A novel p-terphenyl derivative inducing cell-cycle arrest and apoptosis in MDA-MB-435 cells through topoisomerase inhibition

European Journal of Medicinal Chemistry

Volumn 68, Issue , 2013, Pages 192-202

  Qiu, Jin ^a,b   Zhao, Baobing ^a   Shen, Yan ^a   Chen, Wang ^a   Ma, Yudao ^a   Shen, Yuemao ^a  

^a SHANDONG UNIVERSITY   (China)

^b SHANDONG UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

Apoptosis; Suppressors; Terphenyls; Topoisomerase

Indexed keywords

1,4 DIBROMO 2,3 DIMETHOXYBENZENE; 4 BROMO 2,6 DIMETHOXYPHENOL; ANTINEOPLASTIC AGENT; DNA TOPOISOMERASE; TERPHENYL DERIVATIVE; UNCLASSIFIED DRUG; [1,1' BIPHENYL] 4' MONOL, 4 BROMO 2,3 DIMETHOXY; [1,1':4',1'' TEPHENYL] 2',3,4,4'',6' PENTAOL; [1,1':4',1'' TERPHENYL] 2',3,3',4,4'' PENTAOL; [1,1':4',1'' TERPHENYL] 2',3,4,4'' TETOL; [1,1':4',1'' TERPHENYL] 2',3,4,4'',6' PENTAMETHOXY; [1,1':4',1'' TERPHENYL] 2,,3,4,4'' TETMETHOXY; [1,1':4',1'' TERPHENYL] 3,4,4'' TRIOL; [1,1':4',1'' TERPHENYL] 4'' MONOL 3,4 DIMETHOXY; [1,1':4',1'' TERPHENYL] 4'' MONOL,2',3,3',4 TETMETHOXY;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CATALYSIS; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CONTROLLED STUDY; CYTOTOXICITY TEST; DNA CONTENT; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50;

APOPTOSIS; SUPPRESSORS; TERPHENYLS; TOPOISOMERASE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; TERPHENYL COMPOUNDS; TOPOISOMERASE INHIBITORS;

EID: 84884469516     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.07.020     Document Type: Article

References (43)

1. J.C. Wang DNA topoisomerases Annu. Rev. Biochem. 65 1996 635 692 (Pubitemid 26250622)
2. J.J. Champoux DNA topoisomerases: structure, function, and mechanism Annu. Rev. Biochem. 70 2001 369 413 (Pubitemid 32662215)
3. S. Salerno, F. Da Settimo, S. Taliani, F. Simorini, C. La Motta, G. Fornaciari, and A.M. Marini Recent advances in the development of dual topoisomerase I and II inhibitors as anticancer drugs Curr. Med. Chem. 17 2010 4270 4290
4. W.A. Denny Dual topoisomerase I/II poisons as anticancer drugs Expert Opin. Invest. Drugs 6 1997 1845 1851 (Pubitemid 27517588)
5. K. Chikamori, A.G. Grozav, T. Kozuki, D. Grabowski, R. Ganapathi, and M.K. Ganapathi DNA topoisomerase II enzymes as molecular targets for cancer chemotherapy Curr. Cancer Drug Targets 10 2010 758 771
6. V. Calì, C. Spatafora, and C. Tringali Polyhydroxy-p-terphenyls and related p-terphenylquinones from fungi: overview and biological properties R. Atta ur, Studies in Natural Products Chemistry 2003 Elsevier 263 307
7. T. Kamigauchi, R. Sakazaki, K. Nagashima, Y. Kawamura, Y. Yasuda, K. Matsushima, H. Tani, Y. Takahashi, K. Ishii, R. Suzuki, K. Koizumi, H. Nakai, Y. Ikenishi, and Y. Terui Terprenins, novel immunosuppressants produced by Aspergillus candidus J. Antibiot. (Tokyo) 51 1998 445 450 (Pubitemid 28226910)
8. S.S. Liu, B.B. Zhao, C.H. Lu, J.J. Huang, and Y.M. Shen Two new p-terphenyl derivatives from the marine fungal strain Aspergillus sp. AF119 Nat. Prod. Commun. 7 2012 1057 1062
9. A. Barzilai, and K. Yamamoto DNA damage responses to oxidative stress DNA Repair (Amst) 3 2004 1109 1115 (Pubitemid 38997954)
10. G. Iliakis, Y. Wang, J. Guan, and H. Wang DNA damage checkpoint control in cells exposed to ionizing radiation Oncogene 22 2003 5834 5847 (Pubitemid 37176704)
11. V.A. Rao, C. Conti, J. Guirouilh-Barbat, A. Nakamura, Z.H. Miao, S.L. Davies, B. Sacca, I.D. Hickson, A. Bensimon, and Y. Pommier Endogenous gamma-H2AX-ATM-Chk2 checkpoint activation in Bloom's syndrome helicase deficient cells is related to DNA replication arrested forks Mol. Cancer Res. 5 2007 713 724 (Pubitemid 47105490)
12. Y. Tsujimoto Bcl-2 family of proteins: life-or-death switch in mitochondria Biosci. Rep. 22 2002 47 58 (Pubitemid 35217479)
13. A.K. Larsen, A.E. Escargueil, and A. Skladanowski Catalytic topoisomerase II inhibitors in cancer therapy Pharmacol. Ther. 99 2003 167 181 (Pubitemid 36897748)
14. J.M. Fortune, and N. Osheroff Topoisomerase II as a target for anticancer drugs: when enzymes stop being nice Prog. Nucleic Acid Res. Mol. Biol. 64 2000 221 253
15. W. Shi, S.L. Marcus, and T.L. Lowary Cytotoxicity and topoisomerase I/II inhibition of glycosylated 2-phenyl-indoles, 2-phenyl-benzo[b]thiophenes and 2-phenyl-benzo[b]furans Bioorg. Med. Chem. 19 2011 603 612
16. Y. Pommier, J. Covey, D. Kerrigan, W. Mattes, J. Markovits, and K.W. Kohn Role of DNA intercalation in the inhibition of purified mouse leukemia (L1210) DNA topoisomerase II by 9-aminoacridines Biochem. Pharmacol. 36 1987 3477 3486 (Pubitemid 18012223)
17. A.R. Chowdhury, S. Sharma, S. Mandal, A. Goswami, S. Mukhopadhyay, and H.K. Majumder Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I Biochem. J. 366 2002 653 661 (Pubitemid 35001710)
18. H.L. Gomez, J.A. Pinto, M. Olivera, T. Vidaurre, F.D. Doimi, C.E. Vigil, R.G. Velarde, J.E. Abugattas, E. Alarcon, and C.S. Vallejos Topoisomerase II-alpha as a predictive factor of response to therapy with anthracyclines in locally advanced breast cancer Breast 20 2011 39 45
19. K. Kawachi, T. Sasaki, A. Murakami, T. Ishikawa, A. Kito, I. Ota, D. Shimizu, A. Nozawa, Y. Nagashima, R. Machinami, and I. Aoki The topoisomerase II alpha gene status in primary breast cancer is a predictive marker of the response to anthracycline-based neoadjuvant chemotherapy Pathol. Res. Pract. 206 2010 156 162
20. R. van Gijn, R. Lendfers, J. Schellens, A. Bult, and J. Beijnen Dual topoisomerase I/II inhibitors J. Oncol. Pharm. Pract. 6 2000 92 108
21. A.M. Azarova, Y.L. Lyu, C.P. Lin, Y.C. Tsai, J.Y. Lau, J.C. Wang, and L.F. Liu Roles of DNA topoisomerase II isozymes in chemotherapy and secondary malignancies Proc. Natl. Acad. Sci. U. S. A. 104 2007 11014 11019 (Pubitemid 47175218)
22. K. Luo, and Z. Lou Dual roles of topoisomerase II Cell Cycle 8 2009 679
23. D.J. Clarke, A.C. Vas, C.A. Andrews, L.A. Diaz-Martinez, and J.F. Gimenez-Abian Topoisomerase II checkpoints: universal mechanisms that regulate mitosis Cell Cycle 5 2006 1925 1928 (Pubitemid 44435296)
24. G.K. Schwartz, and M.A. Shah Targeting the cell cycle: a new approach to cancer therapy J. Clin. Oncol. 23 2005 9408 9421
25. L.A. Diaz-Martinez, and D.J. Clarke Chromosome cohesion and the spindle checkpoint Cell Cycle 8 2009 2733 2740
26. N. Fujikawa, T. Ohta, T. Yamaguchi, T. Fukuda, F. Ishibashi, and M. Iwao Total synthesis of lamellarins D, L, and N Tetrahedron 62 2006 594 604 (Pubitemid 41779378)
27. K. Nishizawa, and J.Y. Satoh The reaction of cycloalkanones with copper(II) halides. II. The reaction of cyclohexanones with copper(II) bromide Bull. Chem. Soc. Jpn. 48 1975 1875 1877
28. K. Nishizawa, and J.Y. Satoh A convenient synthesis of substituted pyrocatechols Bull. Chem. Soc. Jpn. 48 1975 2215 2216
29. M. Albrecht Synthesis of linear oligo(catechol) ligands for the metal directed self-assembling of helicates Synthesis 2 1996 230 236 (Pubitemid 26079458)
30. M.E.L. Jung, Patrick Yuk Sun, Mansuri, M. Muzzamil, Speltz, and M. Laurine Stereoselective synthesis of an analog of podophyllotoxin by an intramolecular Diels-Alder reaction J. Org. Chem. 50 1985 1087 1105 (Pubitemid 15115663)
31. A.L.K. Jarugu Narasimha Moorthy, Subhas Samanta, Ankur Roy, and Werner M. Nau*[b] Modulation of spectrokinetic properties of o-quinonoid reactive intermediates by electronic factors: time-resolved laser flash and steady-state photolysis investigations of photochromic 6- and 7-Arylchromenes Chem. Eur. J. 15 2009 4289 4300
32. J.S.F.H.E. Landis An expeditious aqueous Suzuki-Miyaura methodology for the arylation of bromophenols Tetrahedron Lett. 47 2006 4275 4279
33. S.M.N. Widyastuti, Fukuji, Keisuke Watanabe, Nobumichi Sako, and Kinji Tanaka Isolation and characterization of two aucuparin-related phytoalexins from Photinia glabra Maxim Ann. Phytopathol. Soc. Jpn. 58 1992 228 233
34. M. Roberti, D. Pizzirani, M. Recanatini, D. Simoni, S. Grimaudo, A. Di Cristina, V. Abbadessa, N. Gebbia, and M. Tolomeo Identification of a terphenyl derivative that blocks the cell cycle in the G0-G1 phase and induces differentiation in leukemia cells J. Med. Chem. 49 2006 3012 3018
35. D.E. Frantz, D.G. Weaver, J.P. Carey, M.H. Kress, and U.H. Dolling Practical synthesis of aryl triflates under aqueous conditions Org. Lett. 4 2002 4717 4718
36. J. Carmichael, W.G. DeGraff, A.F. Gazdar, J.D. Minna, and J.B. Mitchell Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing Cancer Res. 47 1987 936 942 (Pubitemid 17027905)
37. Y. Huang, J. Wang, G. Li, Z. Zheng, and W. Su Antitumor and antifungal activities in endophytic fungi isolated from pharmaceutical plants Taxus mairei, Cephalataxus fortunei and Torreya grandis FEMS Immunol. Med. Microbiol. 31 2001 163 167 (Pubitemid 32822881)
38. T. Ohtsuki, T. Koyano, T. Kowithayakorn, N. Yamaguchi, and M. Ishibashi Isolation of austroinulin possessing cell cycle inhibition activity from Blumea glomerata and revision of its absolute configuration Planta Med. 70 2004 1170 1173 (Pubitemid 40101099)
39. J. Wang, B. Zhao, W. Zhang, X. Wu, R. Wang, Y. Huang, D. Chen, K. Park, B.C. Weimer, and Y. Shen Mycoepoxydiene, a fungal polyketide, induces cell cycle arrest at the G2/M phase and apoptosis in HeLa cells Bioorg. Med. Chem. Lett. 20 2010 7054 7058
40. M. Fukuda, K. Nishio, F. Kanzawa, H. Ogasawara, T. Ishida, H. Arioka, K. Bojanowski, M. Oka, and N. Saijo Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells Cancer Res. 56 1996 789 793
41. J.F. Barrett, J.A. Sutcliffe, and T.D. Gootz In vitro assays used to measure the activity of topoisomerases Antimicrob. Agents Chemother. 34 1990 1 7 (Pubitemid 20019953)
42. Y. Yamashita, N. Fujii, C. Murakata, T. Ashizawa, M. Okabe, and H. Nakano Induction of mammalian DNA topoisomerase I mediated DNA cleavage by antitumor indolocarbazole derivatives Biochemistry 31 1992 12069 12075 (Pubitemid 23011350)
43. L. Du, H.C. Liu, W. Fu, D.H. Li, Q.M. Pan, T.J. Zhu, M.Y. Geng, and Q.Q. Gu Unprecedented citrinin trimer tricitinol B functions as a novel topoisomerase IIalpha inhibitor J. Med. Chem. 54 2011 5796 5810