Stereochemistry-dependent inhibition of RAS farnesylation by farnesyl phosphonic acids

Lipids

Volumn 33, Issue 1, 1998, Pages 39-46

  Hohl, Raymond J ^a,c   Lewis, Kriste A ^a   Cermak, Diana M ^b   Wiemer, David F ^b  

^a UNIVERSITY OF IOWA   (United States)

^b University of Iowa   (United States)

^c UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYFARNESYLPHOSPHONIC ACID; GERANYLGERANYL PROTEIN TRANSFERASE; GERANYLTRANSFERASE; PROTEIN TRANSFERASE; SQUALENE SYNTHASE; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME STRUCTURE; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; LEUKEMIA CELL; STEREOCHEMISTRY;

ALKYL AND ARYL TRANSFERASES; CHOLESTEROL; ENZYME INHIBITORS; FARNESOL; FARNESYL-DIPHOSPHATE FARNESYLTRANSFERASE; HUMANS; LEUKEMIA; MOLECULAR CONFORMATION; PHOSPHONIC ACIDS; PROTEIN ISOPRENYLATION; RAS PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TUMOR CELLS, CULTURED;

EID: 0031933368     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-998-0178-x     Document Type: Article

References (31)

1. Bos, J.L. (1989) ras Oncogenes in Human Cancer: A Review, Cancer Res. 49, 4682-4689.
2. Clark, S. (1992) Protein Isoprenylation and Methylation at Carboxy-Terminal Cysteine Residues, Annu. Rev. Biochem. 61, 355-386.
3. Schafer, W.R., and Rine, J. (1992) Protein Prenylation: Genes, Enzymes, Targets, and Functions, Annu. Rev. Genet. 25, 209-238.
4. Glomset, J.A., and Farnsworth, C.C. (1994) Role of Protein Modification Reactions in Programming Interactions Between Ras-Related GTPases and Cell Membranes, Annu. Rev. Cell Biol. 10, 181-205.
5. Schafer, W.R., Kim, R., Sterne, R., Thorner, J., Kim, S.H., and Rine, J. (1989) Genetic and Pharmacologic Suppression of Oncogenic Mutations of Ras Genes of Yeast and Humans, Science 245, 379-385.
6. Hancock, J.F., Magee, A.M., Childs, J.E., and Marshall, C.J. (1989) All Ras Proteins Are Polyisoprenylated But Only Some Are Palmitoylated, Cell 57, 1167-1187.
7. Jackson, J.H., Cochrane, C.G., Bourne, J.R., Solski, P.A., Buss, J.E., and Der, C.J. (1990) Farnesol Modification of Kirsten-Ras Exon 4B Protein Is Essential for Transformation, Proc. Natl. Acad. Sci. USA 87, 3042-3046.
8. ras Farnesyl-Protein Transferase by Cys-AAX Tetrapeptides, Cell 62, 81-86.
9. Gibbs, J., Pompliano, D., Mosser, S., Rands, E., Lingham, R., Singh, S., Scolnick, E., Kohl, N., and Oliff, A. (1993) Selective Inhibition of Farnesyl-Protein Transferase Blocks Ras Processing In Vivo, J. Biol. Chem. 268, 7617-7620.
10. Kohl, N., Mosser, S., deSolms, S., Giuliani, E., Pompliano, D., Graham, S., Smith, R., Scolnick, E., Oliff, A., and Gibbs, J. (1993) Selective Inhibition of Ras-Dependent Transformation by a Farnesyltransferase Inhibitor, Science 260, 1934-1937.
11. James, G., Goldstein, J., Brown, M., Rawson, T., Somers, T., McDowell, R., Crowley, C., Lucas, B., Levinson, A., and Marsters, J. (1993) Benzodiazepine Peptidomimetics: Potent Inhibitors of Ras Farnesylation in Animal Cells, Science 260, 1937-1941.
12. Garcia, A.M., Rowell, C., Ackermann, K., Kowalczyk, J.J., and Lewis, M.D. (1993) Peptidomimetic Inhibitors of Ras Farnesylation and Function in Whole Cells, J. Biol. Chem. 268, 18415-18418.
13. 2X Peptidomimetics, J. Biol. Chem. 268, 20695-20698.
14. Patel, D.V., Schmidt, R.J., Biller, S.A., Gordon, E.M., Robinson, S.S., and Manne, V. (1995) Farnesyl Diphosphate-Based Inhibitors of Ras Farnesyl Protein Transferase, J. Med. Chem. 38, 2906-2921.
15. Schaber, M.D., O'Hara, M.B., Garsky, V.M., Mosser, S.D., Bergstrom, J.D., Moores, S.L., Marshall, M.S., Freidman, P.A., Dixon, R.A.F., and Gibbs, J.B. (1990) Polysioprenylation of Ras In Vitro by a Farnesyl-Protein Transferase, J. Biol. Chem. 265, 14701-14704.
16. Moores, S.L, Schaber, M.D., Mosser, S.D., Rands, E., O'Hara, M.B., Garsky, V.B., Marshall, M.S., Popliono, D.L., and Gibbs, J.B. (1991) Sequence Determination of Protein Isoprenylation, J. Biol. Chem. 266, 14603-14610.
17. Lerner, E.C., Quian, Y., Blaskivich, M.A., Fossum, R.D., Vogt, A., Sun, J., Cox, A.D., Der, C.J., Hamilton, A.D., and Sebti, S.M. (1995) Ras CAAX Peptidomimetic FTI-277 Selectively Blocks Oncogenic Ras Signaling by Inducing Cytoplasmic Accumulation of Inactive Ras-Raf Complexes, J. Biol. Chem. 270, 26802-26806.
18. Pompliano, D.L., Rands, E., Schaber, M.D., Mosser, S.D., Anthony, N.J., and Gibbs, J.B. (1992) Steady-State Kinetic Mechanism of Ras Farnesyl:Protein Transferase, Biochemistry 31, 3800-3807.
19. Corey, E.J., and Schmidt, G. (1979) Useful Procedures for the Oxidation of Alcohols Involving Pyridinium Dichromate in Aprotic Media, Tetrahedron Lett. 5, 399-402.
20. Froehlich, M.L., Swartling, D.G., Lind, R.E., Mott, A.W., and Bergstrom, D.E. (1989) An Improved Synthesis of 3′-Keto-5′-O-tritylthymidine, Nucleosides Nucleotides 8, 1529-1535.
21. Lowry, O.H., Rosenbrough, N.J., Farr, A.L., and Randall, R.J. (1951) Protein Measurement with the Folin Phenol Reagent, J. Biol. Chem. 193, 265-275.
22. Kanai, T., Hirohashi, S., Noguchi, M., Shimoyama, Y., Shimosato, Y., Noguchi, S., Nishimura, S., and Abe, O. (1987) Monoclonal Antibody Highly Sensitive for the Detection of Ras p21 in Immunoblotting Analysis, Jpn. J. Cancer Res. (Gann) 78, 1314-1318.
23. Hohl, R.J., and Lewis, K. (1995) Differential Effects of Monoterpenes and Lovastatin on RAS Processing, J. Biol Chem. 270, 17508-17512.
24. Khan, S.G., Hasan, M., and Agarwal, R.J. (1995) A Rapid and Convenient Filter-Binding Assay for Ras p21 Processing Enzyme Farnesyltransferase, J. Biochem. Biophys. Methods 30, 133-144.
25. Harwood, K.J., Jr. (1995) Protein Farnesyltranferase: Measurement of Enzymatic Activity in 96-Well Format Using TopCount Microplate Scintillation Counting Technology, Analyt. Biochem. 226, 268-278.
26. Hohl, R.J., Larson, R.A., Mannickarottu, V., and Yachnin, S. (1991) Inhibition of Hydroxymethylglutaryl Coenzyme A Reductase Activity Induces a Paradoxical Increase in DNA Synthesis in Myeloid Leukemia Cells, Blood 77, 1064-1070.
27. Yachnin, S., Golomb, H.M., West, E.J., and Saffold, C. (1983) Increased Cholesterol Biosynthesis in Leukemic Cells from Patients with Hairy Cell Leukemia, Blood 61, 50-60.
28. Ciosek, C.P., Magnin, D.R., Harrity, T.W., Logan, J.V.H., Dickson, J.K., Gordon, E.M., Hamilton, K.A., Jolibois, K.G., Kunselman, L.K., Lawrence, R.M., Mooktiar, K.A., Rich, L.C., Slusarchyk, D.A., Sulsky, R.B., and Biller, S.A. (1993) Lipophilic 1,1-Bisphosphonates Are Potent Squalene Synthase Inhibitors and Orally Active Cholesterol Lowering Agents in vivo, J. Biol Chem. 268, 24832-24837.
29. McEldoon, W.L., and Wiemer, D.F. (1995) Synthesis of Nucleoside 3′-Phosphonates via Nucleoside Ketones, Tetrahedron 51, 7131-7148.
30. Hohl, R.J. (1996) Monoterpenes as Regulators of Malignant Cell Proliferation, Dietary Phytochemicals in Cancer Prevention and Treatment, pp. 137-146, Plenum Press, New York.
31. Moomaw, J.F., and Casey, P.J. (1992) Mammalian Protein Geranylgeranyltransferase. Subunit Composition and Metal Requirements, J. Biol. Chem. 267, 17438-17443.