Abstract
A variety of synthetic and naturally occurring DNA ligands have been shown to bind partially or totally within the minor groove of B-form DNA. The distamycins, netropsin, stilbamidine, and SN18071 all associate noncovalently with the minor groove1,2 while the intercalators adriamycin and actinoraycin have substituents which reside in the minor groove and stabilize their respective complexes. The pyrrolo(l,4)benzodiazepine [P(1,4)B] antitumor antibiotics, anthramycin, tomaymycin, and sibiromycin (see Figure 1) bind covalently in the minor groove to N2 of guanine.3,4 CC-1065, another antitumor antibiotic, binds covalently to N3 of adenine in the minor groove of DNA.5,6
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References
C. Zimmer, Molecular Aspects of the Specific Interaction of Nonintercalatinq Oligopeptide Antibiotics with DNA, Comments Mol. Cell. Biophys., 1: 399 (1983).
B. Pullman, Electrostatics and Specificity in Nucleic Acid Reactions, in: Specificity in Biological Interactions, C. Chagas and B. Pullman, eds., The Vatican Press. (1984).
L.H. Hurley and R.L. Petrusek. Proposed Structure of the Anthramycin DNA Adduct, Nature, 282: 529 (1980).
R.L. Petrusek, G.L. Anderson, T.F. Garner, Q.L. Fannin, D.J. Kaplan. S.G. Zimmer, and L.H. Hurley, Pyrrolo(l,4)Benzodiazepine Antiobitics, Proposed Structures and Characteristics of the in vitro DNA Adducts of Anthramycin, Tomaymycin, Sibiromycin and Neothramycins A and B, Biochemistry, 20: 1111 (1981).
L.H. Hurley, V.L. Reynolds, D.H. Swenson, T. Scahill, Reaction of the Antitumor Antibiotic CC-1065 with DNA: Structure of a DNA Adduct with DNA Sequence Specificity, Science, 226: 843 (1984).
V.L. Reynolds, I.J. Molineux, D.J. Kaplan, D.H. Swenson and L.H. Hurley, DNA Sequence Specificity of the Antitumor Antibiotic CC-1065, Biochemistry, in press (1985).
K. Zakrzewska, R. Lavery, and B. Pullman, The Solvation Contribution to the Binding Energy of DNA with Non-Intercalating Antibiotics, Nucleic Acids Research, 12: 6559 (1984).
L.H. Hurley, C. Gairola and M.J. Zmijewski, Studies on the In Vitro Reactivity of the Pyrrolo(l,4)Benzodiazepine Antibiotics Towards DNA, Using Specifically Radiolabelled Molecules, Biochem. Biophys. Acta, 475: 5215 (1977).
D.E. Graves, C. Pattaroni, C. Balakrishnan, J.M. Ostrander. L.H. Hurley and T.R. Krugh, The Reaction of Anthramycin with DNA: Proton and Carbon Nuclear Magnetic Resonance Studies on the Structure of the Anthramycin-DNA Adduct, J. Biol. Chem. 259: 8202 (1984).
M. Barkley, S. Cheatham, D.E. Thurston and L.H. Hurley, Pyrrolo(l, 4)-Benzodiazepine Antitumor Antibiotics, Evidence for Two Forms of Tomaymycin Bound to DNA, Submitted for publication.
J.C. Dabrowiak, Sequence Specificity of Drug DNA Interactions, Life Sciences, 32: 2915 (1983).
M.W. Van Dyke and P.B. Dervan, Methidium-EDTA-FE(II) and DNase I Foot-printing Report Different Small Molecule Binding Site Sizes on DNA, Nucleic Acids Res. 11: 5555 (1983).
J.S. Taylor, P.G. Schultz and P.B. Dervan, DNA Affinity Cleaving, Sequence Specific Cleavage of DNA by Distamycin-EDTA-Fe(II) and EDTA-Distamycin-Fe(II), Tetrahedron, 40: 457 (1984).
R.P. Hertzberg, S.M. Hecht, V.L. Reynolds, I.J. Molineux and L.H. Hurley, DNA Sequence Specificity of the Pyrrolo(l,4)Benzodiazepine Antitumor Antibiotics. MPE-Fe(II) Footprinting Analysis of DNA Binding Sites for Anthramycin and Related Drugs, Submitted for publication.
M.W. Van Dyke and P.B. Dervan, Footprinting with MPE-Fe(II). Complimentary-Strand Analysis of Distamycin and Actinomycin-Binding Sites on Heterogeneous DNA, Cold Spring Harbor Symposium on Quantitative Biology, 47: 347 (1983).
D.R. Needham-VanDevanter, L.H. Hurley, V.L. Reynolds, N.Y. Theriault, W.C. Krueger and W. Wierenga, Characterization of an Adduct Between CC-1065 and a Defined Oligodeoxynucleotide Duplex, Nucleic Acids Research, 12: 6159 (1984).
T.A. Scahill, unpublished results.
D.E. Graves, M.P. Stone and T.R. Krugh, Structure of the Anthramycin-d(ATGCAT), Adduct from One and Two Dimensional Proton NMR Experimentation in Solution, Biochemistry, in press (1985).
R.L. Petrusek, E.L. Uhlenhopp, N. Duteau and L.H. Hurley, Reaction of Anthramycin with DNA. Biological Consequences of DNA Damage in Normal and Xeroderma Pigmentosum Cell Lines, J. Biol. Chem. 257: 6207 (1982).
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© 1986 Plenum Press, New York
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Hurley, L.H., Needham-VanDevanter, D.R. (1986). Sequence Specificity and Biological Consequences of Drugs that Bind Covalently in the Minor Groove of DNA. In: Simic, M.G., Grossman, L., Upton, A.C., Bergtold, D.S. (eds) Mechanisms of DNA Damage and Repair. Basic Life Sciences, vol 189. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9462-8_21
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DOI: https://doi.org/10.1007/978-1-4615-9462-8_21
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