Inhibitors of protein prenylation 2000

Bibliography

• WILLIAMS TM: Inhibitors of protein prenylation 1999. Exp. Opin. Ther. Patents (1999) 9 (9) :1263–1280.
   Web of Science ®Google Scholar
• BOS JL: ras oncogenes in human cancer: a review. Cancer Res. (1989) 49:4682–4689.
   PubMed Web of Science ®Google Scholar
• CLARK GJ, DER CJ: ras proto-oncogene activation in human malignancy. In: Cellular Cancer Markers. Garrett CT, Sell S (Eds.), Humana Press, Totowa, NJ (1995):17–52.
   Google Scholar
• WILLUMSEN BM, NORRIS K, PAPAGEORGE AG, HUBBERTNL, LOWY DR: Harvey murine sarcoma virus p21 ras protein: biological and biochemical significance of the cysteine nearest the carboxy terminus. EMBO J. (1984) 3:2581–2585.
   PubMed Web of Science ®Google Scholar
• CASEY PJ, SOLSKI PA, DER C, BUSS JE: p21 Ras is modified by a farnesyl isoprenoid. Proc. Natl. Acad. Sci. USA (1989) 86:8323–8327.
   PubMed Web of Science ®Google Scholar
• GRAHAM SL: Inhibitors of protein farnesylation: a new approach to cancer chemotherapy. Exp. Opin. Ther. Patents (1995) 5(12):1269–1285.
   Google Scholar
• ADJEI AA, ERLICHMAN C, DAVIS JN et al.: APhase I trial of the farnesyl transferase inhibitor SCH66336: evidence for biological and clinical activity. Cancer Res. (2000) 60:1871–1877.
   PubMed Web of Science ®Google Scholar
• ••The first published suggestions of clinical activity for an FTI.
   Google Scholar
• ZUJEWSKI J, HORAK ID, BOL CJ et al: Phase I and pharmacokinetic study of farnesyl protein transferase inhibitor R115777 in advanced cancer. J. Clin. Oncol. (2000) 18:927–941.
   PubMed Web of Science ®Google Scholar
• •Detailed description of pharmacokinetics and toxicity profile for R115777.
   Google Scholar
• BRITTEN CD, YAO S-L, SOIGNET S et al.: The farnesyl protein transferase (FPTase) inhibitor L-778,123 in patients with solid cancers. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, USA (1999). Abstract 597.
   Google Scholar
• RYAN DP, EDER JP, SUPKO JG et al.: Phase I clinical trialof the farnesyltransferase (FT) inhibitor BMS-214662 in patients with advanced solid tumors. American Society of Clinical Oncology 366 Annual Meeting. New Orleans, USA (2000). Abstract 720.
   Google Scholar
• ADJEI AA, DAVIS JN, ERLICHMAN C, SVINGEN PA,KAUFMANN SH: Comparison of potential markers of far n esyltr an sfer ase inhibition. Clin. Cancer Res. (2000) 6:2318–2325.
   PubMed Web of Science ®Google Scholar
• PETIT T, IZBICKA E, LAWRENCE RA et al.: Activity ofSCH66336, a tricyclic farnesyltransferase inhibitor against human tumor colony-forming units. Ann. Oncol. (1999) 10:449–453.
   PubMed Web of Science ®Google Scholar
• ESKENS F, AWADA A, VERWEIJ J et al.: Phase I andpharmacologic study of continuous daily oral SCH66336, a novel farnesyl transferase inhibitor. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, USA (1999). Abstract 600.
   Google Scholar
• HURWITZ HI, AMADO R, PRAGER D et al.: Phase I pharmacokinetic trial of the farnesyl transferase inhibitor SCH66336 plus gemcitabine in advanced cancers. American Society of Clinical Oncology 36t1 Annual Meeting. New Orleans, USA (2000). Abstract 717.
   Google Scholar
• KHURI FR, GLISSON BS, MEYERS ML et al.: Phase I study of farnesyl transferase inhibitor (Ell) SCH66336 with paclitaxel in solid tumors: dose finding, pharmacoki-netics, efficacy/safety. American Society of Clinical Oncology 366 Annual Meeting. New Orleans, USA (2000). Abstract 799.
   Google Scholar
• JOHNSTON SR, ELLIS PA, HOUSTON S et al.: A Phase IIstudy of the farnesyl transferase inhibitor R115777 in patients with advanced breast cancer. American Society of Clinical Oncology 366 Annual Meeting. New Orleans, USA (2000). Abstract 318.
   Google Scholar
• ••Efficacy of R115777 for the treatment of breast cancer.
   Google Scholar
• LANCET JE, ROSENBLATT JD, LIESVELD JL et al.: Use of farnesyl transferase inhibitor R115777 in relapsed and refractory acute leukemias: preliminary results of a Phase I trial. American Society of Clinical Oncology 36th Annual Meeting. New Orleans, USA (2000). Abstract 5B.
   Google Scholar
• ••Efficacy of R115777 for the treatment of leukaemias.
   Google Scholar
• PATNAIK A, ECKHARDT SG, IZBICKA E et al.: A Phase Iand pharmacokinetic (PK) study of the farnesyltrans-ferase inhibitor R115777 in combination with gemcitabine. American Society of Clinical Oncology 366 Annual Meeting. New Orleans, USA (2000). Abstract 5A.
   Google Scholar
• SIEGL P: Case studies of QT interval. PhRIVIA PreclinicalDrug Safety Steering Committee Annual Meeting. Washington, USA (2000).
   Google Scholar
• HUBER HE, ABRAMS M, ANTHONY N et al.: Biochemical evaluation of specific ger anylger anyltransfer ase inhibitors. Proc. Am. Assoc. Cancer Res. (2000) 41 :446. Abstract 2838.
   Google Scholar
• •Discovery of a variety of GGTIs and dual FTI/GGTIs including Merck's clinical candidate L-778,123.
   Google Scholar
• MANNE V, RICCA C, GULLO-BROWN J et af: BMS-214662, a highly potent apoptotic farnesyltransferase inhibitor. Proc. Am. Assoc. Cancer Res. (2000) 41:219. Abstract 1399.
   Google Scholar
• •Potent FTI which causes regression of tumour xenografts in mice.
   Google Scholar
• SONNICHSEN D, DAMLE B, MANNING J et al.: Pharma-cokinetics (PK) and pharmacodynamics (PD) of the farnesyltransferase (FT) inhibitor BMS-214662 in patients with advanced solid tumors. American Society of Clinical Oncology 366 Annual Meeting. New Orleans, USA (2000). Abstract 691.
   Google Scholar
• LIU M, BRYANT MS, CHEN J et al.: Antitumor activity of SCH66336, an orally bioavailable tricyclic inhibitor of farnesyl protein transferase, in human tumor xenograft models and wap-ras transgenic mice. Cancer Res. (1998) 58:4947–4956.
   PubMed Web of Science ®Google Scholar
• MOASSER MM, SEPP-LORENZINO L, KOHL NE et al.: Farnesyl transferase inhibitors cause enhanced mitotic sensitivity to tax ol and epothilones. Proc. Nati Acad. Sci. USA (1998) 95:1369–1374.
   PubMed Web of Science ®Google Scholar
• SUN J, BLASKOVICH MA, KNOWLES D et al.: Antitumor efficacy of a novel class of non-thiol-containing peptidomimetic inhibitors of farnesyltransferase and geranylgeranyltransferase I: combination therapy with the cytotoxic agents cisplatin, tax ol and gemcita-bine. Cancer Res. (1999) 59:4919–4926.
   PubMed Web of Science ®Google Scholar
• BERNHARD EJ, MCKENNA WG, HAMILTON AD et al.: Inhibiting Ras prenylation increases the radiosensi-tivity of human tumor cell lines with activating mutations of ras oncogen es. Cancer Res. (1998) 58:1754–1761.
   PubMed Web of Science ®Google Scholar
• COHEN-JONATHAN E, TOULAS C, ADER I et al.: The farnesyltransferase inhibitor F11-277 suppresses the 24-kDa FGF2-induced radioresistance in HeI2. cells expressing wild-type RAS. Radiation Res. (1999) 152:404–411.
   Google Scholar
• •Demonstration that FTIs can radiosensitise cells even in the absence of mutant ras.
   Google Scholar
• PRENDERGAST GC, DAVIDE JP, DESOLMS SJ et al: Farnesyltransferase inhibition causes morphological reversion of ras-transformed cells by a complex mechanism that involves regulation of the actin cytoskeleton. Mol. Cell. Biol. (1994) 14:4193–4202.
   PubMed Web of Science ®Google Scholar
• SEPP-LORENZINO L, MA Z, RANDS E et al: A p eptidomi-metic inhibitor of farnesyl:protein transferase blocks the anchorage-dependent and -independent growth of human tumor cell lines. CancerRes. (1995) 55:5302–5309.
   Web of Science ®Google Scholar
• WHYTE DB, KIRSCHMEIER P, HOCKENBERRY TN et al: K-and N-Ras are geranylgeranylated in cells treated with farnesyl protein transferase inhibitors. J Biol. Chem. (1997) 272:14459–14464.
   PubMed Web of Science ®Google Scholar
• OLIFF A: Farnesyltransferase inhibitors: targeting the molecular basis of cancer. Biochim. Biophys. Acta (1999) 1423:C19–C30.
   PubMed Web of Science ®Google Scholar
• •Historical overview of FTIs and discussion of their mechanism of action.
   Google Scholar
• ADAMSON P, MARSHALL CJ, HALL A, TILBROOK PA: Post-translational modifications of p21 rho proteins. J Biol. Chem. (1992) 267:20033–20038.
   PubMed Web of Science ®Google Scholar
• PRENDERGAST GC: Farnesyltransferase inhibitors:antineoplastic mechanism and clinical prospects. Curr. Opin. Cell Biol. (2000) 12:166–173.
   PubMed Web of Science ®Google Scholar
• •Comprehensive review of the role of RhoB in the biological effects of FTIs.
   Google Scholar
• LIU A, DU W, LIU J-P, JESSELL TM, PRENDERGAST GC: The role of RhoB in the response to farnesyltransferase inhibitors defined by targeted gene disruption. Proc. Am. Assoc. Cancer Res. (2000) 41:219. Abstract 1395.
   Google Scholar
• CHEN Z, SUN J, PRADINES A et al.: Both farnesylated and geranylgeranylated RhoB inhibit malignant transfor-mation and suppress human tumor growth in nude mice. J. Biol. Chem. (2000) 275:17974–17978.
   PubMed Web of Science ®Google Scholar
• ASHAR HR, JAMES L, GRAY K et al.: The farnesyl transfe-rase inhibitor SCH 66336 induces cell cycle changes in sensitive human tumor cell lines and prevents the farnesylation of the centromere associated proteins CENP-E and CENP-F. Proc. Am. Assoc. Cancer Res. (2000) 41:219. Abstract 1398.
   Google Scholar
• ••Evidence that CENP-E and CENP-F may be the targets ofFTIs in HTLs.
   Google Scholar
• PIDOUX AL, ALLSHIRE RC: Centromeres: getting a grip of chromosomes. Curr. Opin. Cell Biol. (2000) 12:308–319.
   PubMedGoogle Scholar
• JIANG K, COPPOLA D, CRESPO NC et al.: The phosphoi-nositide 3-0Hkinase/AKT2 pathway as a critical target for farnesyltransferase inhibitor-induced apoptosis. Mol. Cell. Biol (2000) 20:139–148.
   PubMed Web of Science ®Google Scholar
• FELDKAMP MM, LAU N, GUHA A: Growth inhibition ofastrocytoma cells by farnesyl transferase inhibitors is mediated by a combination of anti-proliferative, pr o-apop to tic and an ti-an gio gen ic effects. Oncogene (1999) 18:7514–7526.
   PubMed Web of Science ®Google Scholar
• SUN J, QUIAN Y, HAMILTON AD, SEBTI SM: 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.
   PubMed Web of Science ®Google Scholar
• OMER CA, CHEN Z, DIEHL RE et al.: Mouse mammarytumor virus-Ki-rasB transgenic mice develop mammary carcinomas that can be growth-inhibited by a farnesyl:protein transferase inhibitor. Cancer Res. (2000) 60:2680–2688.
   PubMed Web of Science ®Google Scholar
• KLOOG Y, COX AD, SINENSKY M: Concepts in Ras-directed therapy. Exp. Opin. Invest. Drugs (1999) 8 (12):2121–2140.
   PubMedGoogle Scholar
• AHMADIAN MR, ZOR T, VOGT D et al.: Guanosine triphosphatase stimulation of oncogenic Ras mutants. Proc. Natl. Acad. Sci. USA (1999) 96:7065–7070.
   PubMed Web of Science ®Google Scholar
• LONG SB, CASEY PJ, BEESE LS: The basis for K-Ras4Bbinding specificity to protein farnesyltransferase revealed by 2A resolution ternary complex structures. Structure (2000) 8:209–222.
   PubMedGoogle Scholar
• •Interesting structural study revealing details of the catalytic mechanism of FTase.
   Google Scholar
• JAMES GL, GOLDSTEIN JL, BROWN MS: Polylysine and CVIM sequences of K-RasB dictate specificity of prenylation and confer resistance to benzodiazepine peptidomimetic in vitro. J. Biol. Chem. (1995) 270:6221–6226.
   PubMed Web of Science ®Google Scholar
• ROZEMA DB, POULTER CD: Yeast protein farnesyltrans-ferase. p Kas of peptide substrates bound as zinc thiolates. Biochemistry (1999) 38:13138–13146.
   Google Scholar
• WU Z, DEMMA M, STRICKLAND CL et al.: Farnesyl protein transferase: identification of K164a and Y30013 as catalytic residues by mutagenesis and kinetic studies. Biochemistry (1999) 38:11239–11249.
   PubMedGoogle Scholar
• ANDRES DA, GOLDSTEIN JL, HO YK, BROWN MS: Mutational analysis of a-subunit of protein farnesyl-transferase. J Biol. Chem. (1993) 268:1383–1390.
   PubMed Web of Science ®Google Scholar
• KRAL AM, DIEHL RE, DESOLMS SJ et al.: Mutational analysis of conserved residues of the I3-subunit of human farnesyl:protein transferase. j Biol. Chem. (1997) 272:27319–27323.
   PubMedGoogle Scholar
• LONG SB, CASEY PJ, BEESE LS: Co-crystal structure of mammalian protein farnesyltransferase complex ed with a farnesyl diphosphate substrate. Biochemistry (1998) 37:9612–9618.
   PubMed Web of Science ®Google Scholar
• STRICKLAND CL, WEBER PC, WINDSOR WT et al.: Tricyclic farnesyl protein transferase inhibitors: crystallographic and calorimetric studies of structure-activity relationships. J Med. Chem. (1999) 42:2125–2135.
   PubMed Web of Science ®Google Scholar
• •Detailed study of the interaction of 5CH66336 and related compounds with FTase.
   Google Scholar
• PREVOST GP, PRADINES A, VIOSSAT I et al: Inhibition of human tumor cell growth in vitro and in vivo by a specific inhibitor of human farnesyltransferase: BIM-46068. Int. J. Cancer (1999) 83:283–287.
   PubMed Web of Science ®Google Scholar
• O'CONNELL CE, ACKERMANN K, ROWELL CA et al: Synthesis and evaluation of hydroxyproline-derived isoprenyltransferase inhibitors. Bioorg. Med. Chem. Lett. (1999) 9:2095–2100.
   PubMedGoogle Scholar
• QIAN Y, MARUGAN JJ, FOSSUM RD et al.: Probing thehydrophobic pocket of farnesyltransferase: aromatic substitution of CAAX peptidomimetics leads to highly potent inhibitors. Bioorg. Med. Chem. (1999) 7:3011–3024.
   PubMedGoogle Scholar
• •SAR studies on FTI-276 and related peptidomimetic inhibitors.
   Google Scholar
• KELLY R, CARD D, REGISTER E et al: Geranylgeranyl-transferase I of Candida albicans: null mutants or enzyme inhibitors produce unexpected phenotypes. J Bacteriol. (2000) 182:704–713.
   PubMed Web of Science ®Google Scholar
• ANTHONY NJ, GOMEZ RP, SCHABER MD et al: Design and in vivo analysis of potent non-thiol inhibitors of farnesyl protein transferase. J Med. Chem. (1999) 42:3356–3368.
   PubMed Web of Science ®Google Scholar
• •Discovery of the widely-used cyanobenzylimidazole moiety.
   Google Scholar
• WILLIAMS TM, CICCARONE TM, MACTOUGH SC et al:2-Substituted piperazines as constrained amino acids. Application to the synthesis of potent, non carboxylic acid inhibitors of farnesyl transferase. J Med. Chem. (1996) 39:1345–1348.
   Google Scholar
• WILLIAMS TM, BERGMAN JM, BRASHEAR K et al.: N-Arylpiperazinone inhibitors of farnesyltransferase: discovery and biological activity. J Med. Chem. (1999) 42:3779–3784.
   PubMed Web of Science ®Google Scholar
• •Discovery of highly cell potent FTIs related to the Merck clinical candidate.
   Google Scholar
• CICCARONE TM, MACTOUGH SC, WILLIAMS TM et al:Non-thiol 3-aminomethylbenzamide inhibitors of farnesyl-protein transferase. Bioorg. Med. Chem. Lett. (1999) 9:1991–1996.
   PubMedGoogle Scholar
• BURNS CJ, GUITTON J-D, BAUDOIN B et al: Novelconformationally extended naphthalene-based inhibitors of farnesyltransferase. J Med. Chem. (1997) 40:1763–1767.
   PubMedGoogle Scholar
• DING CZ, BATORSKY R, BHIDE R et al: Discovery andstructure-activity relationships of imidazole-containing tetrahydrobenzodiazepine inhibitors of farnesyltransferase. J Med. Chem. (1999) 42:5241–5253.
   PubMed Web of Science ®Google Scholar
• •Development of FTIs related to the Bristol-Myers Squibb clinical candidate.
   Google Scholar
• HENRY KJ, WASICAK J, TASKER AS et al.: Discovery of a series of cyclohexylethylamine-containing protein farnesyltransferase inhibitors exhibiting potent cellular activity. J Med. Chem. (1999) 42:4844–4852.
   PubMedGoogle Scholar
• O'CONNOR SJ, BARR KJ, WANG L et al.: Second-generation peptidomimetic inhibitors of protein farnesyltransferase demonstrating improved cellular potency and significant in vivo efficacy. J. Med. Chem. (1999) 42:3701–3710.
   Google Scholar
• AFONSO A, WEINSTEIN J, KELLY J et al: Analogues of 1-(3,10-dibromo-8-chloro-6,11-dihydro- 5H- benzo-[5,6]- cyclohepta[1,2-b]pyridin-11-yl)piperidine as inhibitors of farnesyl protein transferase. Bioorg. Med. Chem. (1999) 7:1845–1855.
   PubMedGoogle Scholar
• TAVERAS AG, DESKUS J, CHAO J et al: Identification of pharmacokinetically stable 3,10-dibromo-8-chlorobenzocycloheptapyridine farnesyl protein transferase inhibitors with potent enzyme and cellular activities. J Med. Chem. (1999) 42:2651–2661.
   PubMedGoogle Scholar
• SCHLITZER M, SATTLER I: Design, synthesis and evalua-tion of novel modular bisubstrate analogue inhibitors of farnesyltransferase. Angew. Chem. Int. Ed. (1999) 38:2032–2034.
   PubMed Web of Science ®Google Scholar
• GIBBS BS, ZAHN TJ, MU Y, SEBOLT-LEOPOLD JS, GIBBSRA: Novel farnesol and geranylgeraniol analogues: a potential new class of anticancer agents directed against protein prenylation. J Med. Chem. (1999) 42:3800–3808.
   PubMed Web of Science ®Google Scholar
• SINGH SB, JAYASURIYA H, SILVERMAN KC et al.: Efficient syntheses, human and yeast farnesyl-protein transfe-rase inhibitory activities of chaetomellic acids and analogues. Bioorg. Med. Chem. (2000) 8:571–580.
   PubMed Web of Science ®Google Scholar
• BOGUSKY MJ, CULBERSON JC, PITZENBERGER SM et al: Conformation of a novel tetrapetide inhibitor NI-12-D-Trp-D-Met-Ph e(pC1)-Gla-NI-12 bound to farn e syl-protein transferase. J. Peptide Res. (1999) 54: 66–73.
   PubMedGoogle Scholar
• VRIGNAUD P, BELLO A, BISSERY MC et al: RPR130401, a non-peptidomimetic farnesyltransferase inhibitor with in vivo activity. Proc. Am. Assoc. Cancer Res. (1998) 39:270.
   Google Scholar