Design, synthesis, and kinetic characterization of protein N-terminal acetyltransferase inhibitors

ACS Chemical Biology

Volumn 8, Issue 6, 2013, Pages 1121-1127

  Foyn, Håvard ^a,b,c   Jones, Justin E ^c   Lewallen, Dan ^c   Narawane, Rashmi ^a   Varhaug, Jan Erik ^a,b   Thompson, Paul R ^c   Arnesen, Thomas ^a,b  

^a UNIVERSITY OF BERGEN   (Norway)

^b HAUKELAND UNIVERSITY HOSPITAL   (Norway)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLTRANSFERASE INHIBITOR; COENZYME A; GUANINE NUCLEOTIDE BINDING PROTEIN; PEPTIDE ALPHA N ACETYLTRANSFERASE;

AMINO TERMINAL SEQUENCE; ARTICLE; CANCER CELL; CELL DEATH; CELL PROLIFERATION; CHROMOSOME SEGREGATION; COMPETITIVE INHIBITION; CYTOTOXICITY; DEVELOPMENT; DRUG DESIGN; DRUG SYNTHESIS; ENZYME SPECIFICITY; HUMAN; NEOPLASM; PRIORITY JOURNAL;

ACETYLATION; ACETYLTRANSFERASES; AMINO ACID SEQUENCE; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; KINETICS; MODELS, MOLECULAR; PEPTIDES; SUBSTRATE SPECIFICITY;

EID: 84879771440     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400136s     Document Type: Article

References (31)

1. Starheim, K. K., Gevaert, K., and Arnesen, T. (2012) Protein N-terminal acetyltransferases: when the start matters Trends Biochem. Sci. 37, 152-161
2. Arnesen, T. (2011) Towards a functional understanding of protein N-terminal acetylation PLoS Biol. 9, e1001074
3. Hwang, C. S., Shemorry, A., and Varshavsky, A. (2010) N-terminal acetylation of cellular proteins creates specific degradation signals Science 327, 973-977
4. Forte, G. M., Pool, M. R., and Stirling, C. J. (2011) N-terminal acetylation inhibits protein targeting to the endoplasmic reticulum PLoS Biol. 9, e1001073
5. Scott, D. C., Monda, J. K., Bennett, E. J., Harper, J. W., and Schulman, B. A. (2011) N-terminal acetylation acts as an avidity enhancer within an interconnected multiprotein complex Science 334, 674-678
6. Behnia, R., Panic, B., Whyte, J. R., and Munro, S. (2004) Targeting of the Arf-like GTPase Arl3p to the Golgi requires N-terminal acetylation and the membrane protein Sys1p Nat. Cell Biol. 6, 405-413
7. Setty, S. R., Strochlic, T. I., Tong, A. H., Boone, C., and Burd, C. G. (2004) Golgi targeting of ARF-like GTPase Arl3p requires its Nalpha-acetylation and the integral membrane protein Sys1p Nat. Cell Biol. 6, 414-419
8. Mullen, J. R., Kayne, P. S., Moerschell, R. P., Tsunasawa, S., Gribskov, M., Colavito-Shepanski, M., Grunstein, M., Sherman, F., and Sternglanz, R. (1989) Identification and characterization of genes and mutants for an N-terminal acetyltransferase from yeast EMBO J. 8, 2067-2075
9. Park, E. C. and Szostak, J. W. (1992) ARD1 and NAT1 proteins form a complex that has N-terminal acetyltransferase activity EMBO J. 11, 2087-2093
10. Arnesen, T., Anderson, D., Baldersheim, C., Lanotte, M., Varhaug, J. E., and Lillehaug, J. R. (2005) Identification and characterization of the human ARD1-NATH protein acetyltransferase complex Biochem. J. 386, 433-443
11. Arnesen, T., Van Damme, P., Polevoda, B., Helsens, K., Evjenth, R., Colaert, N., Varhaug, J. E., Vandekerckhove, J., Lillehaug, J. R., Sherman, F., and Gevaert, K. (2009) Proteomics analyses reveal the evolutionary conservation and divergence of N-terminal acetyltransferases from yeast and humans Proc. Natl. Acad. Sci. U.S.A. 106, 8157-8162
12. Polevoda, B., Norbeck, J., Takakura, H., Blomberg, A., and Sherman, F. (1999) Identification and specificities of N-terminal acetyltransferases from Saccharomyces cerevisiae EMBO J. 18, 6155-6168
13. Van Damme, P., Evjenth, R., Foyn, H., Demeyer, K., De Bock, P. J., Lillehaug, J. R., Vandekerckhove, J., Arnesen, T., and Gevaert, K. (2011) Proteome-derived peptide libraries allow detailed analysis of the substrate specificities of N (alpha)-acetyltransferases and point to hNaa10p as the post-translational actin N (alpha)-acetyltransferase Mol. Cell. Proteomics 10, M110 004580
14. Gautschi, M., Just, S., Mun, A., Ross, S., Rucknagel, P., Dubaquie, Y., Ehrenhofer-Murray, A., and Rospert, S. (2003) The yeast N (alpha)- acetyltransferase NatA is quantitatively anchored to the ribosome and interacts with nascent polypeptides Mol. Cell. Biol. 23, 7403-7414
15. Arnesen, T., Anderson, D., Torsvik, J., Halseth, H. B., Varhaug, J. E., and Lillehaug, J. R. (2006) Cloning and characterization of hNAT5/hSAN: An evolutionarily conserved component of the NatA protein N -α- acetyltransferase complex Gene 371, 291-295
16. Evjenth, R., Hole, K., Karlsen, O. A., Ziegler, M., Arnesen, T., and Lillehaug, J. R. (2009) Human Naa50p (Nat5/San) displays both protein N α- and N Ïμ-acetyltransferase activity J. Biol. Chem. 284, 31122-31129
17. Kalvik, T. V. and Arnesen, T. (2013) Protein N-terminal acetyltransferases in cancer Oncogene 32, 269-276
18. Lee, C. F., Ou, D. S., Lee, S. B., Chang, L. H., Lin, R. K., Li, Y. S., Upadhyay, A. K., Cheng, X., Wang, Y. C., Hsu, H. S., Hsiao, M., Wu, C. W., and Juan, L. J. (2010) hNaa10p contributes to tumorigenesis by facilitating DNMT1-mediated tumor suppressor gene silencing J. Clin. Invest. 120, 2920-2930
19. Arnesen, T., Gromyko, D., Pendino, F., Ryningen, A., Varhaug, J. E., and Lillehaug, J. R. (2006) Induction of apoptosis in human cells by RNAi-mediated knockdown of hARD1 and NATH, components of the protein N -α- acetyltransferase complex Oncogene 25, 4350-4360
20. Lim, J. H., Park, J. W., and Chun, Y. S. (2006) Human arrest defective 1 acetylates and activates beta-catenin, promoting lung cancer cell proliferation Cancer Res. 66, 10677-10682
21. Kuo, H. P., Lee, D. F., Chen, C. T., Liu, M., Chou, C. K., Lee, H. J., Du, Y., Xie, X., Wei, Y., Xia, W., Weihua, Z., Yang, J. Y., Yen, C. J., Huang, T. H., Tan, M., Xing, G., Zhao, Y., Lin, C. H., Tsai, S. F., Fidler, I. J., and Hung, M. C. (2010) ARD1 stabilization of TSC2 suppresses tumorigenesis through the mTOR signaling pathway Sci. Signal. 3, ra9
22. Hua, K. T., Tan, C. T., Johansson, G., Lee, J. M., Yang, P. W., Lu, H. Y., Chen, C. K., Su, J. L., Chen, P. B., Wu, Y. L., Chi, C. C., Kao, H. J., Shih, H. J., Chen, M. W., Chien, M. H., Chen, P. S., Lee, W. J., Cheng, T. Y., Rosenberger, G., Chai, C. Y., Yang, C. J., Huang, M. S., Lai, T. C., Chou, T. Y., Hsiao, M., and Kuo, M. L. (2011) N -alpha-acetyltransferase 10 protein suppresses cancer cell metastasis by binding PIX proteins and inhibiting Cdc42/Rac1 activity Cancer Cell 19, 218-231
23. Yi, C. H., Pan, H., Seebacher, J., Jang, I. H., Hyberts, S. G., Heffron, G. J., Vander Heiden, M. G., Yang, R., Li, F., Locasale, J. W., Sharfi, H., Zhai, B., Rodriguez-Mias, R., Luithardt, H., Cantley, L. C., Daley, G. Q., Asara, J. M., Gygi, S. P., Wagner, G., Liu, C. F., and Yuan, J. (2011) Metabolic regulation of protein N -alpha-acetylation by Bcl-xL promotes cell survival Cell 146, 607-620
24. Gromyko, D., Arnesen, T., Ryningen, A., Varhaug, J. E., and Lillehaug, J. R. (2010) Depletion of the human Nα-terminal acetyltransferase A induces p53-dependent apoptosis and p53-independent growth inhibition Int. J. Cancer 127, 2777-2789
25. Hou, F., Chu, C. W., Kong, X., Yokomori, K., and Zou, H. (2007) The acetyltransferase activity of San stabilizes the mitotic cohesin at the centromeres in a shugoshin-independent manner J. Cell Biol. 177, 587-597
26. Williams, B. C., Garrett-Engele, C. M., Li, Z., Williams, E. V., Rosenman, E. D., and Goldberg, M. L. (2003) Two putative acetyltransferases, san and deco, are required for establishing sister chromatid cohesion in drosophila Curr. Biol. 13, 2025-2036
27. Pimenta-Marques, A., Tostoes, R., Marty, T., Barbosa, V., Lehmann, R., and Martinho, R. G. (2008) Differential requirements of a mitotic acetyltransferase in somatic and germ line cells Dev. Biol. 323, 197-206
28. Evjenth, R. H., Brenner, A. K., Thompson, P. R., Arnesen, T., Froystein, N. A., and Lillehaug, J. R. (2012) Human protein N-terminal acetyltransferase hNaa50p (hNAT5/hSAN) follows ordered sequential catalytic mechanism: combined kinetic and NMR study J. Biol. Chem. 287, 10081-10088
29. Sagar, V., Zheng, W., Thompson, P. R., and Cole, P. A. (2004) Bisubstrate analogue structure-activity relationships for p300 histone acetyltransferase inhibitors Bioorg. Med. Chem. 12, 3383-3390
30. Liszczak, G., Arnesen, T., and Marmorstein, R. (2011) Structure of a ternary Naa50p (NAT5/SAN) N-terminal acetyltransferase complex reveals the molecular basis for substrate-specific acetylation J. Biol. Chem. 286, 37002-37010
31. Thompson, P. R., Wang, D., Wang, L., Fulco, M., Pediconi, N., Zhang, D., An, W., Ge, Q., Roeder, R. G., Wong, J., Levrero, M., Sartorelli, V., Cotter, R. J., and Cole, P. A. (2004) Regulation of the p300 HAT domain via a novel activation loop Nat. Struct. Mol. Biol. 11, 308-315