Structure-activity relationships of novel substituted naphthalene diimides as anticancer agents

European Journal of Medicinal Chemistry

Volumn 57, Issue , 2012, Pages 417-428

  Milelli, Andrea ^a   Tumiatti, Vincenzo ^a   Micco, Marialuisa ^a   Rosini, Michela ^a   Zuccari, Guendalina ^a   Raffaghello, Lizzia ^b   Bianchi, Giovanna ^b   Pistoia, Vito ^b   Fernando Diaz J ^c   Pera, Benet ^c   Trigili, Chiara ^c   Barasoain, Isabel ^c   Musetti, Caterina ^d   Toniolo, Marianna ^d   Sissi, Claudia ^d   Alcaro, Stefano ^e   Moraca, Federica ^e   Zini, Maddalena ^a   Stefanelli, Claudio ^a   Minarini, Anna ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b G GASLINI INSTITUTE   (Italy)

^c CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^d UNIVERSITY OF PADOVA   (Italy)

^e UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

Author keywords

Anticancer; Cytotoxicity; Multitarget directed ligands; Naphthalene diimides

Indexed keywords

2,7 BIS[3 (2,3,4 TRIMETHOXYBENZYLAMINO)PROPYL]BENZO[LMN][3,8]PHENANTHROLINE 1,3,6,8 TETRAONE; ANTINEOPLASTIC AGENT; CARBENE; CASPASE; GUANINE QUADRUPLEX; IMIDE; MITOGEN ACTIVATED PROTEIN KINASE 1; NAPHTHALENE DERIVATIVE; TAQ POLYMERASE; TELOMERASE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; COLON CANCER; CONTROLLED STUDY; CYTOSTASIS; CYTOTOXICITY; DNA STRUCTURE; DOWN REGULATION; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME PHOSPHORYLATION; HUMAN; HUMAN TISSUE; MICROTUBULE; MOLECULAR MODEL; OVARY CANCER; OXIDATION; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASES; CELL LINE, TUMOR; CYTOTOXINS; DRUG SCREENING ASSAYS, ANTITUMOR; EXTRACELLULAR SIGNAL-REGULATED MAP KINASES; G-QUADRUPLEXES; GENE EXPRESSION; HUMANS; IMIDES; MOLECULAR DOCKING SIMULATION; NAPHTHALENES; PHOSPHORYLATION; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TAQ POLYMERASE; TELOMERASE; THERMODYNAMICS;

EID: 84870059174     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.045     Document Type: Article

References (47)

1. S. Takenaka, and M. Takagi Threading intercalators as a new DNA structural probe Bull. Chem. Soc. Jpn. 72 1999 327 337
2. M.F. Brana, M. Cacho, A. Gradillas, B. de Pascual-Teresa, and A. Ramos Intercalators as anticancer drugs Curr. Pharm. Des. 7 2001 1745 1780
3. R. Martinez, and L. Chacon-Garcia The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work Curr. Med. Chem. 12 2005 127 151
4. L.M. Tumir, and I. Piantanida Recognition of single stranded and double stranded DNA/RNA sequences in aqueous medium by small bis-aromatic derivatives Mini Rev. Med. Chem. 10 2010 299 308
5. L. Strekowski, and B. Wilson Noncovalent interactions with DNA: an overview Mutat. Res. 623 2007 3 13
6. T. Nojima, K. Ohtsuka, T. Nagamatsu, and S. Takenaka Bis-naphthalene diimide exhibiting an effective bis-threading intercalating ability Nucleic Acids Res. Suppl. 2003 123 124
7. D.A. Gianolio, and L.W. McLaughlin Tethered naphthalene diimide intercalators enhance DNA triplex stability Bioorg. Med. Chem. 9 2001 2329 2334
8. S. Balasubramanian, and S. Neidle G-quadruplex nucleic acids as therapeutic targets Curr. Opin. Chem. Biol. 13 2009 345 353
9. M. Di Antonio, F. Doria, S.N. Richter, C. Bertipaglia, M. Mella, C. Sissi, M. Palumbo, and M. Freccero Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents J. Am. Chem. Soc. 131 2009 13132 13141
10. M. Gunaratnam, S. Swank, S.M. Haider, K. Galesa, A.P. Reszka, M. Beltran, F. Cuenca, J.A. Fletcher, and S. Neidle Targeting human gastrointestinal stromal tumor cells with a quadruplex-binding small molecule J. Med. Chem. 52 2009 3774 3783
11. Z.R. Liu, K.H. Hecker, and R.L. Rill Selective DNA binding of (N-alkylamine)-substituted naphthalene imides and diimides to G+C-rich DNA J. Biomol. Struct. Dynam. 14 1996 331 339
12. A. Minarini, A. Milelli, V. Tumiatti, L. Ferruzzi, M.R. Marton, E. Turrini, P. Hrelia, and C. Fimognari Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality Eur. J. Med. Chem. 48 2012 124 131
13. V. Tumiatti, A. Milelli, A. Minarini, M. Micco, A. Gasperi Campani, L. Roncuzzi, D. Baiocchi, J. Marinello, G. Capranico, M. Zini, C. Stefanelli, and C. Melchiorre Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent J. Med. Chem. 52 2009 7873 7877
14. H.J. Schneider Ligand binding to nucleic acids and proteins: does selectivity increase with strength? Eur. J. Med. Chem. 43 2008 2307 2315
15. V. Tumiatti, M. Rosini, M. Bartolini, A. Cavalli, G. Marucci, V. Andrisano, P. Angeli, R. Banzi, A. Minarini, M. Recanatini, and C. Melchiorre Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 2. Role of the substituents on the phenyl ring and nitrogen atoms of caproctamine J. Med. Chem. 46 2003 954 966
16. A. Cavalli, M.L. Bolognesi, A. Minarini, M. Rosini, V. Tumiatti, M. Recanatini, and C. Melchiorre Multi-target-directed ligands to combat neurodegenerative diseases J. Med. Chem. 51 2008 347 372
17. A. Petrelli, and G. Valabrega Multitarget drugs: the present and the future of cancer therapy Expert Opin. Pharmacother. 10 2009 589 600
18. W.K. Hagmann The many roles for fluorine in medicinal chemistry J. Med. Chem. 51 2008 4359 4369
19. M.R. Grever, S.A. Schepartz, and B.A. Chabner The National Cancer Institute: cancer drug discovery and development program Semin. Oncol. 19 1992 622 638
20. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, and A. Vaigro-Wolff Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines J. Natl. Cancer Inst. 83 1991 757 766
21. J.N. Weinstein, T.G. Myers, P.M. O'Connor, S.H. Friend, A.J. Fornace Jr., K.W. Kohn, T. Fojo, S.E. Bates, L.V. Rubinstein, N.L. Anderson, J.K. Buolamwini, W.W. van Osdol, A.P. Monks, D.A. Scudiero, E.A. Sausville, D.W. Zaharevitz, B. Bunow, V.N. Viswanadhan, G.S. Johnson, R.E. Wittes, and K.D. Paull An information-intensive approach to the molecular pharmacology of cancer Science 275 1997 343 349
22. I.N. Lavrik, A. Golks, and P.H. Krammer Caspases: pharmacological manipulation of cell death J. Clin. Invest. 115 2005 2665 2672
23. J.D. Robertson, and S. Orrenius Molecular mechanisms of apoptosis induced by cytotoxic chemicals Crit. Rev. Toxicol. 30 2000 609 627
24. K. Balmanno, and S.J. Cook Tumour cell survival signalling by the ERK1/2 pathway Cell Death Differ. 16 2009 368 377
25. A.R. Morgan, J.S. Lee, D.E. Pulleyblank, N.L. Murray, and D.H. Evans Review: ethidium fluorescence assays. Part 1. Physicochemical studies Nucleic Acids Res. 7 1979 547 569
26. A.W. McConnaughie, and T.C. Jenkins Novel acridine-triazenes as prototype combilexins: synthesis, DNA binding, and biological activity J. Med. Chem. 38 1995 3488 3501
27. C. Sissi, L. Lucatello, A. Paul Krapcho, D.J. Maloney, M.B. Boxer, M.V. Camarasa, G. Pezzoni, E. Menta, and M. Palumbo Tri-, tetra- and heptacyclic perylene analogues as new potential antineoplastic agents based on DNA telomerase inhibition Bioorg. Med. Chem. 15 2007 555 562
28. F. Cuenca, O. Greciano, M. Gunaratnam, S. Haider, D. Munnur, R. Nanjunda, W.D. Wilson, and S. Neidle Tri- and tetra-substituted naphthalene diimides as potent G-quadruplex ligands Bioorg. Med. Chem. Lett. 18 2008 1668 1673
29. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne The Protein Data Bank Nucleic Acids Res. 28 2000 235 242
30. A. Canals, M. Purciolas, J. Aymami, and M. Coll The anticancer agent ellipticine unwinds DNA by intercalative binding in an orientation parallel to base pairs Acta Crystallogr. D Biol. Crystallogr. 61 2005 1009 1012
31. G.N. Parkinson, F. Cuenca, and S. Neidle Topology conservation and loop flexibility in quadruplex-drug recognition: crystal structures of inter- and intramolecular telomeric DNA quadruplex-drug complexes J. Mol. Biol. 381 2008 1145 1156
32. S. Alcaro, F. Ortuso, and R.S. Coleman DNA cross-linking by azinomycin B: Monte Carlo simulations in the evaluation of sequence selectivity J. Med. Chem. 45 2002 861 870
33. S. Alcaro, F. Gasparrini, O. Incani, S. Mecucci, D. Misiti, M. Pierini, and C. Villani A "quasi-flexible" automatic docking processing for studying stereoselective recognition mechanisms. Part I. Protocol validation J. Comput. Chem. 21 2000 515 530
34. S. Alcaro, A. Artese, J.N. Iley, S. Missailidis, F. Ortuso, L. Parrotta, R. Pasceri, F. Paduano, C. Sissi, F. Trapasso, and M.G. Vigorita Rational design, synthesis, biophysical and antiproliferative evaluation of fluorenone derivatives with DNA G-quadruplex binding properties ChemMedChem 5 2010 575 583
35. S. Alcaro, G. Costa, S. Distinto, F. Moraca, F. Ortuso, L. Parrotta, and A. Artese The polymorphisms of DNA G-quadruplex investigated by docking experiments with telomestatin enantiomers Curr. Pharm. Des. 18 2011 1873 1879
36. R.M. Buey, E. Calvo, I. Barasoain, O. Pineda, M.C. Edler, R. Matesanz, G. Cerezo, C.D. Vanderwal, B.W. Day, E.J. Sorensen, J.A. Lopez, J.M. Andreu, E. Hamel, and J.F. Diaz Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites Nat. Chem. Biol. 3 2007 117 125
37. C. de Ines, D. Leynadier, I. Barasoain, V. Peyrot, P. Garcia, C. Briand, G.A. Rener, and C. Temple Jr. Inhibition of microtubules and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumor drug, CI 980, and by its chiral isomer, NSC 613863 Cancer Res. 54 1994 75 84
38. F. Oosawa, and S. Asakura Thermodynamics of the Polymerization of Proteins London 1975
39. R.M. Buey, I. Barasoain, E. Jackson, A. Meyer, P. Giannakakou, I. Paterson, S. Mooberry, J.M. Andreu, and J.F. Diaz Microtubule interactions with chemically diverse stabilizing agents: thermodynamics of binding to the paclitaxel site predicts cytotoxicity Chem. Biol. 12 2005 1269 1279
40. J. McGhee, and P. von Hippel Theoretical aspects of DNA-protein interactions: co-operative and non co-operative binding of large ligands to a one-dimensional homogeneous lattice J. Mol. Biol. 86 1974 469 489
41. LigPrep, Version 2.3 2009 Schroedinger LLC New York
42. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still Macromodel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics J. Comput. Chem. 11 1990 440 467
43. D.Q. Mcdonald, and W.C. Still Amber-asterisk torsional parameters for the peptide backbone Tetrahedron Lett. 33 1992 7743 7746
44. D. Hasel, T.F. Hendrickson, and W.C. Still A rapid approximation to the solvent accessible surface areas of atoms Tetrahedron Comput. Methodol. 1 1988 103 116
45. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 19 1998 1639 1662
46. S. Alcaro, F. Gasparrini, O. Incani, L. Caglioti, M. Pierini, and C. Villani "Quasi flexible" automatic docking processing for studying stereoselective recognition mechanisms, part 2: prediction of Delta Delta G of complexation and H-1-NMR NOE correlation J. Comput. Chem. 28 2007 1119 1128
47. G. Wolber, and T. Langer LigandScout: 3-d pharmacophores derived from protein-bound Ligands and their use as virtual screening filters J. Chem. Inf. Model. 45 2005 160 169