A one-pot synthesis and biological activity of ageladine A and analogues

Journal of Medicinal Chemistry

Volumn 54, Issue 7, 2011, Pages 2492-2503

  Shengule, Sudhir R ^a   Loa Kum Cheung, Wendy L ^a   Parish, Christopher R ^b   Blairvacq, Mélina ^c   Meijer, Laurent ^c   Nakao, Yoichi ^d   Karuso, Peter ^a  

^a MACQUARIE UNIVERSITY   (Australia)

^b Biology and Environment   (Australia)

^c STATION BIOLOGIQUE   (France)

^d WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGELADINE A; AGELADINE A DERIVATIVE; ALDEHYDE DERIVATIVE; ANTINEOPLASTIC AGENT; MATRIX METALLOPROTEINASE; NATURAL PRODUCT; PHOSPHOTRANSFERASE; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; MARINE SPECIES; NONHUMAN; ONE POT SYNTHESIS; PICTET SPENGLER REACTION; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MATRIX METALLOPROTEINASE 14; MATRIX METALLOPROTEINASE 2; NEOVASCULARIZATION, PATHOLOGIC; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; PYRROLES;

EID: 79953767989     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200039m     Document Type: Article

References (44)

1. Fujita, M.; Nakao, Y.; Matsunaga, S.; Seiki, M.; Itoh, Y.; Yamashita, J.; van Soest, R. W. M.; Fusetani, N. Ageladine A: an antiangiogenic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai J. Am. Chem. Soc. 2003, 125, 15700-15701 (Pubitemid 37553660)
2. Nakao, Y.; Fusetani, N. Enzyme inhibitors from marine invertebrates J. Nat. Prod. 2007, 70, 689-710 (Pubitemid 46797884)
3. Meketa, M. L.; Weinreb, S. M. Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai Org. Lett. 2006, 8, 1443-1446 (Pubitemid 43587459)
4. Meketa, M. L.; Weinreb, S. M.; Nakao, Y.; Fusetani, N. Application of a 6-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues J. Org. Chem. 2007, 72, 4892-4899 (Pubitemid 46981836)
5. Andrade, P.; Willoughby, R.; Pomponi, S. A.; Kerr, R. G. Biosynthetic studies of the alkaloid, stevensine, in a cell culture of the marine sponge Teichaxinella morchella Tetrahedron Lett. 1999, 40, 4775-4778 (Pubitemid 29281780)
6. Shengule, S. R.; Karuso, P. Concise total synthesis of the marine natural product ageladine A Org. Lett. 2006, 8, 4083-4084 (Pubitemid 44432858)
7. Meketa, M. L.; Weinreb, S. M. A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine a featuring a biogenetically patterned 6 β-2-azatriene electrocyclization Org. Lett. 2007, 9, 853-855
8. Ando, N.; Terashima, S. Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs Bioorg. Med. Chem. Lett. 2007, 17, 4495-4499 (Pubitemid 47058956)
9. Mannello, F.; Tonti, G.; Papa, S. Matrix metalloproteinase inhibitors as anticancer therapeutics Curr. Cancer Drug Targets 2005, 5, 285-298 (Pubitemid 40910561)
10. Brown, K. J.; Maynes, S. F.; Bezos, A.; Maguire, D. J.; Ford, M. D.; Parish, C. R. A novel in vitro assay for human angiogenesis Lab. Invest. 1996, 75, 539-555 (Pubitemid 26346804)
11. Parish, C. R.; Freeman, C.; Brown, K. J.; Francis, D. J.; Cowden, W. B. Identification of sulfated oligosaccharide-based inhibitors of tumor growth and metastasis using novel in vitro assays for angiogenesis and heparanase activity Cancer Res. 1999, 59, 3433-3441 (Pubitemid 29334505)
12. Shoemaker, R. H. The NCI60 human tumour cell line anticancer drug screen Nature Rev. Cancer 2006, 6, 813-823 (Pubitemid 44450469)
13. Ando, N.; Terashima, S. Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs Bioorg. Med. Chem. Lett. 2007, 17, 4495-4499 (Pubitemid 47058956)
14. Mahboobi, S.; Wiegrebe, W.; Popp, A. Synthesis of enantiomerically pure (B)-(S)-brevicolline J. Nat. Prod. 1999, 62, 577-579
15. Lohmander, L. S.; Hoerrner, L. A.; Lark, M. W. Metalloproteinases, tissue inhibitor, and proteoglycan fragments in knee synovial fluid in human osteoarthritis Arthritis Rheum. 1993, 36, 181-189 (Pubitemid 23059328)
16. Murphy, G.; Hembry, R. M. Proteinases in rheumatoid arthritis J. Rheumatol. 1992, 19, 61-64
17. Peress, N.; Perillo, E.; Zucker, S. Localization of tissue inhibitor of matrix metalloproteinases in Alzheimer's disease and normal brain J. Neuropathol. Exp. Neurol. 1995, 54, 16-22
18. Chang, C.; Werb, Z. The many faces of metalloproteases: cell growth, invasion, angiogenesis and metastasis Trends Cell Biol. 2001, 11, S37-S43
19. Tosetti, F.; Ferrari, N.; De Flora, S.; Albini, A. " Angioprevention": angiogenesis is a common and key target for cancer chemopreventive agents FASEB J. 2002, 16, 2-14 (Pubitemid 34027945)
20. Pendás, A. M.; Kneuper, V.; Puente, X. S.; Llano, E.; Mattei, M.-G.; Apte, S.; Murphy, G.; López-Otín, C. Identification and characterization of a novel human matrix metalloproteinase with unique structural characteristics, chromosomal location, and tissue distribution J. Biol. Chem. 1997, 272, 4281-4286 (Pubitemid 27078499)
21. Matter, H.; Schudok, M. Recent advances in the design of matrix metalloprotease inhibitors Curr. Opin. Drug Discovery Dev. 2004, 7, 513-535 (Pubitemid 44383558)
22. Folkman, J. Angiogenesis: an organizing principle for drug discovery Nature Rev. Drug Discovery 2007, 6, 273-286 (Pubitemid 46505878)
23. Folkman, J. Angiogenesis Annu. Rev. Med. 2006, 57, 1-18 (Pubitemid 43261975)
24. Sydnes, M. O.; Bezos, A.; Burns, C.; Kruszelnicki, I.; Parish, C. R.; Su, S.; Rae, A. D.; Willis, A. C.; Banwell, M. G. Synthesis and biological evaluation of some enantiomerically pure C8c-C15 monoseco analogues of the phenanthroquinolizidine-type alkaloids cryptopleurine and julandine Aust. J. Chem. 2008, 61, 506-520
25. Khachigian, L. M.; Parish, C. R. Phosphomannopentaose sulfate (PI-88): heparan sulfate mimetic with clinical potential in multiple vascular pathologies Cardiovasc. Drug Rev. 2004, 22, 1-6 (Pubitemid 38375049)
26. Ohya, T. Identification of 4-methylspinaceamine, a Pictet-Spengler condensation reaction product of histamine with acetaldehyde, in fermentated foods and its metabolite in human urine J. Agric. Food. Chem. 2006, 54, 6909-6915 (Pubitemid 44426976)
27. Manning, G.; Whyte, D. B.; Martinez, R.; Hunter, T.; Sudarsanam, S. The protein kinase complement of the human genome Science 2002, 298, 1912-1934 (Pubitemid 35425239)
28. Kostich, M.; English, J.; Madison, V.; Gheyas, F.; Wang, L.; Qiu, P.; Greene, J.; Thomas, M. Human members of the eukaryotic protein kinase family Genome Biol. 2002, 3, research0043.1-research0043.12
29. Neidner, R. H.; Buzko, O. V.; Hatse, N. M.; Taylor, A.; Gribskov, M.; Taylors, S. S. Protein kinase resource: an integrated environment for phosphorylation research Proteins 2006, 63, 78-86
30. Fischer, P. M. The design of drug candidate molecules as selective inhibitors of therapeutically relevant protein kinases Curr. Med. Chem. 2004, 11, 1563-1583 (Pubitemid 38735797)
31. Weinmann, H.; Metternich, R. Drug discovery process for kinase inhibitors ChemBioChem 2005, 6, 455-459 (Pubitemid 40868133)
32. Smith, P. J.; Yue, E. CDK Inhibitors of Cyclin-Dependent Kinases As Anti-tumor Agents; Monographs on Enzyme Inhibitors; CRC Press, Taylor & Francis: Boca Raton, FL, 2006; Vol. 2, p 448.
33. Meijer, L.; Flajolet, M.; Greengard, P. Pharmacological inhibitors of glycogen synthase kinase 3 Trends Pharmacol. Sci. 2004, 25, 471-480 (Pubitemid 39149703)
34. Wan, Y. Q.; Hur, W. Y.; Cho, C. Y.; Liu, Y.; Adrian, F. J.; Lozach, O.; Bach, S.; Mayer, T.; Fabbro, D.; Meijer, L.; Gray, N. S. Synthesis and target identification of hymenialdisine analogs Chem. Biol. 2004, 11, 247-259 (Pubitemid 38305843)
35. Meijer, L.; Thunnissen, A. M. W. H.; White, A. W.; Garnier, M.; Nikolic, M.; Tsai, L. H.; Walter, J.; Cleverley, K. E.; Salinas, P. C.; Wu, Y. Z.; Biernat, J.; Mandelkow, E. M.; Kim, S. H.; Pettit, G. R. Inhibition of cyclin-dependent kinases, GSK-3′ and CK1 by hymenialdisine, a marine sponge constituent Chem. Biol. 2000, 7, 51-63 (Pubitemid 30141925)
36. Fabian, M. A.; Biggs, W. H., III; Treiber, D. K.; Atteridge, C. E.; Azimioara, M. D.; Benedetti, M. G.; Carter, T. A.; Ciceri, P.; Edeen, P. T.; Floyd, M.; Ford, J. M.; Galvin, M.; Gerlach, J. L.; Grotzfeld, R. M.; Herrgard, S.; Insko, D. E.; Insko, M. A.; Lai, A. G.; Lelias, J. M.; Mehta, S. A.; Milanov, Z. V.; Velasco, A. M.; Wodicka, L. M.; Patel, H. K.; Zarrinkar, P. P.; Lockhart, D. J. A small molecule-kinase interaction map for clinical kinase inhibitors Nature Biotechnol. 2005, 23, 329-336 (Pubitemid 41094421)
37. Karaman, M. W.; Herrgard, S.; Treiber, D. K.; Gallant, P.; Atteridge, C. E.; Campbell, B. T.; Chan, K. W.; Ciceri, P.; Davis, M. I.; Edeen, P. T.; Faraoni, R.; Floyd, M.; Hunt, J. P.; Lockhart, D. J.; Milanov, Z. V.; Morrison, M. J.; Pallares, G.; Patel, H. K.; Pritchard, S.; Wodicka, L. M.; Zarrinkar, P. P. A quantitative analysis of kinase inhibitor selectivity Nature Biotechnol. 2008, 26, 127-132
38. Baek, K.-H.; Zaslavsky, A.; Lynch, R. C.; Britt, C.; Okada, Y.; Siarey, R. J.; Lensch, M. W.; Park, I.-H.; Yoon, S. S.; Minami, T.; Korenberg, J. R.; Folkman, J.; Daley, G. Q.; Aird, W. C.; Galdzicki, Z.; Ryeom, S. Down's syndrome suppression of tumour growth and the role of the calcineurin inhibitor DSCR1 Nature 2009, 459, 1126-1130
39. Itoh, Y.; Takamura, A.; Ito, N.; Maru, Y.; Sato, H.; Suenaga, N.; Aoki, T.; Seiki, M. Homophilic complex formation of MT1-MMP facilitates proMMP-2 activation on the cell surface and promotes tumor cell invasion EMBO J. 2001, 20, 4782-4793 (Pubitemid 32848631)
40. Kinoshita, T.; Sato, H.; Takino, T.; Itoh, M.; Akizawa, T.; Seiki, M. Processing of a precursor of 72-kilodalton type IV collagenase/gelatinase A by a recombinant membrane-type 1 matrix metalloproteinase Cancer Res. 1996, 56, 2535-2538 (Pubitemid 26170690)
41. Knight, C. G.; Willenbrock, F.; Murphy, G. A novel coumarin-labeled peptide for sensitive continuous assays of the matrix metalloproteinases FEBS Lett. 1992, 296, 263-266
42. Davies, B.; Brown, P. D.; East, N.; Crimmin, M. J.; Balkwill, F. R. A synthetic matrix metalloproteinase inhibitor decreases tumor burden and prolongs survival of mice bearing human ovarian carcinoma xenografts Cancer Res. 1993, 53, 2087-2091 (Pubitemid 23145731)
43. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay Cancer Res. 1988, 48, 589-601 (Pubitemid 18056527)
44. Reinhardt, J.; Ferandin, Y.; Meijer, L. Purification of CK1 by affinity chromatography on immobilised axin Protein Expression Purif. 2007, 54, 101-109 (Pubitemid 46636329)