Intercalation of proflavine and a platinum derivative of proflavine into double-helical poly(A)

Biophysical Journal

Volumn 77, Issue 5, 1999, Pages 2717-2724

  Ciatto, Carlo ^a   D'Amico, Maria L ^b   Natile, Giovanni ^c   Secco, Fernando ^b   Venturini, Marcella ^b  

^a FRITZ LIPMANN INSTITUTE   (Germany)

^b UNIVERSITY OF PISA   (Italy)

^c UNIVERSITY OF BARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; PLATINUM DERIVATIVE; POLYADENYLIC ACID; PROFLAVINE;

ARTICLE; CHEMICAL REACTION KINETICS; COVALENT BOND; DIFFUSION; ELECTRIC FIELD; EQUILIBRIUM CONSTANT; INTERCALATION COMPLEX; IONIC STRENGTH; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0032750499     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(99)77105-5     Document Type: Article

References (43)

1. Benesi, H. A., and J. H. Hildebrand. 1949. Spectropholometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71:2703-2707.
2. Bowler, B. E., K. J. Ahmed, W. I. Sundquist, L. S. Hollis, E. E. Whang, and S. J. Lippard. 1989. Synthesis, characterization, and DNA-binding properties of (1,2-diaminoethane)platinum(II) complex linked to the DNA intercalator acridine orange by trimethylene and hexamethylene chains. J. Am. Chem. Soc. 111:1299-1306.
3. Bowler, B. E., L. S. Hollis, and S. J. Lippard. 1984. Synthesis and DNA binding and photonicking properties of acridine orange linked by a polymethylene tether to (1,2-diamminoethane) dichloroplatinum(II). J. Am. Chem. Soc. 106:6102-6104.
4. Bowler, B. E., and S. J. Lippard. 1986. Modulation of platinum antitumor drug binding to DNA by linked and free intercalates. Biochemistry. 25:3031-3038.
5. Brabec, V., and M. Leng. 1993. DNA interstrand cross-links of transdiamminedichloroplatinum(II) are preferentially formed between guanine and complementary cytosine residues. Proc. Natl. Acad. Sci. USA. 90:5345-5349.
6. Bresloff, J. L., and D. M. Crothers. 1975. DNA-ethidium reaction kinetics: demonstration of direct ligand transfer between DNA binding sites. J. Mol. Biol. 95:103-123.
7. Brown, M. D., L. S. Ripley, and D. H. Hall. 1993. A proflavine induced frameshift hotspot in the thymidylate synthase gene of bacteriophage T4. Mutat. Res. 286:189-197.
8. Bruhn, S. L., J. H. Toney, and S. J. Lippard. 1990. Biological processing of DNA modified by platinum compounds. In Progress in Inorganic Chemistry: Bioinorganic Chemistry, Vol. 38. S. J. Lippard, editor. John Wiley and Sons, New York. 477-516.
9. Capranico, G., K. W. Khon, and Y. Pommier. 1990. Local sequence requirements for DNA cleavage by mammalian topoisomerase II in the presence of deoxorubicin. Nucleic Acids Res. 18:6611-6619.
10. Ceci, E., R. Cini, A. Karaulov, M. B. Hurthouse, L. Maresca, and G. Natile. 1993. Preparation of same platinum-linked acridines and crystal structure of [3,6-bis(dimethylamino)acridinioethyl]chloro-(N,N,N′ ,N′-tetramethylethylenediamine)platinum(II). J. Chem. Soc. Dalton Trans. 2491-2497.
11. Ciatto, C. 1994. Studio cinetico e termodinamico dell'interazione di acidi nucleici con agenti intercalanti: il sistema poly(A)-proflavina. Thesis, University of Pisa, Pisa.
12. Corbett, A. H., D. Hong, and N. Osheroff. 1993. Exploiting mechanistic differences between drug classes to define functional drug interaction domains on topoisomerase II. Evidence that several DNA cleavage-enhancing agent share a common site of action on the enzyme. J. Biol. Chem. 268:14394-14398.
13. De Isabella, P., G. Capranico, M. Palumbo, C. Sissi, P. Krapcho, and F. Zunino. 1993. Sequence selectivity of topoisomerase II DNA cleavage stimulated by mitoxantrone derivatives: relationships to drug DNA binding and cellular effects. Mol. Pharmacol. 43:715-721.
14. Diebler, H., F. Secco, and M. Venturini. 1987. The binding of Mg(II) and Ni(II) to synthetic polynucleotides. Biophys. Chem. 26:193-205.
15. Dourlent, M., and C. Helene. 1971. Quantitative analysis of proflavine binding to polyadenylic acid, polyuridylic acid, and transfer RNA. Eur. J. Biochem. 23:86-95.
16. Dourlent, M., J. F. Hogrel, and C. Helene. 1974. Anisotropy effects in temperature-jump relaxation studies on solutions containing linear polymers. J. Am. Chem. Soc. 96:3398-3406.
17. Ferguson, L. R., and W. A. Denny. 1991. The genetic toxicology of acridines. Mutat. Res. 258:123-160.
18. Fichtinger-Schepman, A. M., P. H. Lohman, F. Berends, J. Reedijk, and A. T. van Oosterom. 1986. Interaction of the antitumour drug cisplatin with DNA in vitro and in vivo. IARC Sci. Publ. 78:83-99.
19. Hammes, G. G., and C. D. Hubbard. 1966. The interaction of acridine orange and proflavine with polyadenylic acid. J. Phys. Chem. 70: 2889-2895.
20. Janik, B. 1971. Physicochemical Characteristics of Oligonucleotides and Polynucleotides. IFI/Plenum, New York. 76-96.
21. Jovin, T. M., and G. Striker. 1977. Chemical relaxation kinetic studies of E. coli RNA polymerase binding to poly[d(A-T)] using ethidium as a fluorescence probe. In Chemical Relaxation in Molecular Biology. I. Pecht and R. Riegler, editors. Springer-Verlag, New York, 245-281.
22. Lerman, L. S. 1961. Structural considerations in the interaction of deoxyribonucleic acids with acridines. J. Mol. Biol. 3:18-30.
23. Lerner, D. B., and D. R. Kearns. 1981. Proton and phosphorus NMR investigation of the conformational states of polyadenylic acid double helix. Biopolymers. 20:803-816.
24. Li, H. J., and D. M. Crothers. 1969. Relaxation studies of the proflavine-DNA complex: the kinetics of an intercalation reaction. J. Mol. Biol. 39:461-477.
25. Lippard, S. J. 1983. Platinum, Gold, and Other Metal Chemotherapeutic Agents. ACS Symposium Series 209. American Chemical Society, Washington, DC.
26. Macgregor, R. B., R. M. Clegg, and T. M. Jovin. 1985. Pressure-jump study of the kinetics of ethidium bromide binding to DNA. Biochemistry. 24:5503-5510.
27. Maggini, R., F. Secco, M. Venturini, and H. Diebler. 1994. Kinetic study of double-helix formation and double-helix dissociation of polyadenylic acid. J. Chem. Soc. Faraday Trans. 90:2359-2363.
28. Maggini, R., F. Secco, M. Venturini, and H. Diebler. 1998. Proton transfer involving nucleic acids: a temperature-jump study of the systems sulphonephthaleins-double stranded poly(A) and sulphonephthaleins-double stranded poly(C). Int. J. Chem. Kinetics. 30:161-169.
29. Marcandalli, B., G. Stange, and J. F. Holzwarth. 1988. Kinetics of the interaction of acridine dyes with nucleic acids. J. Chem. Soc. Faraday Trans. 1 84:2807-2819.
30. McGhee, J. D., and P. H. von Hippel. 1974. Theoretical aspects of DNA-protein intercalation: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J. Mol. Biol. 86: 469-489.
31. Meyer-Almes, F. J., and D. Porschke. 1993. Mechanism of intercalation into DNA double helix by ethidium. Biochemistry. 32:4246-4253.
32. Pizzocaro, G., R. Salvioni, M. Pasi, F. Zanoni, A. Milani, S. Pilotti, and S. Monfardini. 1985. Early resection of residual tumor during cisplatin, vinblastine, bleomycin combination chemotherapy in stage III and bulky stage II nonseminomatous testicular cancer. Cancer. 56:249-255.
33. Porschke, D. 1998. Time-resolved analysis of macromolecular structures during reactions by stopped-flow electrooptics. Biophys. J. 75:528-537.
34. Provencher, S. W. 1976. An eigenfunction expansion method for the analysis of exponential decay curves. J. Chem. Phys. 64:2772-2777.
35. Rich, A., D. R. Davies, F. H. C. Crick, and J. D. Watson. 1961. Molecular structure of polyadenylic acid. J. Mol. Biol. 3:71-86.
36. Ripley, L. S., J. S. Dubins, J. G. De Boer, D. M. De Marini, A. M. Bogerd, and K. N. Kreuzer. 1988. Hotspot sites for acridine-induced frameshift mutations in bacteriophage T4 correspond to sites of action of the T4 type II topoisomerase. J. Mol. Biol. 200:665-680.
37. Scatchard, G. 1949. The attraction of proteins for small molecules and ions. Ann. N.Y. Acad. Sci. 51:660-672.
38. Schelhorn, T., S. Kretz, and H. W. Zimmermann. 1992. Reinvestigation of the binding of proflavine to DNA. Is intercalation the dominant binding effect? Cell. Mol. Biol. 38:345-365.
39. Schmechel, D. E. V., and D. M. Crothers. 1971. Kinetic and hydrodynamic studies of the complex of proflavine with polyA.polyU. Biopolymers. 10:465-480.
40. Schwarz, G., S. Klose, and W. Balthasar. 1970. Cooperative binding to linear biopolymers. 2. Thermodynamic analysis of the proflavinepoly(L-glutamic acid) system. Eur. J. Biochem. 12:454-467.
41. Scovell, W. M. 1978. Structural and conformational studies of polyriboadenylic acid in neutral and acid solution. Biopolymers. 17:969-984.
42. Sundquist, W. I., D. P. Bancroft, and S. J. Lippard. 1990. Synthesis, characterization and biological activity of cis-diammineplatinum(II) complex of the DNA intercalators 9-aminoacridine and chloroquine. J. Am. Chem. Soc. 112:1590-1596.
43. Wakelin, L. P. G., and M. J. Waring. 1980. Kinetics of Drug-DNA Interaction. Biopolymers. 144:183-214.