New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles: Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties

Journal of Medicinal Chemistry

Volumn 47, Issue 6, 2004, Pages 1391-1399

  Braña, Miguel F ^a   Cacho, Mónica ^a   García, Mario A ^a   De Pascual Teresa, Beatriz ^a   Ramos, Ana ^a   Domínguez, M Teresa ^a   Pozuelo, José M ^a   Abradelo, Cristina ^a   Rey Stolle, María Fernanda ^a   Yuste, Mercedes ^a   Báñez Coronel, Mónica ^b   Lacal, Juan Carlos ^b  

^a UNIVERSIDAD SAN PABLO CEU   (Spain)

^b INSTITUTO DE INVESTIGACIONES BIOMÉDICAS ALBERTO SOLS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

5 [2 (DIMETHYLAMINO)ETHYL]BENZ[DE]FURO[2,3 G]ISOQUINOLINE 4,6(5H) DIONE; 5 [2 (DIMETHYLAMINO)ETHYL]BENZ[DE]THIENO[2,3 G]ISOQUINOLINE 4,6(5H) DIONE; 5 [2 (DIMETHYLAMINO)ETHYL]BENZ[DE]THIENO[3,2 G]ISOQUINOLINE 4,6(5H) DIONE; AMONAFIDE; ANTINEOPLASTIC AGENT; ELINAFIDE; FURAN; IMIDE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]FURO[2,3 G]ISOQUINOLIN 5 YL)ETHYL] N,N' DIMETHYL 1,3 PROPANEDIAMINE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]FURO[2,3 G]ISOQUINOLIN 5 YL]ETHYL) 1,3 PROPANEDIAMINE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]FURO[3,2 G]ISOQUINOLIN 5 YL)ETHYL] N,N' DIMETHYL 1,3 PROPANEDIAMINE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]THIENO[2,3 G]ISOQUINOLIN 5 Y)ETHYL] N,N' DIMETHYL 1,3 PROPANEDIAMINE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]THIENO[2,3 G]ISOQUINOLIN 5 YL)ETHYL] 1,3 PROPANEDIAMINE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]THIENO[3,2 G]ISOQUINOLIN 5 YL)ETHYL] 1,3 PROPANEDIAMINE; N,N' BIS[2 (4,6 DIOXO 5,6 DIHYDRO 4H BENZ[DE]THIENO[3,2 G]ISOQUINOLIN 5 YL)ETHYL] N,N' DIMETHYL 1,3 PROPANEDIAMINE; NAPHTHALIMIDE; THIOPHENE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING KINETICS; COMPLEX FORMATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; GEL ELECTROPHORESIS; HUMAN; HUMAN CELL; MOLECULAR DYNAMICS; MOLECULAR MODEL; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; CELL LINE, TUMOR; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; HUMANS; IMIDES; INTERCALATING AGENTS; ISOQUINOLINES; MICE; MICE, NUDE; MODELS, MOLECULAR; NAPHTHALIMIDES; NEOPLASM TRANSPLANTATION; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TRANSPLANTATION, HETEROLOGOUS;

EID: 12144286685     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0308850     Document Type: Article

References (27)

1. Malviya, V. K.; Liu, P. Y.; Alberts, D. S.; Surwit, E. A.; Craig, J. B.; Hanningan, E. V. Evaluation of Amonafide in Cervical Cancer, Phase II. A SWOG Study. Am. J. Clin. Oncol. 1992, 15, 41-44.
2. Bousquet, P. F.; Braña, M. F.; Conlon, D.; Fitzgerald, K. M.; Perron, D.; Cocchiaro, C.; Miller, R.; Moran, M.; George, J.; Qian, X.-D.; Keilhauer, G.; Romerdahl, C. A. Preclinical Evaluation of LU79553: a Novel Bis-naphthalimide with Potent Antitumor Activity. Cancer Res. 1995, 55, 1176-1180.
3. Braña, M. F.; Cacho, M.; García, M. A.; de Pascual-Teresa, B.; Ramos, A.; Acero, N.; Llinares, F.; Muñoz-Mingarro, D.; Abradelo, C.; Rey-Stolle, M. F.; Yuste, M. Synthesis, Antitumor Activity, Molecular Modelling and DNA Binding Properties of a New Series of Imidazonaphthalimides. J. Med. Chem. 2002, 45, 5813-5816.
4. Braña, M. F.; Cacho, M.; Ramos, A.; Dominguez, M. T.; Pozuelo, J. M.; Abradelo, C.; Rey-Stolle, M. F.; Yuste, M.; Carrasco, C.; Bailly, C. Synthesis, Biological Evaluation and DNA Binding Properties of Novel Mono and Bisnaphthalimides. Org. Biomol. Chem. 2003, 1, 648-654.
5. Patten, A. D.; Pacofsky, G.; Seitz, S. P.; Akamike, E. A.; Cherney, R. J.; Kaltenbach, R. F.; Orwat, M. J. Polycyclic and Heterocyclic Chromophores for Bis-imide Tumoricidals. Patent WO 9500490, 1995.
6. Bailly, C.; Carrasco, C.; Joubert, A.; Bal, C.; Wattez, N.; Hildebrand, M.-P.; Lansiaux, A.; Colson, P.; Houssier, C.; Cacho, M.; Ramos, A.; Braña, M. F. Chromophore-modified Bis-naphthalimides: DNA Recognition, Topoisomerase Inhibition and Cytotoxic Properties of Two Mono- and Bis-furonaphthalimides. Biochemistry 2003, 42, 4136-4150.
7. Deady, L. W.; Desneves, J.; Kaye, A. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. Synthesis and Antitumor Activity of Some Indeno[1,2-b]quinoline-based Bis-carboxamides. Bioorg. Med. Chem. 2000, 8, 977-984.
8. Gamage, S. A.; Spicer, J. A.; Finlay, G. J.; Stewart, A. J.; Charlton, P.; Baguley, B. C.; Denny, W. A. Dicationic Bis(9-methylphenazine-1-carboxamides): Relationships between Biological Activity and Linker Chain Stucture for a Series of Potent Topoisomerase Targeted Anticancer Drugs. J. Med. Chem. 2001, 44, 1407-1415.
9. Braña, M. F.; Castellano, J. M.; Morán, M.; Pérez de Vega, M. J.; Perron, D.; Conlon, D.; Bousquet, P. F.; Romerdahl, C. A.; Robinson, S. P. Bis-naphthalimides 3: Synthesis and Antitumor Activity of N,N′-Bis[2-(1,8-naphthalimido)ethyl]alkanediamines. Anti-Cancer Drug Des. 1996, 11, 297-309.
10. Gallego, J.; Reid, B. R. Solution Structure and Dynamics of a Complex Between DNA and the Antitumor Bisnaphthalimide LU-79553: Intercalated Ring Flipping on the Millisecond Time Scale. Biochemistry 1999, 38, 15104-15114.
11. de Pascual-Teresa, B.; Gallego, J.; Ortiz, A. R.; Gago, F. Molecular Dynamics Simulations of the Bis-Intercalated Complexes of Ditercalinium and Flexi-Di with the Hexanucleotide d(GCGCGC)2: Theoretical Analysis of the Interaction and Rationale for the Sequence Binding Specificity. J. Med. Chem. 1996, 39, 4810-4824.
12. Braña, M. F.; Casarrubios, C.; Domínguez, G.; Fernández, C.; Pérez, J. M.; Quiroga, A. G.; Navarro-Ranninger, C.; de Pascual-Teresa, B. Synthesis, Cytotoxic Activities and Proposed Mode of Binding of a Series of Bis{[(9-oxo-9,10-dihydroacridine-4-carbonyl)amino]alkyl}alkylamines. Eur. J. Med. Chem. 2002, 37, 301-313.
13. Bailly, C.; Braña, M.; Waring, J. Sequence-selective Intercalation of Antitumor Bis-naphthalimides into DNA. Evidence for an Approach Via the Major Groove. Eur. J. Biochem. 1996, 240, 195-208.
14. Young, M. A.; Beveridge, D. L. Molecular Dynamics Simulations of an Oligonucleotide Duplex with Adenine Tracts Phased by a Full Helix Turn. J. Mol. Biol. 1998, 281, 675-687.
15. Sherer, E. C.; Harris, S. A.; Soliva, R.; Orozco, M.; Laughton, C. A. Molecular Dynamics Studies of DNA A-Tract Structure and Flexibility. J. Am. Chem. Soc. 1999, 121, 5981-5991.
16. 2-C5): Effects of Sequence Polarity on DNA Curvature. J. Mol. Biol. 1999, 285, 1623-1632.
17. Pastor, N.; Pardo, L.; Weinstein, H. Does TATA Matter? A Structural Exploration of the Selectivity Determinants in its Complexes with TATA Box-binding Protein. Biophys. J. 1997, 73, 640-652.
18. Cheatham, T. E. r.; Kollman, P. A. Observation of the A-DNA to B-DNA Transition During Unrestrained Molecular Dynamics in Aqueous Solution. J. Mol. Biol. 1996, 259, 434-444.
19. Garcia-Nieto, R.; Manzanares, I.; Cuevas, C.; Gago, F. Bending of DNA upon Binding of Ecteinascidin 743 and Phthalascidin 650 Studied by Unrestrained Molecular Dynamics Simulations. J. Am. Chem. Soc. 2000, 122, 7172-7182.
20. Cory, M.; Mckee, D. D.; Kagan, J.; Henry, D. W.; Miller, J. A. Design, Synthesis, and DNA Binding Properties of Bifunctional Intercalators. Comparison of Polymethylene and Diphenyl Ether Chains Connecting Phenanthridine. J. Am. Chem. Soc. 1985, 107, 2528-2536.
21. Cohen, G.; Eisenberg, H. Deoxyribonucleate Solutions: Sedimentation in a Density Gradient, Partial Specific Volumes, Density and Refractive Index Increments, and Preferential Interactions. Biopolymers 1968, 6, 1077-1100.
22. Wakelin, L. P. G. Polyfunctional DNA Intercalating Agents. Med. Res. Rev. 1986, 6, 275-340.
23. Moinet-Hedin, V.; Tabka, T.; Poulain, L.; Godard, T.; Lechevrel, M.; Saturnino, C.; Lancelot, J. C.; Le Talaër, J. Y.; Gauduchon, P. Biological Properties of 5,11-Dimethyl-6H-pyrido[3,2-b]carbazoles: A New Class of Potent Antitumor Drugs. Anti-Cancer Drug Des. 2000, 15, 109-118.
24. Sheehan, J. C.; O'Neill, R. C. The Formation of Five and Six-membered Rings by the Acyloin Condensation. II. The Cyclization of Dimethyl Hexahydrohomophthalate. J. Am. Chem. Soc. 1950, 72, 4614-4616.
25. El-Rayyes, N. R.; Ali, A. H. A. The Stobbe Condensation with Dimethyl Homophthalate II. J. Heterocycl. Chem. 1976, 13, 83-88.
26. Eigner, J.; Doty, P. The Native, Denatured and Renatured States of Deoxyribonucleic Acid. J. Mol. Biol. 1965, 12, 549-580.
27. Müller, W.; Crothers, D. M.; Ihara, T. Interactions of Heteroaromatic Compounds with Nucleic Acids. 1. Influence of Heteroatoms and Polarizability on the Base Specificity of Intercalating Ligands. Eur. J. Biochem. 1975, 54, 267-277.