Specific targeting of protein-DNA complexes by DNA-reactive drugs (+)- CC-1065 and pluramycins

Journal of Molecular Recognition

Volumn 9, Issue 2, 1996, Pages 75-87

  Henderson, Douglas ^a   Hurley, Laurence H ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

(+) CC 1065; minor groove DNA binding; pluramycin; TATA box; TBP

Indexed keywords

AMINOGLYCOSIDE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC ANTIBIOTIC; DNA BINDING PROTEIN; INDOLE DERIVATIVE; KITASAMYCIN DERIVATIVE; MYOGLOBIN; PLURAMYCIN; RACHELMYCIN; TATA BINDING PROTEIN; TRANSCRIPTION FACTOR; TRANSCRIPTION FACTOR SP1;

BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; CONFERENCE PAPER; CONFORMATION; DRUG EFFECT; GENETICS; HUMAN; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE REPEAT; NUCLEOTIDE SEQUENCE; TATA BOX;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; BASE SEQUENCE; BINDING SITES; DNA-BINDING PROTEINS; HUMANS; INDOLES; LEUCOMYCINS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MYOGLOBIN; NUCLEIC ACID CONFORMATION; REPETITIVE SEQUENCES, NUCLEIC ACID; SP1 TRANSCRIPTION FACTOR; TATA BOX; TATA-BOX BINDING PROTEIN; TRANSCRIPTION FACTORS;

EID: 0030111082     PISSN: 09523499     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1352(199603)9:2<75::AID-JMR247>3.0.CO;2-4     Document Type: Conference Paper

References (59)

1. Adams, E. G., Badiner, G. J. and Bhuyan, B. K. (1988). Effects of U-7, 184 and several other CC-1065 analogues on cell survival and cell cycle of Chinese hamster ovary cells. Cancer Res. 48, 109-116.
2. Banerji, J., Rusconi, S. and Schaffner, W. (1981). Expression of a β-globin gene is enhanced by remote SV40 DNA sequences. Cell 27, 299-308.
3. Basu, A. K. and Essigmann, J. M. (1988). Site-specifically modified oligodeoxynucleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol. 1, 1-18.
4. Buratowski, S., Hahn, S., Guarante, L. and Sharp, P. A. (1989). Five intermediate complexes in transcription initiation by RNA polymerase II. Cell 56, 549-561.
5. Churchill, M. E. A., Tullius, T. D. and Klug, A. (1990). Mode of interaction of the zinc finger protein TFIIA with a 5S RNA gene of Xenopus. Proc. Natl. Acad. Sci. USA 87, 5528-5532.
6. Cortes, P., Flores, O. and Reinberg, O. (1994). Factors involved in specific transcription by mammalian RNA polymerase II: purification and analysis of transcription factor IIA and identification of transcription factor IIJ. J. Mol. Cell. Biol. 12, 413-421.
7. Courey, A. J. and Tjian, R. (1988). Analysis of Sp1 in vivo reveals multiple transcriptional domains, including a novel gluta- mine-rich activation motif. Cell 55, 887-898
8. Courey, A. J., Holtzman, D. A., Jackson, S. P. and Tjian, R. (1989). Synergistic activation by the glutamine-rich domains of human transcription factor Sp1. Cell 59, 827-836.
9. Davison, B. L., Egly, J.-M., Mulvihil, E. R. and Chambon, P. (1983). Formation of stable preinitiation complexes between eukaryotic class B transcription factors and promoter sequences. Nature 301, 680-686.
10. Devlin, B. H., Wefald, F. C., Kraus, W. E., Bernard, T. S. and Williams, R. S. (1989). Identification of a muscle-specific enhancer within the 5′-flanking region of the human myoglobin gene. J. Biol. Chem. 264, 13896-13901.
11. Dynan, W. S. and Tjian, R. (1983). The promoter-specific transcription factor Sp1 binds to upstream sequence in the SV40 early promoter. Cell 35, 79-87.
12. Everett, R. D., Baty, D. and Chambon, P. (1983). The repeated GC-rich motifs upstream from the TATA box are important elements of the SV40 early promoter. Nucl. Acids. Res. 11, 2447-2464.
13. Gidoni, D., Dynan, W. S. and Tjian, R. (1984). Multiple specific contacts between a mammalian transcription factor and its cognate promoters. Nature (London) 312, 409-413.
14. Hai, T., Horikoshi, M., Reeder, R. G. and Green, M. R. (1988). Analysis of the role of the transcription factor ATF in the assembly of a functional preinitiation complex. Cell 54, 1043-1051.
15. Hanka, J. J., Dietz, A., Gerpheide, S. A., Kuentzil, S. I. and Martin, D. G. (1978). CC-1065 (NSC-298223), a new antitumor antibiotic. Production, in vitro biological activity, microbiological assays and taxonomy of the producing microorganisms. J. Antibiot. 31, 1211-1217.
16. Hansen, M. and Hurley, L. H. (1995). Altromycin B threads the DNA helix interacting with both the major and the minor grooves to position itself for site-directed alkylation of guanine N7. J. Am. Chem. Soc. 117, 2421-2429.
17. Hansen, M., Sang, Y. and Hurley, L. H. (1995). Hedamycin intercalates the DNA helix and, through carbohydrate-mediated recognition in the minor groove, directs N7-alkyiation of guanine in the major groove in a sequence specific manner. Chemistry & Biology 2, 229-240.
18. Ho, S. N., Boyer, S. H., Schreiber, S. L., Danishefsky, S. J. and Crabtree, G. R. (1994). Specific inhibition of formation of transcription complexes by a calicheamicin oligosaccharide: A paradigm for the development of transcriptional antagonists. Proc. Natl. Acad. Sci. USA 91, 9203-9207.
19. Hurley, L. H. (1989). DNA and associated targets for drug design. J. Med. Chem. 32, 2027-2033.
20. Hurley, L. H. and Draves, P. H. (1993). Molecular aspects of the interaction of (+)-CC-1065 with DNA. In: Molecular Aspects of Anticancer Drug-DNA Interactions Vol. I, eds S. Neidle and M. J. Waring, pp. 89-133, Macmillan.
21. Hurley, L. H., Reynolds, V. L., Swenson, D. H. and Scahill, T. A. (1984). Reaction of the antitumor antibiotic CC-1065 with DNA. Structure of a DNA adduct with DNA sequence specificity. Science 226, 843-844.
22. Janson, L. and Pettersson, U. (1990). Cooperative interactions between transcription factors Sp1 and OTF-1. Proc. Natl. Acad. Sci. USA 87, 4732-4736.
23. Johnson, P. F. and McKnight, S. L. (1989). Eukaryotic transcriptional regulatory proteins. Annu. Rev. Biochem. 58, 799-839.
24. Kadonaga, J. T., Jones, K. A. and Tjian, R. (1986). Promoter-specific activation of RNA polymerase II transcription by Sp1. Trends Biochem. 11, 20-23.
25. Kadonaga, J. T., Carner, K. R., Masiarz, F. R. and Tjian, R. (1987). Isolation of cDNA encoding transcription factor Sp1 and functional analysis of the DNA bending domain. Cell 51, 1079-1090.
26. Kadonaga, J. T., Courey, A. J., Ladika, J. and Tjian, R. (1988). Distinct regions of Sp1 modulate DNA binding and transcriptional activation. Science 242, 1566-1570.
27. Kahn, J. D. and Crothers, D. M. (1992). Protein-induced bending and DNA cyclization. Proc. Natl. Acad. Sci. USA 89, 6343-6347.
28. Kim, Y., Geiger, J. H., Hahn, S. and Sigler, P. B. (1993). Crystal structure of a yeast TBP/TATA-box complex. Nature (London) 365, 512-520.
29. Kim, J. L., Nikolov, D. B. and Burley, S. K. (1993). Co-crystal structure of TBP recognizing the minor groove of a TATA element. Nature (London) 365, 520-527.
30. Kim, J. L. and Burley, S. K. (1994). 1.9 Å resolution refined structure of TBP recognizing the minor groove of TATAAAAG. Nature Struct. Biol. 1, 638-653.
31. Koo, H.-S. and Crothers, D. M. (1988). Calibration of DNA curvature and a unified description of sequence-directed bending. Proc. Natl. Acad. Sci. USA 85, 1763-1767.
32. Lee, C.-S., Sun, D., Kizu, R. and Hurley, L. H. (1991). Determination of the structural features of (+)-CC-1065 that are responsible for bending, winding and stiffening of DNA. Chem. Res. Toxicol. 4, 203-213.
33. Lin, C. H., Sun, D. and Hurley, L. H. (1991). (+)-CC-1065 produces bending of DNA that appears to resemble adenine/thymine tracts. Chem. Res. Toxicol. 4, 21-26.
34. Lyubschenko, Y., Shlyakhtenko, L., Chernov, B. and Harrington, R. E. (1991). DNA bending induced by Cro protein binding as demonstrated by gel electrophoresis. Proc. Natl. Acad. Sci. USA 88, 5331-5334.
35. MacLeod, M. C., Powell, K. L. and Tran, N. (1995). Binding of the transcription factor Sp1 to non-target sites in DNA modified by benzo[a]pyrene diol epoxide. Carcinogenesis 16, 975-983.
36. Maher, L. J., III, Dervan, P. B. and Wold, B. (1992). Analysis of promoter-specific repression by triple-helical DNA complexes in a eukaryotic cell-free transcription system. Biochemistry 31, 70-81.
37. Mitchell, P. J. and Tjian, R. (1989). Transcriptional regulation in mammalian cells by sequence-specific DNA binding proteins. Science 245, 371-378.
38. Mitscher, L. A. and Shen, L. L. (1992). A cooperative quinolone- DNA binding model for DNA gyrase inhibition. In: Nucleic Acid Targeted Drug Design, eds C. L. Propst and T. J. Perun, pp. 375-421. Marcel Dekker, New York.
39. Müller, H.-P., Sogo, J. M. and Schaffner, W. (1989). Transcrip- tional enhancers can act in trans. CelI 58, 767-777.
40. Müller, H.-P. and Schaffner, W. (1990). An enhancer stimulates transcription in trans when attached to the promoter via a protein bridge. Trends Genet. 6, 300-304.
41. Nikolov, D. B. et al. and Burley, S. K. (1992). Crystal structure of TFIID TATA-box binding protein. Nature (London) 260, 40-46.
42. Ptashne, M. (1988). How eukaryotic transcriptional activators work. Nature (London) 335, 683-689.
43. Pugh, B. F. and Tijian, R. (1990). Mechanism of transcriptional activation by Sp1: Evidence for coactivators. Cell 61, 1187-1197.
44. Potmesil, M. (1994). Camptothecins: From bench research to hospital wards. Cancer Res. 54, 1431-1439 and references therein.
45. Reynolds, V. L., Molineux, I. J., Kaplan, D. J., Swenson, D. H. and Hurley, L. H. (1985). Location of the site of thermally induced strand breakage and analysis of DNA sequence specificity. Biochemistry 24, 6228-6237.
46. Roeder, R. G. (1991). The complexities of eukaryotic transcription initiation: regulation of preinitiation complex assembly. Trends Biochem. Sci. 16, 402-408.
47. Scahill, T. A., Jensen, R. M., Swenson, D. H., Hatzenbuhler, N.T., Petzold, G. L., Wierenga, W. and Brahme, N. D. (1990). An NMR study of the covalent and noncovalent interaction of CC-1065 and DNA. Biochemistry 29, 2852-2860.
48. Sun, D. and Hurley, L. H. (1992). Inhibition of T4 DNA ligase activity by (+)-CC-1065: demonstration of the importance of the stiffening and winding effects of (+)-CC-1065 on DNA. Anti-Cancer Drug Design 7, 15-36.
49. Sun, D., Hansen, M., Clement, J. J. and Hurley, L. H. (1993a). Structure of the altromycin B (N7-guanine)-DNA adduct. A proposed prototypic DNA adduct structure for the pluramycin antitumor antibiotics. Biochemistry 32, 8068-8074.
50. Sun, D., Lin, C. H. and Hurley, L. H. (1993b). A-tract and (+)-CC-1065-induced bending of DNA. Comparison of structural features using nondenaturing gel analysis, hydroxyl-radical footprinting and high-field NMR. Biochemistry 32, 4487-4495.
51. Sun, D. and Hurley, L. H. (1994). Cooperative bending of the 21-base-pair repeats of the SV40 viral early promoter by human Sp1. Biochemistry 33, 9578-9587.
52. Sun, D., Hansen, M. and Hurley, L. H. (1995). Molecular basis for the DNA sequence specificity of the pluramycins. A novel mechanism involving groove interactions transmitted through the helix via intercalation to achieve sequence selectivity at the covalent bonding step. J. Am. Chem. Soc. 117, 2430-2440.
53. Sun, D. and Hurley, L. H. (1995). TBP binding to the TATA box induces a specific downstream unwinding site that is targeted by pluramycin. Chemistry & Biology 2, 457-469.
54. Tanese, N., Pugh, B. F. and Tjian, T. (1991). Coactivators for a proline-rich activator purified from the multisubunit human TFIID complex. Genes & Dev. 5, 2212-2224.
55. Treiber, D. K., Zhai, X., Jantzen, H. and Essigmann, J. M. (1994). Cisplatin-DNA adducts are molecular decoys for the ribosomal RNA transcription factor hUBF (human upstream binding factor). Proc. Natl. Acad. Sci. USA 91, 5672-5674.
56. Van Dyke, M. W., Roeder, R. G. and Sawadogo, M. (1988). Physical analysis of transcription preinitiation complex assembly on a class II gene promoter. Science 241, 1335-1338.
57. Wefald, F. C., Devlin, B. H. and Williams, R. S. (1990). Functional heterogeneity of mammalian TATA-box sequences revealed by interaction with a cell-specific enhancer. Nature (London) 344, 260-262.
58. Yang, C.-C. and Nash, H. A. (1989). The interaction of E. coli IHF protein with its specific binding site. Cell 57, 869-880.
59. Zhou, O., Lieberman, P. M., Boyer, T. G. and Berk, A. J. (1992). Holo-TFIID supports transcriptional stimulation by diverse activators and from a TATA-less promoter. Genes & Dev. 6, 1964-1974.