Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2011 | 46 | 9 | 3570-3580
Tytuł artykułu

Design, synthesis and antiproliferative activities of biarylolefins based on polyhydroxylated and carbohydrate scaffolds

Treść / Zawartość
Abstrakt, słowa kluczowe
Źródło
Twórcy
Bibliografia
Dodatkowe informacje
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A series of diversely substituted biarylolefins based on carbohydrate and dihydroxyethylene scaffolds were synthesized and evaluated for antiproliferative activity against a panel of human tumor cell lines. Among the thirty-five yet unknown biarylolefins prepared, six displayed potent antiproliferative activities with IC 50 values in the micromolar and submicromolar range. As a new type of antiproliferative agent, the most potent compound 26 showed an IC 50 value of 70nM against SK-OV3 cell line (ovarian cancer). All the synthesized compounds exhibited a poor or modest tubulin polymerization inhibitory activity suggesting another mode of action for these compounds. Molecular docking simulations to the colchicine binding site of tubulin of representative compounds have been used to explain the lack of activity as inhibitors of tubulin polymerization.
Czasopismo
Rocznik
Tom
46
Numer
9
Strony
3570-3580
Opis fizyczny
Twórcy
  • UMR 7565 SRSMC, Nancy Université-CNRS, Groupe S.U.C.R.E.S, BP 239, F-54506 Nancy Vandœuvre, France
  • UMR 7565 SRSMC, Nancy Université-CNRS, Groupe S.U.C.R.E.S, BP 239, F-54506 Nancy Vandœuvre, France
  • Fédération de Recherche Physique et Chimie du Vivant, Université d’Orléans, CNRS, FR 2708, Rue Charles Sadron, 45071 Orléans Cedex 2, France
  • Institut de Chimie des Substances Naturelles, UPR2301 CNRS, Avenue de la Terrasse, F-91198 Gif sur Yvette Cedex, France
  • Institut de Chimie des Substances Naturelles, UPR2301 CNRS, Avenue de la Terrasse, F-91198 Gif sur Yvette Cedex, France
  • Institut de Chimie des Substances Naturelles, Ciblothèque cellulaire, UPR2301 CNRS, Avenue de la terrasse, F-91198 Gif sur Yvette Cedex, France
  • Institut de Chimie des Substances Naturelles, Ciblothèque cellulaire, UPR2301 CNRS, Avenue de la terrasse, F-91198 Gif sur Yvette Cedex, France
Bibliografia
  • 1. Saleem, M.& Kim, H.J.& Ali, M.S.& Lee, Y.S., "An update on bioactive plant lignans", Nat. Prod. Rep., vol. 22, 2005, p.696-716
  • 2. Lin, C.M.& Singh, S.B.& Chu, P.S.& Dempcy, R.O.& Schmidt, J.M.& Pettit, G.R.& Hamel, E., "Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin: a structure–activity study", Mol. Pharmacol., vol. 34, 1988, p.200-208
  • 3. Pettit, G.R.& Singh, S.B.& Boyd, M.R.& Hamel, E.& Pettit, R.K.& Schmidt, J.M.& Hogan, F., "Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6(1a)", J. Med. Chem., vol. 38, 1995, p.1666-1672
  • 4. Pettit, G.R.& Grealish, M.P.& Herald, D.L.& Boyd, M.R.& Hamel, E.& Pettit, R.K., "Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug", J. Med. Chem., vol. 43, 2000, p.2731-2737
  • 5. Lin, C.M.& Ho, H.H.& Pettit, G.R.& Hamel, E., "Antimitotic natural products combretastatin A-4 and combretastatin A-2: studies on the mechanism of their inhibition of the binding of colchicine to tubulin", Biochemistry, vol. 28, 1989, p.6984-6991
  • 6. Hinnen, P.& Eskens, F.A.L.M., "Vascular disrupting agents in clinical development", Br. J. Cancer, vol. 96, 2007, p.1159-1165
  • 7. Chaplin, D.J.& Pettit, G.R.& Hill, S.A., "Anti-vascular approaches to solid tumor therapy: evaluation of combretastatin A4 phosphate", Anticancer Res., vol. 19, 1999, p.189-196
  • 8. Mooney, C.J.& Nagaiah, G.& Fu, P.& Wasman, J.K.& Cooney, M.M.& Savvides, P.S.& Bokar, J.A.& Dowlati, A.& Wang, D.& Agarwala, S.S.& Flick, S.M.& Hartman, P.H.& Ortiz, J.D.& Lavertu, P.& Remick, S.C., "A phase II trial of fosbretabulin in advanced anaplastic thyroid carcinoma and correlation of baseline serum-soluble intracellular adhesion molecule-1 with outcome", Thyroid, vol. 19, 2009, p.233-240
  • 9. Tron, G.C.& Pirali, T.& Sorba, G.& Pagliai, F.& Busacca, S.& Genazzani, A.A., "Medicinal chemistry of combretastatin A4: present and future directions", J. Med. Chem., vol. 49, 2006, p.3033-3044
  • 10. Liou, J.-P.& Chang, J.-Y.& Chang, C.-W.& Chang, C.-Y.& Mahindroo, N.& Kuo, F.-M.& Hsieh, H.-P., "Synthesis and structure–activity relationships of 3-aminobenzophenones as antimitotic agents", J. Med. Chem., vol. 47, 2004, p.2897-2905
  • 11. Banwell, M.G.& Hamel, E.& Hockless, D.C.R.& Verdier-Pinard, P.& Willis, A.C.& Wong, D.J., "4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: synthesis and evaluation as anti-mitotic and cytotoxic agents", Bioorg. Med. Chem., vol. 14, 2006, p.4627-4638
  • 12. Barbosa, E.G.& Bega, L.A.S.& Beatriz, A.& Sarkar, T.& Hamel, E.& do Amaral, M.S.& Pires de Lima, D., "A diaryl sulfide, sulfoxide, and sulfone bearing structural similarities to combretastatin A-4", Eur. J. Med. Chem., vol. 44, 2009, p.2685-2688
  • 13. Romagnoli, R.& Baraldi, P.G.& Carrion, M.D.& Cruz-Lopez, O.& Lopez Cara, C.& Basso, G.& Viola, G.& Khedr, M.& Balzarini, J.& Mahboobi, S.& Sellmer, A.& Brancale, A.& Hamel, E., "2-Arylamino-4-amino-5-aroylthiazoles. One-pot synthesis and biological evaluation of a new class of inhibitors of tubulin polymerization", J. Med. Chem., vol. 52, 2009, p.5551-5555, Romagnoli, R.& Baraldi, P.G.& Cruz-Lopez, O.& Lopez Cara, C.& Carrion, M.D.& Brancale, A.& Hamel, E.& Chen, L.& Bortolozzi, R.& Basso, G.& Viola, G., "Synthesis and antitumor activity of 1,5-disubstituted 1,2,4-triazoles as cis-restricted combretastatin analogues", J. Med. Chem., vol. 53, 2010, p.4248-4258
  • 14. Burja, B.& Cimbora-Zovko, T.& Tomic, S.& Jelusic, T.& Kocevar, M.& Polanc, S.& Osmak, M., "Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies", Bioorg. Med. Chem., vol. 18, 2010, p.2375-2387
  • 15. Odlo, K.& Fournier-Dit-Chabert, J.& Ducki, S.& Gani, O.A.B.S.M.& Sylte, I.& Hansen, T.V., "1,2,3-Triazole analogs of combretastatin A-4 as potential microtubule-binding agents", Bioorg. Med. Chem., vol. 18, 2010, p.6874-6885, Bailly, C.& Bal, C.& Barbier, P.& Combes, S.& Finet, J.-P.& Hildebrand, M.-P.& Peyrot, V.& Wattez, N., "Synthesis and biological evaluation of 4-arylcoumarin analogues of combretastatins", J. Med. Chem., vol. 46, 2003, p.5437-5444
  • 16. Ty, N.& Kaffy, J.& Arrault, A.& Thoret, S.& Pontikis, R.& Dubois, J.& Morin-Allory, L.& Florent, J.-C., "Synthesis and biological evaluation of cis-locked vinylogous combretastatin-A4 analogues: derivatives with a cyclopropyl-vinyl or a cyclopropyl-amide bridge", Bioorg. Med. Chem. Lett., vol. 19, 2009, p.1318-1322
  • 17. Maya, A.B.S.& Perez-Melero, C.& Mateo, C.& Alonso, D.& Fernandez, J.L.& Gajate, C.& Mollinedo, F.& Pelaez, R.& Caballero, E.& Medarde, M., "Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety", J. Med. Chem., vol. 48, 2005, p.556-568
  • 18. Sanchez Maya, A.B.& Perez-Melero, C.& Salvador, N.& Pelaez, R.& Caballero, E.& Medarde, M., "New naphthylcombretastatins. Modifications on the ethylene bridge", Bioorg. Med. Chem., vol. 13, 2005, p.2097-2107
  • 19. Pettit, G.R.& Toki, B.& Herald, D.L.& Verdier-Pinard, P.& Boyd, M.R.& Hamel, E.& Pettit, R.K., "Antineoplastic agents. 379. Synthesis of phenstatin phosphate", J. Med. Chem., vol. 41, 1998, p.1688-1695
  • 20. Alvarez, C.& Alvarez, R.& Corchete, P.& Perez-Melero, C.& Pelaez, R.& Medarde, M., "Exploring the effect of 2,3,4-trimethoxyphenyl moiety as a component of indolephenstatins", Eur. J. Med. Chem., vol. 45, 2010, p.588-597
  • 21. Pettit, G.R.& Grealish, M.P.& Jung, M.K.& Hamel, E.& Pettit, R.K.& Chapuis, J.C.& Schmidt, J.M., "Antineoplastic agents. 465. Structural modification of resveratrol: sodium resverastatin phosphate", J. Med. Chem., vol. 45, 2002, p.2534-2542
  • 22. Romagnoli, R.& Baraldi, P.G.& Jung, M.K.& Iaconinoto, M.A.& Carrion, M.D.& Remusat, V.& Preti, D.& Tabrizi, M.A.& Francesca, F.& De Clercq, E.& Balzarini, J.& Hamel, E., "Synthesis and preliminary biological evaluation of new anti-tubulin agents containing different benzoheterocycles", Bioorg. Med. Chem. Lett., vol. 15, 2005, p.4048-4052, Romagnoli, R.& Baraldi, P.G.& Pavani, M.G.& Tabrizi, M.A.& Preti, D.& Fruttarolo, F.& Piccagli, L.& Jung, M.K.& Hamel, E.& Borgatti, M.& Gambari, R., "Synthesis and biological evaluation of 2-amino-3-(3′,4′,5′-trimethoxybenzoyl)-5-aryl thiophenes as a new class of potent antitubulin agents", J. Med. Chem., vol. 49, 2006, p.3906-3915, Romagnoli, R.& Baraldi, P.G.& Remusat, V.& Carrion, M.D.& Cara, C.L.& Preti, D.& Fruttarolo, F.& Pavani, M.G.& Tabrizi, M.A.& Tolomeo, M.& Grimaudo, S.& Balzarini, J.& Jordan, M.A.& Hamel, E., "Synthesis and biological evaluation of 2-(3′,4′,5′-trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors", J. Med. Chem., vol. 49, 2006, p.6425-6428
  • 23. Alvarez, C.& Alvarez, R.& Corchete, P.& Perez-Melero, C.& Pelaez, R.& Medarde, M., "Synthesis and biological activity of naphthalene analogues of phenstatins: naphthylphenstatins", Bioorg. Med. Chem. Lett., vol. 17, 2007, p.3417-3420, Alvarez, C.& Alvarez, R.& Corchete, P.& Perez-Melero, C.& Pelaez, R.& Medarde, M., "Naphthylphenstatins as tubulin ligands: synthesis and biological evaluation", Bioorg. Med. Chem., vol. 16, 2008, p.8999-9008
  • 24. Jiang, S.& Crogan-Grundy, C.& Drewe, J.& Tseng, B.& Cai, S.X., "Discovery of (naphthalen-4-yl)(phenyl)methanones and N-methyl-N-phenylnaphthalen-1-amines as new apoptosis inducers using a cell- and caspase-based HTS assay", Bioorg. Med. Chem. Lett., vol. 18, 2008, p.5725-5728
  • 25. Ducki, S.& MacKenzie, G.& Greedy, B.& Armitage, S.& Fournier Dit Chabert, J.& Bennett, E.& Nettles, J.& Snyder, J.P.& Lawrence, N.J., "Combretastatin-like chalcones as inhibitors of microtubule polymerisation. Part 2: structure-based discovery of alpha-aryl chalcones", Bioorg. Med. Chem., vol. 17, 2009, p.7711-7722
  • 26. Romagnoli, R.& Baraldi, P.G.& Carrion, M.D.& Cruz-Lopez, O.& Tolomeo, M.& Grimaudo, S.& Di Cristina, A.& Pipitone, M.R.& Balzarini, J.& Brancale, A.& Hamel, E., "Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors", Bioorg. Med. Chem., vol. 18, 2010, p.5114-5122
  • 27. Liou, J.-P.& Chang, Y.-L.& Kuo, F.-M.& Chang, C.-W.& Tseng, H.-Y.& Wang, C.-C.& Yang, Y.-N.& Chang, J.-Y.& Lee, S.-J.& Hsieh, H.-P., "Concise synthesis and structure–activity relationships of combretastatin A-4 analogues, 1-aroylindoles and 3-aroylindoles, as novel classes of potent antitubulin agents", J. Med. Chem., vol. 47, 2004, p.4247-4257
  • 28. Dupeyre, G.& Chabot, G.G.& Thoret, S.& Cachet, X.& Seguin, J.& Guenard, D.& Tillequin, F.& Scherman, D.& Koch, M.& Michel, S., "Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents", Bioorg. Med. Chem., vol. 14, 2006, p.4410-4426
  • 29. Liou, J.-P.& Mahindroo, N.& Chang, C.-W.& Guo, F.-M.& Lee, S.W.-H.& Tan, U.-K.& Yeh, T.-K.& Kuo, C.-C.& Chang, Y.-W.& Lu, P.-H.& Tung, Y.-S.& Lin, K.-T.& Chang, J.-Y.& Hsieh, H.-P., "Structure–activity relationship studies of 3-aroylindoles as potent antimitotic agents", ChemMedChem, vol. 1, 2006, p.1106-1118
  • 30. Jin, Y.& Zhou, Z.Y.& Tian, W.& Yu, Q.& Longa, Q.Y., "4′-Alkoxyl substitution enhancing the anti-mitotic effect of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8-nitroquinazolines as a novel class of anti-microtubule agents", Bioorg. Med. Chem. Lett., vol. 16, 2006, p.5864-5869
  • 31. Alvarez, C.& Alvarez, R.& Corchete, P.& Lopez, J.L.& Perez-Melero, C.& Pelaez, R.& Medarde, M., "Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization", Bioorg. Med. Chem., vol. 16, 2008, p.5952-5961
  • 32. Messaoudi, S.& Treguier, B.& Hamze, A.& Provot, O.& Peyrat, J.-F.& De Losada, J.R.& Liu, J.-M.& Bignon, J.& Wdzieczak-Bakala, J.& Thoret, S.& Dubois, J.& Brion, J.-D.& Alami, M., "Isocombretastatins A versus combretastatins A: the forgotten isoCA-4 isomer as a highly promising cytotoxic and antitubulin agent", J. Med. Chem., vol. 52, 2009, p.4538-4542
  • 33. Alvarez, R.& Alvarez, C.& Mollinedo, F.& Sierra, B.G.& Medarde, M.& Pelaez, R., "Isocombretastatins A: 1,1-diarylethenes as potent inhibitors of tubulin polymerization and cytotoxic compounds", Bioorg. Med. Chem., vol. 17, 2009, p.6422-6431
  • 34. Novoa, A.& Pellegrini-Moïse, N.& Lamandé-Langle, S.& Chapleur, Y., "Efficient access to disubstituted exo-glycals. Application to the preparation of C-glycosyl compounds", Tetrahedron Lett., vol. 50, 2009, p.6484-6487
  • 35. Chattopadhyay, S.K.& Kumar, T.R.S.& Maulik, P.R.& Srivastava, S.& Garg, A.& Sharon, A.& Negi, A.S.& Khanuja, S.P.S., "Absolute configuration and anticancer activity of taxiresinol and related lignans of Taxus wallichiana", Bioorg. Med. Chem., vol. 11, 2003, p.4945-4948
  • 36. Taillefumier, C.& Chapleur, Y., "Synthesis and uses of exo-glycals", Chem. Rev., vol. 104, 2004, p.263-292, Lakhrissi, Y.& Taillefumier, C.& Chrétien, F.& Chapleur, Y., "Facile dibromoolefination of lactones using bromomethylene triphenylphosphorane", Tetrahedron Lett., vol. 42, 2001, p.7265-7268
  • 37. Feldman, K.S., "Cyclization pathways of a (Z)-stilbene-derived bis(ortho quinone monoketal)", J. Org. Chem., vol. 62, 1997, p.4983-4990, Ocasio, C.A.& Scanlan, T.S., "Characterization of thyroid hormone receptor alpha (TRα)-specific analogs with varying inner- and outer-ring substituents", Bioorg. Med. Chem., vol. 16, 2008, p.762-770
  • 38. National Cancer Institute (NCI), Bethesda. Available from: http://dtp.nci.nih.gov.
  • 39. Ravelli, R.B.G.& Gigant, B.& Curmi, P.A.& Jourdain, I.& Lachkar, S.& Sobel, A.& Knossow, M., "Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain", Nature (London, U.K, vol. 428, 2004, p.198-202
  • 40. 3D structure of phenstatin and phenstatin-like compounds were next built from the best CA-4 docked pose and then optimized again by minimization. Available from: http://www.rcsb.org/pdb/home/home.do.
  • 41. Bai, R.& Paull, K.D.& Herald, C.L.& Malspeis, L.& Pettit, G.R.& Hamel, E., "Halichondrin B and homohalichondrin B, marine natural products binding in the vinca domain of tubulin. Discovery of tubulin-based mechanism of action by analysis of differential cytotoxicity data", J. Biol. Chem., vol. 266, 1991, p.15882-15889
  • 42. Paull, K.D.& Lin, C.M.& Malspeis, L.& Hamel, E., "Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data", Cancer Res., vol. 52, 1992, p.3892-3900
  • 43. Bellina, F.& Cauteruccio, S.& Montib, S.& Rossia, R., "Novel imidazole-based combretastatin A-4 analogues: evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin", Bioorg. Med. Chem. Lett., vol. 16, 2006, p.5757-5762
  • 44. Minocha, A.& Long, B.H., "Inhibition of the DNA catenation activity of type II topoisomerase by VP16-213 and VM26", Biochem. Biophys. Res. Commun., vol. 122, 1984, p.165-170
  • 45. Meresse, P.& Dechaux, E.& Monneret, C.& Bertounesque, E., "Etoposide: discovery and medicinal chemistry", Curr. Med. Chem., vol. 11, 2004, p.2443-2466
  • 46. Xu, H.& Lv, M.& Tian, X., "Review on hemisynthesis, biosynthesis, biological activities, mode of action, and structure-activity relationship of podophyllotoxins: 2003–2007", Curr. Med. Chem., vol. 16, 2009, p.327-349
  • 47. Zavala, F.& Guenard, D.& Robin, J.-P.& Brown, E., "Structure–antitubulin activity relationships in steganacin congeners and analogues. Inhibition of tubulin polymerization in vitro by isodeoxypodophyllotoxin", J. Med. Chem., vol. 23, 1980, p.546-549
  • 48. Maestro, version 9.1, Glide, version 5.6, MacroModel, version 9.8, Schrödinger, LLC, New York, NY, 2010.
  • 49. Available from: http://www.molecular-networks.com/products/corina.
  • 50. Sadowski, J.& Gasteiger, J., "From atoms and bonds to three-dimensional atomic coordinates: automatic model builders", Chem. Rev., vol. 93, 1993, p.2567-2581
Kolekcja
Elsevier
Identyfikator YADDA
bwmeta1.element.elsevier-89228d43-a8ac-314a-bcba-24707ffcce79
Identyfikatory
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.