 70 2010 257
28. C. Méplan, M.-J. Richard, and P. Hainaut Oncogene 19 2000 5227
29. A. Morita, S. Ariyasu, S. Ohya, I. Takahashi, B. Wang, K. Tanaka, T. Uchida, H. Okazaki, K. Hanaya, A. Enomoto, M. Nenoi, M. Ikekita, and S. Aoki Oncotarget 4 2013 2439
30. L.M. Ramenskaya, and O.V. Kraeva Russ. J. Phys. Chem. 80 2006 90
31. A. Lakatos, É. Zsigó, D. Hollender, N.V. Nagy, L. Fülöp, D. Simon, Z. Bozsó, and T. Kiss Dalton Trans. 39 2010 1302
32. P. Crouch, and K.J. Barnham Acc. Chem. Res. 45 2012 1604
33. K. Hanaya, M. Suetsugu, S. Saijo, I. Yamato, and S. Aoki J. Biol. Inorg. Chem. 17 2012 517
34. S. Ariyasu, Y. Mizuseda, K. Hanaya, and S. Aoki Chem. Pharm. Bull. 2014 in press
35. V. Prachayasittikul, S. Prachayasittikul, S. Ruchirawat, and V. Prachayasittikul Drug Des. Dev. Ther. 7 2013 1157
36. J. Billiard, J.B. Dennison, J. Briand, R.S. Annan, D. Chai, M. Colón, C.S. Dodson, S.A. Gilbert, J. Greshock, J. Jing, H. Lu, J.E. McSurdy-Freed, L.A. Orband-Miller, G.B. Mills, C.J. Quiin, J.L. Schneck, G.F. Scott, A.N. Shaw, G.M. Waitt, R.F. Wooster, and K.J. Duffy Cancer Metab. 1 2013 19 10.1186/2049-3002-1-19
37. S. Shoaib, A. Shah, G. Rivera, and M. Ashfaq Mini-Rev. Med. Chem. 13 2013 70
38. P. Zajdel, A. Partyka, K. Marciniec, A.J. Bojarski, M. Pawlowski, and A. Wesolowska Future Med. Chem. 6 2014 57
39. K. Kaur, M. Jain, R.P. Reddy, and R. Jain Eur. J. Med. Chem. 45 2010 3245
40. D.A. Pearce, N. Jotterand, I.S. Carrico, and B. Imperiali J. Am. Chem. Soc. 123 2001 5160
41. R. Pallavizini, M. Boiocchi, G. Dacarro, and C. Mangano New J. Chem. 31 2007 927
42. R. Ohshima, M. Kitamura, A. Morita, M. Shiro, Y. Yamada, M. Ikekita, E. Kimura, and S. Aoki Inorg. Chem. 49 2010 888
43. Y. Kageyama, R. Ohshima, K. Sakurama, Y. Fujiwara, Y. Tanimoto, Y. Yamada, and S. Aoki Chem. Pharm. Bull. 57 2009 1257
44. S. Aoki, N. Matsuo, K. Hanaya, Y. Yamada, and Y. Kageyama Bioorg. Med. Chem. 2009 17 2009 3405
45. S. Ariyasu, K. Hanaya, M. Tsunoda, M. Kitamura, M. Hayase, R. Abe, and S. Aoki Chem. Pharm. Bull. 59 2011 1355
46. Q. Jiang, Y. Wang, T. Li, K. Shi, Z. Li, Y. Ma, F. Li, H. Luo, Y. Yang, and C. Xu Mol. Biol. Cell 22 2011 1167
47. J. Cehng, and M. Haas Mol. Biol. Cell 10 1990 5502
48. E. Sekine-Suzuki, I. Nakanishi, T. Shimokawa, M. Ueno, K. Matsumoto, and T. Murakami Anal. Chem. 85 2013 7650