DNA binders: 1. Evaluation of DNA-interactive ability, design, and synthesis of novel intercalating agents

Letters in Drug Design and Discovery

Volumn 6, Issue 1, 2009, Pages 56-62

  Sechi, Mario ^a   Derudas, Marco ^a   Dallocchio, Roberto ^b   Dessì, Alessandro ^b   Cosseddu, Alessia ^c   Paglietti, Giuseppe ^a  

^a UNIVERSITY OF SASSARI   (Italy)

^b CNR Consiglio Nazionale delle Ricerche   (Italy)

^c UNIVERSITY OF SIENA   (Italy)

Author keywords

2,3,6,7 Tetrahydro 1H pyrrolo 1,2 a indole 1,8(5H) dione; DNA binders; Docking; Intercalation; Two armed derivatives

Indexed keywords

2,3,6,7 TETRAHYDRO 1H PYRROLO[1,2 A]INDOLE 1,8(5H) DIONE; DACTINOMYCIN; DISTAMYCIN A; DNA BINDING PROTEIN; ETHIDIUM BROMIDE; INTERCALATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DNA BINDING; DNA TEMPLATE; DRUG DESIGN; DRUG DNA INTERACTION; DRUG SYNTHESIS; ENZYME INHIBITION; MATHEMATICAL COMPUTING; NONHUMAN; PRIORITY JOURNAL;

EID: 61849130722     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009787158472     Document Type: Article

References (22)

1. Hurley, L.H. DNA and its associated process as targets for cancer therapy. Nat. Rev. Cancer, 2002, 2, 188-200.
2. Demeunynck, M.; Bailly, C.; Wilson, W.D. DNA and RNA Binders. From Small Molecules to Drugs, Wiley-VCH, Weinheim; 2003, Vol. 1 and 2.
3. Hurley, L.H. Advances in DNA Sequence-Specific Agents. Jai Press Inc., Greenwich, CT, 1992, Vol. 1.
4. Silverman R.B. The organic chemistry of drug design and drug action. 2nd ed., Elsevier, Academic Press, USA, 2004.
5. Neidle, S.; Thurston, D. E. Chemical approaches to the discovery and development of cancer therapies. Nat. Rev. Cancer, 2005, 5, 285-96.
6. Parril, A. L.; Reddy, M. R. Rational Drug Design: novel methodology and practical applications. ACS, Oxford University Press, 1999.
7. Kandimalla, E. R.; Agrawal, S. Hoogsteen DNA Duplexes of 3′-3′-and 5′-5′-Linked Oligonucleotides and Triplex Formation with RNA and DNA Pyrimidine Single Strand: Experimental and Molecular Modeling Studies. Biochemistry, 1996, 35, 15332-9.
8. Graves, D.E.; Velea, L.M. Intercalative binding of small molecules to nucleic acids. Curr. Org. Chem., 2000, 4, 915-29.
9. Christmann-Franck, S.; Bertrand, H. -O.; Goupil-Lamy, A.; Arsène der Garabedian, P.; Mauffret, O.; Hoffmann, R.; Fermandjian, S. Structure-based virtual screening: an application to human topoisomerase II α. J. Med. Chem., 2004, 47, 6840-53.
10. Amutha, R. ; Subramanian, V.; Nair, B. U. Interaction of benzidine with DNA: experimental and modelling studies. Chem. Phys. Lett., 2001, 344, 40-8.
11. Brana, M. F.; Cacho, M.; Garcia, M. A.; de Pascual-Teresa, B.; Ramos, A.; Acero, N.; Llinares, F.; Munoz-Mingarro, D.; Abradelo, C.; Rey-Stolle, M. F.; Yuste, M. Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties of a New Series of Imidazonaphthalimides. J. Med. Chem., 2002, 45, 5813-6.
12. Morris, G.M.; Goodsell, D. S.; Huey, R.; Olson, A. Distributed automated docking of flexible ligands to proteins: Parallel application of AutoDock 2.4*. J. Comp. Aid. Mol. Des., 1996, 10, 293-304.
13. Sechi, M.; Mura, A.; Sannia, L.; Orecchioni, M.; Paglietti, G. Synthesis of pyrrolo[1,2-a]indole-1,8(5H)-diones as new synthons for developing novel tryciclic compounds of pharmaceutical interest. ARKIVOC, 2004, (v), 97-106.
14. Pinna, G.A.; Sechi, M.; Paglietti, G.; Pirisi, M.A. Addition reactions of acetylenic esters to 6,7-dihydrobenzo[b]furan-4(5H)-one, 6,7-dihydroindol-4(5H)-one, 5,6-dihydrobenzo[b]furan-7(6H)- one and 5,6-dihydroindol-7(6H)-one ketoximes. Formation of reduced furo[g]- and pyrrolo[g]-indoles. J. Chem. Res. (S), 2003, 117-120,
15. (M), 2003, 362-80.
16. Murdock, K.C.; Child, R.G.; Lin, Y.; Warren, J.D.; Fabio, P.F.; Lee, V.J.; Izzo, P.T.; Lang, S.A., Jr.; Angier, R.B.; Citarella, R.V.; Wallace, R.E.; Durr, F.E. Antitumor Agents. 2. Bisguanylhydrazones of anthracene-9,10- dicarbxaldehydes. J. Med. Chem., 1982, 25, 505-18.
17. Gasteiger, J.; Marsili, M. Iterative partial equilization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron, 1980, 36, 3219-28.
18. SYBYL, version 6.3; Tripos Inc., St. Louis, MO., 2001.
19. Weiner, S.J.; Kollman, P. A.; Case, D.A.; Singh, U.C.; Ghio, C.; Alagona, G.; Profeta, S.; Weiner. P. J. Am. Chem. Soc., 1984, 106, 765-84.
20. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem., 1998, 19, 1639-62.
21. Estep, K.G. An Efficient Synthesis of 4-hydroxy-1H-indole-2- carbonitrile and its Conversion to DPI 201-106. Synth. Comm., 1995, 25, 507-14.
22. Seemann, F.; Wiskott, E.; Niklaus, P.; Troxler, F. Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen. Helv. Chim. Acta, 1971, 54, 2411-9.