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Sequence-Specific DNA Minor Groove Binders. Design and Synthesis of Netropsin and Distamycin Analogues
Abstract
ADVERTISEMENT RETURN TO ISSUEReviewNEXTSequence-Specific DNA Minor Groove Binders. Design and Synthesis of Netropsin and Distamycin AnaloguesChristian Bailly and Jonathan B. ChairesView Author Information INSERM U-124 et Laboratoire de Pharmacologie Antitumorale Moléculaire du Centre Oscar Lambret, IRCL, Place de Verdun, 59045 Lille, France, and Department of Biochemistry, University of Mississippi Medical Center, 2500 North State Street, Jackson, Mississippi 39216-4505Cite this: Bioconjugate Chem. 1998, 9, 5, 513–538Publication Date (Web):June 23, 1998Publication History Received13 January 1998Revised5 May 1998Published online23 June 1998Published inissue 1 September 1998https://pubs.acs.org/doi/10.1021/bc980008mhttps://doi.org/10.1021/bc980008mreview-articleACS PublicationsCopyright © 1998 American Chemical SocietyRequest reuse permissionsArticle Views2147Altmetric-Citations216LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Conjugate acid-base pairs,Genetics,Molecules,Nucleic acid structure,Peptides and proteins Get e-Alerts
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Citations
Cites
A caspase-activated DNase that degrades DNA during apoptosis, and its inhibitor ICAD
Enari, M., Sakahira, H., Yokoyama, H., Okawa, K., Iwamatsu, A., & Nagata, S. (1998) · Nature · doi:10.1038/34112 · Cited by 3,189
Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage
Meunier, B. (1992) · Chemical Reviews · doi:10.1021/cr00014a008 · Cited by 2,090
Chemistry and Biology of the Enediyne Anticancer Antibiotics
Nicolaou, K. C., & Dai, W. (1991) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199113873 · Cited by 991
Sigman, D. S., Mazumder, A., & Perrin, D. M. (1993) · Chemical Reviews · doi:10.1021/cr00022a011 · Cited by 921
Design of Sequence-Specific DNA-Binding Molecules
Dervan, P. B. (1986) · Science · doi:10.1126/science.2421408 · Cited by 838
The molecular origin of DNA-drug specificity in netropsin and distamycin.
Kopka, M. L., Yoon, C. N., Goodsell, D. S., et al. (1985) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.82.5.1376 · Cited by 817
Zimmer, C., & Wähnert, U. (1986) · Progress in Biophysics and Molecular Biology · doi:10.1016/0079-6107(86)90005-2 · Cited by 764
Waring, M. J. (1981) · Annual Review of Biochemistry · doi:10.1146/annurev.bi.50.070181.001111 · Cited by 687
Coll, M., Frederick, C. A., Wang, A. H., & Rich, A. (1987) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.84.23.8385 · Cited by 684
Recognition of the four Watson–Crick base pairs in the DNA minor groove by synthetic ligands
White, S., Szewczyk, J. W., Turner, J. M., Baird, E. E., & Dervan, P. B. (1998) · Nature · doi:10.1038/35106 · Cited by 499
Regulation of gene expression by small molecules
Gottesfeld, J. M., Neely, L., Trauger, J. W., Baird, E. E., & Dervan, P. B. (1997) · Nature · doi:10.1038/387202a0 · Cited by 470
Binding of an antitumor drug to DNA
Kopka, M. L., Yoon, C., Goodsell, D. S., Pjura, P. E., & Dickerson, R. E. (1985) · Journal of Molecular Biology · doi:10.1016/0022-2836(85)90171-8 · Cited by 426
Molecular electrostatic potential of the nucleic acids
Pullman, A., & Pullman, B. (1981) · Quarterly Reviews of Biophysics · doi:10.1017/s0033583500002341 · Cited by 411
Lee, M., Rhodes, A. L., Wyatt, M. D., Forrow, S., & Hartley, J. A. (1993) · Biochemistry · doi:10.1021/bi00067a011 · Cited by 404
Recognition of DNA by designed ligands at subnanomolar concentrations
Trauger, J. W., Baird, E. E., & Dervan, P. B. (1996) · Nature · doi:10.1038/382559a0 · Cited by 397
Structural characterization of a 2:1 distamycin A.d(CGCAAATTGGC) complex by two-dimensional NMR.
Pelton, J. G., & Wemmer, D. E. (1989) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.86.15.5723 · Cited by 393
Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids
Baird, E. E., & Dervan, P. B. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960720z · Cited by 360
Molecular Aspects of Anticancer Drug-DNA Interactions
(1994) · doi:10.1007/978-1-349-13330-7 · Cited by 345
Van Dyke, M. W., Hertzberg, R. P., & Dervan, P. B. (1982) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.79.18.5470 · Cited by 328
CC‐1065 and the Duocarmycins: Understanding their Biological Function through Mechanistic Studies
Boger, D. L., & Johnson, D. S. (1996) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199614381 · Cited by 319
Wartell, R. M., Larson, J. E., & Wells, R. D. (1974) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)42119-4 · Cited by 276
Chemistry and biology of natural and designed enediynes.
Nicolaou, K. C., Smith, A. L., & Yue, E. W. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.13.5881 · Cited by 258
Gene Transfer with a Series of Lipophilic DNA-Binding Molecules
Remy, J.-S., Sirlin, C., Vierling, P., & Behr, J.-P. (1994) · Bioconjugate Chemistry · doi:10.1021/bc00030a021 · Cited by 221
Binding modes of distamycin A with d(CGCAAATTTGCG)2 determined by two-dimensional NMR
Pelton, J. G., & Wemmer, D. E. (1990) · Journal of the American Chemical Society · doi:10.1021/ja00160a016 · Cited by 219
Wade, W. S., Mrksich, M., & Dervan, P. B. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00049a006 · Cited by 218
Coll, M., Aymami, J., Van der Marel, G. A., Van Boom, J. H., Rich, A., & Wang, A. H. J. (1989) · Biochemistry · doi:10.1021/bi00427a042 · Cited by 213
Bleomycins: A Structural Model for Specificity, Binding, and Double Strand Cleavage
Stubbe, J., Kozarich, J. W., Wu, W., & Vanderwall, D. E. (1996) · Accounts of Chemical Research · doi:10.1021/ar9501333 · Cited by 213
NITROGEN MUSTARDS IN THE TREATMENT OF NEOPLASTIC DISEASE: Official Statement
RHOADS, C. P. (1946) · Journal of the American Medical Association · doi:10.1001/jama.1946.02870250010003 · Cited by 198
Complexes of the Minor Groove of DNA
Geierstanger, B. H., & Wemmer, D. E. (1995) · Annual Review of Biophysics and Biomolecular Structure · doi:10.1146/annurev.bb.24.060195.002335 · Cited by 197
Lown, J. W., Krowicki, K., Bhat, U. G., Skorobogaty, A., Ward, B., & Dabrowiak, J. C. (1986) · Biochemistry · doi:10.1021/bi00371a024 · Cited by 189
Marky, L. A., & Breslauer, K. J. (1987) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.84.13.4359 · Cited by 185
Mrksich, M., Wade, W. S., Dwyer, T. J., Geierstanger, B. H., Wemmer, D. E., & Dervan, P. B. (1992) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.89.16.7586 · Cited by 184
Targeting the minor groove of DNA
Wemmer, D. E., & Dervan, P. B. (1997) · Current Opinion in Structural Biology · doi:10.1016/s0959-440x(97)80051-6 · Cited by 179
Growth-modulating plasma tripeptide may function by facilitating copper uptake into cells
Pickart, L., Freedman, J. H., Loker, W. J., Peisach, J., Perkins, C. M., Stenkamp, R. E., & Weinstein, B. (1980) · Nature · doi:10.1038/288715a0 · Cited by 175
On the pairing rules for recognition in the minor groove of DNA by pyrrole-imidazole polyamides
White, S., Baird, E. E., & Dervan, P. B. (1997) · Chemistry & Biology · doi:10.1016/s1074-5521(97)90243-x · Cited by 161
DNA and associated targets for drug design
Hurley, L. H. (1989) · Journal of Medicinal Chemistry · doi:10.1021/jm00129a001 · Cited by 153
Taylor, J., Schultz, P. G., & Dervan, P. B. (1984) · Tetrahedron · doi:10.1016/0040-4020(84)85050-4 · Cited by 152
Pluramycins. Old Drugs Having Modern Friends in Structural Biology
Hansen, M. R., & Hurley, L. H. (1996) · Accounts of Chemical Research · doi:10.1021/ar950167a · Cited by 147
Patel, D. J. (1982) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.79.21.6424 · Cited by 139
Chemical and photochemical probing of DNA complexes
Nielsen, P. E. (1990) · Journal of Molecular Recognition · doi:10.1002/jmr.300030102 · Cited by 127
Comparison of binding sites in DNA for berenil, netropsin and distamycin
Portugal, J., & Waring, M. J. (1987) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1987.tb13334.x · Cited by 125
Synthesis, DNA-binding properties, and antitumor activity of novel distamycin derivatives
Arcamone, F., Animati, F., Barbieri, B., Configliacchi, E., D’Alessio, R., Geroni, C., Giuliani, F. C., Lazzari, E., & Menozzi, M. (1989) · Journal of Medicinal Chemistry · doi:10.1021/jm00124a008 · Cited by 122
Kopka, M. L., Goodsell, D. S., Baikalov, I., Grześkowiak, K., Cascio, D., & Dickerson, R. E. (1994) · Biochemistry · doi:10.1021/bi00250a011 · Cited by 111
Herman, D., Baird, E. E., & Dervan, P. B. (1998) · Journal of the American Chemical Society · doi:10.1021/ja9737228 · Cited by 107
Kopka, M. L., Goodsell, D. S., Han, G. W., Chiu, T. K., Lown, J. W., & Dickerson, R. E. (1997) · Structure · doi:10.1016/s0969-2126(97)00255-4 · Cited by 104
Broggini, M., Coley, H. M., Mongelli, N., Pesenti, E. A., Wyatt, M. D., Hartley, J. A., & D’Incalci, M. (1995) · Nucleic Acids Research · doi:10.1093/nar/23.1.81 · Cited by 90
Microwave and infrared spectra of free radicals and molecular ions
Hirota, E. (1992) · Chemical Reviews · doi:10.1021/cr00009a006 · Cited by 89
Optimization of the Hairpin Polyamide Design for Recognition of the Minor Groove of DNA
Parks, M. E., Baird, E. E., & Dervan, P. B. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960721r · Cited by 83
Sriram, M., van der MAREL, G. A., Roelen, H. L. P. F., et al. (1992) · Biochemistry · doi:10.1021/bi00162a022 · Cited by 81
Hansma, H. G., Browne, K. A., Bezanilla, M., & Bruice, T. C. (1994) · Biochemistry · doi:10.1021/bi00194a007 · Cited by 80
Manderville, R. A., Ellena, J. F., & Hecht, S. M. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00135a007 · Cited by 79
Sequence-specific double-strand cleavage of DNA by penta-N-methylpyrrolecarboxamide-EDTA X Fe(II).
Schultz, P. G., & Dervan, P. B. (1983) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.80.22.6834 · Cited by 78
Refinement of Netropsin Bound to DNA: Bias and Feedback in Electron Density Map Interpretation
Goodsell, D. S., Kopka, M. L., & Dickerson, R. E. (1995) · Biochemistry · doi:10.1021/bi00015a009 · Cited by 76
Bailly, C., & Waring, M. J. (1995) · Journal of Biomolecular Structure and Dynamics · doi:10.1080/07391102.1995.10508782 · Cited by 73
Self-citationTurner, J. M., Baird, E. E., & Dervan, P. B. (1997) · Journal of the American Chemical Society · doi:10.1021/ja971208w · Cited by 71
Binding site size limit of the 2:1 pyrrole-imidazole polyamide-DNA motif.
Kelly, J. J., Baird, E. E., & Dervan, P. B. (1996) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.93.14.6981 · Cited by 69
WOYNAROWSKI, J. M., Sigmund, R. D., & Beerman, T. A. (1989) · Biochemistry · doi:10.1021/bi00435a034 · Cited by 67
Wu, W., Vanderwall, D. E., Stubbe, J., Kozarich, J. W., & Turner, C. J. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00102a083 · Cited by 65
Chen, X., Ramakrishnan, B., & Sundaralingam, M. (1997) · Journal of Molecular Biology · doi:10.1006/jmbi.1997.0941 · Cited by 64
Orientation Preferences of Pyrrole−Imidazole Polyamides in the Minor Groove of DNA
White, S. W., Baird, E. E., & Dervan, P. B. (1997) · Journal of the American Chemical Society · doi:10.1021/ja971569b · Cited by 63
Distamycin A and tallimustine inhibit TBP binding and basal in vitro transcription
Bellorini, M., Moncollin, V., D’lncalci, M., Mongelli, N., & Mantovani, R. (1995) · Nucleic Acids Research · doi:10.1093/nar/23.10.1657 · Cited by 62
Effect of minor groove binding drugs on mammalian topoisomerase I activity
McHugh, M. M., WOYNAROWSKI, J. M., Sigmund, R. D., & Beerman, T. A. (1989) · Biochemical Pharmacology · doi:10.1016/0006-2952(89)90472-3 · Cited by 62
Structure of the glycyl-L-histidyl-L-lysine-copper(II) complex in solution
Freedman, J. H., Pickart, L., Weinstein, B., Mims, W. B., & Peisach, J. (1982) · Biochemistry · doi:10.1021/bi00262a004 · Cited by 59
DNA recognition by lexitropsins, minor groove binding agents
Lown, J. W. (1994) · Journal of Molecular Recognition · doi:10.1002/jmr.300070205 · Cited by 54
Cyclic polyamides for recognition in the minor groove of DNA.
Cho, J., Parks, M. E., & Dervan, P. B. (1995) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.92.22.10389 · Cited by 52
Kahne, D. E. (1995) · Chemistry & Biology · doi:10.1016/1074-5521(95)90075-6 · Cited by 51
The purine 2-amino group as a critical recognition element for binding of small molecules to DNA
Waring, M. J., & Bailly, C. (1994) · Gene · doi:10.1016/0378-1119(94)90414-6 · Cited by 50
Self-citationBrowne, K. A., & Bruice, T. C. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00039a001 · Cited by 43
Bailly, C., Payet‐Bornet, D., TRAVERS, A. A., & Waring, M. J. (1996) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.93.24.13623 · Cited by 40
Self-citationMarchand, C., Bailly, C., McLean, M. J., Moroney, S. E., & Waring, M. J. (1992) · Nucleic Acids Research · doi:10.1093/nar/20.21.5601 · Cited by 38
Self-citationBailly, C., Helbecque, N., Hénichart, J., Colson, P., Houssier, C., Rao, K. E., Shea, R. G., & Lown, J. W. (1990) · Journal of Molecular Recognition · doi:10.1002/jmr.300030103 · Cited by 37
Self-citationLee, S. H., & GOLDBERG, I. H. (1989) · Biochemistry · doi:10.1021/bi00429a015 · Cited by 35
Sequence-selective binding of an ellipticine derivative to DNA
Bailly, C., Ó’hUigín, C., Rivalle, C., Bisagni, É., Hénichart, J., & Waring, M. J. (1990) · Nucleic Acids Research · doi:10.1093/nar/18.21.6283 · Cited by 32
Self-citationOrientation of non-blue cupric complexes on DNA fibers.
Chikira, M., Sato, T., Antholine, W. E., & Petering, D. H. (1991) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)49926-7 · Cited by 30
Crystal structures of B-form DNA–RNA chimers complexed with distamycin
Chen, X., Ramakrishnan, B., & Sundaralingam, M. (1995) · Nature Structural & Molecular Biology · doi:10.1038/nsb0995-733 · Cited by 30
Bailly, C., Sun, J. S., Colson, P., Houssier, C., Hélène, C., Waring, M. J., & Henichart, J. P. (1992) · Bioconjugate Chemistry · doi:10.1021/bc00014a002 · Cited by 30
Self-citationStructure of a dicationic monoimidazole lexitropsin bound to DNA
Goodsell, D. S., Ng, H. L., Kopka, M. L., et al. (1995) · Biochemistry · doi:10.1021/bi00051a013 · Cited by 28
Design and development of sequence selective lexitropsin DNA minor groove binders
Lown, J. W. (1995) · Drug Development Research · doi:10.1002/ddr.430340207 · Cited by 27
DNA Minor-Groove Binding Drugs
Zunino, F., Animati, F., & Capranico, G. (1995) · Current Pharmaceutical Design · doi:10.2174/1381612801666220524192103 · Cited by 25
Huang, L., Quada, J. C., & Lown, J. W. (1995) · Bioconjugate Chemistry · doi:10.1021/bc00031a003 · Cited by 24
Cooperative Triple-Helix Formation via a Minor Groove Dimerization Domain
Szewczyk, J. W., Baird, E. E., & Dervan, P. B. (1996) · Journal of the American Chemical Society · doi:10.1021/ja960831y · Cited by 24
Boyd, F. L., Cheatham, S., Remers, W. A., Hill, G. C., & Hurley, L. H. (1990) · Journal of the American Chemical Society · doi:10.1021/ja00165a004 · Cited by 23
Perrée‐Fauvet, M., & Gresh, N. (1994) · Journal of Biomolecular Structure and Dynamics · doi:10.1080/07391102.1994.10508064 · Cited by 19
Fagan, P. A. (1996) · Nucleic Acids Research · doi:10.1093/nar/24.8.1566 · Cited by 19
Bruice, T. C., Sengupta, D., Blaskó, A., Chiang, S.-Y., & Beerman, T. A. (1997) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(97)00011-4 · Cited by 16
Ketterlé, C., Gabarro‐Arpa, J., Ouali, M., Bouziane, M., Auclair, C., Helissey, P., Giorgi‐Renault, S., & Bret, M. L. (1996) · Journal of Biomolecular Structure and Dynamics · doi:10.1080/07391102.1996.10508911 · Cited by 16
Fosse, P., René, B., Saucier, J.-M., Hénichart, J., Waring, M. J., Colson, P., Houssier, C., & Bailly, C. (1994) · Biochemistry · doi:10.1021/bi00199a007 · Cited by 16
Self-citationDesign of B‐DNA cross‐linking and sequence‐reading molecules
Walker, W. L., Kopka, M. L., Filipowsky, M., Dickerson, R. E., & Goodsell, D. S. (1995) · Biopolymers · doi:10.1002/bip.360350513 · Cited by 13
Riou, J., Grondard, L., Naudin, A., & Bailly, C. (1995) · Biochemical Pharmacology · doi:10.1016/0006-2952(95)00132-j · Cited by 11
Self-citationDistamycin paradoxically stimulates the copying of oligo(dA).cntdot.poly(dT) by DNA polymerases
Levy, A., Weisman-Shomer, P., & Fry, M. (1989) · Biochemistry · doi:10.1021/bi00444a018 · Cited by 9
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Metadata
- Authors
- Bailly, C., & Chaires, J. B.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-06-23
- Volume
- 9
- Issue
- 5
- Pages
- 513-538
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2055487676
- Cited by
- 254
- References
- 90
- FWCI
- 4.95
- Type
- journal article
- Language
- en
- Open access
- closed
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