Anticancer activity of novel unnatural synthetic isoprenoids

Anticancer Research

Volumn 30, Issue 7, 2010, Pages 2505-2512

  Adams, Val R ^a,b   Deremer, David L ^a   Stevich, Bojana ^a   Mattingly, Cynthia A ^a   Gallt, Becky ^a   Subramanian, Thangaiah ^b   Troutman, Jerry M ^c   Peter Spielmann, H ^a,b,c  

^a UNIVERSITY OF KENTUCKY   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

^c UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Breast cancer; Farnesyl diphosphate analogues; Lung cancer; RAS protein farnesylation

Indexed keywords

ANTINEOPLASTIC AGENT; ISOPRENOID; K RAS PROTEIN; MEVINOLIN; MITOGEN ACTIVATED PROTEIN KINASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CYTOTOXICITY; DRUG ACTIVITY; DRUG INHIBITION; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HUMAN CELL; LUNG CANCER; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEIN PHOSPHORYLATION;

ADENOCARCINOMA; ALKYL AND ARYL TRANSFERASES; BREAST NEOPLASMS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; GENES, RAS; HUMANS; LUNG NEOPLASMS; MAP KINASE SIGNALING SYSTEM; MITOGEN-ACTIVATED PROTEIN KINASES; POLYISOPRENYL PHOSPHATES; PROTO-ONCOGENE PROTEINS; RAS PROTEINS; SESQUITERPENES; TERPENES;

EID: 77955777881     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (47)

1. Jemal A, Siegel R, Ward E, Hao Y, Xu J and Thun MJ: Cancer Statistics, 2009. CA Cancer J Clin 59: 225-249, 2009.
2. Singletary SE and Connolly JL: Breast cancer staging: working with the sixth edition of the AJCC Cancer Staging Manual. CA Cancer J Clin 56: 37-47; quiz 50-31, 2006.
3. Mountain CF: Revisions in the International System for Staging Lung Cancer. Chest 111: 1710-1717, 1997. (Pubitemid 27260107)
4. Malumbres M and Barbacid M: RAS oncogenes: the first 30 years. Nat Rev Cancer 3: 459-465, 2003.
5. Ding L, Getz G, Wheeler DA, Mardis ER, McLellan MD, Cibulskis K et al: Somatic mutations affect key pathways in lung adenocarcinoma. Nature 455: 1069-1075, 2008.
6. Adjei AA: The role of mitogen-activated ERK-kinase inhibitors in lung cancer therapy. Clin Lung Cancer 7: 221-223, 2005.
7. Michaelson D, Ali W, Chiu VK, Bergo M, Silletti J, Wright L et al: Postprenylation CAAX processing is required for proper localization of Ras but not Rho GTPases. Mol Biol Cell 16: 1606-1616, 2005. (Pubitemid 40471934)
8. Rowinsky EK, Windle JJ and Von Hoff DD: Ras protein farnesyltransferase: A strategic target for anticancer therapeutic development. J Clin Oncol 17: 3631-3652, 1999.
9. Sousa SF, Fernandes PA and Ramos MJ: Unraveling the mechanism of the farnesyltransferase enzyme. J Biol Inorg Chem 10: 3-10, 2005.
10. Doll RJ, Kirschmeier P and Bishop WR: Farnesyltransferase inhibitors as anticancer agents: critical crossroads. Curr Opin Drug Discov Devel 7: 478-486, 2004. (Pubitemid 44383554)
11. Gibbs JB, Oliff A and Kohl NE: Farnesyltransferase inhibitors: Ras research yields a potential cancer therapeutic. Cell 77: 175-178, 1994. (Pubitemid 24138615)
12. Karp JE, Kaufmann SH, Adjei AA, Lancet JE, Wright JJ and End DW: Current status of clinical trials of farnesyltransferase inhibitors. Curr Opin Oncol 13: 470-476, 2001. (Pubitemid 33027899)
13. Basso AD, Kirschmeier P and Bishop WR: Lipid posttranslational modifications. Farnesyl transferase inhibitors. J Lipid Res 47: 15-31, 2006.
14. Sousa SF, Fernandes PA and Ramos MJ: Farnesyltransferase inhibitors: a detailed chemical view on an elusive biological problem. Curr Med Chem 15: 1478-1492, 2008.
15. Morgillo F and Lee HY: Lonafarnib in cancer therapy. Expert Opin Investig Drugs 15: 709-719, 2006.
16. Mesa RA: Tipifarnib: farnesyl transferase inhibition at a crossroads. Expert Rev Anticancer Ther 6: 313-319, 2006.
17. Cox AD and Der CJ: Farnesyltransferase inhibitors and cancer treatment: targeting simply Ras? Biochim Biophys Acta 1333: F51-71, 1997.
18. James GL, Brown MS and Goldstein JL: Assays for inhibitors of CAAX farnesyltransferase in vitro and in intact cells. Methods Enzymol 255: 38-46, 1995.
19. Sebti SM: Blocked pathways: FTIs shut down oncogene signals. Oncologist 8(Suppl 3): 30-38, 2003.
20. Cox AD, Hisaka MM, Buss JE and Der CJ: Specific isoprenoid modification is required for function of normal, but not oncogenic, Ras protein. Mol Cell Biol 12: 2606-2615, 1992.
21. Morgan MA, Sebil T, Aydilek E, Peest D, Ganser A and Reuter CW: Combining prenylation inhibitors causes synergistic cytotoxicity, apoptosis and disruption of RAS-to-MAP kinase signalling in multiple myeloma cells. Br J Haematol 130: 912-925, 2005. (Pubitemid 43899732)
22. Lobell RB, Omer CA, Abrams MT, Bhimnathwala HG, Brucker MJ, Buser CA et al: Evaluation of farnesyl:protein transferase and geranylgeranyl:protein transferase inhibitor combinations in preclinical models. Cancer Res 61: 8758-8768, 2001.
23. Sebti SM and Der CJ: Opinion: Searching for the elusive targets of farnesyltransferase inhibitors. Nat Rev Cancer 3: 945-951, 2003.
24. Chehade KA, Andres DA, Morimoto H and Spielmann HP: Design and synthesis of a transferable farnesyl pyrophosphate analogue to Ras by protein farnesyltransferase. J Org Chem 65: 3027-3033, 2000. (Pubitemid 30329163)
25. Chehade KA, Kiegiel K, Isaacs RJ, Pickett JS, Bowers KE, Fierke CA et al: Photoaffinity analogues of farnesyl pyrophosphate transferable by protein farnesyl transferase. J Am Chem Soc 124: 8206-8219, 2002. (Pubitemid 34875379)
26. Coffinier C, Hudon SE, Lee R, Farber EA, Nobumori C, Miner JH et al: A potent HIV protease inhibitor, darunavir, does not inhibit ZMPSTE24 or lead to an accumulation of farnesylprelamin A in cells. J Biol Chem 283: 9797-9804, 2008.
27. Troutman JM, Roberts MJ, Andres DA and Spielmann HP: Tools to analyze protein farnesylation in cells. Bioconjug Chem 16: 1209-1217, 2005.
28. Henriksen BS, Zahn TJ, Evanseck JD, Firestine SM and Gibbs RA: Computational and conformational evaluation of FTase alternative substrates: insight into a novel enzyme binding pocket. J Chem Inf Model 45: 1047-1052, 2005.
29. Troutman JM, Subramanian T, Andres DA and Spielmann HP: Selective modification of CaaX peptides with ortho-substituted anilinogeranyl lipids by protein farnesyl transferase: competitive substrates and potent inhibitors from a library of farnesyl diphosphate analogues. Biochemistry 46: 11310-11321, 2007. (Pubitemid 47556758)
30. Roberts MJ, Troutman JM, Chehade KA, Cha HC, Kao JP, Huang X et al: Hydrophilic anilinogeranyl diphosphate prenyl analogues are Ras function inhibitors. Biochemistry 45: 15862-15872, 2006. (Pubitemid 46032507)
31. Subramanian T, Liu S, Troutman JM, Andres DA and Spielmann HP: Protein farnesyltransferase-catalyzed isoprenoid transfer to peptide depends on lipid size and shape, not hydrophobicity. Chembiochem 9: 2872-2882, 2008.
32. Subramanian T, Wang Z, Troutman JM, Andres DA and Spielmann HP: Directed library of anilinogeranyl analogues of farnesyl diphosphate via mixed solid- and solution-phase synthesis. Org Lett 7: 2109-2112, 2005. (Pubitemid 40826061)
33. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D et al: New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82: 1107-1112, 1990. (Pubitemid 20213250)
34. Anonymous: Screening Services - DTP human tumor cell line screen. In: D.T.P.N.C. Institute, ed. Bethesda: National Cancer Institute, 2004.
35. Chou TC and Talalay P: Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors. Adv Enzyme Regul 22: 27-55, 1984.
36. Ikediobi ON, Davies H, Bigneli G, Edkins S, Stevens C, O'Meara S et al: Mutation analysis of 24 known cancer genes in the NCI-60 cell line set. Mol Cancer Ther 5: 2606-2612, 2006. (Pubitemid 44848987)
37. Konstantinopoulos PA, Karamouzis MV and Papavassiliou AG: Post-translational modifications and regulation of the RAS superfamily of GTPases as anticancer targets. Nat Rev Drug Discov 6: 541-555, 2007.
38. Ogata H, Sato H, Takatsuka J and De Luca LM: Human breast cancer MDA-MB-231 cells fail to express the neurofibromin protein, lack its type I mRNA isoform and show accumulation of p-MAPK and activated Ras. Cancer Lett 172: 159-164, 2001. (Pubitemid 32889711)
39. Zhou C, Shao Y and Gibbs RA: Aromatic farnesyl diphosphate analogues: vinyl triflate-mediated synthesis and preliminary enzymatic evaluation. Bioorg Med Chem Lett 12: 1417-1420, 2002. (Pubitemid 34454825)
40. Adjei AA, Davis JN, Bruzek LM, Erlichman C and Kaufmann SH: Synergy of the protein farnesyltransferase inhibitor SCH66336 and cisplatin in human cancer cell lines. Clin Cancer Res 7: 1438-1445, 2001. (Pubitemid 32708700)
41. Shi B, Yaremko B, Hajian G, Terracina G, Bishop WR, Liu M et al: The farnesyl protein transferase inhibitor SCH66336 synergizes with taxanes in vitro and enhances their antitumor activity in vivo. Cancer Chemother Pharmacol 46: 387-393, 2000.
42. Warnberg F, White D, Anderson E, Knox F, Clarke RB, Morris J et al: Effect of a farnesyl transferase inhibitor (R115777) on ductal carcinoma in situ of the breast in a human xenograft model and on breast and ovarian cancer cell growth in vitro and in vivo. Breast Cancer Res 8: R21, 2006.
43. Dechat T, Shimi T, Adam SA, Rusinol AE, Andres DA, Spielmann HP et al: Alterations in mitosis and cell cycle progression caused by a mutant lamin A known to accelerate human aging. Proc Natl Acad Sci USA 104: 4955-4960, 2007. (Pubitemid 47186158)
44. Davies BS, Yang SH, Farber E, Lee R, Buck SB, Andres DA et al: Increasing the length of progerin's isoprenyl anchor does not worsen bone disease or survival in mice with Hutchinson-Gilford progeria syndrome. J Lipid Res 50: 126-134, 2009.
45. Yang SH, Andres DA, Spielmann HP, Young SG and Fong LG: Progerin elicits disease phenotypes of progeria in mice whether or not it is farnesylated. J Clin Invest 118: 3291-3300, 2008.
46. Fong LG, Vickers TA, Farber EA, Choi C, Yun UJ, Hu Y et al: Activating the synthesis of progerin, the mutant prelamin A in Hutchinson-Gilford progeria syndrome, with antisense oligonucleotides. Hum Mol Genet 18: 2462-2471, 2009.
47. Wong WW, Dimitroulakos J, Minden MD and Penn LZ: HMG-CoA reductase inhibitors and the malignant cell: the statin family of drugs as triggers of tumor-specific apoptosis. Leukemia 16: 508-519, 2002.