Amino derivatives of indole as potent inhibitors of isoprenylcysteine carboxyl methyltransferase

Journal of Medicinal Chemistry

Volumn 53, Issue 19, 2010, Pages 6838-6850

  Go, Mei Lin ^a   Leow, Jo Lene ^a   Gorla, Suresh Kumar ^a   Schüller, Andreas Peter ^b   Wang, Mei ^b   Casey, Patrick J ^b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b DUKE NUS MEDICAL SCHOOL   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 METHYLBUT 2 ENYL) 5 M TOLYL 1H INDOLE; 1 OCTYL 5 M TOLYL 1H INDOL 3 YL)METHANAMINE; 1 OCTYL 5 M TOLYL 1H INDOLE; 1 OCTYL 5 M TOLYL 1H INDOLE 3 CARBALDEHYDE; 1 OCTYL 5 M TOLYL 1H INDOLE 3 CARBALDEHYDE OXIME; 1 OCTYL 5 M TOLYL 1H INDOLE 3 CARBOXAMIDE; 1 OCTYL 5 M TOLYL 1H INDOLE 3 CARBOXYLIC ACID; 2 (5 BROMO 1 OCTYL 1H INDOL 3 YL)ACETIC ACID; 2 (5 BROMO 1H INDOL 3 YL)ACETAMIDE; 2 (5 BROMO 1H INDOL 3 YL)ACETONITRILE; 2 (5 BROMO 1H INDOL 3 YL)ETHANOL; 2 (5 BROMO 1H INDOL 3 YL)PROPANAMIDE; 2 (5 BROMO 1H INDOL 3 YL)PROPANENITRILE; 2 [5 (3 ETHOXYPHENYL) 1 OCTYL 1H INDOL 3 YL)N,N DIETHYL ACETAMIDE; 2-[5 FLUORO 1 (3 METHYLBUT 2 ENYL) 1H INDOL 3 YL]ACETAMIDE; 3 (1 OCTYL 5 M TOLYL 1H INDOL 3 YL)PROPANAMIDE; 3 (5 M TOLYL 1H INDOL 3 YL)PROPANAMIDE; 5 BROMO 1 OCTYL 1H INDOLE; 5 BROMO 1 OCTYL 1H INDOLE 3 CARBALDEHYDE; 5 FLUORO 1 OCTYL 1H INDOLE; METHYL 2 (5 BROMO 1H INDOL 3 YL)ACETATE; METHYLTRANSFERASE INHIBITOR; N ETHYL N[(5 FLUORO 1 OCTYL 1H INDOL 3 YL)METHYL]ETHANAMINE; N ETHYL N[[1 (3 METHYLBUT 2 ENYL) 1H INDOL 3 YL]METHYL]ETHANAMINE; N ETHYL N[[5 FLUORO 1 (3 METHYLBUT 2 ENYL) 1H INDOL 3 YL]METHYL]ETHANAMINE; N,N DIETHYL 2 [5 (3 METHOXYPHENYL) 1 OCTYL 1H INDOL 3 YL]ACETAMIDE; N[(1 OCTYL 5 M TOLYL 1H INDOL 3 YL)METHYL]ACETAMIDE; N[(1 OCTYL 5 M TOLYL 1H INDOL 3 YL)METHYL]METHANESULFONAMIDE; PROTEIN S ISOPRENYLCYSTEINE O METHYLTRANSFERASE; UNCLASSIFIED DRUG; AMINE; ANTINEOPLASTIC AGENT; CYSMETHYNIL; INDOLE DERIVATIVE; PROTEIN METHYLTRANSFERASE; PROTEIN-S-ISOPRENYLCYSTEINE O-METHYLTRANSFERASE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; IC 50; LIPOPHILICITY; ANTAGONISTS AND INHIBITORS; CELL PROLIFERATION; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; HUMAN; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

AMINES; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; PROTEIN METHYLTRANSFERASES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77957900386     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1002843     Document Type: Article

References (50)

1. Zhang, F. L.; Casey, P. J. Protein prenylation: molecular mechanisms and functional consequences Annu. Rev. Biochem. 1996, 65, 241-269
2. Kloog, Y.; Cox, A. D. Prenyl-binding domains: potential targets for Ras inhibitors and anti-cancer drugs Semin. Cancer Biol. 2004, 14, 253-261
3. Casey, P. J.; Seabra, M. C. Protein prenyltransferases J. Biol. Chem. 1996, 271, 5289-5292
4. Boyartchuk, V. L.; Ashby, M. N.; Rine, J. Modulation of Ras and a-factor function by carboxyl-terminal proteolysis Science 1997, 275, 1796-1800
5. Otto, J. C.; Kim, E.; Young, S. G.; Casey, P. J. Cloning and characterization of a mammalian prenyl protein-specific protease J Biol.Chem 1999, 274, 8379-8382
6. Clarke, S.; Vogel, J. P.; Deschenes, R. J.; Stock, J. Posttranslational modification of the Ha-ras oncogene protein: evidence for a third class of protein carboxyl methyltransferases Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4643-4647
7. Hrycyna, C. A.; Sapperstein, S. K.; Clarke, S; Michaelis, S. The Saccharomyces cerevisiae STE14 gene encodes a methyltransferase that mediates C-terminal methylation of a-factor and Ras proteins EMBO J. 1991, 10, 1699-1709
8. Dai, Q.; Choy, E.; Chiu, V.; Romano, J.; Slivka, S. R.; Steitz, S. A.; Michaelis, S.; Philips, M. R. Mammalian prenylcysteine carboxyl methyltransferase is in the endoplasmic reticulum J Biol.Chem 1998, 273, 15030-15034
9. Glomset, J. A.; Farnsworth, C. C. Role of protein modification reactions in programming interactions between ras-related GTPases and cell membranes Annu. Rev. Cell Biol. 1994, 10, 181-205
10. Downward, J. Targeting Ras signaling pathways in cancer therapy Nature Rev. Cancer 2003, 3, 11-22
11. Bos, J. L. Ras oncogenes in human cancer: a review Cancer Res. 1989, 49, 4682-4689
12. Malumbres, M.; Barbacid, M. RAS oncogenes: the first 30 years Nature Rev. Cancer 2003, 3, 459-465
13. Schlessinger, J. Cell signalling by receptor tyrosine kinases Cell 2000, 103, 211-225
14. Gschwind, A.; Fischer, O. M.; Ullrich, A. The discovery of receptor tyrosine kinases: targets for cancer therapy Nature Rev. Cancer 2004, 4, 361-370 (Pubitemid 38579482)
15. Willumsen, B. M.; Christensen, A.; Hubbert, N. L.; Papageorge, A. G.; Lowy, D. R. The p21 ras C-terminus is required for transformation and membrane association Nature 1984, 310, 583-586
16. Seabra, M. C. Membrane association and targeting of prenylated Ras-like GTPases Cell. Signalling 1998, 10, 167-172
17. Gibbs, J. B.; Oliff, A.; Kohl, N. E. Farnesyltransferase inhibitors: Ras research yields a potential cancer therapeutic Cell 1994, 77, 175-178
18. Mazieres, J.; Pradines, A.; Favre, G. Perspectives on farnesyl transferase inhibitors in cancer therapy Cancer Lett. 2004, 206, 159-167
19. Sousa, S. F.; Fernandes, P. A.; Ramos, M. J. Farnesyltransferase inhibitors: a detailed chemical view on an elusive biological problem Curr. Med. Chem. 2008, 15, 1478-1492
20. Rowell, C. A.; Kowalczyk, J. J.; Lewis, M. D.; Garcia, A. M. Direct Demonstration of Geranylgeranylation and Farnesylation of Ki-Ras in Vivo J. Biol. Chem. 1997, 272, 14093-14097
21. Whyte, D. B.; Kirschmeier, P.; Hockenberry, T. N.; Nunez-Oliva, I.; James, L.; Catino, J. J.; Bishop, W. R.; Pai, J. K. K- and N-Ras are geranylgeranylated in cells treated with farnesyl protein transferase inhibitors J. Biol. Chem. 1997, 272, 14459-14464 (Pubitemid 27232866)
22. Bergo, M. O.; Gavino, B. J.; Hong, C.; Beigneux, A. P.; McMahon, M.; Casey, P. J.; Young, S. G. Inactivation of Icmt inhibits transformation by oncogenic K-Ras and B-Raf J. Clin. Invest. 2004, 113, 539-550
23. Wahlstrom, A. M.; Cutts, B. A.; Liu, M.; Lindskog, A.; Karlsson, C.; Sjogren, A. K.; Andersson, K. M.; Young, S. G.; Bergo, M. O. Inactivating Icmt ameliorates K-RAS-induced myeloproliferative disease Blood 2008, 112, 1357-1365
24. Wahlstrom, A. M.; Cutts, B. A.; Karlsson, C.; Andersson, K. M.; Liu, M.; Sjogren, A. K.; Swolin, B.; Young, S. G.; Bergo, M. O. Rce1 deficiency accelerates the development of K-RAS-induced myeloproliferative disease Blood 2007, 109, 763-768
25. Anderson, J. L.; Henriksen, B. S.; Gibbs, R. A.; Hrycyna, C. A. The isoprenoid substrate specificity of isoprenylcysteine carboxylmethyltransferase: development of novel inhibitors J. Biol. Chem. 2005, 280, 29454-29461
26. Buchanan, M. S.; Carroll, A. R.; Fechner, G. A.; Boyle, A.; Simpson, M.; Addepalli, R.; Avery, V. M.; Forster, P. I.; Guymer, G. P.; Cheung, T.; Chen, H.; Quinn, R. J. Small-molecule inhibitors of the cancer target, isoprenylcysteine carboxyl methyltransferase, from Hovea parvicalyx Phytochemistry 2008, 69, 1886-1889
27. Donelson, J. L.; Hodges, H. B.; MacDougall, D. D.; Henriksen, B. S.; Hrycyna, C. A.; Gibbs, R. A. Amide-substituted farnesylcysteine analogs as inhibitors of human isoprenylcysteine carboxyl methyltransferase Bioorg. Med. Chem. Lett. 2006, 16, 4420-4423
28. Buchanan, M. S.; Carroll, A. R.; Fechner, G. A.; Boyle, A.; Simpson, M.; Addepalli, R.; Avery, V. M.; Hooper, J. N.; Cheung, T.; Chen, H.; Quinn, R. J. Aplysamine 6, an alkaloidal inhibitor of isoprenylcysteine carboxyl methyltransferase from the sponge Pseudoceratina sp J. Nat. Prod. 2008, 71, 1066-1067
29. Buchanan, M. S.; Carroll, A. R.; Fechner, G. A.; Boyle, A.; Simpson, M. M.; Addepalli, R.; Avery, V. M.; Hooper, J. N.; Su, N.; Chen, H.; Quinn, R. J. Spermatinamine, the first natural product inhibitor of isoprenylcysteine carboxyl methyltransferase, a new cancer target Bioorg. Med. Chem. Lett. 2007, 17, 6860-6863
30. Marciano, D.; Ben-Baruch, G.; Marom, M.; Egozi, Y.; Haklai, R.; Kloog, Y. Farnesyl derivatives of rigid carboxylic acids: Inhibitors of ras-dependent cell growth J. Med. Chem. 1995, 38, 1267-1272
31. Goldberg, L.; Haklai, R.; Bauer, V.; Heiss, A.; Kloog, Y. New derivatives of farnesylthiosalicylic acid (salirasib) for cancer treatment: farnesylthiosalicylamide inhibits tumor growth in nude mice models J. Med. Chem. 2009, 52, 197-205
32. Winter-Vann, A. M.; Baron, R. A.; Wong, W.; dela Cruz, J.; York, J. D.; Gooden, D. M.; Bergo, M. O.; Young, S. G.; Toone, E. J.; Casey, P. J. A small-molecule inhibitor of isoprenylcysteine carboxyl methyltransferase with antitumor activity in cancer cells Proc. Natl. Acad. Sci. U.S.A 2005, 102, 4336-4341
33. Wang, M.; Tan, W.; Zhou, J.; Leow, J.; Go, M.; Lee, H. S.; Casey, P. J. A small molecule inhibitor of isoprenylcysteine carboxymethyltransferase induces autophagic cell death in PC3 prostate cancer cells J. Biol. Chem. 2008, 283, 18678-18684
34. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discover and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25
35. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates J. Med. Chem. 2002, 45, 2615-2623
36. Kerns, E. H.; Di, L. Drug-like Properties: Concepts, Structure, Design and Methods; Academic Press: Burlington, MA, 2008; pp 56 - 84; 187-195.
37. Yamada, F.; Tamura, M.; Hasegawa, A.; Somei, M. Synthetic studies of psilocin analogs having either a formyl group or bromine atom at the 5- or 7-position Chem. Pharm. Bull. (Tokyo) 2002, 50, 92-99
38. Roy, S.; Eastman, A.; Gribble, G. W. Synthesis of N -alkyl substituted bioactive indolocarbazoles related to Gö6976 Tetrahedron 2006, 62, 7838-7845
39. Jansen, M.; Potschka, H.; Brandt, C.; Loscher, W.; Dannhardt, G. Hydantoin-substituted 4,6-dichloroindole-2-carboxylic acids as ligands with high affinity for the glycine binding site of the NMDA receptor J. Med. Chem. 2003, 46, 64-73
40. Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Roda, A.; Guardigli, M.; Traniello, S.; Spisani, S. N -Benzyl-2-chloroindole-3-carboxylic acids as potential anti-inflammatory agents. Synthesis and screening for effects on human neutrophil functions and on COX1/COX2 activity Eur. J. Med. Chem. 2004, 39, 785-791
41. Bascop, S. I.; Laronze, J. Y.; Sapi, J. Synthesis of 2-aminopropyle-3- indole-acetic(propionic) acid derivatives ARKIVOC 2003, 46-61
42. Wildman, S. A.; Crippen, G. M. Prediction of Physiochemical Parameters by Atomic Contributions J. Chem. Inf. Comput. Sci. 1999, 39, 868-873
43. Chou, J. T.; Jurs, P. C. Computer assisted computation of partition coefficients from molecular structures using fragment constants J. Chem. Inf. Comput. Sci. 1979, 19, 172-178
44. Baron, R. A.; Peterson, Y. K.; Otto, J. C.; Rudolph, J.; Casey, P. J. Time-dependent inhibition of isoprenylcysteine carboxyl methyltransferase by indole-based small molecules Biochemistry 2007, 46, 554-560
45. Leow, J. L.; Gorla, S. K.; Go, M. L.; Wang, M.; Casey, P. J. Analogues of cysmethynil with improved antiproliferative activity against breast and prostate cancer cells. Manuscript submitted for publication.
46. Li, Z.; Lucas, N. T.; Wang, Z.; Zhu, D. Facile synthesis of Janus "double-concave" tribenzo[ a, g, m ]coronenes J. Org. Chem. 2007, 72, 3917-3920
47. Na, Y. M.; Le Borgne, M.; Pagniez, F.; Le Baut, G.; Le Pape, P. Synthesis and antifungal activity of new 1-halogenobenzyl-3-imidazolylmethylindole derivatives Eur. J. Med. Chem. 2003, 38, 75-87 (Pubitemid 36197856)
48. Winter-Vann, A. M.; Kamen, B. A.; Bergo, M. O.; Young, S. G.; Melnyk, S.; James, S. J.; Casey, P. J. Targeting Ras signaling through inhibition of carboxyl methylation: an unexpected property of methotrexate Proc. Natl. Acad. Sci. U.S.A 2003, 100, 6529-6534
49. Baron, R. A.; Casey, P. J. Analysis of the kinetic mechanism of recombinant human isoprenylcysteine carboxylmethyltransferase (Icmt) BMC Biochem. 2004, 5, 19
50. Theander, K; Pugh, R. J. The influence of pH and temperature on the equilibrium and dynamic surface tension of aqueous solutions of sodium oleate J. Colloid Interface Sci. 2001, 239, 209-216