Synthesis and biological activity of pseudopeptides inhibitors of Ras farnesyl transferase containing unconventional amino acids (533 views)
Farmaco (ISSN: 0014-827x), 1999 Nov; 54(11-12): 785-790.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 0.406, 5-year impact factor: 0
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0033433990&partnerID=40&md5=3a913fc65d28b0b55d70da160b2ca393
Keywords: Cellular In Vitro Activity, Phenol Derivative, Ras Farnesyltransferase Inhibitor, Protein Farnesyltransferase Inhibitor, Pseudopeptide, Amino Acid Sequence, Animal Cell, Antineoplastic Activity, Article, Cancer, Drug Synthesis, Nonhuman, Oncogene Ras, Structure Activity Relation, Alkyl And Aryl Transferases, Brain, Cattle, Cell Line, Transformed, Cell Survival, Enzyme Inhibitors,
Affiliations:
Dipto. Chim. Farmaceut. T., Univ. Napoli 'Federico II', Via D., Naples, Italy
Oncologia Sperimentale 'E', Ist. Naz. Tumori, Via M. S., Naples, Italy
References:
(1984) Eur. J. Biochem., 138, pp. 9-37. , Abbreviations follow the recommendations of the IUPAC-IUB Joint Commission on Biochemical Nomenclature for amino acids and peptide
Bos, J.L., (1989) Cancer Res., 49, pp. 4681-4689
Suarez, H.G., Du Villard, J.A., Severino, M., Caillou, B., Schlumberger, M., Tubiana, M., Parmentier, C., Monier, R., (1990) Oncogene, 5, pp. 565-570
Zhang, F.L., Casey, P.J., (1996) Annu. Rev. Biochem., 65, pp. 241-269
Kato, K., Cox, A.D., Hisaka, M.M., Graham, S.M., Buss, J.E., Der, C.J., (1992) Proc. Natl. Acad. Sci. USA, 89, pp. 6403-6407
Gibbs, J.B., (1991) Cell, 65, pp. 1-4
Schafer, W.R., Rine, J., (1992) Annu. Rev. Genet., 26, pp. 209-237
Sebti, S., Hamilton, A.D., (1997) Curr. Opin. Oncol., 9, pp. 557-561
Omer, C.A., Kohl, N.E., (1997) Trends Pharmacol. Sci., 18, pp. 437-444
Goldstein, J.L., Brown, M.S., Stradley, S.J., Reiss, Y., Gierasch, L.M., (1991) J. Biol. Chem., 266, pp. 15575-15578
Kohl, N.E., Mosser, S.D., DeSolms, S.J., Guiliani, E.A., Pompliano, D.L., Graham, S.L., Smith, R.L., Gibbs, J.B., (1993) Science, 260, p. 1934. , (b)
Graham, S.L., DeSolms, S.J., Guiliani, E.A., Kohl, N.E., Mosser, S.D., Oliff, A., Pompliano, D.L., Smith, R.L., (1994) J. Med. Chem., 37, p. 725. , (c)
Graham, S.L., (1995) Exp. Opin. Ther. Patents, 5, p. 1269. , (d)
Graham, S.L., Williams, T.M., (1996) Exp. Opin. Ther. Patents, 6, p. 1295. , (e)
Sebti, S.M., Hamilton, A.D., (1997) Pharacol. Ter., 74, p. 103. , (f)
Leonard, D.M., (1997) J. Med. Chem., 40, p. 2971. , (g)
Hunt, J.T., Lee, G.V., Leftheris, K., Seizinger, B., Carboni, J., Mabus, J., Ricca, C., Manne, V., (1996) J. Med. Chem., 39, p. 353
E. Merck & Co. Inc. WO9509001 (1995)Patel, D.V., Patel, M.M., Robinson, S.S., Gordon, E.M., (1994) Bioorg. Med. Chem. Lett., 4, p. 1883
Caliendo, G., Fiorino, F., Grieco, P., Perissutti, E., Santagada, V., Ramunno, A., Albrizio, S., Santelli, G., (1998) Eur. J. Med. Chem., p. 1998
Leftheris, K., Kline, T., Vite, G.D., Cho, Y.H., Bhide, R.S., Patel, D.V., Patel, M.M., Manne, V., (1996) J. Med. Chem., 39, p. 224
Byk, G., Lelievre, Y., Duchesne, M., Clerc, F.F., Scherman, D., Guitton, J.D., (1997) Bioorg. Med. Chem., 5, pp. 115-124
Vincent, M., Remond, G., Portevin, B., Serkiz, B., Laubie, M., (1982) Tetrahedron Lett., 23, pp. 1677-1680
Teetz, V., Geiger, R., Gaul, H., (1984) Tetrahedron Lett., 25, pp. 4479-4482
Knorr, R., Trzeciak, A., Bannwarth, W., Gllessen, D., (1989) Tetrahedron Lett., 30, pp. 1927-1930
Kowalczyk, J.J., Ackermann, K., Garcia, A.M., Lewis, M.D., (1995) Bioorg. Med. Chem. Lett., 5, pp. 3073-3078
Hagiwara, D., Miyake, H., Morimoto, H., Murai, M., Fujii, T., Matsuo, M., (1992) J. Med. Chem., 35, pp. 3184-3191
Reiss, Y., Goldstein, J.L., Seabra, M.C., Casey, P.J., Brown, M.S., (1990) Cell, 62, pp. 81-88
Fusco, A., Berlingieri, M.T., Di Fiore, P.P., Portella, G., Grieco, M., Vecchio, G., (1987) Mol. Cell. Biol., 7, pp. 3365-3370
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Boyd, M.R., (1990) J. Natl. Cancer Inst., 82, pp. 1107-1112
Marsters, J.C., McDowell, R.S., Reynolds, M.E., Oare, D.A., Somers, T.C., Stanley, M.S., Rawson, T.E., Tom, J., (1994) J. Bioorg. Med. Chem., 2, pp. 949-957
Clerc, F.F., Guitton, J.L., Fromage, M., Lelievre, Y., Duchesne, M., Tocque, B., James-Surcouf, E., Becauart, J., (1995) Bioorg. Med. Chem. Lett., 5, pp. 1779-1784
Bos, J. L., (1989) Cancer Res., 49, pp. 4681-4689
Suarez, H. G., Du Villard, J. A., Severino, M., Caillou, B., Schlumberger, M., Tubiana, M., Parmentier, C., Monier, R., (1990) Oncogene, 5, pp. 565-570
Zhang, F. L., Casey, P. J., (1996) Annu. Rev. Biochem., 65, pp. 241-269
Kato, K., Cox, A. D., Hisaka, M. M., Graham, S. M., Buss, J. E., Der, C. J., (1992) Proc. Natl. Acad. Sci. USA, 89, pp. 6403-6407
Gibbs, J. B., (1991) Cell, 65, pp. 1-4
Schafer, W. R., Rine, J., (1992) Annu. Rev. Genet., 26, pp. 209-237
Omer, C. A., Kohl, N. E., (1997) Trends Pharmacol. Sci., 18, pp. 437-444
Goldstein, J. L., Brown, M. S., Stradley, S. J., Reiss, Y., Gierasch, L. M., (1991) J. Biol. Chem., 266, pp. 15575-15578
Kohl, N. E., Mosser, S. D., DeSolms, S. J., Guiliani, E. A., Pompliano, D. L., Graham, S. L., Smith, R. L., Gibbs, J. B., (1993) Science, 260, p. 1934. , (b)
Graham, S. L., DeSolms, S. J., Guiliani, E. A., Kohl, N. E., Mosser, S. D., Oliff, A., Pompliano, D. L., Smith, R. L., (1994) J. Med. Chem., 37, p. 725. , (c)
Graham, S. L., (1995) Exp. Opin. Ther. Patents, 5, p. 1269. , (d)
Graham, S. L., Williams, T. M., (1996) Exp. Opin. Ther. Patents, 6, p. 1295. , (e)
Sebti, S. M., Hamilton, A. D., (1997) Pharacol. Ter., 74, p. 103. , (f)
Leonard, D. M., (1997) J. Med. Chem., 40, p. 2971. , (g)
Hunt, J. T., Lee, G. V., Leftheris, K., Seizinger, B., Carboni, J., Mabus, J., Ricca, C., Manne, V., (1996) J. Med. Chem., 39, p. 353
Kowalczyk, J. J., Ackermann, K., Garcia, A. M., Lewis, M. D., (1995) Bioorg. Med. Chem. Lett., 5, pp. 3073-3078
Marsters, J. C., McDowell, R. S., Reynolds, M. E., Oare, D. A., Somers, T. C., Stanley, M. S., Rawson, T. E., Tom, J., (1994) J. Bioorg. Med. Chem., 2, pp. 949-957
Clerc, F. F., Guitton, J. L., Fromage, M., Lelievre, Y., Duchesne, M., Tocque, B., James-Surcouf, E., Becauart, J., (1995) Bioorg. Med. Chem. Lett., 5, pp. 1779-1784
Farmaco (ISSN: 0014-827x), 1999 Nov; 54(11-12): 785-790.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 0.406, 5-year impact factor: 0
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0033433990&partnerID=40&md5=3a913fc65d28b0b55d70da160b2ca393
Keywords: Cellular In Vitro Activity, Phenol Derivative, Ras Farnesyltransferase Inhibitor, Protein Farnesyltransferase Inhibitor, Pseudopeptide, Amino Acid Sequence, Animal Cell, Antineoplastic Activity, Article, Cancer, Drug Synthesis, Nonhuman, Oncogene Ras, Structure Activity Relation, Alkyl And Aryl Transferases, Brain, Cattle, Cell Line, Transformed, Cell Survival, Enzyme Inhibitors,
Affiliations:
Dipto. Chim. Farmaceut. T., Univ. Napoli 'Federico II', Via D., Naples, Italy
Oncologia Sperimentale 'E', Ist. Naz. Tumori, Via M. S., Naples, Italy
References:
(1984) Eur. J. Biochem., 138, pp. 9-37. , Abbreviations follow the recommendations of the IUPAC-IUB Joint Commission on Biochemical Nomenclature for amino acids and peptide
Bos, J.L., (1989) Cancer Res., 49, pp. 4681-4689
Suarez, H.G., Du Villard, J.A., Severino, M., Caillou, B., Schlumberger, M., Tubiana, M., Parmentier, C., Monier, R., (1990) Oncogene, 5, pp. 565-570
Zhang, F.L., Casey, P.J., (1996) Annu. Rev. Biochem., 65, pp. 241-269
Kato, K., Cox, A.D., Hisaka, M.M., Graham, S.M., Buss, J.E., Der, C.J., (1992) Proc. Natl. Acad. Sci. USA, 89, pp. 6403-6407
Gibbs, J.B., (1991) Cell, 65, pp. 1-4
Schafer, W.R., Rine, J., (1992) Annu. Rev. Genet., 26, pp. 209-237
Sebti, S., Hamilton, A.D., (1997) Curr. Opin. Oncol., 9, pp. 557-561
Omer, C.A., Kohl, N.E., (1997) Trends Pharmacol. Sci., 18, pp. 437-444
Goldstein, J.L., Brown, M.S., Stradley, S.J., Reiss, Y., Gierasch, L.M., (1991) J. Biol. Chem., 266, pp. 15575-15578
Kohl, N.E., Mosser, S.D., DeSolms, S.J., Guiliani, E.A., Pompliano, D.L., Graham, S.L., Smith, R.L., Gibbs, J.B., (1993) Science, 260, p. 1934. , (b)
Graham, S.L., DeSolms, S.J., Guiliani, E.A., Kohl, N.E., Mosser, S.D., Oliff, A., Pompliano, D.L., Smith, R.L., (1994) J. Med. Chem., 37, p. 725. , (c)
Graham, S.L., (1995) Exp. Opin. Ther. Patents, 5, p. 1269. , (d)
Graham, S.L., Williams, T.M., (1996) Exp. Opin. Ther. Patents, 6, p. 1295. , (e)
Sebti, S.M., Hamilton, A.D., (1997) Pharacol. Ter., 74, p. 103. , (f)
Leonard, D.M., (1997) J. Med. Chem., 40, p. 2971. , (g)
Hunt, J.T., Lee, G.V., Leftheris, K., Seizinger, B., Carboni, J., Mabus, J., Ricca, C., Manne, V., (1996) J. Med. Chem., 39, p. 353
E. Merck & Co. Inc. WO9509001 (1995)Patel, D.V., Patel, M.M., Robinson, S.S., Gordon, E.M., (1994) Bioorg. Med. Chem. Lett., 4, p. 1883
Caliendo, G., Fiorino, F., Grieco, P., Perissutti, E., Santagada, V., Ramunno, A., Albrizio, S., Santelli, G., (1998) Eur. J. Med. Chem., p. 1998
Leftheris, K., Kline, T., Vite, G.D., Cho, Y.H., Bhide, R.S., Patel, D.V., Patel, M.M., Manne, V., (1996) J. Med. Chem., 39, p. 224
Byk, G., Lelievre, Y., Duchesne, M., Clerc, F.F., Scherman, D., Guitton, J.D., (1997) Bioorg. Med. Chem., 5, pp. 115-124
Vincent, M., Remond, G., Portevin, B., Serkiz, B., Laubie, M., (1982) Tetrahedron Lett., 23, pp. 1677-1680
Teetz, V., Geiger, R., Gaul, H., (1984) Tetrahedron Lett., 25, pp. 4479-4482
Knorr, R., Trzeciak, A., Bannwarth, W., Gllessen, D., (1989) Tetrahedron Lett., 30, pp. 1927-1930
Kowalczyk, J.J., Ackermann, K., Garcia, A.M., Lewis, M.D., (1995) Bioorg. Med. Chem. Lett., 5, pp. 3073-3078
Hagiwara, D., Miyake, H., Morimoto, H., Murai, M., Fujii, T., Matsuo, M., (1992) J. Med. Chem., 35, pp. 3184-3191
Reiss, Y., Goldstein, J.L., Seabra, M.C., Casey, P.J., Brown, M.S., (1990) Cell, 62, pp. 81-88
Fusco, A., Berlingieri, M.T., Di Fiore, P.P., Portella, G., Grieco, M., Vecchio, G., (1987) Mol. Cell. Biol., 7, pp. 3365-3370
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Boyd, M.R., (1990) J. Natl. Cancer Inst., 82, pp. 1107-1112
Marsters, J.C., McDowell, R.S., Reynolds, M.E., Oare, D.A., Somers, T.C., Stanley, M.S., Rawson, T.E., Tom, J., (1994) J. Bioorg. Med. Chem., 2, pp. 949-957
Clerc, F.F., Guitton, J.L., Fromage, M., Lelievre, Y., Duchesne, M., Tocque, B., James-Surcouf, E., Becauart, J., (1995) Bioorg. Med. Chem. Lett., 5, pp. 1779-1784
Bos, J. L., (1989) Cancer Res., 49, pp. 4681-4689
Suarez, H. G., Du Villard, J. A., Severino, M., Caillou, B., Schlumberger, M., Tubiana, M., Parmentier, C., Monier, R., (1990) Oncogene, 5, pp. 565-570
Zhang, F. L., Casey, P. J., (1996) Annu. Rev. Biochem., 65, pp. 241-269
Kato, K., Cox, A. D., Hisaka, M. M., Graham, S. M., Buss, J. E., Der, C. J., (1992) Proc. Natl. Acad. Sci. USA, 89, pp. 6403-6407
Gibbs, J. B., (1991) Cell, 65, pp. 1-4
Schafer, W. R., Rine, J., (1992) Annu. Rev. Genet., 26, pp. 209-237
Omer, C. A., Kohl, N. E., (1997) Trends Pharmacol. Sci., 18, pp. 437-444
Goldstein, J. L., Brown, M. S., Stradley, S. J., Reiss, Y., Gierasch, L. M., (1991) J. Biol. Chem., 266, pp. 15575-15578
Kohl, N. E., Mosser, S. D., DeSolms, S. J., Guiliani, E. A., Pompliano, D. L., Graham, S. L., Smith, R. L., Gibbs, J. B., (1993) Science, 260, p. 1934. , (b)
Graham, S. L., DeSolms, S. J., Guiliani, E. A., Kohl, N. E., Mosser, S. D., Oliff, A., Pompliano, D. L., Smith, R. L., (1994) J. Med. Chem., 37, p. 725. , (c)
Graham, S. L., (1995) Exp. Opin. Ther. Patents, 5, p. 1269. , (d)
Graham, S. L., Williams, T. M., (1996) Exp. Opin. Ther. Patents, 6, p. 1295. , (e)
Sebti, S. M., Hamilton, A. D., (1997) Pharacol. Ter., 74, p. 103. , (f)
Leonard, D. M., (1997) J. Med. Chem., 40, p. 2971. , (g)
Hunt, J. T., Lee, G. V., Leftheris, K., Seizinger, B., Carboni, J., Mabus, J., Ricca, C., Manne, V., (1996) J. Med. Chem., 39, p. 353
Kowalczyk, J. J., Ackermann, K., Garcia, A. M., Lewis, M. D., (1995) Bioorg. Med. Chem. Lett., 5, pp. 3073-3078
Marsters, J. C., McDowell, R. S., Reynolds, M. E., Oare, D. A., Somers, T. C., Stanley, M. S., Rawson, T. E., Tom, J., (1994) J. Bioorg. Med. Chem., 2, pp. 949-957
Clerc, F. F., Guitton, J. L., Fromage, M., Lelievre, Y., Duchesne, M., Tocque, B., James-Surcouf, E., Becauart, J., (1995) Bioorg. Med. Chem. Lett., 5, pp. 1779-1784
Synthesis and biological activity of pseudopeptides inhibitors of Ras farnesyl transferase containing unconventional amino acids
A study was performed on the structure-activity relationships of a series of phenol derivatives, CVFM analogs, derived from the two most active compounds of a first series (1(A) and 1(B)) of inhibitors of Ras farnesyl transferase (FTase) that we have recently described. We report the synthesis and the activity of a second series of compounds in which the phenylalanine residue was replaced by unconventional aromatic and non-aromatic amino acids, with varying electronic, lipophilic, steric and conformational properties. The compounds showed to be significantly less active than reference compounds against FT, with the only exception of derivative 3(A) (IC50 = 3 mu M), which is slightly more active than 1(A) but not 1(B). Subsequently we tested the effects of compounds 1(A), 1(B) and 3(A), 3(B) on the anchorage-dependent growth of two epithelial cell lines of rats, FRTL-5 and the same line v-aa-ras transformed. Compound 3, derived from lead compound 1(A), showed an appreciable selectivity against transformed cells. In contrast, compounds derived from derivative 1(B) had only a modest cellular activity. (C) 1999 Elsevier Science S.A. All rights reserved.
A study was performed on the structure-activity relationships of a series of phenol derivatives, CVFM analogs, derived from the two most active compounds of a first series (1(A) and 1(B)) of inhibitors of Ras farnesyl transferase (FTase) that we have recently described. We report the synthesis and the activity of a second series of compounds in which the phenylalanine residue was replaced by unconventional aromatic and non-aromatic amino acids, with varying electronic, lipophilic, steric and conformational properties. The compounds showed to be significantly less active than reference compounds against FT, with the only exception of derivative 3(A) (IC50 = 3 mu M), which is slightly more active than 1(A) but not 1(B). Subsequently we tested the effects of compounds 1(A), 1(B) and 3(A), 3(B) on the anchorage-dependent growth of two epithelial cell lines of rats, FRTL-5 and the same line v-aa-ras transformed. Compound 3, derived from lead compound 1(A), showed an appreciable selectivity against transformed cells. In contrast, compounds derived from derivative 1(B) had only a modest cellular activity. (C) 1999 Elsevier Science S.A. All rights reserved.
Synthesis and biological activity of pseudopeptides inhibitors of Ras farnesyl transferase containing unconventional amino acids
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Synthesis and biological activity of pseudopeptides inhibitors of Ras farnesyl transferase containing unconventional amino acids
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* Carbonic anhydrase IX: Biochemical and crystallographic characterization of a novel antitumor target (398 views)
Bba-Gen Subjects (ISSN: 1570-9639, 0006-3002, 0925-4439), 2010 Feb; 1804(2): 404-409.
Impact Factor: 2.773
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Arena G, Casnati A, Contino A, Magrì A, Sansone F, Sciotto D, Ungaro R
* Inclusion of naturally occurring amino acids in water soluble calix[4]arenes: A microcalorimetric and 1H NMR investigation supported by molecular modeling (388 views)
Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2006 Jan 21; 4(2): 243-249.
Impact Factor: 2.874
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Menchise V, De Simone G, Tedeschi T, Corradini R, Sforza S, Marchelli R, Capasso D, Saviano M, Pedone C
* Insights into peptide nucleic acid (PNA) structural features: The crystal structure of a D-lysine-based chiral PNA-DNA duplex (519 views)
P Natl Acad Sci Usa (ISSN: 0027-8424, 1091-6490, 0027-8424print), 2003 Oct 14; 100(21): 12021-12026.
Impact Factor: 10.272
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Borgatti M, Lampronti I, Romanelli A, Pedone C, Saviano M, Bianchi N, Mischiati C, Gambari R
* Transcription factor decoy molecules based on a peptide nucleic acid (PNA)-DNA chimera mimicking Sp1 binding sites (522 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 2003 Feb 28; 278(9): 7500-7509.
Impact Factor: 6.482
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Romano M, Giojelli A, Mainenti PP, Tamburrini O, Salvatore M
* Upper thoracic sympathetic chain neurolysis under CT guidance. A two year follow-up in patients with palmar and axillary hyperhidrosis (385 views)
Radiol Med (ISSN: 0033-8362, 1826-6983, 1826-6983electronic), 2002 Nov; 104(5-6): 421-425.
Impact Factor: 1.368
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Morelli G, De Luca S, Tesauro D, Saviano M, Pedone C, Dolmella A, Visentin R, Mazzi U
* CCK8 peptide derivatized with diphenylphosphine for rhenium labelling: Synthesis and molecular mechanics calculations (323 views)
J Pept Sci (ISSN: 1075-2617, 1099-1387, 1075-2617print), 2002 Jul; 8(7): 373-381.
Impact Factor: 1.691
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Monti SM, Ritieni A, Sacchi R, Skog K, Borgen E, Fogliano V
* Characterization of phenolic compounds in virgin olive oil and their effect on the formation of carcinogenic/mutagenic heterocyclic amines in a model system (612 views)
J Agric Food Chem (ISSN: 0021-8561), 2001 Sep; 49(8): 3969-3975.
Impact Factor: 1.576
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Garzillo AM, Colao MC, Buonocore V, Oliva R, Falcigno L, Saviano M, Santoro AM, Zappala R, Bonomo RP, Bianco C, Giardina P, Palmieri G, Sannia G
* Structural and kinetic characterization of native laccases from Pleurotas ostreatus, Rigidoporus lignosus, and Trametes trogii (456 views)
Journal Of Protein Chemistry (ISSN: 0277-8033), 2001 Apr; 20(3): 191-201.
Impact Factor: 1.021
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Fogliano V, Ritieni A, Monti SM, Gallo M, Della Medaglia D, Ambrosino ML, Sacchi R
Antioxidant activity of virgin olive oil phenolic compounds in a micellar system (301 views)
Journal Of The Science Of Food And Agriculture (ISSN: 0022-5142), 1999 Oct; 79(13): 1803-1808.
Impact Factor: 1.097
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13 Records (13 excluding Abstracts).
Total impact factor: 54.13 (54.13 excluding Abstracts).
Total 5 year impact factor: 47.989 (47.989 excluding Abstracts).
Total impact factor: 54.13 (54.13 excluding Abstracts).
Total 5 year impact factor: 47.989 (47.989 excluding Abstracts).
533 views. Last view on Thursday 02 March 2023, 4:04:10
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