Hexylitaconic acid: A new inhibitor of p53-HDM2 interaction isolated from a marine-derived fungus, Arthrinium sp.

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 1, 2006, Pages 69-71

  Tsukamoto, Sachiko ^a   Yoshida, Takushi ^a   Hosono, Hidetaka ^b   Ohta, Tomihisa ^a   Yokosawa, Hideyoshi ^b  

^a KANAZAWA UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Arthriniun sp.; HDM2; Marine derived fungus; p53; Ubiquitin ligase

Indexed keywords

HEXYLITACONIC ACID; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTHRINIUM; ARTICLE; CHEMICAL INTERACTION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME LINKED IMMUNOSORBENT ASSAY; FUNGUS; NONHUMAN; RECEPTOR BINDING; SPECTROSCOPY;

ASCOMYCOTA; CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; ENZYME-LINKED IMMUNOSORBENT ASSAY; FUNGAL PROTEINS; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; PROTEIN BINDING; PROTO-ONCOGENE PROTEINS C-MDM2; SUCCINATES; TUMOR SUPPRESSOR PROTEIN P53;

ARTHRINIUM; FUNGI;

EID: 27744466131     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.09.052     Document Type: Article

References (25)

1. C.M. Pickart Annu. Rev. Biochem. 70 2001 503
2. M.H. Glickman, and A. Ciechanover Physiol. Rev. 82 2002 373
3. R. Honda, H. Tanaka, and H. Yasuda FEBS Lett. 420 1997 25
4. M. Ashcroft, and K.H. Vousden Oncogene 18 1999 7637
5. B. Vogelstein, D. Lane, and A.J. Levine Nature 408 2000 307
6. S. Tsukamoto, M. Tatsuno, R.W.M. van Soest, H. Yokosawa, and T. Ohta J. Nat. Prod. 66 2003 1181
7. S. Tsukamoto, K. Koimaru, and T. Ohta Mar. Drugs 3 2005 29
8. S. Tsukamoto, H. Hirota, M. Imachi, M. Fujimuro, H. Onuki, T. Ohta, and H. Yokosawa Bioorg. Med. Chem. Lett. 15 2005 191
9. S. Tsukamoto, K. Yamashita, K. Tane, R. Kizu, T. Ohta, S. Matsunaga, N. Fusetani, H. Kawahara, and H. Yokosawa Biol. Pharm. Bull. 27 2004 699
10. The fungus was identified on the basis of the morphological evaluation by NCIBM Japan Co., Ltd. (Shizuoka, Japan). A voucher specimen is deposited at Kanazawa University with the code MF571.
11. The fungus was grown in a fermentation broth composed of 1:1 seawater/deionized water with 2.0% malt extract and 0.5% peptone without shaking at 25°C for 3 months.
12. +.
13. A. Isogai, M. Washizu, K. Kondo, S. Murakoshi, and A. Suzuki Agric. Biol. Chem. 48 1984 2607
14. Escherichia coli BL21 cells transformed with pGEX6P1-p53 or pGEX6P1-HDM2 were precultured overnight at 37°C in LB medium supplemented with 100 μg/mL ampicillin, transferred to a 100-fold volume of the same medium, and cultured at 37°C for 2 h. Isopropyl 1-thio-β-d-galactoside was then added at the final concentration of 0.1 mM, and the cells were further cultured at 30°C for 6 h. Two GST-fusion proteins were purified by using glutathione-immobilized agarose beads and the GST tag of GST-p53 or GST-MDM2 was removed by cleavage with PreScission protease (Amersham).
15. Three derivatives were prepared according to the method described in Ref. 13.
16. C. Klemke, S. Kehraus, A.D. Wright, and G.M. Konig J. Nat. Prod. 67 2004 1058
17. M. Varoglu, and P. Crews J. Nat. Prod. 63 2000 41
18. P.H. Kussie, S. Gorina, V. Marechal, B. Elenbaas, J. Moreau, A.J. Levine, and N.P. Pavletich Science 274 1996 948
19. C. Garcia-Echeverria, P. Chene, M.J.J. Blommers, and P. Furet J. Med. Chem. 43 2000 3205
20. R. Stoll, C. Renner, S. Hansen, S. Palme, C. Klein, A. Belling, W. Zeslawski, M. Kamionka, T. Rehm, P. Muhlhahn, R. Schumacher, F. Hesse, B. Kaluza, W. Voelter, R.A. Engh, and T.A. Holak Biochemistry 40 2001 336
21. J. Zhao, M. Wang, J. Chen, A. Luo, X. Wang, M. Wu, D. Yin, and Z. Liu Cancer Lett. 183 2002 69
22. L.T. Vassilev, B.T. Vu, B. Graves, D. Carvajal, F. Podlaski, Z. Filipovic, N. Kong, U. Kammlott, C. Lukacs, C. Klein, N. Fotouhi, and E.A. Liu Science 303 2004 844
23. D.J. Parks, L.V. LaFrance, R.R. Calvo, K.L. Milkiewicz, V. Gupta, J. Lattanze, K. Ramachandren, T.E. Carver, E.C. Petrella, M.D. Cummings, D. Maguire, B.L. Grasberger, and T. Lu Bioorg. Med. Chem. Lett. 15 2005 765
24. S.J. Duncan, S. Gruschow, D.H. Williams, C. McNicholas, R. Purewal, M. Hajek, M. Gerliz, S. Marin, S.K. Wrigley, and M. Moore J. Am. Chem. Soc. 123 2001 554
25. 50 value of 4.6 μM.