Small-Molecule Inhibitors of GGTase-I from the Heterocycle Library Derived from Phosphine Catalysis

Enzymes

Volumn 30, Issue , 2011, Pages 165-177

  Chan, Lai N ^a   Watanabe, Masaru ^a   Kwon, Ohyun ^a   Tamanoi, Fuyuhiko ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Chemical compound library; GGTase I; Pharmacokinetic parameters; RabGGTase; Tumor growth inhibition

Indexed keywords

MUS;

EID: 81255192034     PISSN: 18746047     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-415922-8.00007-0     Document Type: Chapter

References (28)

1. The Enzymes Volume 21: Protein Lipidation 2001, Academic Press. F. Tamanoi, D.S. Sigman (Eds.).
2. Rathinam R., Berrier A., Alahari S.K. Role of Rho GTPases and their regulators in cancer progression. Front Biosci 2011, 17:2561-2571.
3. Lahoz A., Hall A. DLC1: a significant GAP in the cancer genome. Genes Dev 2008, 22:1724-1730.
4. Clark E.A., Golub T.R., Lander E.S., Hynes R.O. Genomic analysis of metastasis reveals an essential role for RhoC. Nature 2000, 406:532-535.
5. Harem A., Sanchez-Sweatman O., You-Ten A., Duncan G., Wakeham A., Khokha R., Mak T.W. RhoC is dispensable for embryogenesis and tumor initiation but essential for metastasis. Genes Dev 2005, 19:1974-1979.
6. Sjogren A.K., Andersson K.M., Liu M., Cutts B.A., Karlsson C., Wahlstrom A.M., Dalin M., Weinbaum C., Casey P.J., Tarkowski A., Swolin B., Young S.G., et al. GGTase-I deficiency reduces tumor formation and improves survival in mice with K-RAS-induced lung cancer. J Clin Invest 2007, 117:1294-1304.
7. Miquel K., Pradines J., Sun J., Qian Y., Hamilton A.D., Sebti S.M., Favre G. GGTI-298 induces G0-G1 block and apoptosis whereas FTI-277 causes G2-M enrichment in A549 cells. Cancer Res 1997, 57:1846-1850.
8. Vasudevan A., Qian Y., Vogt A., Blaskovich M.A., Ohkanda J., Sebti S.M., Hamilton A.D. Potent, highly selective, and non-thiol inhibitors of protein geranylgeranyltransferase-I. J Med Chem 1999, 42:1333-1340.
9. Sun J., Qian Y., Hamilton A.D., Sebti S.M. Both farnesyltransferase and geranylgeranyltransferase I inhibitors are required for inhibition of oncogenic K-Ras prenylation but each alone is sufficient to suppress human tumor growth in nude mouse xenografts. Oncogene 1998, 16:1467-1473.
10. Sun J., Ohkanda J., Coppola D., Yin H., Kothare M., Busciglio B., Hamilton A.D., Sebti S.M. Geranylgeranyltransferase I inhibitor GGTI-2154 induces breast carcinoma apoptosis and tumor regression in H-Ras transgenic mice. Cancer Res 2003, 63:8922-8929.
11. Peterson Y.K., Kelly P., Weinbaum C.A., Casey P.J. A novel protein geranylgeranyltransferase-I inhibitor with high potency, selectivity, and cellular activity. J Biol Chem 2006, 281:12445-12450.
12. Peterson Y.K., Wang X.S., Casey P.J., Tropsha A. Discovery of geranylgeranyltransferase-I inhibitors with novel scaffolds by the means of quantitative structure-activity relationship modeling, virtual screening, and experimental validation. J Med Chem 2009, 52:4210-4220.
13. Castellano S., Fiji H.D., Kinderman S.S., Watanabe M., Leon P., Tamanoi F., Kwon O. Small-molecule inhibitors of protein geranylgeranyltransferase type I. J Am Chem Soc 2007, 129:5843-5845.
14. Watanabe M., Fiji H.D., Guo L., Chan L., Kinderman S.S., Slamon D.J., Kwon O., Tamanoi F. Inhibitors of protein geranylgeranyltransferase I and Rab geranylgeranyltransferase identified from a library of allenoate-derived compounds. J Biol Chem 2008, 283:9571-9579.
15. Lu J., Chan L., Fiji H.D., Dahl R., Kwon O., Tamanoi F. In vivo antitumor effect of a novel inhibitor of protein geranylgeranyltransferase-I. Mol Cancer Ther 2009, 8:1218-1226.
16. Zhu X., Henry C.E., Kwon O. Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes. Tetrahedron 2005, 61:6276-6282.
17. Zhu X.-F., Lan J., Kwon O. An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines. J Am Chem Soc 2003, 125:4716-4717.
18. Zhu X., Henry C.E., Wang J., Dudding T., Kwon O. Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes. Org Lett 2005, 7:1387-1390.
19. Zhu X., Schaffner A., Li R.C., Kwon O. Phosphine-catalyzed synthesis of 6-substituted 2-pyrones: manifestation of E/Z-isomerism in the zwitterionic intermediate. Org Lett 2005, 7:2977-2980.
20. Taylor J.S., Reid T.S., Terry K.L., Casey P.J., Beese L.S. Structure of mammalian protein geranylgeranyltransferase type-I. EMBO J 2003, 22:5963-5974.
21. Pylypenko O., Rakm A., Reents R., Niculae A., Sidorovitch V., Cioaca M.D., Bessolitsyna E., Thomä N.H., Waldmann H., Schlichting I., Goody R.S., Alexandrov K. Structure of Rab escort protein-1 in complex with Rab geranylgeranyltransferase. Mol Cell 2003, 11:483-494.
22. deSolms S.J., Ciccarone T.M., MacTough S.C., Shaw A.W., Buser C.A., Ellis-Hutchings M., Fernandes C., Hamilton K.A., Huber H.E., Kohl N.E., Lobell R.B., Robinson R.G., et al. Dual protein farnesyltransferase-geranylgeranyltransferase-I inhibitors as potential cancer chemotherapeutic agents. J Med Chem 2003, 46:2973-2984.
23. Lobell R.B., Omer C.A., Abrams M.T., Bhimnathwala H.G., Brucker M.J., Buser C.A., Davide J.P., deSolms S.J., Dinsmore C.J., Ellis-Hutchings M.S., Kral A.M., Liu D., et al. Evaluation of farnesyl:protein transferase and geranylgeranyl:protein transferase inhibitor combinations in preclinical models. Cancer Res 2001, 61:8758-8768.
24. 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.
25. Rowell C.A., Kowalczyk J.J., lewis M.D., Garcia A.M. Direct demonstration of geranylgeranylation and farnesylation of K-Ras in vivo. J Biol Chem 1997, 272:14093-14097.
26. Lackner M.R., Kindt R.M., Carroll P.M., Brown K., Cancilla M.R., Chen C., de Silva H., Franke Y., Guan B., Heuer T., Hung T., Keegan K., et al. Chemical genetics identifies Rab geranylgeranyl transferase as an apoptotic target of farnesyl transferase inhibitors. Cancer Cell 2005, 7:325-336.
27. Choi J., Mouillesseaux K., Wang Z., Fiji H.D., Kinderman S.S., Otto G.W., Geisler R., Kwon O., Chen J.N. Aplexone targets the HMG-CoA reductase pathway and differentially regulates arteriovenous angiogenesis. Development 2011, 138:1173-1181.
28. Cruz D., Wang Z., Kibbie J., Modlin R., Kwon O. Diversity through phosphine catalysis identifies octahydro-1,6-naphthyridin-4-ones as activators of endothelium-driven immunity. Proc Natl Acad Sci USA 2011, 108:6769-6774.