Inhibitors of protein prenylation 1999

Bibliography

• WILLIAMS TM: Inhibitors of protein farnesylation 1998. Exp. Opin. Ther. Patents (1998) 8(5):553–569.
   Web of Science ®Google Scholar
• ADJEI AA, ERLICHMAN C, DAVIS JN et al: A Phase I and pharmacologic study of the farnesyl protein transfe-rase inhibitor SCH 66366 in patients with locally advanced or metastatic cancer. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, GA, USA (1999). Abstract 598.
   Google Scholar
• ESKENS F, AWADA A, VERWEIJ J et al. Phase 1 andpharmacologic study of continuous daily oral SCH 66366, a novel farnesyl transferase inhibitor. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, GA, USA (1999). Abstract 600.
   Google Scholar
• HUDES GR, SCHOL J, BAAB J et al.: Phase 1 clinical and pharmacokinetic trial of the farnesyltransferase inhibitor R115777 on a 21-day dosing schedule. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, GA, USA (1999). Abstract 601.
   Google Scholar
• ZUJEWSKI J, HORAK ID, BOL CJJG et al.: A Phase 1 and pharmacokinetic study of farnesyltransferase inhibitor R115777, in advanced cancer. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, GA, USA (1999). Abstract 739.
   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, GA, USA (1999). Abstract 597.
   Google Scholar
• PEETERS M, VAN CUTSEM E, MARSE H et al. Phase 1 combination trial of the farnesyltransferase inhibitor (FT) R115777 with a 5FU/LV regimen in advanced colorectal (CRC) or pancreatic (PC) cancer. American Society of Clinical Oncology 35th Annual Meeting. Atlanta, GA, USA (1999). Abstract 859.
   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
• ••A set of experiments suggesting it is not necessary to achieveunprocessed K-Ras to observe an antitumour effect in mice bearing K-ras tumours.
   Google Scholar
• MANGUES R, CORRAL T, KOHL NE etal. Antitumor effect of a farnesyl protein transferase inhibitor in mammary and lymphoid tumors overexpressing N-ras in transgenic mice. Cancer Res. (1998) 58:1253–1259.
   Google Scholar
• DU W, LEBOWITZ PF, PRENDERGAST GC: Cell growth byfarnesyltransferase inhibitors is mediated by gain of geranylgeranylated RhoB. Ma Cell. Biol. (1999) 19:1831–1840.
   Web of Science ®Google Scholar
• SUZUKI N, URANO J, TAMANOI F: Farnesyltransferase inhibitors induce cytochrome c release and caspase 3 activation preferentially in transformed cells. Proc. Natl. Acad. ScL USA (1998) 95:15356–15361.
   PubMed Web of Science ®Google Scholar
• ••A definitive study establishing a connection betweenprotein farnesylation and apoptosis.
   Google Scholar
• VITALE M, MATOLA TD, ROSSI G, LAEZZA C, FENZI G, BIFULCO M: Prenyltransferase inhibitors induce apoptosis in proliferating thyroid cells through a p53-independent, CrmA-sensitive, and caspase-3-like protease-dependent mechanism. Endocrinology (1999) 140:698–704.
   PubMedGoogle Scholar
• BARRINGTON RE, SUBLER MA, RANDS E et al.: A farnesyl-transferase inhibitor induces tumor regression in transgenic mice harboring multiple oncogenic mutations by mediating alterations in both cell cycle control and apoptosis. Mol. Cell. Biol. (1998) 18:85–92.
   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 oncogenes. Cancer Res. (1998) 58:1754–1761.
   PubMed Web of Science ®Google Scholar
• ••Cell culture study indicating potential utility of radiotherapycombined with prenyltransferase inhibition in treating cancer.
   Google Scholar
• MOASSER MM, SEPP-LORENZINO L, KOHL NE et al.: Farnesyl transferase inhibitors cause enhanced mitotic sensitivity to taxol and epothilones. Proc. Natl. Acad. ScL USA (1998) 95:1369–1374.
   PubMed Web of Science ®Google Scholar
• •Additivity between an FTI and taxanes in cell culture suggests a possible therapeutic combination.
   Google Scholar
• GLENN JS, MARSTERS JC, JR., GREENBERG HB: Use of a prenylation inhibitor as a novel antiviral agent. J. Vim]. (1998) 72:9303–9306.
   Google Scholar
• HIGHTOWER KE, HUANG CC, CASEY PJ, FIERKE CA: H-Ras peptide and protein substrates bind protein farnesyltransferase as an ionized thiolate. Biochemistry (1998) 37:15555–15562.
   PubMed Web of Science ®Google Scholar
• STRICKLAND CL, WINDSOR WT, SYTO R et al.: Crystal structure of farnesyl protein transferase complexed with a CaaX peptide and farnesyl diphosphate analog. Biochemistry (1998) 37:16601–16611.
   PubMed Web of Science ®Google Scholar
• LONG SB, CASEY PJ, BEESE LS: Cocrystal structure of protein farnesyltransferase complexed with a farnesyl diphosphate substrate. Biochemistry (1998) 37:9612–9618.
   PubMed Web of Science ®Google Scholar
• •First crystal structure of FTase complexed with one of its substrates, FPP.
   Google Scholar
• DUNTEN P, KAMMLOTT U, CROWTHER R, WEBER D, PALERMO R, BIRKTOFT J: Protein farnesyltransferase: structure and implications for substrate binding. Biochemistry (1998) 37:7907–7912.
   PubMed Web of Science ®Google Scholar
• BOUTIN JA, MARANDE W, PETIT L et al.: Investigation ofS-farnesyl transferase substrate specificity with combinatorial tetrapeptide libraries. Cell Signal. (1999) 11:59–69.
   PubMedGoogle Scholar
• ARMSTRONG SA, HANNAH VC, GOLDSTEIN JL, BROWN MS: CaaX geranylgeranyl transferase transfers farnesyl as efficiently as geranylgeranyl to RhoB. J. Biol. Chem. (1995) 270:7864–7868.
   PubMed Web of Science ®Google Scholar
• ROSKOSKI R, RICHTIE P: Role of the carboxyterminal residue in peptide binding to protein farnesyltransfe-rase and protein geranylgeranyltransferase. Arch. Biochem. Biophys. (1998) 356:167–176.
   PubMed Web of Science ®Google Scholar
• DESOLMS SJ, GIULIANI EA, GRAHAM SL et al: N-Arylalkyl pseudopeptide inhibitors of farnesyltransferase. Med. Chem. (1998) 41:2651–2656.
   Google Scholar
• QIAN Y, VOGT A, VASUDEVAN A, SEBTI SM, HAMILTONAD: Selective inhibition of Type-I geranylgeranyltrans-ferase in vitro and in whole cells by CAA'. peptidomi-metics. Bioorg. Med. Chem. (1998) 6:293–299.
   PubMed Web of Science ®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 farnesyltransferase. J. Med. Chem. (1996) 39:1345–1348.
   Google Scholar
• NJOROGE FG, VIBULBHAN B, RANE DF et al: Structure-activity relationship of 3-substituted N-(pyridinyla-cety0-4-(8-chloro-5,6-dihydro-11H-benzo [5,6]cyclohe pta[1,2-b]pyridin-11-ylidenelpiperidine inhibitors of farnesyl-protein transferase: design and synthesis of in vivo active antitumor compounds. J. Med. Chem. (1997) 40:4290–4301.
   PubMedGoogle Scholar
• MALLAMS AK, ROSSMAN RR, DOLL RJ et al: Inhibitors offarnesyl protein transferase. 4-amido, 4-carbamoyl, and 4-carboxamido derivatives of 1-(8-chloro-6,11-dihydro-5H- benzo[5,6]-cyclohepta[1,2-b]pyridin-11-y0 piperazine and 1-(3-bromo-8-chloro-6,11-dihydro-5H-benzo[5,6] cyclohepta[1,2-b] pyridin-11-yOpiperazine. J. Med. Chem. (1998) 41:877–893.
   Google Scholar
• LIU M, BRYANT MS, CHEN J et al: Effects of SCH 59228,an orally bioavailable farnesyl protein transferase inhibitor, on the growth of oncogene-transformed fibroblasts and a human colon carcinoma xenograft in nude mice. Cancer Chemother. PharmacoL (1999) 43:50–58.
   PubMedGoogle Scholar
• NJOROGE FG, TAVERAS AG, KELLY J et al.: (444244-(8-Chloro-3,10-dibromo-6,11-dihydro-5H-b enzo[5,6]cyclohepta[1,2-1]-pyridin-11 (R)-3/0-1-piperi diny11-2-oxo-ethyl]-1-piperidinecarboxamide (SCH-66336): a very potent farnesyl protein transfe-rase inhibitor as a novel antitumor agent. J. Med. Chem. (1998) 41:4890–4902.
   PubMed Web of Science ®Google Scholar
• LIU M, BRYANT MS, CHEN J et al.: Antitumor activity of SCH 66336, 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
• •Biological characterisation of an FTI currently in clinical trials.
   Google Scholar
• NJORGE FG, VIBULBHAN B, PINTO P et al: Potent, selective, and orally bioavailable tricyclic pyridyl acetamide N-oxide inhibitors of farnesyl protein transferase with enhanced in vivo antitumor activity. J. Med. Chem. (1998) 41:1561–1567.
   PubMedGoogle Scholar
• KELLY J, WOLIN R, CONNOLLY M et al.: Synthesis of isomeric 3-piperidinyl and 3-pyrrolidinyl benzo[5,6]cyclohepta[1,2-b]pyridines: sulfonamido derivatives as inhibitors of Ras prenylation. Bioorg. Med. Chem. (1998) 6:673–686.
   PubMedGoogle Scholar
• WOLIN R, CONNOLLY M, KELLY J et al.: Inhibitors of farnesyl protein transferase. Synthesis and biological activity of amide and cyanoguanidine derivatives containing a 5,11-dihydro[l]benzthiepin, benzoxepin, and benzazepin [4,3-b]pyridine ring system. Bioorg. Med. Chem. Lett. (1998) 8:2521–2526.
   Google Scholar
• NJOROGE FG, VIBULBHAN B, PINTO P et al.: Highly regioselective nitration reactions provide a versatile method of functionalizing benzocycloheptapyridine tricyclic ring systems: application toward preparation of nanomolar inhibitors of farnesyl protein transfe-rase. J. Org. Chem. (1998) 63:445–451.
   PubMedGoogle Scholar
• AFONSO A, PUAR MS, KELLY J, MCPHAIL AT: Synthesis of a Cit spirocyclopropyl derivative of 8-chloro-6,11-dihydro-5H- benzo[5,6]cyclohepta[1,26 ]pyridine. Tetrahedron Lett. (1998) 39:7657–7660.
   Google Scholar
• AFONSO A, KELLY J, PUAR MS, MCCOMBIE S, MCPHAILAT: Synthesis of a CH spiropiperidino derivative of 8-chloro-6,11-dihydro-5H- benzo[5,6]cyclohepta[1,26 ]pyridine. Tetrahedron Lett. (1998) 39:7661–7664.
   Google Scholar
• VENET M, ANGIBAUD P, SANZ G, POIGNET H, END D,BOWDEN C: Synthesis and in vivo structure-activity relationships of imidazoly1-2(1H) quinolinones as farnesyl transferase inhibitors (FTO. American Associa-tion of Cancer Research. New Orleans, LA, USA (1998).
   Google Scholar
• SKRZAT S, ANGIBAUD P, VENET M, SANZ G, BOWDEN C,END D: R11577, a novel imidazole farnesyl transferase inhibitor (FTO with potent oral antitumor activity. American Association of CancerResearch. New Orleans, LA, USA (1998).
   Google Scholar
• HUANG C-C, CASEY PJ, FIERKE CA: Evidence for acatalytic role of zinc in protein farnesyltransferase. Biol. Chem. (1997) 272:20–23.
   Google Scholar
• BRESLIN MJ, DESOLMS SJ, GIULIANI EA et al: Potent,non-thiol inhibitors of farnesyl-transferase. Bioorg. Med. Chem. (1998) 8:3311–3316.
   Google Scholar
• WILLIAMS TM, DINSMORE CJ, BERGMAN JM et al.: Substrate-based design of farnesyltransferase inhibi-tors: from tetrapeptides to heterocycles. 216th American Chemical Society National Meeting. Boston, MA, USA (1998) 309.
   Google Scholar
• DINSMORE CJ, CULBERSON JC, GIBBS JB et al.:Imidazole-containing farnesyltransferase inhibitors based on the diaryl-X motif. 216th American Chemical Society Meeting. Boston, MA, USA (1998) 307.
   Google Scholar
• CALIENDO G, FIORINO F, GRIECO P et al. Phenol- derived CVFM analog inhibitors of ras farnesyltransferase possessing cellular in vitro activity. Eur. J. Med. Chem. (1998) 33:725–732.
   Google Scholar
• AUGERI DJ, O'CONNER SJ, JANO WICK D et al: Potent andselective non-cysteine-containing inhibitors of protein farnesyltransferase. J. Med. Chem. (1998) 41:4288–4300.
   PubMedGoogle Scholar
• SCHOLTEN JD, ZIMMERMAN K, OXENDER Metal.: Inhibi-tors of farnesyl:protein transferase - a possible cancer chemotherapeutic. Bioorg. Med. Chem. (1996) 4:1537–1543.
   Google Scholar
• AOYAMA T, SATOH T, YONEMOTO M et al: New class ofhighly potent farnesyl diphosphate-competitive inhibitors of farnesyltransferase. J. Med. Chem. (1998) 41:143–147.
   PubMedGoogle Scholar
• YONOMOTO M, SATOH T, ARAKAWA H et al: J-104,871,a novel farnesyltransferase inhibitor, blocks ras farnesylation in vivo in a farnesyl pyrophosphate-competitive manner. Mol. Pharmacol (1998) 54:1–7.
   PubMedGoogle Scholar
• VRIGNAUD P, BELLO A, BISSERY MC et al: RPR 130401, anon-peptidomimetic farnesyltransferase inhibitor with in vivo activity. Proc. Am. Assoc. Cancer Res. (1998) 39:270.
   Google Scholar
• HOLSTEIN SA, CERMAK DM, WIEMER DF, LEWIS K, HOHLRJ: Phosphonate and bisphosphonate analogues of farnesyl pyrophosphate as potential inhibitors of farnesyl protein transferase. Bioorg. Med. Chem. (1998) 6:687–695.
   PubMedGoogle Scholar
• OVERHANS M, STUIVENBERG HR, PIETERMAN E et al.:Inhibitors of protein:farnesyl transferase and protein:geranylgeranyl transferase I: synthesis of homologous diphosphate analogs of isoprenylated pyrophosphate. Bioorg. Chem. (1998) 26:269–282.
   Google Scholar
• HOHL RJ, LEWIS KA, CERMAK DM, WIEMER DF: Stereochemistry-dependent inhibition of ras farnesy-lation by farnesyl phosphonic acids. Lipids (1998) 33:39–46.
   PubMedGoogle Scholar
• GIBBS JB, POMPLIANO DL, MOSSER SD et al.: Selectiveinhibition of farnesyl-protein transferase blocks ras processing in vivo. J. Biol. Chem. (1993) 268:7617–7620.
   PubMed Web of Science ®Google Scholar
• BARBER AM, HARDCASTLE IR, ROWLANDS MG, NUTLEYBP, MARRIOTT JH, JARMAN M: Solid-phase synthesis of novel inhibitors of farnesyl transferase. Bioorg. Med. Chem. (1999) 6:623–626.
   Google Scholar
• LEE S-H, KIM M-J, BOK SH, LEE H eta]: Arteminolide, aninhibitor of farnesyl transferase from artemisia sylvatica. J. Org. Chem. (1998) 63:7111–7113.
   PubMedGoogle Scholar
• SINGH SB, ZINK DL, WILLIAMS M, POLISHOOK JD,SANCHEZ M, SILVERMAN KC: Kampanols: novel ras farnesyl-protein transferase inhibitors from Stachy-botrys kampalensis. Bioorg. Med. Chem. Lett. (1998) 8:2071–2076.
   PubMed Web of Science ®Google Scholar
• LINGHAM RB, SILVERMAN KC, JAYASURIYA H et al.:Clavaric acid and steroidal analogues as ras- and FPP-directed inhibitors of human farnesyl-protein transferase. J. Med. Chem. (1998) 41:4492–4501.
   PubMedGoogle Scholar
• HINTERDING K, HAGENBUCH P, RETEY J, WALDMANN H: Synthesis and in vitro evaluation of the ras farnesyl-transferase inhibitor pepticinnamin E. Angew. Chem. Int. Ed. (1998) 37:1236–1239.
   PubMed Web of Science ®Google Scholar
• COHEN LH, PIETERMAN E, VAN LEEUWEN REW, DU J, NEGRE-AMINOU P, VALENTIJN ARPM: Inhibition of human smooth muscle cell proliferation in culture by farnesyl pyrophosphate analogues, inhibitors of in vitro protein:farnesyl transferase. Biochem. Pharmacol. (1998) 57:365–373.
   Google Scholar
• YOKOYAMA K, TROBRIDGE P, BUCKNER FS, VAN VOORHIS WC, STUART KD, GELD MH: Protein farnesyl-transferase from Trypanosoma brucei. J. Biol. Chem. (1998) 273:26497–26505.
   PubMed Web of Science ®Google Scholar
• SONODA K-H, SAKAMOTO T, YOSHIKAWA H, ASHIZUKAS, OHSHMS Y, KISHIHARA K: Inhibition of corneal inflammation by the topical use of ras farnesyltransfe-rase inhibitors: selective inhibition of macrophage localization. Invest. Ophthal Vis. Sci. (1998) 39:2245–2251.
   PubMedGoogle Scholar