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Volumn 45, Issue 4, 2010, Pages 1304-1313

Design, synthesis and evaluation of analogs of initiation factor 4E (eIF4E) cap-binding antagonist Bn7-GMP

Author keywords

Anticancer; Antifibrotic; CoMFA; CoMSIA; eIF4E; Translation initiation

Indexed keywords

[5 (2 AMINO 7 BENZYL 6 OXO 1H PURIN 1 IUM 9(6H) YL) 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 6 OXO 7 [3 (TRIFLUOROMETHYL)BENZYL] 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (2 CHLORO 5 FLUOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (2 CHLOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (2 FLUOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (2 METHYLBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (2,5 DICHLOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (3 CHLOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (3 FLUOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (3 METHOXYBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (3 METHYLBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (3 NITROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (4 CARBOXYBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (4 CHLOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (4 FLUOROBENZYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; [5 [2 AMINO 7 (NAPHTHALEN 2 YLMETHYL) 6 OXO 1H PURIN 1 IUM 9(6H) YL] 3,4 DIHYDROXYTETRAHYDROFURAN 2 YL]METHYLPHOSPHATE; GUANOSINE DERIVATIVE; INITIATION FACTOR 4E; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

EID: 77349115916     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.11.054     Document Type: Article
Times cited : (44)

References (40)
  • 1
    • 0030940199 scopus 로고    scopus 로고
    • Overexpression of eukaryotic initiation factor 4E (eIF4E) in breast Carcinoma
    • Li B.D.L., Liu L., Dawson M., and Benedetti A.D. Overexpression of eukaryotic initiation factor 4E (eIF4E) in breast Carcinoma. Cancer 79 (1997) 2385-2390
    • (1997) Cancer , vol.79 , pp. 2385-2390
    • Li, B.D.L.1    Liu, L.2    Dawson, M.3    Benedetti, A.D.4
  • 2
    • 0032054816 scopus 로고    scopus 로고
    • The mRNA 5′ cap-binding protein elF4E and control of cell growth
    • Gingrast N.S.a.A.-C. The mRNA 5′ cap-binding protein elF4E and control of cell growth. Curr. Opin. Cell Biol. 10 (1998) 268-275
    • (1998) Curr. Opin. Cell Biol. , vol.10 , pp. 268-275
    • Gingrast, N.S.a.A.-C.1
  • 3
    • 0033044355 scopus 로고    scopus 로고
    • eIF4E Expression in tumors: its possible role in progresstion of malignancies
    • Benedetti A.D., and Harris A.L. eIF4E Expression in tumors: its possible role in progresstion of malignancies. Int. J. Biochem. Cell Biol. 31 (1999) 59-72
    • (1999) Int. J. Biochem. Cell Biol. , vol.31 , pp. 59-72
    • Benedetti, A.D.1    Harris, A.L.2
  • 4
    • 2542506326 scopus 로고    scopus 로고
    • The mRNA cap-binding protein eIF4E in post-transcriptional gene expression
    • v.d. Haar T., Gross J.D., Wagner G., and McCarthy J.E.G. The mRNA cap-binding protein eIF4E in post-transcriptional gene expression. Nat. Struct. Mol. Biol. 11 (2004) 503-511
    • (2004) Nat. Struct. Mol. Biol. , vol.11 , pp. 503-511
    • v.d. Haar, T.1    Gross, J.D.2    Wagner, G.3    McCarthy, J.E.G.4
  • 6
    • 85047696004 scopus 로고    scopus 로고
    • Translation initiation and its deregulation during tumorigenesis
    • Watkins S.J., and Norbury C.J. Translation initiation and its deregulation during tumorigenesis. Br. J. Cancer 86 (2002) 1023-1027
    • (2002) Br. J. Cancer , vol.86 , pp. 1023-1027
    • Watkins, S.J.1    Norbury, C.J.2
  • 7
    • 0030808698 scopus 로고
    • Detection of the proto-oncogene eIF4E in surgical margins may predict recurrence in head and neck cancer
    • Nathan C.-A.O., Liu L., Li B.D., Abreo F.W., Nandy I., and De Benedetti A. Detection of the proto-oncogene eIF4E in surgical margins may predict recurrence in head and neck cancer. Oncogene 15 (1995) 579-584
    • (1995) Oncogene , vol.15 , pp. 579-584
    • Nathan, C.-A.O.1    Liu, L.2    Li, B.D.3    Abreo, F.W.4    Nandy, I.5    De Benedetti, A.6
  • 9
    • 0029070762 scopus 로고
    • Elevated levels of eukaryotic translation initiation factor eIF-4E, mRNA in a broad spectrum of transformed cell lines
    • Miyagi Y., Sugiyama A., Asai A., Okazaki T., Kuchino Y., and Kerr S.J. Elevated levels of eukaryotic translation initiation factor eIF-4E, mRNA in a broad spectrum of transformed cell lines. Cancer Lett. 91 (1995) 247-252
    • (1995) Cancer Lett. , vol.91 , pp. 247-252
    • Miyagi, Y.1    Sugiyama, A.2    Asai, A.3    Okazaki, T.4    Kuchino, Y.5    Kerr, S.J.6
  • 10
    • 0031800113 scopus 로고    scopus 로고
    • Differential expression of vascular endothelial growth factor mRNA vs. protein isoform expression in human breast cancer and relationship to eIF-4E, Br
    • Scott P.A.E., Smith K., Poulsom R., Benedetti A.D., Bicknell R., and Harris A.L. Differential expression of vascular endothelial growth factor mRNA vs. protein isoform expression in human breast cancer and relationship to eIF-4E, Br. J. Cancer 77 (1998) 2120-2128
    • (1998) J. Cancer , vol.77 , pp. 2120-2128
    • Scott, P.A.E.1    Smith, K.2    Poulsom, R.3    Benedetti, A.D.4    Bicknell, R.5    Harris, A.L.6
  • 11
    • 0033521868 scopus 로고    scopus 로고
    • Elevated expression of eIF4E in confined early breast cancer lesions: possible role of hypoxia
    • DeFatta R.J., Turbat-Herrera E.A., Li B.D., Anderson W., and Benedetti A.D. Elevated expression of eIF4E in confined early breast cancer lesions: possible role of hypoxia. Int. J. Cancer 80 (1999) 516-522
    • (1999) Int. J. Cancer , vol.80 , pp. 516-522
    • DeFatta, R.J.1    Turbat-Herrera, E.A.2    Li, B.D.3    Anderson, W.4    Benedetti, A.D.5
  • 14
    • 0030443685 scopus 로고    scopus 로고
    • The eIF4E-binding proteins 1 and 2 are negative regulators of cell growth
    • Rousseau D., Gingras A.C., Pause A., and Sonenberg N. The eIF4E-binding proteins 1 and 2 are negative regulators of cell growth. Oncogene 13 (1996) 2415-2420
    • (1996) Oncogene , vol.13 , pp. 2415-2420
    • Rousseau, D.1    Gingras, A.C.2    Pause, A.3    Sonenberg, N.4
  • 16
    • 0032577691 scopus 로고    scopus 로고
    • 4E-BP3, a new member of the eukaryotic initiation factor 4E-binding protein family
    • Poulin F., Gingras A.-C., Olsen H., Chevalier S., and Sonenberg N. 4E-BP3, a new member of the eukaryotic initiation factor 4E-binding protein family. J. Biol. Chem. (1998) 14002-14007
    • (1998) J. Biol. Chem. , pp. 14002-14007
    • Poulin, F.1    Gingras, A.-C.2    Olsen, H.3    Chevalier, S.4    Sonenberg, N.5
  • 17
    • 13444259647 scopus 로고    scopus 로고
    • Regulation of cap-dependent translation by eIF4E inhibitory proteins
    • Richter J.D., and Sonenberg N. Regulation of cap-dependent translation by eIF4E inhibitory proteins. Nature 433 (2005) 477-480
    • (2005) Nature , vol.433 , pp. 477-480
    • Richter, J.D.1    Sonenberg, N.2
  • 18
    • 0023124676 scopus 로고
    • Regulated phosphorylation and low abundance of HeLa cell initiation factor eIF-4F suggest a role in translational control. Heat shock effects on eIF-4F
    • Duncan R., Milburn S.C., and Hershey J.W.B. Regulated phosphorylation and low abundance of HeLa cell initiation factor eIF-4F suggest a role in translational control. Heat shock effects on eIF-4F. J. Biol. Chem. 262 (1987) 380-388
    • (1987) J. Biol. Chem. , vol.262 , pp. 380-388
    • Duncan, R.1    Milburn, S.C.2    Hershey, J.W.B.3
  • 19
    • 0024390833 scopus 로고
    • Inhibition of eukaryotic translation by nucleoside 5′-monophosphate analogues of mRNA 5′-Cap: changes in N7 substituent affect analogue activity
    • Darzynkiewicz E., Stepinski J., Ekiel I., Goyer C., Sonenberg N., Temeriusz A., Jin Y., Sijuwade T., Haber D., and Tahara S.M. Inhibition of eukaryotic translation by nucleoside 5′-monophosphate analogues of mRNA 5′-Cap: changes in N7 substituent affect analogue activity. Biochemistry 28 (1989) 4771-4778
    • (1989) Biochemistry , vol.28 , pp. 4771-4778
    • Darzynkiewicz, E.1    Stepinski, J.2    Ekiel, I.3    Goyer, C.4    Sonenberg, N.5    Temeriusz, A.6    Jin, Y.7    Sijuwade, T.8    Haber, D.9    Tahara, S.M.10
  • 21
    • 34547788872 scopus 로고    scopus 로고
    • Crystallographic and mass spectrometric characterisation of eIF4E with N7-alkylated cap derivatives
    • Brown C.J., McNae I., Fischer P.M., and Walkinshaw M.D. Crystallographic and mass spectrometric characterisation of eIF4E with N7-alkylated cap derivatives. J. Mol. Biol. 372 (2007) 7-15
    • (2007) J. Mol. Biol. , vol.372 , pp. 7-15
    • Brown, C.J.1    McNae, I.2    Fischer, P.M.3    Walkinshaw, M.D.4
  • 22
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effects of shape on binding of steroids to carrier proteins
    • Cramer R.D., Patterson D.E., and Bruce J.D. Comparative molecular field analysis (CoMFA). 1. Effects of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 110 (1988) 5959-5967
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer, R.D.1    Patterson, D.E.2    Bruce, J.D.3
  • 23
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe G., Abraham U., and Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J. Med. Chem. 37 (1994) 4130-4146
    • (1994) J. Med. Chem. , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 24
    • 0031226772 scopus 로고    scopus 로고
    • Empirical scoring functions: I. the development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes
    • Eldridge M.D., Murray C.W., Auton T.R., Paolini G.V., and Mee R.V. Empirical scoring functions: I. the development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J. Comput. Aided Mol. Des 11 (1997) 425-445
    • (1997) J. Comput. Aided Mol. Des , vol.11 , pp. 425-445
    • Eldridge, M.D.1    Murray, C.W.2    Auton, T.R.3    Paolini, G.V.4    Mee, R.V.5
  • 25
    • 45449104027 scopus 로고    scopus 로고
    • Expression, purification and characterization of recombinant mouse translation initiation factor eIF4E as a dihydrofolate reductase (DHFR) fusion protein
    • Ghosh P., Cheng J., Chou T.-F., Jia Y., Avdulov S., Bitterman P.B., Polunovsky V.A., and Wagner C.R. Expression, purification and characterization of recombinant mouse translation initiation factor eIF4E as a dihydrofolate reductase (DHFR) fusion protein. Protein Expr. Purif. 60 (2008) 132-139
    • (2008) Protein Expr. Purif. , vol.60 , pp. 132-139
    • Ghosh, P.1    Cheng, J.2    Chou, T.-F.3    Jia, Y.4    Avdulov, S.5    Bitterman, P.B.6    Polunovsky, V.A.7    Wagner, C.R.8
  • 27
    • 77349088306 scopus 로고    scopus 로고
    • T.I. SYBYL 7.1, 1699 South Hanley Rd., St. Louis, Missouri, 63144, (USA).
    • T.I. SYBYL 7.1, 1699 South Hanley Rd., St. Louis, Missouri, 63144, (USA).
  • 28
    • 0035829429 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship (3D-QSAR) models for a novel class of piperazine-based stromelysin-1 (MMP-3) Inhibitors: applying a "divide and conquer" strategy
    • Amin E.A., and Welsh W.J. Three-dimensional quantitative structure-activity relationship (3D-QSAR) models for a novel class of piperazine-based stromelysin-1 (MMP-3) Inhibitors: applying a "divide and conquer" strategy. J. Med. Chem. 44 (2001) 3849-3855
    • (2001) J. Med. Chem. , vol.44 , pp. 3849-3855
    • Amin, E.A.1    Welsh, W.J.2
  • 29
    • 33746893424 scopus 로고    scopus 로고
    • Highly predictive CoMFA and CoMSIA models for two series of stromelysin-1 (MMP-3) inhibitors elucidate S1′ and S1-S2′ binding modes
    • Amin E.A., and Welsh W.J. Highly predictive CoMFA and CoMSIA models for two series of stromelysin-1 (MMP-3) inhibitors elucidate S1′ and S1-S2′ binding modes. J. Chem. Inf. Model. 46 (2006) 1775-1783
    • (2006) J. Chem. Inf. Model. , vol.46 , pp. 1775-1783
    • Amin, E.A.1    Welsh, W.J.2
  • 31
  • 33
    • 33744961739 scopus 로고    scopus 로고
    • Stopped-flow kinetic analysis of eIF4E and phosphorylated eIF4E binding to cap analogs and capped oligoribonucleotides
    • Slepenkov S.V., Darzynkiewicz E., and Rhoads R.E. Stopped-flow kinetic analysis of eIF4E and phosphorylated eIF4E binding to cap analogs and capped oligoribonucleotides. J. Biol. Chem. 281 (2006) 14927-14938
    • (2006) J. Biol. Chem. , vol.281 , pp. 14927-14938
    • Slepenkov, S.V.1    Darzynkiewicz, E.2    Rhoads, R.E.3
  • 35
    • 65249127526 scopus 로고    scopus 로고
    • Partial charge calculation method affects CoMFA QSAR prediction accuracy
    • Mittal R.R., Harris L., McKinnon R.A., and Sorich M.J. Partial charge calculation method affects CoMFA QSAR prediction accuracy. J. Chem. Inf. Model. 49 (2009) 704-709
    • (2009) J. Chem. Inf. Model. , vol.49 , pp. 704-709
    • Mittal, R.R.1    Harris, L.2    McKinnon, R.A.3    Sorich, M.J.4
  • 36
    • 38849180436 scopus 로고    scopus 로고
    • Targeting the eukaryotic translation initiation factor 4E for cancer therapy
    • Graff J.R., Konicek B.W., Carter J.H., and Marcusson E.G. Targeting the eukaryotic translation initiation factor 4E for cancer therapy. Cancer Res. 68 (2008) 631-634
    • (2008) Cancer Res. , vol.68 , pp. 631-634
    • Graff, J.R.1    Konicek, B.W.2    Carter, J.H.3    Marcusson, E.G.4
  • 38
    • 0023653185 scopus 로고
    • Inhibition of eurkaryotic translation by analogues of messenger RNA 5′-cap: chemical and biological consequences of 5′-phosphate modifications of 7-methylguanosine 5′-monophosphate
    • Darzynkiewicz E., Ekiel I., Lassota P., and Tahara S.M. Inhibition of eurkaryotic translation by analogues of messenger RNA 5′-cap: chemical and biological consequences of 5′-phosphate modifications of 7-methylguanosine 5′-monophosphate. Biochemistry 26 (1987) 4372-4380
    • (1987) Biochemistry , vol.26 , pp. 4372-4380
    • Darzynkiewicz, E.1    Ekiel, I.2    Lassota, P.3    Tahara, S.M.4
  • 39
    • 0033774871 scopus 로고    scopus 로고
    • Mini-review: computational structure-based design of inhibitors that target protein surfaces
    • Zeng J. Mini-review: computational structure-based design of inhibitors that target protein surfaces. Comb. Chem. High Throughput Screen. 3 (2000) 355-362
    • (2000) Comb. Chem. High Throughput Screen. , vol.3 , pp. 355-362
    • Zeng, J.1


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