Unique base-step recognition by a platinum - Acridinylthiourea conjugate leads to a DNA damage profile complementary to that of the anticancer drug cisplatin

Biochemistry

Volumn 43, Issue 26, 2004, Pages 8560-8567

  Budiman, Michael E ^a   Alexander, Rebecca W ^a   Bierbach, Ulrich ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC SPECTROSCOPY; BIOASSAY; EMISSION SPECTROSCOPY; ENZYMES; HYDROLYSIS; PLATINUM;

INTERCALATOR; NUCLEOBASE;

DNA;

ACRIDINYLTHIOUREA; ANTINEOPLASTIC AGENT; CISPLATIN; PLATINUM; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC EMISSION SPECTROMETRY; COVALENT BOND; DNA ADDUCT; DNA DAMAGE; DNA FOOTPRINTING; ENZYME ISOLATION; HYDROLYSIS; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL; PROTEIN MODIFICATION; SEQUENCE HOMOLOGY; TRANSCRIPTION REGULATION;

BASE SEQUENCE; BINDING SITES; CISPLATIN; DNA; DNA DAMAGE; DNA REPAIR; DNA-DIRECTED RNA POLYMERASES; ELECTROPHORESIS, AGAR GEL; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; PLASMIDS; PLATINUM; PROTEIN BINDING; RNA; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY, ATOMIC; THIOUREA; TIME FACTORS; TRANSCRIPTION FACTORS; TRANSCRIPTION, GENETIC; ULTRAVIOLET RAYS; UREA; VIRAL PROTEINS;

EID: 3142579781     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi049415d     Document Type: Article

References (33)

1. Baguley, B. C. (2002) A brief history of cancer chemotherapy, in Anticancer Drug Development (Baguley, B. C., and Kerr, D. J., Eds.) p 111, Academic Press, San Diego.
2. Gelasco, A., and Lippard, S. J. (1999) Anticancer activity of cisplatin and related complexes, in Topics in Biological Inorganic Chemistry (Clarke, M. J., and Sadler, P. J., Eds.) Vol. 1, pp 1-43, Springer, New York.
3. Farrell, N., Qu, Y., and Roberts, J. D. (1999) Chemistry and biology of multifunctional DNA binding agents, in Topics in Biological Inorganic Chemistry (Clarke, M. J., and Sadler, P. J., Eds.) Vol. I, pp 99-115, Springer, New York.
4. Martins, E. T., Baruah, H., Kramarczyk, J., Saluta, G., Day, C. S., Kucera, G. L., and Bierbach, U. (2001) Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore, J. Med. Chem. 44, 4492-4496.
5. Augustus, T. M., Anderson, J., Hess, S. M., and Bierbach, U. (2003) Bis(acridinylthiourea)platinum(II) complexes: synthesis, DNA affinity, and biological activity in glioblastoma cells, Bioorg. Med. Chem. Lett. 13, 855-858.
6. Ackley, M. C., Barry, C. G., Mounds, A. M., Farmer, M. C., Springer, B.-E., Day, C. S., Wright, M. W., Berners-Price, S. J., Hess, S. M., and Bierbach, U. (2004) Structure-activity relationships in platinum- acridinylthiourea conjugates: effect of the thiourea nonleaving group on drug stability, nucleobase affinity, and in vitro cytotoxicity, J. Biol. Inorg. Chem. (in press).
7. Baruah, H., Rector, C. L., Monnier, S. M., and Bierbach, U. (2002) Mechanism of action of non-cisplatin type DNA-targeted platinum anticancer agents: DNA interactions of novel acridinylthioureas and their platinum conjugates, Biochem. Pharmacol. 64, 191-200.
8. Barry, C. G., Baruah, H., and Bierbach, U. (2003) Unprecedented monofunctional metalation of adenine nucleobase in guanine- and thymine-containing dinucleotide sequences by a cytotoxic platinum-acridine hybrid agent, J. Am. Chem. Soc. 125, 9629-9637.
9. Baruah, H., Day, C. S., Wright M. W., and Bierbach, U. (2004) Metal-intercalator-mediated self-association and one-dimensional aggregation in the structure of the excised major DNA adduct of a platinum-acridine agent, J. Am. Chem. Soc. 126, 4492-4493.
10. Baruah, H., and Bierbach, U. (2004) Biophysical characterization and molecular modeling of the coordinative-intercalative DNA monoadduct of a platinum-acridinylthiourea agent in a site-specifically modified dodecamer, J. Biol. Inorg. Chem. 9, 335-344.
11. Baruah, H., and Bierbach, U. (2003) Unusual intercalation of acridin-9-ylthiourea into the 5′-GA/TC DNA base step from the minor groove: implications for the covalent DNA adduct profile of a novel platinum-intercalator conjugate, Nucleic Acids Res. 31, 4138-4146.
12. Davies, M. S., Berners-Price, S. J., and Hambley, T. W. (1998) Sequence selectivity in the kinetics of formation of intra- and interstrand DNA crosslinks by cisplatin, J. Am. Chem. Soc. 120, 11380-11390.
13. 2], Indian J. Chem. 8, 193-194.
14. Gibbons, G. R., Page, J. D., and Chaney, S. G. (1991) Treatment of DNA with ammonium bicarbonate or thiourea can lead to underestimation of platinum-DNA monoadducts, Cancer Chemother. Pharmacol. 29, 112-116.
15. Axelrod, V. D., and Kramer, F. R. (1985) Transcription from bacteriophage T7 and SP6 RNA polymerases promoters in the presence of 3′- deoxyribonucleoside 5′-triphosphates chain terminators, Biochemistry 24, 5716-5723.
16. Kramer, F. R., and Mills, D. R. (1978) RNA sequencing with radioactive chain-terminating ribonucleotides, Proc. Natl. Acad. Sci. U.S.A. 75, 5334-5338.
17. Cohen, G. L., Ledner, J. A., Bauer, W. R., Ushay, H. M., Caravana, C., and Lippard, S. J. (1980) Sequence dependent binding of cis- dichlorodiammineplatinum(II) to DNA, J. Am. Chem. Soc. 102, 2487-2488.
18. Murray, V., Motyka, H., England, P. R., Wickham, G., Lee, H. H., Denny, W. A., and McFadyen, W. D. (1992) An investigation of the sequence-specific interaction of cis-diamminedichloroplatinum(II) and four analogues, including two acridine-tethered complexes, with DNA inside human cells, J. Biol. Chem. 267, 18805-18809.
19. White, R. J., and Phillips, D. R. (1989) Sequence-dependent termination of bacteriophage T7 transcription in vitro by DNA-binding agents, Biochemistry 28, 4277-4283.
20. Cullinane, C., Wickham, G., McFadyen, W. D., Denny, W. A., Palmer, B. D., and Phillips, D. R. (1993) The use of bidirectional transcription footprinfing to detect platinum-DNA crosslinks by acridine-tethered platinum diamine complexes and cisplatin, Nucleic Acids Res. 21, 393-400.
21. Fichtinger-Schepman, A. M. J., van der Veer, J. L., den Hartog, J. H. J., Lohman, P. H. M., and Reedijk, J. (1985) Adducts of the antitumor drug cis-diamminedichloroplatinum(II) with DNA: formation, identification, and quantitation, Biochemistry 24, 707-713.
22. Elmroth, S. K. C., and Lippard, S. J. (1995) Surface and electrostatic contributions to DNA-promoted reactions of platinum complexes with short oligonucleotides: a kinetic study, Inorg. Chem. 34, 5234-5243.
23. Bowler, B. E., and Lippard, S. J. (1986) Modulation of platinum antitumor drug binding to DNA by linked and free intercalators, Biochemistry 25, 3031-3038.
24. Temple, M. D., McFadyen, W. D., Holmes, R. J., Denny, W. A., and Murray, V. (2000) Interaction of cisplatin and DNA-targeted 9-aminoacridine platinum complexes with DNA, Biochemistry 39, 5593-5599.
25. Temple, M. D., Recabarren, P., McFadyen, W. D., Holmes, R. J., Denny, W. A., and Murray, V. (2002) The interaction of DNA-targeted 9-aminoacridine-4- carboxamide platinum complexes with DNA in intact human cells, Biochim. Biophys. Acta 1574, 223-230.
26. Perrin, L. C., Cullinane, C., McFadyen, W. D., and Phillips, D. R. (1999) Sequence specificity and reactivity of the binding of phenazine-tethered platinum complexes to DNA, Anti-Cancer Drug Des. 14, 243-252.
27. Whittaker, J., McFadyen, W. D., Wickham, G., Wakelin, L. P. G., and Murray, V. (1998) The interaction of DNA-targeted platinum phenanthridinium complexes with DNA, Nucleic Acids Res. 26, 3933-3939.
28. 2, Biochemistry 38, 9221-9233.
29. Palmer, B. D., Lee, H. H., Johnson, P., Baguley, B. C., Wickham, G., Wakelin, L. P. G., McFadyen, W. D., and Denny, W. A. (1990) DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine, J. Med. Chem. 33, 3008-3014.
30. Jou, Z. S., Chiu, T. K., Leiberman, P. M., Baikalov, I., Berk, A. J., and Dickerson, R. E. (1996) How proteins recognize the TATA box, J. Mol. Biol. 261, 239-254.
31. Cohen, S. M., Jamieson, E. R., and Lippard, S. J. (2000) Enhanced binding of the TATA-binding protein to TATA boxes containing planking cisplatin 1,2-cross-links, Biochemistry 39, 8259-8265.
32. Wei, M., Cohen, S. M., Silverman, A. P., and Lippard, S. J. (2001) Effects of spectator ligands on the specific recognition of intrastrand platinum-DNA cross-links by high mobility group box and TATA-binding proteins, J. Biol. Chem. 276, 38774-38780.
33. Jung, Y. W., Mikata, Y., and Lippard, S. J. (2001) Kinetic studies of the TATA-binding protein interaction with cisplatin-modified DNA, J. Biol. Chem. 276, 43589-43596.