Development of a new benzophenone-diketopiperazine-type potent antimicrotubule agent possessing a 2-pyridine structure

ACS Medicinal Chemistry Letters

Volumn 5, Issue 10, 2014, Pages 1094-1098

  Hayashi, Yoshiki ^a   Takeno, Haruka ^a   Chinen, Takumi ^b   Muguruma, Kyohei ^a   Okuyama, Kohei ^c   Taguchi, Akihiro ^a   Takayama, Kentaro ^a   Yakushiji, Fumika ^a   Miura, Masahiko ^c   Usui, Takeo ^b   Hayashi, Yoshio ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

^c TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

anticancer; antimicrotubule agent; Cyclic dipeptide; diketopiperazine

Indexed keywords

2 PYRIDYL DERIVATIVE; BENZOPHENONE; IMIDAZOLE; PIPERAZINEDIONE; PLINABULIN; PYRIDINE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DEPOLYMERIZATION; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; HT 29 CELL LINE; HUMAN; HUMAN CELL; IC50;

EID: 84907969519     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml5001883     Document Type: Article

References (24)

1. Nogales, E. Structual insights into microtubule function. Annu. Rev. Biochem. 2000, 69, 277-302.
2. Zhou, J.; Giannakakou, P. Targeting microtubules for cancer chemotherapy. Curr. Med. Chem. Anti-Cancer Agents 2005, 5, 65-71.
3. Dumontet, C.; Jordan, M. A. Microtubule-binding agents: A dynamic field of cancer therapeutics. Nat. Rev. Drug Discovery 2010, 9, 790-803.
4. Suffness, M.; Wall, M. E. In Taxol: Science and Applications; Suffness, M., Ed.; CRC Press: Boca Raton, FL, 1995; p 3.
5. Mekhail, T. M.; Markman, M. Paclitaxel in cancer therapy. Expert Opin. Pharmacother. 2002, 3, 755-766.
6. Rowinsky, E. K.; Donehower, R. C. The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics. Pharmacol. Ther. 1991, 52, 35-84.
7. Kelly, M.; Hartwell, J. L. The biological effects and the chemical composition of podophyllin. J. Natl. Cancer Inst. 1954, 14, 967-1010.
8. Cortese, F.; Bhattacharyya, B.; Wolff, J. Podophyllotoxin as a probe for the colchicines binding site of tubulin. J. Biol. Chem. 1977, 521, 1134-1140.
9. Lin, C. M.; Ho, H. H.; Pettit, G. R.; Hamel, E. Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of their inhibition of the binding of colchicine to tubulin. Biochemistry 1989, 28, 6984 -6991.
10. Pettit, G. R.; Singh, S. B.; Boyd, M. R.; Hamel, E.; Pettit, R. K.; Schmidt, J. M.; Hogan, F. Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6(1a). J. Med. Chem. 1995, 38, 1666-1672.
11. Wang, R. W-J.; Rebhun, L. I.; Kupchan, S. M. Antimitotic and antitubulin activity of the tumor inhibitor steganacin. Cancer Res. 1977, 37, 3071-3079.
12. Kanoh, K.; Kohno, S.; Asari, T.; Harada, T.; Katada, J.; Muramatsu, M.; Kawashima, H.; Sekiya, H.; Uno, I. (-)-Phenylahistin: A new mammalian cell cycle inhibitor produced by Aspergillus ustus. Bioorg. Med. Chem. Lett. 1997, 7, 2847 -2852.
13. Kanoh, K.; Kohno, S.; Katada, J.; Takahashi, J.; Uno, I. (-)- Phenylahistin arrests cells in mitosis by inhibiting tubulin polymerization. J. Antibiot. 1999, 52, 134-141.
14. Kanoh, K.; Kohno, S.; Katada, J.; Hayashi, Y.; Muramatsu, M.; Uno, I. Antitumor activity of phenylahistin in vitro and in vivo. Biosci., Biotechnol., Biochem. 1999, 63, 1130-1133.
15. Kanoh, K.; Kohno, S.; Katada, J.; Takahashi, J.; Uno, I.; Hayashi, Y. Synthesis and biological activities of phenylahistin derivatives. Bioorg. Med. Chem. 1999, 7, 1451-1457.
16. Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. Total synthesis of anti-microtubule diketopiperazine derivatives: Phenylahistin and aurantiamine. J. Org. Chem. 2000, 65, 8402-8405.
17. Ludford, R. J. Colchicine in the experimental chemotherapy of cancer. J. Natl. Cancer Inst. 1945, 6, 89-101.
18. Remick, S. C. Vascular targeting: Clinical experience. Horizons in Cancer Therapeutics: From Bench to Bedside 2002, 3, 16-23.
19. Pilat, M. J.; LoRusso, P. M. Vascular disrupting agents. J. Cell. Biochem. 2006, 99, 1021-1039.
20. Daenen, L. G. M.; Roodhart, J. M. L.; Shaked, Y.; Voest, E. E. Vascular disrupting agents (VDAs) in anticancer therapy. Curr. Clin. Pharmacol. 2010, 5, 178-185.
21. Tozer, G. M.; Kanthou, C.; Baguley, B. C. Disrupting tumour blood vessels. Nat. Rev. Cancer. 2005, 5, 423-435.
22. Yamazaki, Y.; Tanaka, K.; Nicholson, B.; Deyanat-Yazdi, G.; Potts, B.; Yoshida, T.; Oda, A.; Kitagawa, T.; Orikasa, S.; Kiso, Y.; Yasui, H.; Akamatsu, M.; Chinen, T.; Usui, T.; Shinozaki, Y.; Yakushiji, F.; Miller, B. R.; Neuteboom, S.; Palladino, M.; Kanoh, K.; Lloyd, G. K.; Hayashi, Y. Synthesis and structure - Activity relationship study of antimicrotubule agents phenylahistin derivatives with a didehydropi-perazine- 2,5-dione structure. J. Med. Chem. 2012, 55, 1056-1071.
23. Yamazaki, Y.; Sumikura, M.; Masuda, Y.; Hayashi, Y.; Yasui, H.; Kiso, Y.; Chinen, T.; Usui, T.; Yakushiji, F.; Potts, B.; Neuteboom, S.; Palladino, M.; Lloyd, G. K.; Hayashi, Y. Synthesis and structure - activity relationships of benzophenone-bearing diketopiperazine type antimicrotuble agents. Bioorg. Med. Chem. 2012, 14, 4279 -4289.
24. Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.