DNA Damage and Cytotoxicity Induced by Minor Groove Binding Methyl Sulfonate Esters

Biochemistry

Volumn 42, Issue 48, 2003, Pages 14318-14327

  Varadarajan, Sridhar ^a   Shah, Dharini ^a   Dande, Prasad ^a   Settles, Samuel ^a   Chen, Fa Xian ^a   Fronza, Gilberto ^b   Gold, Barry ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF GENOA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CYTOLOGY; DNA; ESTERS; GELS; HIGH PRESSURE LIQUID CHROMATOGRAPHY; PROTEINS; TOXICITY;

CYTOTOXICITY; PEPTIDES;

BIOCHEMISTRY;

3 METHYLADENINE; 3 METHYLGUANINE; 3-METHYLADENINE; 3-METHYLGUANINE; 7 METHYLGUANINE; 7-METHYLGUANINE; ADENINE; ADENINE DERIVATIVE; ANTIINFECTIVE AGENT; BACTERIAL DNA; BINDING PROTEIN; CONGOCIDINE; CYTOSINE; DNA; DNA FRAGMENT; DNA GLYCOSYLTRANSFERASE; DRUG DERIVATIVE; ESTER; ESTER DERIVATIVE; GUANINE; GUANINE DERIVATIVE; IMIDAZOLE DERIVATIVE; MESYLIC ACID; MESYLIC ACID DERIVATIVE; METHYL LEXITROPSIN; METHYL SULFONATE ESTER DERIVATIVE; N METHYLIMIDAZOLECARBOXAMIDE; N METHYLPYRROLECARBOXAMIDE; PROTEIN SUBUNIT; PYRROLE DERIVATIVE; THYMINE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; BACTERIUM MUTANT; BINDING AFFINITY; BINDING SITE; CHEMISTRY; CONFORMATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYTOTOXICITY; DNA ADDUCT; DNA DAMAGE; DNA METHYLATION; DNA REPAIR; DNA SEQUENCE; DNA STRUCTURE; DRUG DNA BINDING; DRUG EFFECT; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; EXCISION REPAIR; GENETICS; GROWTH, DEVELOPMENT AND AGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; MOLECULAR GENETICS; MOLECULAR RECOGNITION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN DNA BINDING; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; PROTEIN TARGETING; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; WILD TYPE;

ADENINE; ANTI-BACTERIAL AGENTS; BASE SEQUENCE; DNA ADDUCTS; DNA DAMAGE; DNA FRAGMENTATION; DNA METHYLATION; DNA REPAIR; DNA, BACTERIAL; ESCHERICHIA COLI; ESTERS; GUANINE; MESYLATES; MOLECULAR SEQUENCE DATA; NETROPSIN; NUCLEIC ACID CONFORMATION; PROTEIN BINDING;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA;

EID: 0344198160     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0353272     Document Type: Article

References (45)

1. Chemical Carcinogens (1984) 2nd ed., ACS Monograph 182 (Searle, C. E., Ed.) Vols. I and II, American Chemical Society, Washington, DC.
2. The Anticancer Drugs (1994) 2nd ed. (Pratt, W. B., Ruddon, R. W., Ensminger, W. D., and Maybaum, J., Eds.) Oxford Press, New York.
3. Hematology/Oncology Clinics of North America: Therapy-Related Second Malignancies (1993) Vol. 7 (Henry-Amar, M., and Dietrich, P. Y., Eds.) W. B. Saunders, Philadelphia.
4. Smith, M. A., McCaffrey, R. P., and Karp, J. E. (1996) J. Natl. Cancer Inst. 88, 407-418.
5. Karran, P., Lindahl, T., Øfsteng, I., Evensen, G. B., and Seeberg, E. (1980) J. Mol. Biol. 140, 101-127.
6. Lindahl, T. (1982) Annu. Rev. Biochem. 51, 61-87.
7. Larson, K., Sahm, J., Shenkar, R., and Strauss, B. (1985) Mutat. Res. 150, 77-84.
8. Zhang, Y., Chen, F.-X., Mehta, P., and Gold, B. (1993) Biochemistry 32, 7954-7965,
9. Shah, S., Kelly, J., Zhang, Y., Dande, P., Martinez, J., Ortiz, G., Fronza, G., Tran, H., Soto, M. A., Marky, L., and Gold, B. (2001) Biochemistry 40, 1796-1803.
10. Encell, L., Shuker, D. E. G., Foiles, P. G., and Gold, B. (1996) Chem. Res. Toxicol. 9, 563-567.
11. Kelly, J., Inga, A., Chen, F.-X., Dande, P., Shah, D., Monti, P., Aprile, A., Burns, P. A., Scott, G., Abbondandolo, A., Gold, B., and Fronza, G. (1999) J. Biol. Chem. 274, 18327-18334.
12. Monti, P. A., Campomenosi, P., Iannone, R., Ciribilli, Y., Iggo, R., Scott, G., Burns, P. A., Shah, D., Menichini, P., Abbondandolo, A., Gold, B., and Fronza, G. (2002) J. Biol. Chem. 277, 28663-28668.
13. Dinglay, S., Gold, B., and Sedgwick, B. (1998) Mutat. Res. 407, 109-116.
14. Engelward, B., Dreslin, A., Christensen, J., Huszar, D., Kurahara, C., and Samson, L. (1996) EMBO J. 15, 945-952.
15. Tentori, L., Vernole, P., Madaio, R., Portarena, I., Levati, L., Lacal, P. M., Turriziani, M., Dande, P., Gold, B., Bonmassar, E., and Graziani, G. (2000) Leukemia 12, 1451-1459.
16. Tentori, L., Balduzzi, A., Portarena, I., Levati, L., Vernole, P., Gold, B., Bonmassar, E., and Graziani, G. (2001) Cell Death Differ. 8. 817-828.
17. Krowicki, K., and Lown, J. W. (1987) J. Org. Chem. 52, 3493-3501.
18. Baird, E. E., and Dervan, P. B. (1996) J. Am. Chem. Soc. 118, 6141-6146.
19. Beranek, D. T., Weis, C. C., and Swenson, D. H. (1980) Carcinogenesis 1, 595-605.
20. Rhode, S. L., III. (1985) J. Virol. 54, 630-633.
21. Maxam, A. M., and Gilbert, W. (1980) Methods Enzymol. 65, 499-560.
22. Lown, J. W., Krowicki, K., Bhat, U. G., Skorobogaty, A., Ward, B., and Dabrowiak, J. C. (1986) Biochemistry 25, 7408-7416.
23. Mrksich, M., Wade, W. S., Dwyer, T. J., Geierstanger, B. H., Wemmer, D. E., and Dervan, P. B. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 7586-7590.
24. Lindahl, T. (1976) Nature 259, 64-66.
25. Riazuddin, S., and Lindahl, T. (1978) Biochemistry 17, 2110-2118.
26. Lawley, P. D., and Warren, W. (1976) Chem. Biol. Interact. 12, 211-220.
27. Fujii, T., Saito, T., and Nakasaki, T. (1989) Chem. Pharm. Bull. 37, 2601-2609.
28. Pullman, A., and Pullman, B. (1981) Quart. Rev. Biophys. 14, 289-380.
29. Kopka, M. L., Yoon, C., Goodsell, D., Pjura, P., and Dickerson, R. E. (1985) Proc. Natl. Acad. Sci., U.S.A. 82, 1376-1380.
30. Coll, M., Aymami, J., van der Marel, G. A., van Boom, J. H., Rich, A., and Wang, A. H.-J. (1989) Biochemistry 28, 310-320.
31. Burckhardt, G., Luck, G., Zimmer, C., Störl, J., Krowicki, K., and Lown, J. W. (1989) Biochim. Biophys. Acta 1009, 11-18.
32. Lown, J. L., Krowicki, K., Bhat, U. G., Skorobogaty, A., Ward, B., and Dabrowiak, J. C. (1985) Biopolymers 24, 183-197.
33. Thomas, L., Yang, C.-H., and Goldthwait, D. A. (1982) Biochemistry 21, 1162-1169.
34. McCarthy, T. V., Karran, P., and Lindahl, T. (1984) EMBO J. 3, 545-550.
35. Samson, L., and Cairns, J. (1977) Nature 267, 281-283.
36. Lindahl, T., Sedgwick, B., Sekiguchi, M., and Nakabeppu, Y. (1988) Annu. Rev. Biochem. 57, 133-157.
37. Dianov, G., and Lindahl, T. (1994) Curr. Biol. 4, 1069-176.
38. Demple, B., and Harrison, L. (1994) Annu. Rev. Biochem. 63, 915-948.
39. Nakabeppu, Y., Konda, H., and Sekiguchi, M. (1984) J. Biol. Chem. 259, 13723-13729.
40. Bjelland, S., Bjfrås, M., and Seeberg, E. (1993) Nucleic Acids Res. 21, 2045-2049.
41. Karran, P., Hjelmgen, T., and Lindahl, T. (1982) Nature 296, 770-773.
42. Rebeck, G. W., and Samson, L. (1991) J. Bacteriology 173, 2068-2076.
43. Cunningham, R., Saporito, S., Spitzer, S., and Weiss, B. (1986) J. Bacteriol. 168, 1120-1127.
44. Volkert, M., Nguyen, D., and Beard, C. (1986) Genetics 112, 11-26.
45. Boiteux, S. O., Huisman, O., and Laval, J. (1984) EMBO J. 3, 2569-2573.