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Miscellaneous

Inhibitors of protein farnesylation 1998

Pages 553-569 | Published online: 25 Feb 2005

Bibliography

  • GRAHAM SL: Inhibitors of protein farnesylation: a new approach to cancer chemotherapy. Exp. Opin. Ther. Pat-ents (1995) 5 (1 2):1269–1285.
  • GRAHAM SL, WILLIAMS TM: Inhibitors of protein fame-sylation. Exp. Opin. Ther. Patents (1996) 6(12) :1295–1304.
  • OMER CA, KOHL NK: CA1A2X-competitive inhibitors of farnesyltransferase as anti-cancer agents. Trends Pharm. Sci (1997) 18:437–445.
  • SEPP-LORENZINO L, MA Z, RANDS E et al.: A peptidomi-metic inhibitor of farnesyl:protein transferase blocks the anchorage-dependent and independent growth of human tumor cell lines. CancerRes. (1995) 55:5302–5309.
  • •This study demonstrated that the antiproliferative effects of a PFTase inhibitor in a panel of human tumour cell lines are independent of ras mutational status.
  • LERNER EC, ZHANG T-T, KNOWLES DB et al.: Inhibition the prenylation of K-Ras, but not H- or N-Ras, is highly resistant to CaaX peptidomimetics and requires both a farnesyltransferase and a geranyl- I inhibitor in human tumor cell lines. Oncogene (1997) 15:1283–1288.
  • ••One of the first indications that cross-prenylation of K-Rasby PGGTase renders K- ras transformed cells highly resistant to the effects of PFTase inhibition.
  • KOHL NE, OMER CA, CONNER MW et al.: Inhibition of induces regression of mammary and salivary carcinomas in rastransgenic mice. Nature Med. (1995) 1:792–797.
  • ••The first study of a PFTase inhibitor in H-ras transgenic miceresulted in regression of the primary tumour mass.
  • BARRINGTON RE, SUBLER MA, RANDS E et al.: A farnesyl- inhibitor induces tumor regression in transgenic mice harboring multiple oncogenic muta-tions by mediating alterations in both cell cycle con-trol and apoptosis. Mol. Cell Biol. (1998) 18(0:85–92.
  • •A study demonstrating that cells with multiple genetic le-sions, such as are found in human cancer, are sensitive to the anti-proliferative effects of PFTase inhibitors.
  • LEBOWITZ PF, SAKAMURO D, PRENDERGAST GC: Fame-syl transferase inhibitors induce apoptosis of Ras-transformed cells denied substratum attachment. Can-cer Res. (1997) 57:708–713.
  • FOKSTUEN T, RABO YB, ZHOU J-N et al.: The Ras fame-sylation inhibitor BZA-5B increases the resistance to cisplatin in a human melanoma cell line. Anticancer Res. (1997) 17:2347–2352.
  • ROWELL CA, KOWALCZYK JJ, LEWIS MD, GARCIA AM: Di-rect demonstration of geranylgeranylation and fame-sylation of Ki-Ras in vivo. J. Biol. Chem. (1997) 272(22)14093–14097.
  • •The observation that K-Ras can be geranylgeranylated in vi-tro by PGGTase I is demonstrated to occur in vivo in cell cul-ture, under conditions where the farnesylation of K-Ras is suppressed by a PFTase inhibitor.
  • WHYTE DB, KIRSCHMEIER P, HOCKENBERRY TN et al.: K- N-Ras are geranylgeranylated in cells treated with farnesyl protein transferase inhibitors. J. Biol. Chem. (1997) 272 (22) :14459–14464.
  • •A second paper indicating that geranylgeranylation of K-Ras occurs in cell culture when protein farnesylation is blocked by a PFTase inhibitor.
  • THISSEN JA, GROSS JM, SUBRAMANIAN K, MEYER T, CA-SEY P: Prenylation-dependent association of Ki-Ras with microtubles. J. Biol. Chem. (1997) 272(48):30362–30370.
  • END D, SKRZAT S, DEVINE A et al.: R115777, a novel far-nesyl protein transferase inhibitor (PT): biochemical and cellular effects in H-Ras and K-Ras dominant sys-tems. Proc. Am. Assoc. Cancer Res. (1998) 39:270. Abstract 1847.
  • ZUJEWSKI J, HORAK ID, WOESTENBORGHS R et al.: Phase I trial of farnesyltransferase inhibitor, R115777, in advanced cancer. Proc. Am. Assoc. Cancer Res. (1998) 39:270. Abstract 1848.
  • ••Initial results from the first clinical trial of a PFTase inhibitor.
  • LUI M, LEE S, YAREMKO B et al.: SCH 66336, an orally tricyclic farnesyl protein transferase in-hibitor, demonstrates broad and potent in-vivo antitu-mor activity. Proc. Am. Assoc. Cancer Res. (1998) 39:270. Abstract 1843.
  • ••Characterisation of SCH 66336, a PFTase inhibitor that en-tered human clinical trials in late 1997.
  • COWSERT LM: In vitro and in vivo activity of antisense inhibitors of ras: potential for clinical development. Anti Cancer Drug Design (1997) 12:359–371.
  • GIBBS JB, GRAHAM SL, HARTMAN GD et al.: Farnesyl-transferase inhibitors versus Ras inhibitors. Curr. Opin. Chem. Biol. (1997) 1(2):197–203.
  • COX AD, DER CJ: Farnesyltransferase inhibitors and cancer treatment: targeting simply Ras? Biochim. Bio-phys. Acta (1997) 1333:F51–F71.
  • LEBOWITZ PF, CASEY PJ, PRENDERGAST GC, THISSEN JA:Farnesyltransferase inhibitors alter the prenylation and growth-stimulating function of Rho-B. J. Biol. Chem. (1997) 272(25):15591–15594.
  • •Evidence that RhoB is a PFTase substrate involved with cell proliferation.
  • FOSTER R, HU K-Q, LU Y, NOLAN KM, THISSAN J, SETTLE-MAN J: Identification of a novel human Rho-protein with unusual properties - GTPase deficiency and in vivo farnesylation. Mol. Cell. Biol. (1996) 16(6)2689–2699.
  • YAMAGATA K, SANDERS LK, KAUFMAN WE et al.: RheB, agrowth factor-regulated and synaptic activity-regulated gene, encodes a novel Ras-related protein. J. Biol. Chem. (1994) 269(23) :16333–16339.
  • CLARK GJ, KINCH MS, ROGERSGRAHAM K et al.: The Ras-related protein RheB is farnesylated and antagonizes Ras signalling and transformation. J. Biol. Chem. (1997) 272(16):10608–10615.
  • DIAMOND RH, CRESSMAN DE, LAZ TM, ABRAMS CS, TAUB R: PRL-1, a unique nuclear-protein tyrosine phosphatase, affects cell-growth. Mol. Cell. Biol. (1994) 14(6)3752–3762.
  • CATES CA, MICHAEL RL, STAYBROOK KR et al.: Prenyla-tion of oncogenic human PTPCAAX protein-tyrosine phosphatases. Cancer Lett. (1996) 110:49–55.
  • DE SMEDT F, BOOM A, PESESSE X et al. Posttransla- modification of human brain-type-I inosito1-1,4,5-trisphosphate 5-phosphatase by farne-. j Biol Chem. (1996) 271 (17) 10419–10424
  • PARK H-W, BODULURI SR, MOOMAW JF, CASEY PJ, BEESE: Crystal structure of protein farnesyltransferase at 2.25 angstrom resolution. Science (1997) 275:1800–1804.
  • ••The first crystal structure determination of PFTase.
  • PARK H-W, BEESE LS: Protein farnesyltransferase. Curr. Opin. Struct. Biol. (1997) 7:873–880.
  • KRAL AM, DIEHL RE, DESOLMS SJet al: Mutational analy-sis of conserved residues of the 6-subunit of human farnesyl:proteintransferase. J. Biol. Chem. (1997) 272(43)27319–27323.
  • LEONARD DM: Ras farnesyltransferase - a new thera-peutic target. J. Med. Chem. (1997) 40(19):2971–2990.
  • REUVENI H, GITLER A, PORADOSU E, GILON C, LEVITZKI A: Synthesis and biological activity of semipeptoid far-nesyltransferase inhibitors. Bioorg. Med. Chem. (1997) 5 (1):85–92.
  • BURNS CJ, GUITTON J-D, BAUDOIN B et al.: Novel con-formationally extended napthalene-based inhibitors of farnesyltransferase. J. Med. Chem. (1997) 40 (12) :1763–1767.
  • CLERC F-F, GUITTON J-D, FROMAGE N et al.: Constrained analogs of KCVFM with improved inhibitory proper-ties against farnesyl transferase. Bioorg. Med. Chem. Lett. (1995) 5(16):1779–1784.
  • QIAN Y, BLASKOVICH MA, SALEEM M et al.: Design and structural requirements of potent peptidomimetic in-hibitors of p21Ras farnesyltransferase. J. Biol. Chem. (1994) 269:12410–12413.
  • QIAN Y, BLASKOVICH MA, SEONG CM et al.: Peptidomi-metic inhibitors of p21Ras farnesyltransferase: hydro-phobic functionalization leads to disruption of p21Ras membrane association in whole cells. Bioorg. Med. Chem. Lett. (1994) 4(20:2579–2584.
  • BYK G, LELIEVRE Y, DUCHESNE M et al.: Synthesis and conformational analysis of peptide inhibitors of far-nesyltransferase. Bioorg. Med. Chem. (1997) 5 (1) :115–124.
  • BYK G, DUCHESNE M, PARKER F et al.: Local constrained shifty pseudopeptides inhibitors of ras-farnesyl trans-ferase. Bioorg. Med. Chem. Lett. (1995) 5(22):2677–2682.
  • LEFTHERIS K: Highly potent thiol-based inhibitors of Ras farnesyl protein transferase. 25th National Medici-nal Chemistry Symposium. Ann Arbor, MI, USA (1996).
  • STOBER P, SCHELHAAS M, NAGELE E et al.: Synthesis of characteristic lipopeptides of the human N-Ras pro-tein and their evalution as possible inhibitors of pro-tein farnesyl transferase. Bioorg. Med. Chem. (1997) 5 (1):75–83.
  • DINSMORE CJ, WILLIAMS TM, HAMILTON K et al.: Diary-lether inhibitors of farnesyl-protein transferase. Bioorg. Med. Chem. Lett. (1997) 7(101345–1348.
  • VOGT A, YIMIN Q, BLASKOVICH MA eta].: A non-peptide mimic of Ras-CaaX: selective inhibition of farnesyl-transferase and Ras processing. J. Biol. Chem. (1995) 270(2):660–664.
  • QIAN Y, VOGT A, SEBTI SM, HAMILTON AD: Design and synthesis of non-peptide Ras CAAX mimetics as potent farneysltransferase inhibitors. J. Med. Chem. (1996) 39:217–223.
  • MALLAMS AK, NJOROGE FG, DOLL RJ et al.: Antitumor 8-chlorobenzocycloheptapyridines: a new class of selec-tive, non-peptidic, nonsulfhydryl inhibitors of Ras far-nesylation. Bioorg. Med. Chem. (1997) 5(0:93–99.
  • NJOROGE FG, DOLL RJ, VIBULBHAN V: Discovery of novel nonpeptide tricyclic inhibitors of Ras farnesyl protein transferase. Bioorg. Med. Chem. (1997) 5(1):101–113.
  • MALLAMS AK, ROSSMAN RR, DOLL RJ et al: Inhibitors of farnesyl protein transferase. part 2. 4-amido-, 4-carbamoyl and 4-carboxamido derivatives of 143-bromo-8-chloro-6,11-dihydro-511-benz o [5,6]cyclo-hepta[1,2-b]pyridin-11-y1) piperazine. 214th National American Chemical Society Meeting. Las Vegas, NV (Sept. 7–11 1997).
  • NJOROGE FG, VIBULBHAN B, ALVAREZ CS: Novel tricyc-lic aminoacetyl and sulfonamide inhibitors of Ras far-nesyl protein transferase. Bioorg. Med. Chem. Lett. (1996) 6(24)2977–2982.
  • LEONARD DM, SHULER KR, POULTER CJ et al. Structure- relationships of cysteine-lacking pentapeptide derivatives that inhibit Ras farnesyltransferase. J. Med. Chem. (1997) 40(2):192–200.
  • SCHOLTEN JD, ZIMMERMAN KK, OXENDER MG et al. between anions and farnesyldiphosphate competitive inhibitors of farnesyl:protein transferase. J. Biol. Chem. (1997) 272 (29) 18077–18081
  • SCHOLTEN JD, ZIMMERMAN K, OXENDER M eta].: Inhibi-tors of farnesyl: protein transferase - a possible chemo-therapeutic. Bioorg. Merl. Chem. (1996) 4 (9) :1537–1543.
  • MCNAMARA DJ, DOBRUSIN E, LEONARD DM et al.: C-Terminal modifications of histidyl-N-benzylglycin-amides to give improved inhibition of ras farnesyl-transferase, cellular activity, and anticancer activity in mice. J. Med. Chem. (1997) 40(20:3319–3322.
  • WALLACE A, KOBLAN KS, HAMILTON K et al.: Selection of potent inhibitors of farnesyl-protein transferase from a synthetic tetrapeptide combinatorial library. J. Biol. Chem. (1996) 271(49):31306–31311.
  • GAON I, TUREK TC, DISTEFANO MD: Farnesyl and gera-nylgeranyl pyrophosphate analogs incorporating benzoylbenzyl ethers: synthesis and inhibition of yeast protein farnesyltransferase. Tetrahedron Lett. (1996) 37 (49):8833–8836.
  • TUREK TC, GAON I, DISTEFANO MD: Analogs of farnesyl pyrophosphate incorporting internal benzoylbenzo-ate esters: synthesis, inhibition kinetics and photoin-activation of yeast protein farnesyltransferase. Tetrahedron Lett. (1996) 37(28):4845–4848.
  • GAON I, TUREK TC, WELLER VA et al.: Photoactive ana-logs of farnesyl pyrophosphate containing benzoyl-benzoate esters: synthesis and application to photoaffinity labeling of yeast protein farnesyltrans-ferase. J. Org. Chem. (1996) 61(22):7738–7745.
  • CROTEAU R, ALONSO WR, KOEPP AE, SHIM JH, CANE D: Irreversible inactivation of monoterpene cyclases by a mechanism-based inhibitor. Arch. Biochem. Biophys. (1993) 307(2) 397–404.
  • GIBBS RA, KRISHNAN U, DOLENCE JM, POULTER CD: A stereoselective palladium copper-catalyzed route to isoprenoids - synthesis and biological evaluation of 13-methylidenefarnesyl diphosphate. J. Org. Chem. (1995) 60(24):7821–7829.
  • MU YQ, GIBBS RA, EUBANKS LM, POULTER CD: Cuprate-Mediated synthesis and biological evaluation of- and tert-butylfarnesyl diphosphate ana-logs. J. Org. Chem. (1996) 61(23):8010–8015.
  • LINGHAM RB, SILVERMAN KC, BILLS GF et al.: Chae-tomella acutiseta produces chaetomellic acids A and B which are reversible inhibitors of farnesyl-protein transferase. App. Microbiol. Biotech. (1993) 40(2–3)370–374.
  • SINGH SB, ZINK DL, LIESCH JM etal. Isolation and struc- of chaetomellic acids A and B from chaetomella acutisetafarnesyl pyrophosphate mimic inhibitors of Ras farnesylprotein transferase. Tetrahedron (1993) 49(27)5917–5926.
  • RATEMI ES, DOLENCE JM, POULTER CD, VEDERAS JC:Synthesis of protein farnesyltransferase and protein geranylgeranyltransferase inhibitors: rapid access to chaetomellic acid A and its analogues. J. Org. Chem. (1996) 61 (18):6296–6301.
  • JAYASURIYA H, BILLS GF, CASCALES C et al.: Oreganicacid: a potent novel inhibitor of Ras farnesyl-protein transferase from an endophytic fungus. Bioorg. Med. Chem. Lett. (1996) 6(17):2081–2084.
  • SILVERMAN KC, JAYASURIYA H, CASCALES C et al:Oreganic acid, a potent inhibitor of Ras farnesyl-protein transferase. Biochem. Biophys. Res. Comm. (1997) 232(2)478–481.
  • KAMINSKI JJ, RANE DF, SNOW ME et al. Identification of farneyl protein transferase inhibitors using three-dimensional database searching methods. J. Med. Chem. (1997) 40(25):4103–4112.
  • UCHIDA R, SHIOMI K, INOKOSHI J et al.: Kurasoins A andB, new protein farnesyltransferase inhibitors pro-duced by Paecilomyces sp. FO-3684. I. producing strain, fermentation, isolation, and biological activi-ties. J. Antibiot. (1996) 49(9):932–934.
  • UCHIDA R, SHIOMI K, SUNAZUKA T et al: Kurasoins Aand B, new protein farnesyltransferase inhibitors pro-duced by Paecilomyces sp. F0-3684. II. Structure eluci-dation and total synthesis. J. Antibiot. (1996) 49(9)886–889.
  • SUNAZUKA T, HIROSE T, ZHI-MING T et al.: Synthesisand absolute structures of novel protein farnesyltrans-ferase inhibitors, kurasoins A and B. J. Antibiot. (1997) 50(5)453–455.
  • SINGH SB, BALL RG, BILLS GF et al.: Chemistry and biol-ogy of cylindrols: novel inhibitors of Ras farnesyl-protein transferase from Cylindrocarpon lucidum. J. Org. Chem. (1996) 61(22)7727–7737.
  • DABRAH TT, HARWOOD HJ, HUANG LH et al.: CP-225,917 and CP-263,114, novel Ras farnesylation in-hibitors from an unidentified fungus. I. Taxonomy, fermentation, isolation, and biochemical properties. J. Antibiot. (1997) 50(1):1–6.
  • KWON B-M, LEE S-H, KIM K-S et al: Rhombenone: fame-syl protein transferase inhibitor from the leaves of Hedera Rhombea bean. Bioorg. Med. Chem. Lett. (1997) 7 (8):971–974.
  • UCHIDA R, SHIOMI K, INOKOSHI J, TANAKA H, IWAI Y, OMURA S: Andrastatin D, novel protein farnesyltrans-ferase inhibitor produced by Penicillium sp. FO-3929. Antibiot. (1996) 49:1278–1280.
  • BERNHARD EJ, KAO G, COX AD et al.: The farnesyltrans-ferase inhibitor FTI-277 radiosensitizes H-Ras-transformed rat embryo fibroblasts. Cancer Res. (1996) 56:1727–1730.
  • VOGT A, QUIAN Y, MCGUIRE TF, HAMILTON AD, SEBTI SM: Protein geranylgeranylation, not farnesylation, is required for the Gi to S phase transition in mouse fi-broblasts. Oncogene (1996) 13:1991–1999.
  • VOGT A, SUN J, QUIAN Y, HAMILTON AD, SEBTI SM: The geranylgeranyltransferase-I inhibitor GGTI-298 ar- human tumor cells in Go/GI and induces pnwAniciPtisun a p53-independent manner. J. Biol.. (1997) 272(43):27224–27229.
  • MIQUEL K, PRADINES A, SUN J et al: GGTI-298 induces Go-Gi block and apoptsis whereas FTI-277 causes G2-M enrichment in A549 cells. Cancer Res. (1997) 57:1846–1850.

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