Novel 9′-substituted-noscapines: Synthesis with Suzuki cross-coupling, structure elucidation and biological evaluation

European Journal of Medicinal Chemistry

Volumn 84, Issue , 2014, Pages 476-490

  Porcù, Elena ^a   Sipos, Attila ^e   Basso, Giuseppe ^a   Hamel, Ernest ^b   Bai, Ruoli ^b   Stempfer, Verena ^c   Udvardy, Antal ^d   Bényei, Attila Cs ^d,e   Schmidhammer, Helmut ^c   Antus, Sándor ^d   Viola, Giampietro ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c UNIVERSITY OF INNSBRUCK   (Austria)

^d UNIVERSITY OF DEBRECEN   (Hungary)

^e UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Antimicrotubule agents; Apoptosis; Cell cycle arrest; Noscapine; Suzuki reaction

Indexed keywords

9' (2 METHOXYPHENYL) NOSCAPINE; 9' (2 NAPHTHYL) NOSCAPINE; 9' (3 METHOXYPHENYL) NOSCAPINE; 9' (4 METHOXYPHENYL) NOSCAPINE; 9' (4 METHYLPHENYL) NOSCAPINE; 9' BROMONOSCAPINE; 9' METHYLNOSCAPINE; 9' PHENYLNOSCAPINE; CASPASE 3; CASPASE 9; COLCHICINE; NOSCAPINE; PROTEIN BCL 2; PROTEIN MCL 1; TUBULIN; UNCLASSIFIED DRUG; 9' (2 METHYLPHENYL)NOSCAPINE; 9' (2 NAPHTHYL)NOSCAPINE; 9' (3 METHYLPHENYL)NOSCAPINE; 9' (4 METHYLPHENYL)NOSCAPINE; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; REACTIVE OXYGEN METABOLITE; APOPTOSIS REGULATORY PROTEIN;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CIRCULAR DICHROISM; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG HALF LIFE; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; G2 PHASE CELL CYCLE CHECKPOINT; HELA CELL LINE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; JURKAT CELL LINE; LYMPHOCYTE; MICROTUBULE ASSEMBLY; MITOSIS INDEX; PROTEIN DEPHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SUZUKI REACTION; THIN LAYER CHROMATOGRAPHY; B-CELL LEUKEMIA CELL LINE; BREAST ADENOCARCINOMA; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE ARREST; CELL DEATH; CELL PROLIFERATION; COLON ADENOCARCINOMA; COMPARATIVE STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; ENZYME ACTIVATION; IC50; MELTING POINT; MITOCHONDRIAL MEMBRANE POTENTIAL; NON SMALL CELL LUNG CANCER; OVARY CARCINOMA; PROTEIN EXPRESSION; TUMOR GROWTH; UTERINE CERVIX CARCINOMA; WESTERN BLOTTING; X RAY CRYSTALLOGRAPHY; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

APOPTOSIS; APOPTOSIS REGULATORY PROTEINS; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HUMANS; JURKAT CELLS; MOLECULAR DOCKING SIMULATION; NOSCAPINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84904887791     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.07.050     Document Type: Article

References (59)

1. J.A. Hadfield, S. Ducki, N. Hirst, and A.T. McGown Tubulin and microtubules as targets for anticancer drugs Prog. Cell Cycle Res. 5 2003 309 325
2. M.A. Jordan, and L. Wilson Microtubules as a target for anticancer drugs Nat. Rev. Cancer 4 2004 253 265 (Pubitemid 38525281)
3. C. Dumontet, and M.A. Jordan Microtubule-binding agents: a dynamic field of cancer therapeutics Nat. Rev. Drug Discov. 9 2010 790 803
4. K. Ye, Y. Ke, N. Keshava, J. Shanks, J.A. Kapp, R.R. Tekmal, J. Petros, and H.C. Joshi Opium alkaloid noscapine is an antitumor agent that arrests metaphase and induces apoptosis in dividing cells Proc. Natl. Acad. Sci. U. S. A. 95 1998 1601 1606 (Pubitemid 28103439)
5. M. Mahmoudian, and P. Rahimi-Moghaddam The Anti-cancer activity of noscapine: a review Recent Pat. Anticancer Drug Discov. 4 2009 92 97
6. H.C. Joshi, K. Ye, J. Kapp, F. Liu, Noscapine and Noscapine Derivatives Useful as Anticancer Agents, U.S. Patent, 2002, 6,376,516. 04.2002.
7. J. Zhou, K. Gupta, S. Aggarwal, R. Aneja, R. Chandra, D. Panda, and H.C. Joshi Brominated derivatives of noscapine are potent microtubule-interfering agents that perturb mitosis and inhibit cell proliferation Mol. Pharmacol. 63 2003 799 807 (Pubitemid 36368986)
8. R. Aneja, S.N. Vangapandu, M. Lopus, R. Chandra, D. Panda, and H.C. Joshi Development of a novel nitro-derivative of noscapine for the potential treatment of drug-resistant ovarian cancer and T-cell lymphoma Mol. Pharmacol. 69 2006 1801 1809 (Pubitemid 43894296)
9. N.K. Manchukonda, B. Sridhar, P.K. Naik, H.C. Joshi, and S. Kantevari Copper(I) mediated facile synthesis of potent tubulin polymerization inhibitor, 9-amino-alpha-noscapine from natural α-noscapine Bioorg. Med. Chem. Lett. 22 2012 2983 2987
10. P.K. Naik, B.P. Chatterji, S.N. Vangapandu, R. Aneja, R. Chandra, S. Kanteveri, and H.C. Joshi Rational design, synthesis and biological evaluations of amino-noscapine: a high affinity tubulin-binding noscapinoid J. Comput. Aided Mol. Des. 25 2011 443 454
11. R. Bognár, G. Gaál, P. Kerekes, and S. Szabó On the accompanying alkaloids of morphine. 1. Isolation of codeine, thebaine and narcotine (in German) Pharmazie 22 1967 452 456
12. M.M. Baradarani, and R.H. Prager The specific epimerization of phthalideisoquinoline alkaloids Tetrahedron Lett. 40 1999 7403 7406
13. N. Miyaura, and A. Suzuki Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 95 1995 2457 2483
14. S. Berényi, A. Sipos, I. Szabó, and T. Kálai Novel route to 2-arylapomorphines Synth. Commun. 37 2007 467 471
15. A. Sipos, S. Debreceni, R. Szabó, Z. Gyulai, and S. Berényi Synthesis of 3-alkyl and arylapomorphines Synth. Commun. 37 2007 2549 2558 (Pubitemid 47254562)
16. A. Sipos, S. Berényi, B. Kiss, É. Schmidt, and I. Greiner Synthesis and neuropharmacological evaluation of 2-aryl- and alkylapomorphines Bioorg. Med. Chem. 16 2008 3773 3779 (Pubitemid 351484038)
17. R. Martin, and S.L. Buchwald Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands Acc. Chem. Res. 41 2008 1461 1473
18. G. Snatzke, G. Wollenberg, J. Hrbek Jr., F. Santavy, K. Blaha, W. Klyne, and J.R. Swan The optical rotatory dispersion and circular dichroism of the phthalideisoquinoline alkaloids and of their α- hydroxybenzyltetrahydroisoquinoline derivatives Tetrahedron 25 1969 5059 5075
19. J. von Langermann, H. Lorenz, O. Boehm, A. Fleming, A. Bernsdorf, M. Köckerling, D. Schinzer, and A. Seidel-Morgenstern (3R*, 5′S*)-6,7-Dimethoxy-3-(4′-methoxy-6′-methyl-5′, 6′,7′,8′-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5′-yl) isobenzofuran-1(3H)-one (racemic-noscapine) Acta Cryst. E66 2010 o570 o572
20. J. Seetharaman, and S.S. Rajan Crystal and molecular-structure of noscapine Zeit Krist. 210 1995 111 113
21. P.K. Naik, S. Santoshi, and H.C. Joshi Noscapinoids with anti-cancer activity against human acute lymphoblastic leukemia cells (CEM): a three dimensional chemical space pharmacophore modeling and electronic feature analysis J. Mol. Model. 18 2012 307 318
22. E. Hamel Evaluation of antimitotic agents by quantitative comparisons of their effects on the polymerization of purified tubulin Cell Biochem. Biophys. 38 2003 1 22
23. K.G. Pinney, A.D. Bounds, K.M. Dingeman, V.P. Mocharla, G.R. Pettit, R. Bai, and E. Hamel A new anti-tubulin agent containing the benzo[b]thiophene ring system Bioorg. Med. Chem. Lett. 9 1999 1081 1086 (Pubitemid 29204661)
24. D. Raffa, B. Maggio, F. Plescia, S. Cascioferro, S. Plescia, M.V. Raimondi, G. Daidone, M. Tolomeo, S. Grimaudo, A. Di Cristina, R.M. Pipitone, R. Bai, and E. Hamel Synthesis, antiproliferative activity, and mechanism of action of a series of 2-{[2E]-3-phenylprop-2-enoylamino}benzamides Eur. J. Med. Chem. 46 2011 2786 2796
25. E. Hamel, A.V. Blokhin, D.G. Nagle, H.D. Yoo, and W.H. Gerwick Limitations in the use of tubulin polymerization assays as a screen for the identification of new antimitotic agents: the potent marine natural product curacin A as an example Drug Dev. Res. 34 1995 110 120
26. M.C. Edler, G. Yang, M.K. Jung, R. Bai, W.G. Bornmann, and E. Hamel Demonstration of microtubule-like structures formed with (-)-rhazinilam from purified tubulin outside of cells and a simple tubulin-based assay for evaluation of analog activity Arch. Biochem. Biophys. 407 2009 98 104
27. C.M. Lin, G.J. Kang, M.C. Roach, J.B. Jiang, D.P. Hesson, R.F. Ludueña, and E. Hamel Investigation of the mechanism of the interaction of tubulin with derivatives of 2-styrylquinazolin-4(3H)-one Mol. Pharmacol. 40 1991 827 832
28. G.J. Kang, Z. Getahun, A. Muzaffar, A. Brossi, and E. Hamel N-acetylcolchinol O-methyl ether and thiocolchicine, potent analogs of colchicine modified in the C ring: evaluation of the mechanistic basis for their enhanced biological properties J. Biol. Chem. 265 1990 10255 10259
29. P.K. Naik, S. Santoshi, A. Rai, and H.C. Joshi Molecular modeling and competition binding study of Br-noscapine and colchicine provide insight into noscapinoid-tubulin binding site J. Mol. Graph. Model. 29 2011 947 955
30. B. Bhattacharyya, and J. Wolff Promotion of fluorescence upon binding of colchicine to tubulin Proc. Natl. Acad. Sci. U. S. A. 71 1974 2627 2631
31. A. Kubo, and S. Tsukita Non-membranous granular organelle consisting of PCM-1: subcellular distribution and cell-cycle-dependent assembly/disassembly J. Cell Sci. 116 2003 919 928 (Pubitemid 36367641)
32. R. Balczon, L. Bao, and W.E. Zimmer PCM-1, A 228-kD centrosome autoantigen with a distinct cell cycle distribution J. Cell Biol. 124 1994 783 793 (Pubitemid 24085786)
33. C. Didier, A. Merdes, J.E. Gairin, and N. Jabrane-Ferrat Inhibition of proteasome activity impairs centrosome-dependent microtubule nucleation and organization Mol. Biol. Cell 19 2008 1220 1229 (Pubitemid 351481833)
34. P.R. Clarke, and L.A. Allan Cell-cycle control in the face of damage - a matter of life or death Trends Cell Biol. 19 2009 89 98
35. H. Kiyokawa, and D. Ray In vivo roles of cdc25 phosphatases: biological insight into the anti-cancer therapeutic targets Anticancer Agents Med. Chem. 8 2008 832 836
36. M. Donzelli, and G.F. Draetta Regulating mammalian checkpoints through cdc25 inactivation EMBO Rep. 4 2003 671 677 (Pubitemid 36974751)
37. A.O. Walter, W. Seghezzi, W. Korver, J. Sheung, and E. Lees The mitotic serine/threonine kinase aurora2/AIK is regulated by phosphorylation and degradation Oncogene 19 2000 4906 4916
38. F. Quignon, L. Rozier, A.M. Lachages, A. Bieth, M. Simili, and M. Debatisse Sustained mitotic block elicit DNA breaks: one step alteration of ploidy and chromosome integrity in mammalian cells Oncogene 26 2007 165 172 (Pubitemid 46095728)
39. N.J. Ganem, and D. Pellman Linking abnormal mitosis to the acquisition of DNA damage J. Cell Biol. 199 2012 871 881
40. I. Vermes, C. Haanen, H. Steffens-Nakken, and C. Reutelingsperger A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V J. Immunol. Method 184 1995 39 51
41. D.R. Green, and G. Kroemer The pathophysiology of mitochondrial cell death Science 305 2005 626 629 (Pubitemid 39006738)
42. m) in apoptosis: an update Apoptosis 3 2003 115 128 (Pubitemid 36553052)
43. J. Cai, and D.P. Jones Superoxide in apoptosis. Mitochondrial generation triggered by cytochrome c loss J. Biol. Chem. 273 1998 11401 11404 (Pubitemid 28272028)
44. F. Mollinedo, and C. Gajate Microtubules, microtubule-interfering agents and apoptosis Apoptosis 8 2003 413 450 (Pubitemid 37247987)
45. N.J. Chiang, C.I. Lin, J.P. Liou, C.C. Kuo, C.Y. Chang, L.T. Chen, and J.Y. Chang A novel synthetic microtubule inhibitor, MPT0B214 exhibits antitumor activity in human tumor cells through mitochondria-dependent intrinsic pathway Plos One 8 3 2013 e58953
46. R. Romagnoli, P.G. Baraldi, C. Lopez-Cara, M. Kimatrai Salvador, D. Preti, M. Aghazadeh Tabrizi, M. Bassetto, A. Brancale, E. Hamel, I. Castagliuolo, R. Bortolozzi, G. Basso, and G. Viola Synthesis and biological evaluation of 2-alkoxycarbonyl-3-anilino benzo[b]thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents J. Med. Chem. 56 2013 2606 2618
47. J.B. Denault, and G.S. Salvesen Caspases: keys in the ignition of cell death Chem. Rev. 102 2002 4489 4499
48. A.G. Porter, and R.U. Janicke Emerging role of caspase-3 in apoptosis Cell Death Differ. 6 1999 99 104
49. R. Aneja, J. Zhou, S.N. Vangapandu, B. Zhou, R. Chandra, and H.C. Joshi Drug-resistant T-lymphoid tumors undergo apoptosis selectively in response to an antimicrotubule agent, EM011 Blood 107 2006 2486 2492 (Pubitemid 43345572)
50. R. Aneja, T. Miyagi, P. Karna, T. Ezell, D. Shukla, M. Vij Gupta, C. Yates, S.R. Chinni, H. Zhau, L.W. Chung, and H.C. Joshi A novel microtubule-modulating agent induces mitochondrially driven caspase-dependent apoptosis via mitotic checkpoint activation in human prostate cancer cells Eur. J. Cancer 46 2010 1668 1678
51. I.E. Wertz, S. Kusam, C. Lam, T. Okamoto, W. Sandoval, D.J. Anderson, E. Helgason, J.A. Ernst, M. Eby, J. Liu, L.D. Belmont, J.S. Kaminker, K.M. O'Rourke, K. Pujara, P.B. Kohli, A.R. Johnson, M.L. Chiu, J.R. Lill, P.K. Jackson, W.J. Fairbrother, S. Seshagiri, M.J. Ludlam, K.G. Leong, E.C. Dueber, H. Maecker, D.C. Huang, and V.M. Dixit Sensitivity to antitubulin chemotherapeutics is regulated by MCL1 and FBW7 Nature 471 2011 110 114
52. D.R. Matson, and P.T. Stukenberg Spindle poisons and cell fate: a tale of two pathways Mol. Interv. 11 2011 141
53. A.J. DeBono, J.H. Xie, S. Ventura, C.W. Pouton, B. Capuano, and P.J. Scammells Synthesis and biological evaluation of N-substituted noscapine analogues ChemMedChem 7 2012 2122 2133
54. R.C. Mishra, P. Karna, S.R. Gundala, V. Pannu, R.A. Stanton, K.K. Gupta, M. Robindon, M. Lopus, L. Wilson, M. Henary, and R. Aneja Biochem. Pharmacol. 82 2011 110 121
55. P. Karna, P.C. Rida, V. Pannu, K.K. Gupta, W.B. Dalton, H. Joshi, V.W. Yang, J. Zhou, and R. Aneja A novel microtubule-modulating noscapinoid triggers apoptosis by inducing spindle multipolarity via centrosome amplification and declustering Cell Death Differ. 18 2011 632 644
56. G. Viola, D. Vedaldi, F. Dall'Acqua, E. Fortunato, G. Basso, N. Bianchi, C. Zuccato, M. Borgatti, I. Lampronti, and R. Gambari Induction of γ-globin mRNA, erythroid differentiation and apoptosis in UVA-irradiated human erythroid cells in the presence of furocoumarine derivatives Biochem. Pharm. 75 2008 810 825 (Pubitemid 351174109)
57. E. Hamel, and C.M. Lin Separation of active tubulin and microtubule-associated proteins by ultracentrifugation and isolation of a component causing the formation of microtubule bundles Biochemistry 23 1984 4173 4184 (Pubitemid 14042049)
58. P. Verdier-Pinard, J.Y. Lai, H.D. Yoo, J. Yu, B. Márquez, D.G. Nagle, M. Nambu, J.D. White, J.R. Falck, W.H. Gerwick, B.W. Day, and E. Hamel Structure-activity analysis of the interaction of curacin A, the potent colchicine site antimitotic agent, with tubulin and effects of analogs on the growth of MCF-7 breast cancer cells Mol. Pharmacol. 53 1998 62 76 (Pubitemid 28068373)
59. E. Hamel, and C.M. Lin Stabilization of the colchicine-binding activity of tubulin by organic acids Biochim. Biophys. Acta 675 1981 226 231 (Pubitemid 11041378)