Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13

Journal of Medicinal Chemistry

Volumn 46, Issue 18, 2003, Pages 3900-3913

  Bauvois, Brigitte ^a   Puiffe, Marie Line ^a   Bongui, Jean Bernard ^b   Paillat, Sandrine ^b   Monneret, Claude ^b   Dauzonne, Daniel ^b  

^a INSERM   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

(6,8 DIOXO 5,6,7,8 TETRAHYDRO 13 OXA 5,7 DIAZABENZO[3,4]CYCLOHEPTA[1,2 B]NAPHTHALEN 12 YL)ACETIC ACID; (6,8 DIOXO 6,7 DIHYDRO 8H 5,13 DIOXA 7 AZABENZO[3,4]CYCLOHEPTA[1,2 B]NAPHTHALEN 12 YL)ACETIC ACID; 2',3 DINITROFLAVONE 8 ACETIC ACID; BESTATIN; CATHEPSIN G; COMMON ACUTE LYMPHOBLASTIC LEUKEMIA ANTIGEN; DINITROFLAVONE; DIPEPTIDYL CARBOXYPEPTIDASE; DIPEPTIDYL PEPTIDASE IV; FLAVONE DERIVATIVE; GAMMA GLUTAMYLTRANSFERASE; GELATINASE B; MEMBRANE METALLOENDOPEPTIDASE; MICROSOMAL AMINOPEPTIDASE; MITOFLAXONE; SERINE PROTEINASE; UNCLASSIFIED DRUG;

ANGIOGENESIS; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; PROTEIN EXPRESSION; PROTEIN FUNCTION;

ACETIC ACIDS; ANGIOGENESIS INHIBITORS; ANTIGENS, CD13; DRUG SCREENING ASSAYS, ANTITUMOR; FLAVONOIDS; FLOW CYTOMETRY; HUMANS; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0041418313     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm021109f     Document Type: Article

References (63)

1. Antczak, C.; De Meester, I.; Bauvois, B.; Ectopeptidases in pathophysiology. Bioessays 2001, 23, 251-260.
2. Antczak, C.; De Meester, I.; Bauvois, B. Transmembrane proteases as disease markers and targets for therapy. J Biol. Regul. Homeost. Agents 2001, 15, 130-139.
3. Sjostrom, H.; Noren, O.; Olsen, J. Structure and function of aminopeptidase N. In cellular peptidases in immune functions and diseases; Langner, J., Ansorge, S., Eds.; Kluwer Academic/Plenum Publishers: New York, 2000; pp 25.
4. Riemann, D.; Kehlen, A.; Langner, J. CD13 - not just a marker in leukemia typing. Immunol. Today 1999, 20, 83-88.
5. Hooper, N. M. Families of zinc metalloproteases. FEBS Lett. 1994, 354, 1-6.
6. Larsen, S. L.; Pedersen, L. O.; Buus S.; Stryhn A. T cell responses affected by aminopeptidase N (CD13)-mediated trimming of major histocompatibility complex class II-bound peptides. J. Exp. Med. 1996, 184, 183-189.
7. Nanus, D. M.; Papandreou, C. N.; Albino, P. Expression of cell-surface peptidases in neoplastic cells. In Cell surface peptidases in health and disease; Kenny A. J., Boustead, C. M., Eds.; BIOS Scientific Publishers: Oxford, 1997; pp 353-370.
8. Ishii, K.; Usui, S.; Sugimura, Y.; Yoshida, S.; Hioki, T.; Tatematsu, M. ; Yamamoto, H.; Hirano, K. Aminopeptidase N is regulated by zinc in human prostate participates in tumor cell invasion. Int. J. Cancer 2001, 92, 49-54.
9. Fujii, H.; Nakajima, M.; Saiki, I.; Yoneda, J.; Azuma, I.; Tsuruo, T. Human melanoma invasion and metastasis enhancement by high expression of aminopeptidase N/CD13. Clin. Exp. Metastasis 1995, 13, 337-344.
10. Lohn, M.; Mueller, C.; Langner, G. Cell cycle retardation in monocytoid cells induced by aminopeptidase N (CD13). Leuk. Lymphoma 2002, 43, 407-413.
11. Saiki, I.; Fujii, H.; Yoneda, J.; Abe, F.; Nakajima, M.; Tsuruo, T.; Azuma, I. Role of aminopeptidase N (CD13) in tumor-cell invasion and extracellular matrix degradation. Int. J. Cancer 1993, 54, 137-143.
12. Tomanek, R. J.; Schatteman, G. C. Angiogenesis: new insights and therapeutic potential. Anat. Record 2000, 261, 126-135.
13. Pasqualini, R.; Koivunen, E.; Kain, R.; Lahdenranta, J.; Sakamoto, M.; Stryhn, A.; Ashmum, R. A.; Shapiro, L. H.; Arap, W.; Ruoslahti, E. Aminopeptidase N is a receptor for tumor-homing peptides and a target for inhibiting angiogenesis. Cancer Res. 2000, 60, 722-727.
14. Bhagwat, S. V.; Lahdenranta, J.; Giordano, R.; Arap, W.; Pasqualini, R.; Shapiro, L. H. CD13/APN is activated by angiogenic signals and is essential for capillary tube formation. Blood 2001, 97, 652-659.
15. Hashida, H.; Takabayashi, A.; Kanai, M.; Adachi, M.; Kondo, K.; Kohno, M.; Yamaoka, Y.; Miyake, M. Aminopeptidase N is involved in cell motility and angiogenesis: its clinical significance in human colon cancer. Gastroenterology 2002, 122, 376-386.
16. Ota, K.; Kurita, S.; Yamada, K.; Masaoka, T.; uzuka, Y.; Ogawa, N. Immunotherapy with bestatin for acute nonlymphocytic leukemia in adults. Cancer Immunol. Immunother. 1986, 23, 5-10.
17. Urabe, A.; Mutoh, Y.; Mizoguchi, H.; Takaku, F.; Ogawa, N. Ubenimex in the treatment of acute nonlymphocytic leukemia in adults. Ann. Hematol. 1993, 67, 63-66.
18. Scornik, O. A.; Bothol, V. Bestatin as an experimental tool in animals. Curr. Drug Metab. 2001, 2, 67-85.
19. Stoner, G. D.; Mukhtar, H. Polyphenols as cancer chemopreventive agents. J Cell Biochem. 1995, 22, 169-180.
20. Jankun, J., Selman, S. H., Swiercz, R., Skrzypczak-Kanjun, E. Why drinking green tea could prevent cancer. Nature 1997, 387, 561.
21. Birt, D. F.; Hendrich, S.; Wang W. Diatery agents in cancer prevention: flavonoids and isoflavonoids. Pharmacology Therapeutics 2001, 90, 157-177.
22. Cao, Y.; Cao, R. Angiogenesis inhibited by drinking tea. Nature 1999, 398, 381.
23. Melillo, G.; Sausville, E. A.; Cloud, K.; Lahusen, T.; Varesio L.; Senderowicz A. M. Flavopiridol, a protein kinase inhibitor, down-regulates hypoxic induction of vascular endothelial growth factor expresssion in human monocytes. Cancer Res. 1999, 59 (9), 5433-5437.
24. Jung, Y. D.; Kim, M. S.; Shin, B. A.; Chay, K. O.; Ahn, B. W.; Liu, W.; Bucana, C. D.; Gallick, G. E.; Ellis, L. M. EGCG, a major component of green tea, inhibits tumour growth by inhibiting VEGF induction in human colon carcinoma cells. Brit. J. Cancer 2000, 84, 844-850.
25. Scwhartz, G. K.; Ilson, D.; Saltz, L.; O'Reilly, E.; Tong, W.; Maslak, P.; Werner, J.; Perkins, P.; Stoltz, M.; Kelsen, D. Phase II study of the cyclin-dependent kinase inhibitor flavopiridol administered to patients with advanced gastric carcinoma. J. Clin. Oncol. 2001, 19, 1985-1992.
26. Lamy, S.; Gingras, D.; Béliveau, R. Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation. Cancer Res. 2002, 62, 381-385.
27. Garbisa, S.; Sartor, L.; Biggin, S.; Salvato, B.; Benelli, R.; Albini, A. Tumor gelatinases and invasion inhibited by the green tea flavanol epigallocatechin-3-gallate. Cancer 2001, 91, 822-832.
28. Sartor, L.; Pezzato, E.; Garbisa, S. (-)epigallocatechin-3-gallate inhibits leukocyte elastase: potential of the phyto-factor in hindering inflammation, emphysema, and invasion. J. Leuk. Biol. 2002, 71, 73-79.
29. Bormann, H.; Melzig, M. F. Inhibition of metallopeptidases by flavonoids and related compounds. Pharmazie 2000, 55, 129-132.
30. Minagawa, A.; Otani, Y.; Kubota, T.; Wada, N.; Furukawa, T.; Kumai, K.; Kameyama, K.; Ojada, Y.; Fujii, M.; Yano, M.; Sato, T.; Ito, A.; Kitajima, M. The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Jpn. J. Cancer Res. 2001, 92, 1322-1328.
31. Atassi, G.; Briet, P.; Berthelon, J.-J.; Collonges, F. Synthesis and antitumor activity of some 8-substituted-4-oxo-4H-1-benzopyrans. Eur. J. Med. Chem. Chim. Ther. 1985, 20, 393-402.
32. Corbett, T. H.; Bissery, M.-C.; Wozniak, A.; Plowman, J.; Polin, L.; Tapazoglou, E.; Dieckman, J.; Valeriote, F. Activity of flavone acetic acid (NSC 347512) against solid tumors of mice. Invest. New Drugs 1986, 4, 207-220.
33. Finlay, G. J.; Smith, G. P.; Fray, L. M.; Baguley, B. C. Effect of flavone acetic acid (NSC 347512) on Lewis lung carcinoma: evidence for an indirect effect. J. Natl. Cancer Inst. 1988, 80, 241-245.
34. Hill, S. A.; Williams, K. B.; Denekamp, J. Studies with a panel of tumors having a variable sensitivity to FAA, to investigate its mechanism of action. Int. J. Radiat. Biol. 1991, 60, 379-384.
35. Bowler, K.; Pearson, J. A. Long-term effects of flavone acetic acid on the growth of a rat tumor. Anticancer Res. 1992, 12, 1275-1280.
36. Lindsay, C. K.; Gomez, D. E.; Thorgeirsson, U. P. Effect of flavone acetic acid on endothelial cell proliferation: evidence for antiangiogenic properties. Anticancer Res. 1996, 16, 425-432.
37. Bibby, M. C.; Double, J. A. Flavone acetic acid - from laboratory to clinic and back. Anti-Cancer Drugs 1993, 4, 3-17.
38. Dauzonne, D.; Grandjean, C. Synthesis of 2-aryl-3-nitro-4H-1-benzopyran-4-ones. Synthesis 1992, 677-680.
39. Dauzonne, D.; Folléas, B.; Martinez, L.; Chabot, G. G. Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones. Eur. J. Med. Chem. 1997, 32, 71-82.
40. Claisen, L.; Eisleb, O. Über die umlagerung von phenolallyläthern in die isomeren allylphenole. Justus Liebigs Ann. Chem. 1913, 401, 21-119.
41. Dauzonne, D.; Demerseman, P. A convenient synthesis of 3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2-phenyl-2H-1-benzopyrans. Synthesis 1990, 66-70.
42. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. A greatly improved procedure for ruthenium tetraoxide catalyzed oxidations of organic compounds. J. Org. Chem. 1981, 46, 3936-3938.
43. Kim, S.; Park, Y. H.; Kee, I. S. Mild deprotection of methoxymethyl, methylthiomethyl, methoxyethoxymethyl, and β-(trimethylsilyl)ethoxymethyl esters with magnesium bromide in ether. Tetrahedron Lett. 1991, 32, 3099-3100.
44. Mohakhud, P. K.; Goyal, S.; Grover, N.; Saradhi K. P.; Parthasarathy, M. R. Synthesis of some substituted 5,6-dihydro-7H-benzo[c]xanthen-7-one and its aza analogues. Indian J. Chem. Sec. B. 1996, 25B, 904-910.
45. Aitken, R. A.; Bibby, M. C.; Double, J. A.; Laws, A. L.; Ritchie, R. B.; Wilson, D. W. J. Synthesis and antitumour activity of new derivatives of flavone-8-acetic acid (FAA). Part 2: Ring substituted derivatives. Arch. Pharm. Pharm. Med. Chem. 1997, 330, 215-224.
46. Nelson, A. R.; Fingleton, B.; Rothenberg, M. L.; Matrisian, L. M. Matrix metalloproteinases: biologic activity and clinical implications. J. Clin. Oncol. 2000, 18, 1135-1149.
47. Bank, U.; Ansorge, S. More than destructive: neutrophil-derived serine proteases in cytokine bioactivity control. J. Leukoc. Biol. 2001, 69, 197-206.
48. Robinson, M. J.; Cobb, M. H. Mitogen-activated protein kinase pathways. Curr. Opin. Cell. Biol. 1997, 9, 180-186.
49. McCubrey, J. A.; May, W. S.; Duronio, V.; Mufson, A. Serine/threonine phosphorylation in cytokine signal transduction. Leukemia 2000, 14, 9-21.
50. Ono, K.; Han, J. The p38 signal transduction pathway: activation and function. Cell. Signal. 2000, 12, 1-13.
51. Ansorge, S.; Langner, J.; Buhling, F.; Lendeckel, U. Proteolytic signals from Magdeburg. Immunol. Today 2000, 21, 166-167.
52. Lendeckel, U.; Kahne, T.; Arndt, M.; Frank, K.; Ansorge, S. Inhibition of alanyl aminopeptidase induces MAP-kinase p42/ERK2 in the human T cell line KARPAS-299. Biochem. Biophys. Res. Commun. 1998, 252, 5-9.
53. Lendeckel, U.; Arndt, M.; Frank, K.; Wex, T.; Ansorge, S. Role of alanyl aminopeptidase in growth and function of human T cells. Int. J. Mol. Med. 1999, 4, 17-27.
54. Navarrete Santos, A.; Langner, J.; Hermann, M.; Riemann, D. Aminopeptidase N/CD13 is directly linked to signal transduction pathways in monocytes. Cell Immunol. 2000, 201, 22-32.
55. Osuka, A.; Nakajima, S.; Maruyama, K. Synthesis of a 1,2-phenylene-bridged triporphyrin. J. Org. Chem. 1992, 57, 7355-7359.
56. Gautier, N.; Dodd, R. H. The practical use of a glycine anion equivalent for the preparation of 3-carboxy-1,2-dihydro-l-oxo-isoquinoline. Synth. Commun. 1998, 28, 3769-3777.
57. Ersoy, O.; Fleck, R.; Blanco, M.-J.; Masamune, S. Design and syntheses of three haptens to generate catalytic antibodies that cleave amide bonds with nucleophilic catalysis. Bioorg. Med. Chem. 1999, 7, 279-286.
58. Aitken, R. A.; Bibby, M. C.; Double, J. A.; Phillips, R. M.; Sharma, S. K. Synthesis and antitumour activity of new derivatives of flavone-8-acetic acid (FAA). Part 1: 6-methyl derivatives. Arch. Pharm. Pharm. Med. Chem. 1996, 329, 489-497.
59. De Meester, I.; Vanham, G.; Kestens, L.; Vanhoof, G.; Bosmans, E.; Gigase, P.; Scharpe, S. Binding of adenosine deaminase to the lymphocyte surface via CD26. Eur. J. Immunol. 1994, 24, 566-570.
60. Bauvois, B.; Laouar, A.; Rouillard, D.; Wietzerbin, J. Inhibition of y-glutamyl transpeptidase activity at the surface of human myeloid cells is correlated with macrophage maturation and transforming growth factor β production. Cell Growth Differ. 1995, 6, 1163-1170.
61. Klickstein, L. B.; Kaempfer, C. E.; Wintroub, B. U. The granulocyte-angiotensin system. Biol. Chem. 1982, 257, 15042-15046.
62. Chintala, S. K.; Sawaya, R.; Aggarwal, B. B.; Majumder, S.; Giri, D. K.; Kyritsis, A. P.; Gokaslan, Z. L.; Rao, J. S. Induction of matrix metalloproteinase-9 requires a polymerized actin cytoskeleton in human malignant glioma cells. J. Biol. Chem. 1998, 273, 13545-13551.
63. Bauvois, B.; Van Weyenbergh J.; Rouillard, D.; Wietzerbin, J. TGF-beta 1-stimulated adhesion of human mononuclear phagocytes to fibronectin and laminin is abolished by IFN-gamma: dependence on alpha 5 beta 1 and beta 2 integrins. Exp. Cell. Res. 1996, 222, 209-217.