Targeting DNA bulged microenvironments with synthetic agents: Lessons from a natural product

Chemistry and Biology

Volumn 9, Issue 8, 2002, Pages 925-931

  Xi, Zhen ^a   Hwang, Geum Sook ^a   Goldberg, Irving H ^a   Harris, Jeffrey L ^b   Pennington, William T ^b   Fouad, Farid S ^c   Qabaja, Ghassan ^c   Wright, Justin M ^c   Jones, Graham B ^c  

^a HARVARD MEDICAL SCHOOL   (United States)

^b CLEMSON UNIVERSITY   (United States)

^c NORTHEASTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DNA; DRUG DERIVATIVE; ENEDIYNE; LIGAND; OLIGODEOXYRIBONUCLEOTIDE; SPIRO COMPOUND; ZINOSTATIN; ZINOSTATIN CHROMOPHORE;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; GENE LIBRARY; HYDROLYSIS; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CYCLIZATION; DNA; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; ENEDIYNES; GENE LIBRARY; HYDROLYSIS; LIGANDS; NUCLEIC ACID CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; ZINOSTATIN;

EID: 0036669211     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(02)00188-6     Document Type: Article

References (27)

1. Sanger W. Principles of Nucleic Acid Structure. 1994;Springer-Verlag, New York.
2. Turner D.H. Bulges in nucleic acids. Curr. Opin. Struct. Biol. 2:1992;334-337.
3. Chastain M., Tinoco I. Structural elements in RNA. Progress in Nucleic Acid Research and Molecular Biology In. 1991;Academic, W.E. Cohn, K. Moldave. eds. (New York. 41, 131-177.
4. Lilley D.M.S. Kinking of DNA and RNA by base bulges. Proc. Natl. Acad. Sci. USA. 92:1995;7140-7142.
5. Dingwall C., Ernberg I., Gait M.J., Green S.M., Heaphy S., Karn J., Lowe A.D., Singh M., Skinner M.A., Valerio R. HIV-1 tat protein binds trans-activation-responsive region (TAR) RNA in vitro. Proc. Natl. Acad. Sci. USA. 86:1989;6925-6929.
6. Greenblatt J., Nodwell J.R., Mason S.W. Transcriptional antitermination. Nature. 364:1993;401-406.
7. Wells R.D. Molecular bases of genetic instability of triplet repeats. J. Biol. Chem. 271:1996;2875-2878.
8. Perutz M.F. Glutamine repeats and inherited neurodegnerative disease. molecular aspects Curr. Opin. Struct. Biol. 6:1996;848-858.
9. Kunkel T.A. Slipping DNA and diseases. Nature. 365:1993;207-209.
10. Harvey S.C. Slipped structures in DNA triplet repeat sequences. entropic contributions to genetic instabilities Biochemistry. 36:1997;3047-3049.
11. Xi Z., Goldberg I.H. DNA-damaging enediyne compounds. Comprehensive Natural Products Chemistry In. 1999;Pergamon, D.H.R. Barton and K. Nakanishi, eds. (Oxford. 7, 553-592.
12. Xi Z., Mao Q.-K., Goldberg I.H. Mechanistic studies on the base catalyzed transformation of neocarzinostatin chromophore. Roles of bulged DNA Biochemistry. 38:1999;4342-4354.
13. Kappen L.S., Goldberg I.H. DNA conformation-induced activation of an enediyne for site-specific cleavage. Science. 261:1993;1319-1321.
14. Kappen L.S., Goldberg I.H. Site-specific cleavage at a DNA bulge by neocarzinostatin chromophore via a novel mechanism. Biochemistry. 32:1993;13138-13145.
15. Kappen L.S., Goldberg I.H. Bulge-specific cleavage in transactivation response region RNA and its DNA analogue by neocarzinostatin chromophore. Biochemistry. 34:1995;5997-6002.
16. Hensens O.D., Chin D.-H., Stassinopoulos A., Zink D.L., Kappen L.S., Goldberg I.H. Spontaneous generation of a biradical species of neocarzinostatin chromophore. Role in DNA bulge-specific cleavage Proc. Natl. Acad. Sci. USA. 91:1994;4534-4538.
17. Yang C.F., Stassinopoulos A., Goldberg I.H. Specific binding of the biradical analog of neocarzinostatin chromophore to bulged DNA. Implications for thiol-independent cleavage Biochemistry. 34:1995;2267-2275.
18. Stassinopoulos A., Ji J., Gao S., Goldberg I.H. Solution structure of a two-base DNA bulge complexed with an enediyne cleaving analog. Science. 272:1996;1943-1946.
19. Gao X., Stassinopoulos A., Ji J., Kwon Y., Bare S., Goldberg I.H. Induced formation of a DNA bulge structure by a molecular wedge ligand-postactivated neocarzinostatin chromophore. Biochemistry. 41:2002;5131-5143.
20. Myers A.G., Liang J., Hammond M., Harrington P., Wu Y., Kuo E. Total synthesis of the (+)-neocarzinostatin chromophore. J. Am. Chem. Soc. 120:1998;5319-5320.
21. Smith A.L., Nicolaou K.C. The enediyne antibiotics. J. Med. Chem. 39:1996;2103-2117.
22. Grissom J.W., Gunawardena G.U., Klingberg D., Huang D. The chemistry of enediynes, enyne allenes and related compounds. Tetrahedron. 52:1996;6453-6518.
23. Maier, M.E. (1995). Design of enediyne prodrugs. Synlett, 13-26.
24. Xi Z., Jones G.B., Qabaja G., Wright J.W., Johnson F.S., Goldberg I.H. Synthesis and DNA binding of spirocyclic model compounds related to the neocarzinostatin chromophore. Org. Lett. 1:1999;1375-1377.
25. Butkus E., Berg U., Stoncius A., Rimkus A. Chromatographic enantiomer separation and absolute configuration of spiro[benzo-1,3-dioxole-2,9'-bicyclo[3.3.1]nonan]-2'-one and the corresponding diastereomeric hydroxy acetals. J. Chem. Soc. Perkin Trans. 2:1998;2547-2551.
26. Morris J.L., Becker C.L., Fronczek F.R., Daly W.H., McLaughlin M.L. Synthesis of extended linear aromatics using tandem Diels-Alder aromatization reactions. J. Org. Chem. 59:1994;6484-6486.
27. Minuti L., Taticchi A., Gacs-Baitz E., Marrocchi A. High pressure Diels-Alder reactions of 2-vinyl-3,4-dihydronaphthalene. Synthesis of cyclopenta[c]- and Indeno[c]phenanthrenones. Tetrahedron. 51:1995;8953-8958.