A new bisintercalating anthracycline with picomolar DNA binding affinity

Journal of Medicinal Chemistry

Volumn 48, Issue 26, 2005, Pages 8209-8219

  Portugal, José ^a   Cashman, Derek J ^b   Trent, John O ^b   Ferrer Miralles, Neus ^a   Przewloka, Teresa ^c   Fokt, Izabela ^c   Priebe, Waldemar ^c   Chaires, Jonathan B ^b  

^a INSTITUT DE BIOLOGIA MOLECULAR DE BARCELONA   (Spain)

^b University of Louisville School of Medicine   (United States)

^c UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE DERIVATIVE; DAUNORUBICIN; DAUNOSAMINE; DOXORUBICIN; UNCLASSIFIED DRUG; WP 631; WP 762;

ARTICLE; BINDING AFFINITY; CELL CYCLE; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENERGY; ENTROPY; LEUKEMIA CELL LINE; MOLECULAR MODEL; T LYMPHOCYTE;

EID: 29744432643     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050902g     Document Type: Article

References (39)

1. Booser, D. J.; Hortobagyi, G. N. Anthracycline antibiotics in cancer therapy. Focus on drug resistance. Drugs 1994, 47, 223-258.
2. Minotti, G.; Menna, P.; Salvatorelli, E.; Cairo, G.; Gianni, L. Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol. Rev. 2004, 56, 185-229.
3. Gewirtz, D. A. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem. Pharmacol. 1999, 57, 727-741.
4. Binaschi, M.; Bigioni, M.; Cipollone, A.; Rossi, C.; Goso, C.; Maggi, C. A.; Capranico, G.; Animati, F. Anthracyclines: selected new developments. Curr. Med. Chem. - Anti-Cancer Agents 2001, 1, 113-130.
5. Chaires, J. B.; Leng, F.; Przewloka, T.; Fokt, I.; Ling, Y. H.; Perez-Soler, R.; Priebe, W. Structure-based design of a new bisintercalating anthracycline antibiotic. J. Med. Chem. 1997, 40, 261-266.
6. Priebe, W. Anthracycline Antibiotics: New Analogues, Methods of Delivery and Mechanisms of Action. ACS Symposium Series; American Chemical Society: Washington, D. C., 1995.
7. Priebe, W.; Fokt, I.; Przewloka, T.; Chaires, J. B.; Portugal, J.; Trent, J. O. Exploiting anthracycline scaffold for designing DNA-targeting agents. Methods Enzymol. 2001, 340, 529-555.
8. Chaires, J. B. Molecular recognition of DNA by daunorubicin. Advances in DNA sequence specific agents; JAI Press Inc.: Greenwich, CT, 1996; pp 141-167.
9. Chaires, J. B.; Herrera, J. E.; Waring, M. J. Preferential binding of daunomycin to 5′ATCG and 5′ATGC sequences revealed by footprinting titration experiments. Biochemistry 1990, 29, 6145-6153.
10. Frederick, C. A.; Williams, L. D.; Ughetto, G.; van der Marel, G. A.; van Boom, J. H.; Rich, A.; Wang, A. H. Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin. Biochemistry 1990, 29, 2538-2549.
11. Rudnicki, W. R.; Kurzepa, M.; Szczepanik, T.; Priebe, W.; Lesyng, B. A simple model for predicting the free energy of binding between anthracycline antibiotics and DNA. Acta Biochim. Pol. 2000, 47, 1-9.
12. Leng, F.; Priebe, W.; Chaires, J. B. Ultralight DNA binding of a new bisintercalating anthracycline antibiotic. Biochemistry 1998, 37, 1743-1753.
13. Hu, G. G.; Shui, X.; Leng, F.; Priebe, W.; Chaires, J. B.; Williams, L. D. Structure of a DNA-bisdaunomycin complex. Biochemistry 1997, 36, 5940-5946.
14. Robinson, H.; Priebe, W.; Chaires, J. B.; Wang, A. H. Binding of two novel bisdaunorubicins to DNA studied by NMR spectroscopy. Biochemistry 1997, 36, 8663-8670.
15. Record, M. T., Jr.; Anderson, C. F.; Lohman, T. M. Thermodynamic analysis of ion effects on the binding and conformational equilibria of proteins and nucleic acids: the roles of ion association or release, screening, and ion effects on water activity. Q. Rev. Biophys. 1978, 11, 103-178.
16. Chaires, J. B. Dissecting the free energy of drug binding to DNA. Anti-Cancer Drug Des. 1996, 11, 569-580.
17. Lavery, R.; Sklenar, H. The definition of generalized helicoidal parameters and of axis curvature for irregular nucleic acids. Journal of Biomol. Struct. Dynam. 1988, 6, 63-91.
18. Burnett, J. C.; Kellogg, G. E.; Abraham, D. J. Computational methodology for estimating changes in free energies of biomolecular association upon mutation. The importance of bound water in dimer-tetramer assembly for beta 37 mutant hemoglobins. Biochemistry 2000, 39, 1622-1633.
19. Fornabaio, M.; Cozzini, P.; Mozzarelli, A.; Abraham, D. J.; Kellogg, G. E. Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 2. Computational titration and pH effects in molecular models of neuraminidase-inhibitor complexes. J. Med. Chem. 2003, 46, 4487-4500.
20. Cashman, D. J.; Kellogg, G. E. A computational model for anthracycline binding to DNA: tuning groove-binding intercalators for specific sequences. J. Med. Chem. 2004, 47, 1360-1374.
21. Cashman, D. J.; Scarsdale, J. N.; Kellogg, G. E. Hydropathic analysis of the free energy differences in anthracycline antibiotic binding to DNA. Nucleic Acids Res. 2003, 31, 4410-4416.
22. o/w. More than the Sum of its Parts? Eur. J. Med. Chem. 2000, 35, 651-661.
23. Villamarin, S.; Mansilla, S.; Ferrer-Miralles, N.; Priebe, W.; Portugal, J. A comparative analysis of the time-dependent antiproliferative effects of daunorubicin and WP631. Eur. J. Biochem. 2003, 270, 764-770.
24. Mansilla, S.; Pina, B.; Portugal, J. Daunorubicin-induced variations in gene transcription: commitment to proliferation arrest, senescence and apoptosis. Biochem. J. 2003, 372, 703-711.
25. Dervan, P. B.; Burli, R. W. Sequence-specific DNA recognition by polyamides. Curr. Opin. Chem. Biol. 1999, 3, 688-693.
26. Dervan, P. B.; Edelson, B. S. Recognition of the DNA minor groove by pyrrole-imidazole polyamides. Curr. Opin. Struct. Biol. 2003, 13, 284-299.
27. Dervan, P. B. Molecular recognition of DNA by small molecules. Bioorg. Med. Chem. 2001, 9, 2215-2235.
28. Dervan, P. B. D., R. M.; Marques, M. A. Programmable DNA Binding Oligomers for Control of Transcription. Curr. Med. Chem. 2005, 5, 373-387.
29. Waring, M. J.; Wakelin, L. P. Echinomycin: a bifunctional intercalating antibiotic. Nature 1974, 252, 653-657.
30. Cuesta-Seijo, J. A.; Sheldrick, G. M. Structures of Complexes between Echinomycin and Duplex DNA. Acta Crystallogr. D Biol. Crystallogr. 2005, 61, 442-448.
31. Leng, F.; Chaires, J. B.; Waring, M. J. Energetics of echinomycin binding to DNA. Nucleic Acids Res. 2003, 31, 6191-6197.
32. Villamarin, S.; Ferrer-Miralles, N.; Mansilla, S.; Priebe, W.; Portugal, J. Induction of G(2)/M arrest and inhibition of c-myc and p53 transcription by WP631 in Jurkat T lymphocytes. Biochem. Pharmacol. 2002, 63, 1251-1258.
33. Martin, B.; Vaquero, A.; Priebe, W.; Portugal, J. Bisanthracycline WP631 inhibits basal and Sp1-activated transcription initiation in vitro. Nucleic Acids Res. 1999, 27, 3402-3409.
34. Mansilla, S.; Priebe, W.; Portugal, J. Sp1-targeted inhibition of gene transcription by WP631 in transfected lymphocytes. Biochemistry 2004, 43, 7584-7592.
35. Perego, P.; Corna, E.; De Cesare, M.; Gatti, L.; Polizzi, D.; Pratesi, G.; Supino, R. Zunino, F. Role of apoptosis and apoptosis-related genes in cellular response and antitumor efficacy of anthracyclines. Curr. Med. Chem. 2001, 8, 31-37.
36. McGhee, J. D. Theoretical calculations of the helix-coil transition of DNA in the presence of large, cooperatively binding ligands. Biopolymers 1976, 15, 1345-1375.
37. Trent, J. O. Molecular modeling of drug-DNA complexes: an update. Methods Enzymol. 2001, 340, 290-326.
38. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunol. Methods 1983, 65, 55-63.
39. Doyle, A.; Griffiths, J. B.; Newell, D. G. Cell & Tissue Culture: Laboratory Procedures; John Wiley & Sons: New York, 1995.