Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2

Journal of the American Chemical Society

Volumn 132, Issue 19, 2010, Pages 6827-6833

  Binda, Claudia ^a   Valente, Sergio ^b   Romanenghi, Mauro ^c   Pilotto, Simona ^a,b   Cirilli, Roberto ^d   Karytinos, Aristotele ^a   Ciossani, Giuseppe ^a   Botrugno, Oronza A ^c   Forneris, Federico ^a,e   Tardugno, Maria ^b   Edmondson, Dale E ^f   Minucci, Saverio ^c,g   Mattevi, Andrea ^a   Mai, Antonello ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c EUROPEAN INSTITUTE OF ONCOLOGY   (Italy)

^d UTRECHT UNIVERSITY   (Netherlands)

^e ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^f EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^g UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL ACTIVITIES; BIOLOGICAL EVALUATION; CELL DIFFERENTIATION; CELLULAR MODEL; COFACTORS; COVALENT MODIFICATIONS; CRYSTALLOGRAPHIC STUDIES; DEMETHYLASE; EVOLUTIONARY ORIGIN; FLAVOENZYMES; INHIBITORY ACTIVITY; LIGAND BINDING; MONOAMINE OXIDASE; PATHOLOGICAL PROCESS; PROMYELOCYTIC LEUKEMIA; RACEMIC MIXTURES; SUBSTRATE SPECIFICITY; SYNERGISTIC ACTIVITY; TUMOR PROGRESSIONS; TUMORIGENESIS; VIRUS INFECTION;

BINDING ENERGY; CATALYSTS; CHROMOSOMES; SYNTHESIS (CHEMICAL); VIRUSES;

ENZYMES;

ENZYME INHIBITOR; FLAVOPROTEIN; HISTONE DEMETHYLASE INHIBITOR; PROTEIN LSD1; PROTEIN LSD2; RETINOIC ACID; TRANYLCYPROMINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENTIATION; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; LIGAND BINDING; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; DRUG SYNERGISM; ENZYME INHIBITORS; HISTONE DEMETHYLASES; HUMANS; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TRANYLCYPROMINE;

EID: 77952355653     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101557k     Document Type: Article

References (33)

1. Best, J. D. and Carey, N. Drug Discovery Today 2009, 15, 65
2. Bhaumik, S. R., Smith, E., and Shilatifard, A. Nat. Struct. Mol. Biol. 2007, 14, 1008
3. Anand, R. and Marmorstein, R. J. Biol. Chem. 2007, 282, 35425
4. Forneris, F., Binda, C., Battaglioli, E., and Mattevi, A. Trends Biochem. Sci. 2008, 33, 181
5. Shi, Y., Lan, F., Matson, C., Mulligan, P., Whetstine, J. R., Cole, P. A., Casero, R. A., and Shi, Y. Cell 2004, 119, 941
6. Karytinos, A., Forneris, F., Profumo, A., Ciossani, G., Battaglioli, E., Binda, C., and Mattevi, A. J. Biol. Chem. 2009, 284, 17775
7. Lee, M. G., Wynder, C., Cooch, N., and Shiekhattar, R. Nature 2005, 437, 432
8. Schulte, J. H., Lim, S., Schramm, A., Friedrichs, N., Koster, J., Versteeg, R., Ora, I., Pajtler, K., Klein-Hitpass, L., Kuhfittig-Kulle, S., Metzger, E., Schüle, R., Eggert, A., Buettner, R., and Kirfel, J. Cancer Res. 2009, 69, 2065
9. Hu, X., Li, X., Valverde, K., Fu, X., Noguchi, C., Qiu, Y., and Huang, S. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 10141
10. Gu, H. and Roizman, B. J. Virol. 2009, 83, 4376
11. Ciccone, D. N., Su, H., Hevi, S., Gay, F., Lei, H., Bajko, J., Xu, G., Li, E., and Chen, T. Nature 2009, 461, 415
12. Yang, Z., Jiang, J., Stewart, D. M., Qi, S., Yamane, K., Li, J., Zhang, Y., and Wong, J. Cell. Res. 2010, 20, 276
13. Edmondson, D. E., Binda, C., Wang, J., Upadhyay, A. K., and Mattevi, A. Biochemistry 2009, 48, 4220
14. Yang, M., Culhane, J. C., Szewczuk, L. M., Gocke, C. B., Brautigam, C. A., Tomchick, D. R., Machius, M., Cole, P. A., and Yu, H. Nat. Struct. Mol. Biol. 2007, 14, 535
15. Lee, M. G., Wynder, C., Schmidt, D, M., McCafferty, D. G., and Shiekhattar, R. Chem. Biol. 2006, 13, 563
16. Schmidt, D. M. and McCafferty, D. G. Biochemistry 2007, 46, 4408
17. Yang, M., Culhane, J. C., Szewczuk, L. M., Jalili, P., Ball, H. L., Machius, M., Cole, P. A., and Yu, H. Biochemistry 2007, 46, 8058
18. Mimasu, S., Sengoku, T., Fukuzawa, S., Umehara, T., and Yokoyama, S. Biochem. Biophys. Res. Commun. 2008, 366, 15
19. Binda, C., Li, M., Hubalek, F., Restelli, N., Edmondson, D. E., and Mattevi, A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9750
20. Forneris, F., Binda, C., Adamo, A., Battaglioli, E., and Mattevi, A. J. Biol. Chem. 2007, 282, 20070
21. Collaborative Computational Project, Number 4 Acta Crystallogr. 1994, D50, 760
22. Ronzoni, S., Faretta, M., Ballarini, M., Pelicci, P., and Minucci, S. Cytometry, Part A 2005, 66, 52
23. Minucci, S. Blood 2002, 100, 2989
24. Di Croce, L., Raker, V. A., Corsaro, M., Fazi, F., Fanelli, M., Faretta, M., Fuks, F., Lo Coco, F., Kouzarides, T., Nervi, C., Minucci, S., and Pelicci, P. G. Science 2002, 295, 1079
25. Zirkle, C. L., Kaiser, C., Tedeschi, D. H., Tedeschi, R. E., and Burger, A. J. Med. Pharm. Chem. 1962, 91, 1265
26. Son, S. Y., Ma, J., Kondou, Y., Yoshimura, M., Yamashita, E., and Tsukihara, T. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 5739
27. Culhane, J. C., Wang, D., Yen, P. M., and Cole, P. A. J. Am. Chem. Soc. 2010, 132 (9) 3164
28. De Colibus, L., Li, M., Binda, C., Lustig, A., Edmondson, D. E., and Mattevi, A. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 12684
29. Hubalek, F., Pohl, J., and Edmondson, D. E. J. Biol. Chem. 2003, 278, 28612
30. Botrugno, O. A., Santoro, F., and Minucci, S. Cancer. Lett. 2009, 280, 134
31. Silverman, R. B. J. Biol. Chem. 1983, 258, 14766
32. Walker, W. H., Hemmerich, P., and Massey, V. Helv. Chim. Acta 1967, 50, 2269
33. Ueda, R., Suzuki, T., Mino, K., Tsumoto, H., Nakagawa, H., Hasegawa, M., Sasaki, R., Mizukami, T., and Miyata, N. J. Am. Chem. Soc. 2009, 131, 17536