The geometry of intercalation complex of antitumor mitoxantrone and ametantrone with DNA: Molecular dynamics simulations

Acta Biochimica Polonica

Volumn 45, Issue 1, 1998, Pages 1-11

  Mazerski, Jan ^a   Martelli, Sante ^b   Borowski, Edward ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Anthracenedione antitumor drugs; Molecular dynamics simulations; Structure of intercalation complex

Indexed keywords

AMETANTRONE; ANTINEOPLASTIC AGENT; DNA; DRUG DERIVATIVE; INTERCALATING AGENT; MITOXANTRONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; HYDROGEN BOND;

ANTINEOPLASTIC AGENTS; COMPUTER SIMULATION; DNA; HYDROGEN BONDING; INTERCALATING AGENTS; MITOXANTRONE; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION;

EID: 0031610288     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Cheng, C.C. & Zee-Cheng, R.K.Y. (1983) The design, synthesis, and development of a new class of potential antineoplastic anthraquinones; in Progress of Medicinal Chemistry (Ellis, G.P. & West, G.B., eds.) pp. 83-118, Elsevier, Amsterdam, and references cited therein.
2. Zee-Cheng, R.K.Y. & Cheng, C.C. (1978) Anti-neoplastic agents. Structure-activity relationship study of bis(substituted aminoalkylo-amino)anthraquinones. J. Med. Chem. 21, 291-294.
3. Zee-Cheng, R.K.Y., Podrebarac, E.G., Menon, C.S. & Cheng, C.C. (1979) Structural modification study of bis(substituted aminoalkylo-amino)anthraquinones. An evaluation of the relationship of the [2-[(2-hydroxyethyl)amino]ethyl]amino side chain with antineoplastic activity. J. Med. Chem. 22, 501-505.
4. Murdock, K.C., Child, R.G., Fabio, P.F., Angier, R.B., Wallace, R.E., Durr, F.E. & Citarella, R.V. (1979) Antitumor agents. 1. 1,4-Bis [(aminoalkyl)amino]-9,10-anthracenediones. J. Med. Chem. 22, 1024-1030.
5. Cheng, C.C. & Zee-Cheng, R.K.Y. (1983) The design, synthesis and development of a new class of potent antineoplastic anthraquinones. Progr. Med. Chem. 20, 83-118.
6. Krapcho, A.P., Shaw, K.J., Landi, J.J., Jr., Phinney, D.G., Hacker, M.P. & McCormack, J.J. (1986) Synthesis and antitumor activities of asymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones and related systems. J. Med. Chem. 29, 1370-1375.
7. Durr, F.E. (1988) Biochemical pharmacology and tumor biology of mitoxantrone and ametantrone; in Anthracycline and Anthracenedione-Based Anticancer Agents (Lown, J.W., ed.) pp. 401-445, Elsevier, Amsterdam.
8. Baguley, B.C. (1991) DNA intercalating antitumor agents. Anti-Cancer Drug Design 6, 1-35.
9. VanGunsteren, W.F., Berendsen, H.J.C., Geursten, R.G. & Zwinderman, H.R.J. (1986) A molecular computer dynamics simulation if an eight-base-pair DNA fragment in aqueous solution: Comparison with experimental two-dimensional NMR data. Ann. N. Y. Acad. Sci. 482, 287-303.
10. Subraminian, P.S., Ravishanker, G. & Beveridge, D.L. (1988) Theoretical considerations on the "spine of hydration" in the minor groove of d(CGCGAATTCGCG) · d(CGCGAATTCGCG): Monte Carlo computer simulation. Proc. Natl Acad. Sci. U.S.A. 85, 1836-1840.
11. 6 minihelix including counterions and water. Biopolymers 29, 1027-1044.
12. Dang, L. & Kollman, P.A. (1990) Molecular dynamics simulations study of the free energy of association of 9-methyladenine and 1-methyl-thymine bases in water. J. Am. Chem. Soc. 112 , 503-507.
13. Cieplak, P., Rao, S.N., Grootenhuis, P.D.J. & Kollman, P.A. (1990) Free energy calculations on base specificity of drug-DNA interactions: Application to daunomycin and acridine intercalation into DNA. Biopolymers 29, 717-727.
14. Swaminathan, S., Beveridge, D.L. & Herman, H.H. (1990) Molecular dynamics simulation of a deoxynucleotide-drug intercalation complex: d(CpG)/proflavine. J. Phys. Chem. 94, 4660-4665.
15. Langley, D.R., Doyle, T.W. & Beveridge, D.L. (1991) The dyneimicin-DNA intercalation complex. A model based on DNA affinity cleavage and molecular dynamics simulations. J. Am. Chem. Soc. 113, 4395-4403.
16. Chuprina, V.P., Heinemann, U., Nurislamov, A.A., Zielenkiewicz, P., Dickerson, R.E. & Saenger, W. (1991) Molecular dynamics simulation of the hydration shell of a B-DNA dodecamer reveals two main types of minor-groove hydration depending on groove width. Proc. Natl. Acad. Sci. U.S.A. 88, 593-597.
17. Herzyk, P., Neidle, S. & Goodfellow, J.M. (1992) Conformation and dynamics of drug-DNA intercalation. J. Biomol. Struct. Dyn. 10, 97-139.
18. Subraminian, P.S., Ravishanker, G. & Beveridge, D.L. (1991) Molecular dynamics of B-DNA including water and counterions. A 140-ps trajectory for d(CGCGAATTCGCG) based on the GROMOS Force Field. J. Am. Chem. Soc. 113, 5027-5040.
19. Herzyk, P., Goodfellow, J.M. & Neidle, S. (1991) Molecular dynamics simulations of dinucleoside and dinucleoside-drug crystal hydrates. J. Biomol. Struct. Dyn. 9, 363-386.
20. VanGunsteren, W.F. & Berendsen, H.J.C. (1987) GROMOS Library Manual, Biomos Groningen, The Netherlands.
21. Ryckeart, J.P., Ciccotti, G. & Berendsen, H.J.C. (1977) Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes. J. Comput. Phys. 23, 327-341.
22. Gago, F. & Richargs, W.G. (1990) Netropsin binding to poly[d(IC)]+poly[d(IC)] and poly[d(GC)] + poly[d(GC)]: A computer simulation. Mol. Pharmacol. 37, 341-346.
23. Frederick, Ch.A., Williams, J.D., Ughetto, G., van der Marel, G.A., van Boom, J.H., Rich, A. & Wang, A.H. J. (1990) Structural camparison of anticancer drug-DNA complexes: Adramycin and daunomycin. Biochemists, 29, 2538-2549.
24. Cirilli, M., Bachechi, F., Ughetto, G., Colonna, F.P. & Capobianco, M.L. (1993) Interactions between morpholinyl anthracyclines and DNA. The crystal structure of a morpholinodoxorubicin bound to d(CGTACG). J. Mol. Biol. 230, 878-883.
25. Denny, W.A. & Wakelin, L.P.G. (1990) Kinetics of the binding of mitoxantrone, ametantrone and analogs to DNA: Relationship with binding mode and antitumor activity. Anti-Cancer Drug Design 5, 189-196.