Preliminary studies of new proteasome inhibitors in the tumor targeting approach: Synthesis and in vitro cytotoxicity

Journal of Medicinal Chemistry

Volumn 48, Issue 21, 2005, Pages 6731-6740

  Vivier, Magali ^a   Jarrousse, Anne Sophie ^a   Bouchon, Bernadette ^a   Galmier, Marie Josephe ^a   Auzeloux, Philippe ^a   Sauzieres, Jacques ^b   Madelmont, Jean Claude ^a  

^a INSERM   (France)

^b OTL Pharma   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL; BORTEZOMIB; EPOXIMICIN; N (2 DIETHYLAMINOETHYL)BENZAMIDE DERIVATIVE; N1 (DIETHYLAMINO)ETHYL N4 [4 METHYL 1 [4 METHYL 1 (4 METHYL 1 OXOPENTAN 2 YLAMINO) 1 OXOPENTAN 2 YLAMINO] 1 OXOPENTAN 2 YL]TEREPHTHALAMIDE; PROTEASOME INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CATALYSIS; CHEMICAL COMPOSITION; CONTROLLED STUDY; DRUG CYTOTOXICITY; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME INHIBITOR INTERACTION; FLUORESCENCE ACTIVATED CELL SORTING; HUMAN; HUMAN CELL; IC 50; MELANOMA CELL; PEPTIDE SYNTHESIS; UBIQUITINATION; WESTERN BLOTTING;

ALDEHYDES; ANTINEOPLASTIC AGENTS; BENZAMIDES; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; HUMANS; MELANOMA, EXPERIMENTAL; NEOPLASM TRANSPLANTATION; OLIGOPEPTIDES; PEPTIDES; PHTHALIC ACIDS; PROTEASOME ENDOPEPTIDASE COMPLEX; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 27144491965     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050181l     Document Type: Article

References (62)

1. Coux, O.; Tanaka, K.; Goldberg, A. L. Structure and Functions of the 20S and 26S Proteasomes. Annu. Rev. Biochem. 1996, 65, 801-847.
2. Goldberg, A. L.; Rock, K. L. Proteolysis, Proteasomes and Antigen Presentation. Nature 1992, 357, 375-378.
3. Groettrup, G.; Schmidtke, G. Selective Proteasome Inhibitors: Modulators of Antigen Presentation? DDT 1999, 4 (2), 63-71.
4. Elliott, P. J.; Zollner T. M.; Boehncke, W.-H. Proteasome Inhibition: a New Anti-inflammatory Strategy. J. Mol. Med. 2003, 81, 235-245.
5. Price, S. R. Increased Transcription of Ubiquitin-proteasome System Components: Molecular Responses Associated with Muscle Atrophy. Int. J. Biochem. Cell Biol. 2003, 35, 617-628.
6. Goellner, G. M.; Rechsteiner, M. Are Hungtington's and Polyglutamine-based Ataxias Proteasome Storage Diseases? Int. J. Biochem. Cell Biol. 2003, 35, 562-571.
7. Naidoo, N.; Song, W.; Hunter-Ensor, M.; Sehgal, A. A Role for the Proteasome in the Light Response of the Timeless Clock Protein. Science 1999, 285, 1737-1741.
8. Hilt, W.; Wolf, D. H. Proteasomes: Destruction as a Programme. Trends Biochem. Sci. 1996, 21, 96-102.
9. Myung, J.; Kim, K. B.; Crews, C. M. The Ubiquitin-Proteasome Pathway and Proteasome Inhibitors. Med. Res. Rev. 2001, 21 (4), 245-273.
10. Adams, J.; Palombella, V. J.; Sausville, E. A.; Johson, J.; Destree, A.; Lazarus, D. D.; Maas, J.; Pien, C. S.; Prakash, S.; Elliott, P. J. Proteasome Inhibitors: a Novel Class of Potent and Effective Antitumor Agents. Cancer Res. 1999, 59, 2615-2622.
11. Kisselev, A. F.; Goldberg, A. L. Proteasome Inhibitors: from Research Tools to Drug Candidates. Chem. Biol. 2001, 8, 739-758.
12. Gillessen, S.; Groettrup, M.; Cerny, T. The proteasome, a New Target for Cancer Therapy. Onkologie 2002, 25, 534-539.
13. Adams, J. Potential for Proteasome Inhibition in the Treatment of Cancer. Drug Discovery Today 2003, 8 (7), 307-315.
14. Los, M.; Burek, C. J.; Stroh, C.; Benediyk, K., Hug, H.; Mackiewicz, A. Anticancer Drugs of Tomorrow: Apoptotic Pathways as Targets for Drug Design. Drug Discovery Today 2003, 8 (2), 67-77.
15. Masse, C. E.; Morgan, A. J., Adams, J.; Panek, J. S. Syntheses and Biological Evaluation of (+)-Lactacystin and Analogues. Eur. J. Org. Chem. 2000, 2513-2528.
16. Dick, L. R.; Cruikshank, A. A.; Destree, A. D.; Grenier, L.; McCormack, T. A.; Melandri, F. D.; Nunes, S. L.; Palombella, V. J.; Parent, L. A.; Plamondon, L.; Stein, R. L. Mechanistic Studies on the Inactivation of the Proteasome by Lactacystin in Cultured Cells. J. Biol. Chem. 1997, 272, 182-188.
17. Fenteany, G.; Schreiber, S. L. Lactacystin, Proteasome Function, and Cell Fate. J. Biol. Chem. 1998, 273 (15), 8545-8548.
18. Kohno, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Kuroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. Structures of TMC-95A-D: Novel Proteasome Inhibitors from Apiospora montagnei Sacc. TC 1093. J. Org. Chem. 2000, 65, 990-995.
19. Vinitsky, A.; Michaud, C.; Powers, J. C.; Orlowski, M. Inhibition of the Chymotrypsin-like Activity of the Pituitary Multicatalytic Proteinase Complex. Biochemistry 1992, 31, 9421-9428.
20. Wilk, S.; Figueiredo-Preira, M. E. Synthetic Inhibitors of the Multicatalytic Proteinase Complex (Proteasome). Enzyme Proteine 1993, 47, 306-313.
21. Vinitsky, A.; Cardozo, C.; Sepp-Lorenzino, L.; Michaud, C.; Orlowski, M. Inhibition of the Proteolytic Activity of the Multicatalytic Proteinase Complex (Proteasome) by Substrate-related Peptidyl Aldehydes. J. Biol. Chem. 1994, 269, 29860-29866.
22. Cardozo, C.; Vinitsky, A.; Michaud, C.; Orlowski, M. Evidence That the Nature of Amino Acid Residues in the P3 Position Directs Substrates to Distinct Catalytic Sites of the Pituitary Multicatalytic Proteinase Complex (Proteasome). Biochemistry 1994, 33 (21), 6483-6489.
23. Adams, J.; Behnke, M.; Chen, S.; Cruickshank, A. A.; Dick, L. R.; Grenier, L.; Klunder, J. M.; Ma, Y.-T.; Plamondon, L.; Stein, R. L. Potent and Selective Inhibitors of the Proteasome: Dipeptidyl Boronic Acids. Bioorg. Med. Chem. Lett. 1998, 8, 333-338
24. Lightcap, E. S.; McCormack, T. A.; Pien, C. S.; Chau, V.; Adams, J.; Elliott, P. J. Proteasome Inhibition Measurements: Clinical Application. Clin. Chem. 2000, 46 (5), 673-683.
25. Bogyo, M.; McMaster, J. S.; Gaczynska, M.; Tortorella, D.; Goldberg, A. L.; Ploegh, H. Covalent Modification of the Active Site Threonine of Proteosomal β-subunits and the Escherichia coli Homologue HsIV by a New Class of Inhibitors. Proc. Natl. Acad. Sci. U.S.A. 1997, 94 (13), 6629-6634.
26. Bogyo, M.; Shin, S.; McMaster, J. S.; Ploegh, H. L. Substrate Binding and Sequence Preference of the Proteasome Revealed by Active-site-directed Affinity Probes. Chem. Biol. 1998, 5 (6), 307-320.
27. Elofsson, M.; Splittgerber, U.; Myung, J.; Mohan, R.; Crews, C. M. Towards Subunit-Specific Proteasome Inhibitors: Synthesis and Evaluation of Peptide α′,β′-epoxycetones. Chem. Biol. 1999, 6(11), 811-822.
28. Lynas, J. F.; Harriott, P.; Healy, A.; McKervey, M. A.; Walker, B. Inhibitors of the Chymotrypsin-like Activity of Proteasome Based on di- and tri-peptidyl α-keto aldehydes (glyoxals). Bioorg. Med. Chem. Lett. 1998, 8, 373-378.
29. Lum, R. T.; Nelson, M. G.; Joly, A.; Horsma, A. G.; Lee, G.; Meyer, S. M.; Wick, M. M.; Schow, S. R. Selective Inhibition of the Chymotrypsin-like Activity of the 20S Proteasome by 5-methoxy-1-indanone Dipeptide Benzamides. Bioorg. Med. Chem. Lett. 1998, 8, 209-214.
30. Loidl, G.; Groll, M.; Musiol, H. J.; Huber, R.; Moroder, L. Bivalency as a Principle for Proteasome Inhibition. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 5418-5422.
31. Loidl, G.; Groll, M.; Musiol, H.-J.; Ditzel, L.; Huber, R.; Moroder, L. Bifunctional Inhibitors of the Trypsin-like Activity of Eukaryotic Proteasomes. Chem. Biol. 1999, 6 (4), 197-204.
32. Löwe, J.; Stock, D.; Jap, B.; Zwickl, P.; Baumeister, W.; Hubert, R. Crystal Structure of the 20S Proteasome from the Archaeon T. acidophilum at 3.4 Å Resolution. Science 1995, 268 (5210), 533-539.
33. Groll, M.; Ditzel, L.; Löwe, J.; Stock, D.; Bochtler, M.; Bartunik, H. D.; Huber, R. Structure of 20S Proteasome from Yeast at 2.4 Å Resolution. Nature 1997, 386 (6624), 463-471.
34. Goldberg, A. L.; Akopian, T. N.; Kisselev, A. F.; Lee, A. H.; Rohrwild, M. New Insights into the Mechanisms and Importance of the Proteasome in Intracellular Protein Degradation. Biol. Chem. 1997, 378, 131-140.
35. Ditzel, L.; Stock, D.; Löwe, J. Structural Investigation of Proteasome Inhibition. Biol. Chem. 1997, 378, 239-247.
36. Groll, M.; Heinemeyer, W.; Jäger, S.; Ullrich, T.; Bochtler, M.; Wolf, D. H.; Huber, R. The Catalytic Sites of 20S Proteasomes and their Role in Subunit Maturation: A Mutational and Crystallographic Study. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10976-10983.
37. Teicher, B. A.; Ara, G.; Herbst, R.; Palombella, V. J.; Adams, J. The Proteasome Inhibitor PS-341 in Cancer Therapy. Clin. Cancer Res. 1999, 5, 2638-2645.
38. Adams, J. Development of the Proteasome Inhibitor PS-341. Oncologist 2002, 7, 9-16.
39. Stein, R. L.; Ma, Y.-T.; Brand, S. Inhibitors of The 26S Proteolytic Complex And The 20S Proteasome Contained Therein. U.S. Patent 5,693,617, December 2, 1997.
40. Moreau, M. F.; Michelot, J.; Veyre, A.; Madelmont, J. C.; Godenèche, D.; Labarre, P.; Parry, D.; Meyniel, G. Agents pour le Diagnostic et le Traitement des Mélanomes, Dérivés Halogénés Aromatiques Utilisables comme de tels Agents et leur Préparation. French patent 8901898, February 14, 1989.
41. 125 radio pharmaceutical as Potential Tracers for Malignant Melanoma. J. Nucl. Med. 1991, 32, 1573-1580.
42. 125I-radiopharmaceuticals for Diagnosis and Treatment for Malignant Melanoma. Eur. J. Nucl. Med. 1993, 18, 538.
43. 123I-BZA. Melanoma Res. 1993, 3, 83.
44. 123-N-(2-diethylaminoethyl-4-iodobenzamide). J. Nucl. Med. 1993, 34, 1260-1266.
45. Moreau, M. F.; Michelot, J.; Papon, J.; Bayle, M.; Labarre, P.; Madelmont, J. C.; Parry, D.; Boire, J. Y.; Segquin, H.; Veyre, A.; Mauclaire, L. Synthesis, Radiolabeling, and Preliminary Evaluation in Mice of some (N-diethylaminoethyl)-4-iodobenzamide Derivates as Melanoma Imaging Agents. Nucl. Med. Biol. 1995, 22, 737-747.
46. Chehade, F.; Michelot, J.; Hindie, E.; Papon, J.; Delabriolle-Vaylet, C.; Zhang, L.; Escaig, F.; Moreau, M. F.; Veyre, A. Localization of N-(2-diethylaminoethyl)-4-iodobenzamide in the Pigmented Mouse Eye: a Microanalytical Study. Cell. Mol. Biol. 1996, 42, 343-350.
47. 123I-N-(2- diethyleminoethyl)-2-iodobenzamide: a potential imaging agent for cutaneous melanoma staging. Eur. J. Nucl. Med. 2002, 29, 1478-1484.
48. Maul, W. Synthese von 14C-markiertem Noxiptilin. J. Labelled Compd. 1969, 3, 251-256.
49. Gilman, H. Some Personnal Notes on More Than One-Half Century of Organometallic Chemistry. Organomet. Chem. 1968, 7, 1-52.
50. Corey, E. J.; Székely, I.; Shiner, C. S. Tetrahedron Lett. 1977, 3529.
51. Klausner, Y. S.; Bodansky, M. Coupling Reagents in Peptide Synthesis. Synthesis 1972, 453-463.
52. Sheeman, J.C.; Goodman, M.; Hess, G. P. Peptide Derivatives Containing Hydroxyamino Acids. J. Am. Chem. Soc. 1956, 78, 1367-1369.
53. Sheeman, J. C.; Hess, G. P. A New Method of Forming Peptide Bonds. J. Am. Chem. Soc. 1955, 77, 1067-1068.
54. 1 Observations on the Reactions of Carbodiimides with Acids and Some New Applications in the Synthesis of Phosphoric Acid Esters. J. Am. Chem. Soc. 1958, 80, 6204-6212.
55. Khorana, H. G. The Chemistry of Carbodiimides. Chem. Rev. 1953, 53, 145-166.
56. DeTar, D. F.; Silverstein, R. Reactions of Carbodiimides. I. The Mechanisms of the Reactions of Acetic Acid with Dicyclohexyl-carbodiimide. J. Am. Chem. Soc. 1966, 88, 1013-1019.
57. DeTar, D. F.; Silverstein, R. Reactions of Carbodiimides. II. The Reactions of Dicyclohexylcarbodiimide with Carboxylic Acids in the Presence of Amines and Phenols. J. Am. Chem. Soc. 1966, 88, 1020-1023.
58. DeTar, D. F.; Silverstein, R.; Rogers, F. F., Jr.; Reactions of Carbodiimides. III. The reactions of Carbodiimides with Peptide Acids. J. Am. Chem. Soc. 1966, 88, 1024-1030.
59. Lebreton, L.; Annat, J.; Derrepas, P.; Dutartre, P.; Renaut, P. Structure-Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin.1. Structural Modifications of the Hydroglycine Moiety. J. Med. Chem. 1999, 42, 277-290.
60. Hochstrasser, M. Ubiquitin, Proteasomes, and the Regulation of Intracellular Protein Degradation. Curr. Opin. Cell Biol. 1995, 7, 215-223.
61. Viestra, R. D. The Ubiquitin/26S Proteasome Pathway, the Complex Last Chapter in the Life of Many Plant Proteins. Trends Plant Sci. 2003, 8 (3), 135-142.
62. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantitities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248.