Developing an irreversible inhibitor of human DDAH-1, an enzyme upregulated in melanoma

ChemMedChem

Volumn 9, Issue 4, 2014, Pages 792-797

  Wang, Yun ^a   Hu, Shougang ^a   Gabisi, Abdul M ^d   Er, Joyce A V ^a   Pope, Arthur ^c   Burstein, Gayle ^b   Schardon, Christopher L ^b   Cardounel, Arturo J ^c   Ekmekcioglu, Suhendan ^d   Fast, Walter ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b University of Texas at Austin   (United States)

^c THE OHIO STATE UNIVERSITY WEXNER MEDICAL CENTER   (United States)

^d UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

covalent inhibitors; dimethylaminohydrolase; dimethylarginine; melanoma; nitric oxide

Indexed keywords

ARGININE; DIMETHYLARGININE DIMETHYLAMINOHYDROLASE 1; ENZYME INHIBITOR; N(G),N(G) DIMETHYLARGININE; N5 (1 IMINO 2 CHLOROETHYL) LEVO ORNITHINE; NITRIC OXIDE; UNCLASSIFIED DRUG; AMIDASE; DIMETHYLARGININASE; N(5)-(1-IMINO-2-CHLOROETHYL)ORNITHINE; ORNITHINE;

ARTICLE; CANCER CELL CULTURE; CELL STRAIN HEK293; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG POTENCY; DRUG SELECTIVITY; DRUG TARGETING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IMMUNOHISTOCHEMISTRY; MELANOCYTE; MELANOMA; PRIORITY JOURNAL; PROTEIN EXPRESSION; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; BIOSYNTHESIS; CELL SURVIVAL; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; ENZYMOLOGY; HEK293 CELL LINE; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; UPREGULATION;

AMIDOHYDROLASES; CELL LINE, TUMOR; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; HEK293 CELLS; HUMANS; MELANOMA; MOLECULAR CONFORMATION; NITRIC OXIDE; ORNITHINE; STRUCTURE-ACTIVITY RELATIONSHIP; UP-REGULATION;

EID: 84897990572     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300557     Document Type: Article

References (33)

1. T. Shirakawa, K. Kako, T. Shimada, Y. Nagashima, A. Nakamura, J. Ishida, A. Fukamizu, Mol. Med. Report 2011, 4, 615-620.
2. J. Leiper, M. Nandi, Nat. Rev. Drug Discovery 2011, 10, 277-291
3. B. Caplin, J. Leiper, Arterioscler. Thromb. Vasc. Biol. 2012, 32, 1343-1353
4. A. Kittel, R. Maas, Curr. Pharm. Des. 2013, DOI:.
5. J. Strobel, F. Muller, O. Zolk, B. Endress, J. Konig, M. F. Fromm, R. Maas, Amino Acids 2013, 45, 989-1002.
6. B. Caplin, Z. Wang, A. Slaviero, J. Tomlinson, L. Dowsett, M. Delahaye, A. Salama, D. C. Wheeler, J. Leiper, Arterioscler. Thromb. Vasc. Biol. 2012, 32, 2892-2900.
7. A. J. Pope, K. Karrupiah, P. N. Kearns, Y. Xia, A. J. Cardounel, J. Biol. Chem. 2009, 284, 35338-35347
8. X. Hu, X. Xu, G. Zhu, D. Atzler, M. Kimoto, J. Chen, E. Schwedhelm, N. Luneburg, R. H. Boger, P. Zhang, Y. Chen, Circulation 2009, 120, 2222-2229
9. X. Hu, D. Atzler, X. Xu, P. Zhang, H. Guo, Z. Lu, J. Fassett, E. Schwedhelm, R. H. Boger, R. J. Bache, Y. Chen, Arterioscler. Thromb. Vasc. Biol. 2011, 31, 1540-1546
10. J. Leiper, M. Nandi, B. Torondel, J. Murray-Rust, M. Malaki, B. O'Hara, S. Rossiter, S. Anthony, M. Madhani, D. Selwood, C. Smith, B. Wojciak-Stothard, A. Rudiger, R. Stidwill, N. Q. McDonald, P. Vallance, Nat. Med. 2007, 13, 198-203.
11. M. Knipp, ChemBioChem 2006, 7, 879-889
12. M. Nandi, P. Kelly, B. Torondel, Z. Wang, A. Starr, Y. Ma, P. Cunningham, R. Stidwill, J. Leiper, Arterioscler. Thromb. Vasc. Biol. 2012, 32, 2589-2597
13. S. S. Pullamsetti, R. Savai, R. Dumitrascu, B. K. Dahal, J. Wilhelm, M. Konigshoff, D. Zakrzewicz, H. A. Ghofrani, N. Weissmann, O. Eickelberg, A. Guenther, J. Leiper, W. Seeger, F. Grimminger, R. T. Schermuly, Sci. Transl. Med. 2011, 3, 87ra 53.
14. Y. Wang, A. F. Monzingo, S. Hu, T. H. Schaller, J. D. Robertus, W. Fast, Biochemistry 2009, 48, 8624-8635
15. M. Lluis, Y. Wang, A. F. Monzingo, W. Fast, J. D. Robertus, ChemMedChem 2011, 6, 81-88.
16. M. A. Moscarello, H. Lei, F. G. Mastronardi, S. Winer, H. Tsui, Z. Li, C. Ackerley, L. Zhang, R. Raijmakers, D. D. Wood, Dis. Models Mech. 2013, 6, 467-478
17. J. S. Knight, W. Zhao, W. Luo, V. Subramanian, A. A. O'Dell, S. Yalavarthi, J. B. Hodgin, D. T. Eitzman, P. R. Thompson, M. J. Kaplan, J. Clin. Invest. 2013, 123, 2981-2993
18. J. L. Slack, C. P. Causey, Y. Luo, P. R. Thompson, ACS Chem. Biol. 2011, 6, 466-476.
19. J. Kotthaus, D. Schade, N. Muschick, E. Beitz, B. Clement, Bioorg. Med. Chem. 2008, 16, 10205-10209.
20. E. M. Stone, T. H. Schaller, H. Bianchi, M. D. Person, W. Fast, Biochemistry 2005, 44, 13744-13752.
21. J. Kotthaus, D. Schade, B. Clement, J. Enzyme Inhib. Med. Chem. 2012, 27, 24-28.
22. G. J. Southan, C. Szabo, Biochem. Pharmacol. 1996, 51, 383-394.
23. E. I. Closs, F. Z. Basha, A. Habermeier, U. Forstermann, Nitric Oxide 1997, 1, 65-73.
24. Y. Wang, S. Hu, W. Fast, J. Am. Chem. Soc. 2009, 131, 15096-15097.
25. E. A. Grimm, A. G. Sikora, S. Ekmekcioglu, Clin. Cancer. Res. 2013, 19, 5557-5563
26. Z. Yang, B. Misner, H. Ji, T. L. Poulos, R. B. Silverman, F. L. Meyskens, S. Yang, Antioxid. Redox Signaling 2013, 19, 433-447.
27. W. L. Stone, H. Yang, M. Qui, Methods Mol. Biol. 2006, 315, 245-256.
28. M. Knipp, M. Vasak, Anal. Biochem. 2000, 286, 257-264
29. E. M. Stone, M. D. Person, N. J. Costello, W. Fast, Biochemistry 2005, 44, 7069-7078.
30. C. L. Tsou, Adv. Enzymol. Relat. Areas Mol. Biol. 1988, 61, 381-436.
31. Y. Cheng, W. H. Prusoff, Biochem. Pharmacol. 1973, 22, 3099-3108.
32. L. J. Druhan, S. P. Forbes, A. J. Pope, C. A. Chen, J. L. Zweier, A. J. Cardounel, Biochemistry 2008, 47, 7256-7263.
33. J. Sun, L. J. Druhan, J. L. Zweier, Arch. Biochem. Biophys. 2010, 494, 130-137.