Molecular modelling studies, synthesis and biological activity of a series of novel bisnaphthalimides and their development as new DNA topoisomerase II inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 1, 2009, Pages 13-24

  Filosa, Rosanna ^a   Peduto, Antonella ^a   Di Micco, Simone ^a   Caprariis, Paolo de ^a   Festa, Michela ^a   Petrella, Antonello ^a   Capranico, Giovanni ^b   Bifulco, Giuseppe ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Anticancer naphthalimides; DNA topoisomerase II inhibitors

Indexed keywords

BISNAPHTHALIMIDE DERIVATIVE; CASPASE; GYRASE INHIBITOR; N,N' BIS[2 (5 NITRO 1,3 DIOXO 2,3 DIHYDRO 1H BENZ[DE]ISOQUINOLIN 2 YL)]PROPANE 2 ETHANEDIAMINE; N,N' BIS[2 (5 NITRO 1,3 DIOXO 2,3 DIHYDRO 1H BENZ[DE]ISOQUINOLIN 2 YL)BUTYLAMINOETHYL] 2 PROPANEDIAMINE; NAPHTHALIMIDE DERIVATIVE; PURINE; PYRIMIDINE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BINDING SITE; CANCER INHIBITION; COLON CARCINOMA; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA BINDING; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ENZYME ACTIVATION; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; THREE DIMENSIONAL IMAGING;

CELL LINE, TUMOR; COLONIC NEOPLASMS; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; NAPHTHALIMIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 57849137376     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.024     Document Type: Article

References (23)

1. Braña M.F., and Ramos A. Curr. Med. Chem. Anticancer Agents 1 (2001) 237
2. Nitiss J.L., Zhou J., Rose A., Hsiung Y., Gale K.C., and Osheroff N. Biochemistry 37 (1998) 3078
3. Malviya V.K., Liu P.Y., Alberts D.S., Surwit E.A., Craig J.B., and Hanningan E.V. Am. J. Clin. Oncol. 15 (1992) 41
4. 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., and Romerdahl C. Cancer Res. 55 (1995) 1176
5. Bailly C., Braña M.F., and Waring J. Eur. J. Biochem. 240 (1996) 195
6. Gamage S.A., Spicer J.A., Finlay G.J., Stewart A.J., Charlton P., Baguley B.C., and Denny W.A. J. Med. Chem. 44 (2001) 1407
7. Cholody W.C., Kosakowska-Cholody T., Hollingshead M.G., Hariprakasha H.K., and Michejda C.J. J. Med. Chem. 48 (2005) 4474
8. Holden J.A. Curr. Med. Chem. Anticancer Agents 1 (2001) 1
9. Filosa R., Peduto A., de Caprariis P., Festa M., Petrella A., Pau A., Pinna G.A., La Colla P., Busonera B., and Loddo R. Eur. J. Med. Chem. 42 (2007) 293
10. Payne G.B. J. Org. Chem. 32 (1967) 3351
11. Witiak D.T., Lee H.J., Hart R.W., and Gibson R.E. J. Med. Chem. 20 (1977) 630
12. Capranico G., Binaschi M., Borgnetto M.E., Zunino F., and Palumbo M. Trends Pharmacol. Sci. 18 (1997) 323
13. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comp. Chem. 19 (1998) 1639
14. Breneman C.M., and Wiberg K.B. J. Comp. Chem. 11 (1990) 361
15. Oliveira J., Ralton L., Tavares J., Codeiro-da-Silva A., Bestwick C.S., McPherson A., and Lin P.K.T. Bioorg. Med. Chem. Lett. 10 (2007) 541
16. Lin P.K.T., and Pavlov V.A. Bioorg. Med. Chem. Lett. 10 (2000) 1609
17. McCoy L.L. J. Am. Chem. Soc. 80 (1958) 6568
18. Nicoletti I., Migliorati G., Pagliacci M.C., Grignani F., and Riccardi C. J. Immunol. Methods 139 (1991) 271
19. Guano F., Pourquier P., Tinelli S., Binaschi M., Bigioni M., Animati F., Manzini S., Zunino F., Kohlhagen G., Pommier Y., and Capranico G. Mol. Pharmacol. 56 (1999) 77
20. MacroModel, version 8.5, Schrödinger LLC, New York, NY, 2003.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery J. A.; Jr, Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H. Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.
22. Sanner M.F. J. Mol. Graph. Model. 17 (1999) 57-61
23. Sanner M.F., Olson A.J., and Spehner J.C. Biopolymers 38 (1996) 305-320