Probing platinum-adenine-N3 adduct formation with DNA minor-groove Binding agents

Chemical Research in Toxicology

Volumn 23, Issue 7, 2010, Pages 1148-1150

  Rao, Lu ^a   West, Tiffany K ^b   Saluta, Gilda ^b   Kucera, Gregory L ^b   Bierbach, Ulrich ^a  

^a WAKE FOREST UNIVERSITY   (United States)

^b WAKE FOREST UNIVERSITY HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; CELL DNA; CONGOCIDINE; DNA; GUANINE; PLATINUM;

ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL; CELL PROLIFERATION; CYTOTOXICITY; DNA CLEAVAGE; HUMAN; HUMAN CELL;

ADENINE; ALKYLATING AGENTS; DNA ADDUCTS; DNA CLEAVAGE; NETROPSIN; ORGANOPLATINUM COMPOUNDS;

EID: 77955343918     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100170p     Document Type: Article

References (24)

1. Lovejoy, K. S. and Lippard, S. J. (2009) Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting Dalton Trans. 10651-10659
2. Ma, Z., Choudhury, J. R., Wright, M. W., Day, C. S., Saluta, G., Kucera, G. L., and Bierbach, U. (2008) A non-cross-linking platinum-acridine agent with potent activity in non-small-cell lung cancer J. Med. Chem. 51, 7574-7580
3. Guddneppanavar, R. and Bierbach, U. (2007) Adenine-N3 in the DNA minor groove: an emerging target for platinum containing anticancer pharmacophores Anticancer Agents Med. Chem. 7, 125-138
4. Guddneppanavar, R., Choudhury, J. R., Kheradi, A. R., Steen, B. D., Saluta, G., Kucera, G. L., Day, C. S., and Bierbach, U. (2007) Effect of the diamine nonleaving group in platinum-acridinylthiourea conjugates on DNA damage and cytotoxicity J. Med. Chem. 50, 2259-2263
5. Guddneppanavar, R., Saluta, G., Kucera, G. L., and Bierbach, U. (2006) Synthesis, biological activity, and DNA-damage profile of platinum-threading intercalator conjugates designed to target adenine J. Med. Chem. 49, 3204-3214
6. Ackley, M. C., Barry, C. G., Mounce, 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. 9, 453-461
7. Jamieson, E. R. and Lippard, S. J. (1999) Structure, recognition, and processing of cisplatin-DNA adducts Chem. Rev. 99, 2467-2498
8. Budiman, M. E., Alexander, R. W., and Bierbach, U. (2004) Unique base-step recognition by a platinum-acridinylthiourea conjugate leads to a DNA damage profile complementary to that of the anticancer drug cisplatin Biochemistry 43, 8560-8567
9. 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
10. Weston, S. A., Lahm, A., and Suck, D. (1992) X-ray structure of the Dnase I-D(Ggtatacc)(2) complex at 2.3-Angstrom resolution J. Mol. Biol. 226, 1237-1256
11. Monti, P., Traverso, I., Casolari, L., Menichini, P., Inga, A., Ottaggio, L., Russo, D., Iyer, P., Gold, B., and Fronza, G. (2010) Mutagenicity of N3-methyladenine: a multi-translesion polymerase affair Mutat. Res. 683, 50-56
12. Russo, D., Fronza, G., Ottaggio, L., Monti, P., Inga, A., Iyer, P., Gold, B., and Menichini, P. (2009) High frequency of genomic deletions induced by Me-lex, a sequence selective N3-adenine methylating agent, at the Hprt locus in Chinese hamster ovary cells Mutat. Res. 671, 58-66
13. Fronza, G. and Gold, B. (2004) The biological effects of N3-methyladenine J. Cell. Biochem. 91, 250-257
14. Varadarajan, S., Shah, D., Dande, P., Settles, S., Chen, F. X., Fronza, G., and Gold, B. (2003) DNA damage and cytotoxicity induced by minor groove binding methyl sulfonate esters Biochemistry 42, 14318-14327
15. Lown, J. W. (1994) DNA recognition by lexitropsins, minor groove binding agents J. Mol. Recognit. 7, 79-88
16. Colombier, C., Lippert, B., and Leng, M. (1996) Interstrand cross-linking reaction in triplexes containing a monofunctional transplatin-adduct Nucleic Acids Res. 24, 4519-4524
17. Ourliac Garnier, I. and Bombard, S. (2007) GG sequence of DNA and the human telomeric sequence react with cis-diammine-diaquaplatinum at comparable rates J. Inorg. Biochem. 101, 514-524
18. Ourliac-Garnier, I., Elizondo-Riojas, M. A., Redon, S., Farrell, N. P., and Bombard, S. (2005) Cross-links of quadruplex structures from human telomeric DNA by dinuclear platinum complexes show the flexibility of both structures Biochemistry 44, 10620-10634
19. Barry, C. G., Day, C. S., and Bierbach, U. (2005) Duplex-promoted platination of adenine-N3 in the minor groove of DNA: challenging a longstanding bioinorganic paradigm J. Am. Chem. Soc. 127, 1160-1169
20. Shah, D. and Gold, B. (2003) Evidence in Escherichia coli that N3-methyladenine lesions and cytotoxicity induced by a minor groove binding methyl sulfonate ester can be modulated in vivo by netropsin Biochemistry 42, 12610-12616
21. Reddy, B. S., Sharma, S. K., and Lown, J. W. (2001) Recent developments in sequence selective minor groove DNA effectors Curr. Med. Chem. 8, 475-508
22. Woynarowski, J. M. (2002) Targeting critical regions in genomic DNA with AT-specific anticancer drugs Biochim. Biophys. Acta 1587, 300-308
23. Woynarowski, J. M., Trevino, A. V., Rodriguez, K. A., Hardies, S. C., and Benham, C. J. (2001) AT-rich islands in genomic DNA as a novel target for AT-specific DNA-reactive antitumor drugs J. Biol. Chem. 276, 40555-40566
24. Woynarowski, J. M. and Beerman, T. A. (1997) Effects of bizelesin (U-77,779), a bifunctional alkylating minor groove binder, on replication of genomic and simian virus 40 DNA in BSC-1 cells Biochim. Biophys. Acta 1353, 50-60