Email this article 
DNA Minor Groove Binder Hoechst 33258 and its Analogues: a Review
(*) Corresponding author
DOI's assignment:
the author of the article can submit here a request for assignment of a DOI number to this resource!
Cost of the service: euros 10,00 (for a DOI)
Abstract
The synthetic dye Hoechst 33258, i.e. 2-(4-hydroxyphenyl)-5-[5-(4-methylpiperazine-1-yl) benzimidazo-2-yl]-benzimidazole is known to bind strongly to the minor groove of double-stranded B-DNA with specificity for AT-rich sequences. It is an N-methyl piperazine derivative with two benzimidazole groups and one phenol group. It is the best known of the bis-benzimidazole family of minor groove binders. Since the early 1970s, Hoechst 33258 has been widely used as a fluorescent DNA stain because it has ready access into cells. Hoechst derivatives are used in plant cell biology for chromosome and nuclear staining, analysis of nuclear DNA content values (flow cytometry), analysis of plant chromosomes, etc. Hoechst analogues also find uses as radioprotectors and topoisomerase inhibitors. This family of drugs therefore provides a starting point for rational drug design. It is also a good model system with which to investigate the molecular basis for DNA sequence recognition and binding. The existing literature on this family of drugs is reviewed here
Copyright © 2013 Praise Worthy Prize - All rights reserved.
Keywords
References
L.H. Hurley, DNA and associated targets for drug design, Journal of Medicinal Chemistry, Volume 32, (Issue 9), September 1989, Pages 2027-2033.
P.B. Dervan, Molecular recognition of DNA by small molecules, Bioorganic and Medicinal Chemistry, Volume 9, (Issue 9), September 2001, Pages 2215–2235.
D.A. Denham, R.R. Suswillo, et al., Studies on Brugia pahangi. 13. The anthelmintic effect of compounds F151 (Friedheim), HOE 33258 (Hoechst) and their reaction product, Journal of Helminthology, Volume 50, (Issue 4), December 1976, Pages 243-250.
C. Bailly, P. Colson, et al., The different binding modes of Hoechst 33258 to DNA studied by electric linear dichroism, Nucleic Acids Research, Volume 21, (Issue 16), August 1993, Pages 3705-3709.
K.J. Embrey, M.S. Searle, et al., Interaction of Hoechst 33258 with the minor groove of the AT-rich DNA duplex d(GGTAATTACC)2 studied in solution by NMR spectroscopy, European Journal of Biochemistry, Volume 211, (Issue 3), February 1993, Pages 437-447.
S.A. Latt, E. Sahar, et al., Interactions between pairs of DNA binding dyes: results and implications for chromosome analysis, Cytometry, Volume 1, (Issue 1), April 1980, Pages 2-12.
S.A. Latt, J.C. Wohlleb, Optical studies of the interaction of 33258 Hoechst with DNA, chromatin, and metaphase chromosomes, Chromosoma (Berlin), Volume 52, (Issue 4), November 1975, Pages 297-316.
A.K. Singh, J.W. Lown, Synthesis of substituted imidazo[4,5-b]pyridines as analogs of the DNA binding fluorochrome Hoechst 33258, Synthetic Communications, Volume 28, (Issue 21), May 1998, Pages 4059-4066.
A.K. Singh, J.W. Lown, Synthesis of Hoechst 33258 analogues designed to target human tumor helicases, Heterocyclic Communications, Volume 5, (Issue 1), February 1999, Pages 11-18.
K. Steinmetzer, K.-E. Reinert, Multimode interaction of Hoechst 33258 with eukaryotic DNA; quantitative analysis of the DNA conformational changes, Journal of Biomolecular Structure and Dynamics, Volume 15, (Issue 4), February 1998, Pages 779-791.
C. Bailly, Topoisomerase I poisons and suppressors as anticancer drugs, Current Medicinal Chemistry, Volume 7, (Issue 1), January 2000, Pages 39-58.
K.J. Soderlind, B. Gorodetsky, et al., Bis-benzimidazole anticancer agents: Targeting human tumour helicases, Anticancer Drug Design., Volume 14, (Issue 1), February 1999, Pages 19-36.
P.R. Turner, W.A. Denny, The genome as a drug target: sequence specific minor groove binding ligands, Current Drug Targets, Volume 1, (Issue 1), July 2000, Pages 1-14.
A.K. Jain, S. Bhattacharya, Groove binding ligands for the interaction with parallel-stranded ps-duplex DNA and triplex DNA, Bioconjugate Chemistry, Volume 21, (Issue 8), August 2010, Pages 1389-1403.
A. Lauria, A. Montalbano, et al., DNA Minor Groove Binders: an overview on molecular modeling and QSAR Approaches, Current Medicinal Chemistry, Volume 14, (Issue 20), August 2007, Pages 2136-2160.
S.M. Nelson, L.R. Ferguson, et al., Non-covalent ligand/DNA interactions: Minor groove binding agents, Mutation Research, Volume 623, (Issue 1-2), October 2007, Pages 24-40.
K.J. Embrey, D.J. Craik, 13C NMR relaxation study of molecular motion in the DNA-binding ligand Hoechst 33258, Journal of Physical Chemistry, Volume 99, (Issue 13), March 1995, Pages 4831-4836.
C. Alemán, An ab initio study of the conformational preferences of Hoechst 33258 in gas-phase and aqueous solution environments, Theoretical Chemistry Accounts, Volume 99, (Issue 5), September1998, Pages 312-319.
R. Kakkar, R. Garg, Structures of some Hoechst analogues in gas phase and in aqueous solution, Indian Journal of Chemistry, Volume 41B, (Issue 9), September 2002, Pages 1929-1936.
A.-M. Sapse, M. Mezei, et al., Solvent effect on the conformation of the Hoechst 33258 agent, Journal of Molecular Structure (Theochem), Volume 393, (Issue 1-3), April 1997, Pages 25-30.
M.C. Vega, M. Coll, et al., Intrinsic conformational preferences of the Hoechst dye family and their influence on DNA binding, European Journal of Biochemistry, Volume 239, (Issue 2), July 1996, Pages 376-383.
I. Haq, J.E. Ladbury, et al., Specific binding of Hoechst 33258 to the d(CGCAAATTTGCG)2 duplex: Calorimetric and spectroscopic studies, Journal of Molecular Biology, Volume 271, (Issue 2), August 1997, Pages 244-257.
H.-J. Wang, M.-K. Teng, Molecular recognition of DNA minor groove binding drugs. In: Crystallographic and modeling method in molecular design (Springer-Verlag, New York, Bugg. C. E. & Ealick, S. E., eds 1990, pp. 123-150).
R. Jin, K.J. Breslauer, Characterization of the minor groove environment in a drug-DNA complex: bisbenzimide bound to the poly[d(AT)]. poly[d(AT)] duplex, Proceedings of the National Academy of Sciences of the United States of America, Volume 85, (Issue 23), December 1988, Pages 8939-8942.
X.-H. Ju, W.-J. Wang, et al., Ab initio and DFT studies on the structure, infrared spectrum, and thermodynamic properties of Hoechst 33258, Journal of Chinese Chemical Society, Volume 52, (Issue 3), 2005, Pages 421-427.
H. Görner, Direct and sensitized photoprocesses of bis-benzimidazole dyes and the effects of surfactants and DNA, Photochemistry Photobiology, Volume 73, (Issue 4), April 2001, Pages 339-348.
M. Ladinig, W. Leupin, et al., Protonation equilibria of Hoechst 33258 in aqueous solution, Helvetica Chimica Acta, Volume 88, (Issue 1), January 2005, Pages 53-67.
V.N. Umetskaya, Y.M. Rozanov, Mechanism of the interaction of DNA with the fluorescent dye Hoechst 33258, Biofizika, Volume 35, (Issue 3), May-June 1990, Pages 399-401, Russian.
V.N. Umetskaya, A.A. Roslov, et al., Fluorescence characteristics of DNA complexes with dyes of the bis-benzimidazole series, Molecular Biology (Moscow), Volume 23, (Issue 2), March-April 1989, Pages 379-387.
C. Alemán, A. Adhikary, et al., On the protonation equilibrium for the benzimidazole derivative Hoechst 33258: An electronic molecular orbital study, Journal of Biomolecular Structure and Dynamics, Volume 20, (Issue 2), October 2002, Pages 301-310.
C. Alemán, A.M. Namba, et al., Acid-base and electronic structure dependent properties of Hoechst 33342, Journal of Biomolecular Structure and Dynamics, Volume 23, (Issue 1), August 2005, Pages 29-36.
J. Bontemps, C. Houssier, et al., Physico-chemical study of the complexes of "33258 Hoechst" with DNA and nucleohistone, Nucleic Acids Research, Volume 2, (Issue 6), June 1975, Pages 971-984.
K.K. Kalninsh, D.V. Pestov, et al., (1994) Absorption and fluorescence spectra of the probe Hoechst 33258, Photochemistry Photobiology A: Chemistry, Volume 83, (Issue 1), September 1994, Pages 39-47.
F. Geinguenaud, J.A. Mondragon-Sanchez, et al., Parallel DNA double helices incorporating isoG or m5isoC bases studied by FTIR, CD and molecular modelling, Spectrochimica Acta Part A, Volume 61, (Issue 4), February 2005, Pages 579-587.
Y. Guan, R. Shi, et al., Multiple binding modes for dicationic Hoechst 33258 to DNA, Journal of Physical chemistry B, Volume 111, (Issue 25), June 2007, Pages 7336-7344.
R. Kakkar, R. Garg, et al., Theoretical study of tautomeric structures and fluorescence spectra of Hoechst 33258, Journal of Molecular Structure (Theochem), Volume 579, (Issue 1-3), March 2002, Pages 109-113.
C.F. Cesarone, C. Bolognesi, et al., Improved microfluorometric DNA determination in biological material using 33258 Hoechst, Analytical Biochemistry, Volume 100, (Issue 1), November 1979, Pages 188-197.
T.R. Downs, W.W. Wilfinger, Fluorometric quantification of DNA in cells and tissue, Analytical Biochemistry, Volume 131, (Issue 2), June 1983, Pages 538-547.
D.L. Stout, F.F. Becker, Fluorometric quantitation of single-stranded DNA: A method applicable to the technique of alkaline elution, Analytical Biochemistry, Volume 127, (Issue 2), December 1982, Pages 302-307.
A. Adhikary, E. Bothe, et al., Pulse radiolysis of the DNA-binding bisbenzimidazole derivatives Hoechst 33258 and 33342 in aqueous solutions, International Journal of Radiation Biology, Volume 76, (Issue 9), September 2000, Pages 1157-1166.
H. Du, A. Fuh, et al., (1998) Photochem CAD: a computer-aided design and research tool in photochemistry, Photochemistry Photobiology, Volume 68, (Issue 2), August 1998, Pages 141-142.
R.P. Haugland, Handbook of Fluorescent Probes and Research Chemicals (Molecular Probes Eugene: Oregon, USA, 1992).
J.W. Ellwart, P. Dormer, Vitality measurement using spectrum shift in Hoechst 33342 stained cells, Cytometry, Volume 11, (Issue 2), March 1990, Pages 239-243.
T. Stokke, H.B. Steen, Multiple binding modes for Hoechst 33258 to DNA, Journal of Histochemistry & Cytochemistry, Volume 33, (Issue 4), April 1985, Pages 333-338.
H. Loewe, J. Urbanietz, (1974) Basic substituted 2,6-bisbenzimidazole derivatives, a novel series of substances with chemotherapeutic activity, Arzneimittelforschung, Volume 24, (Issue 12), December 1974, Pages 1927-1933.
I. Hilwig, A. Gropp, Staining of constitutive heterochromatin in mammalian chromosomes with a new fluorochrome, Experimental Cell Research, Volume 75, (Issue 1), November 1972, Pages 122-126.
S.A. Latt, Microfluorometric detection of deoxyribonucleic acid replication in human metaphase chromosomes, Proceedings of the National Academy of Sciences of the United States of America, Volume 70, (Issue 12), December 1973, Pages 3395-3399.
B. Weisblum, E. Haenssler, Fluorometric properties of the bibenzimidazole specific for AT [adenine-thymine] concentration in chromosomal DNA, Chromosoma, Volume 46, (Issue 3), 1974, Pages 255-260.
G. Holmquist, Hoechst 33258 fluorescent staining of Drosophila chromosomes, Chromosoma, Volume 49, (Issue 4), 1975, Pages 333-356.
D.J. Arndt-Jovin, T.M. Jovin, Multivariate chromosome analysis and complete karyotyping using dual labeling and fluorescence digital imaging microscopy, Cytometry, Volume 11, (Issue 1), April 1990, Pages 80-93.
S. Frau, J. Bernadou, et al., Hoechst 33258, a specific DNA minor groove binder, Bulletin de la Societe Chimique de France, Volume 133, (Issue 11), 1996, Pages 1053-1070.
D.J. Arndt-Jovin, T.M. Jovin, Analysis and sorting of living cells according to deoxyribonucleic acid content, Journal of Histochemistry and Cytochemistry, Volume 25, (Issue 7), July 1977, Pages 585-589.
H.A. Crissman, G.T. Hirons, Staining of DNA in live and fixed cells (Methods in Cell Biology, Flow Cytometry Second Edition, Part A, Volume 41, 1994, pp. 195–209,)
J.M. Petit, M. Denis-Gay, et al., Assessment of fluorochromes for cellular structure and function studies by flow cytometry, Biology of the Cell, Volume 78, (Issue 1-2), 1993, Pages 1-13.
S.A. Latt, G. Stetten, Spectral studies on 33258 Hoechst and related bisbenzimidazole dyes useful for fluorescent detection of deoxyribonucleic acid synthesis, Journal of Histochemistry and Cytochemistry, Volume 24, (Issue 1), January 1976, Pages 24-33.
Y. Guan, W. Zhou, et al., Determination of nucleic acids based on the fluorescence quenching of Hoechst 33258 at pH 4.5, Analytica Chimica Acta, Volume 570, (Issue 1), January 2006, Pages 21-28.
G. Cosa, K.-S. Focsaneanu, et al., Photophysical properties of fluorescenct DNA-dyes bound to single and double-stranded DNA in aqueous buffered solution, Photochemistry and Photobiology, Volume 73, (Issue 6), June 2001, Pages 585-599.
N. Barooah, J. Mohanty, et al., pH and temperature dependent relaxation dynamics of Hoechst-33258: A time resolved fluorescence study, Photochemical and Photobiological Sciences, Volume 10, (Issue 1), January 2011, Pages 35-41.
W. Müller, F. Gautier, Interactions of heteroaromatic compounds with nucleic acids. AT-specific nonintercalating DNA ligands, European Journal of Biochemistry, Volume 54, (Issue 2), June 1975, Pages 385-394.
C. Zimmer, U. Wähnert, Nonintercalating DNA-binding ligands: Specificity of the interaction and their use as tools in biophysical, biochemical and biological investigations of the genetic material, Progress in Biophysics and Molecular Biology, Volume 47, (Issue 1), 1986, Pages 31-112.
R.F. Martin, N. Holmes, Use of 125I-labeled DNA ligand to probe DNA structure, Nature, Volume 302, (Issue 5907), March 1983, Pages 452-454.
K.D. Harshman, P.B. Dervan, Molecular recognition of B-DNA by Hoechst 33258, Nucleic Acids Research, Volume 13, (Issue 13), July 1985, Pages 4825-4835.
M.V. Mikhailov, A.S. Zasedatelev, et al., Mechanism of recognition of AT pairs in DNA by "Hoechst 33258" dye, Molekulyarnaya Biologiya (Moscow), Volume 15, (Issue 3), May-June 1981, Pages 690-705.
A.S. Zasedatelev, M.V. Mikhailov, et al., Mechanism of the "recognition" of AT pairs in DNA by molecules of Hoechst 33258 dye, Doklady Akademii Nauk SSSR, Volume 255, (Issue 3), January 1980, Pages 756-760.
P.E. Pjura, K. Grzeskowiak, et al., Binding of Hoechst 33258 to the Minor Groove of B-DNA, Journal of Molecular Biology, Volume 197, (Issue 2), September 1987, Pages 257-271.
M.-K. Teng, N. Usman, et al., The molecular structure of the complex of Hoechst 33258 and the DNA dodecamer d(CGCGAATTCGCG), Nucleic Acids Research, Volume 16, (Issue 6), March 1988, Pages 2671-2690.
M. A. A. F. de C. T. Carrondo, M. Coll, et al., Binding of a Hoechst dye to d(CGCGATATCGCG) and its influence on the conformation of the DNA fragment, Biochemistry, Volume 28, (Issue 19), September 1989, Pages 7849-7859.
J.R. Quintana, A.A Lipanov, et al., Low-temperature crystallographic analyses of the binding of Hoechst 33258 to the double-helical DNA dodecamer C-G-C-G-A-A-T-T-C-G-C-G, Biochemistry, Volume 30, (Issue 42), October 1991, Pages 10294-10306.
N. Spink, D.G. Brown, et al., Sequence-dependent effects in drug-DNA interaction: The crystal structure of Hoechst 33258 bound to the d(CGCAAATTTGCG)2 duplex, Nucleic Acids Research, Volume 22, (Issue 9), May 1994, Pages 1607-1612.
M.C. Vega, I. Garcia Saez, et al., Three-dimensional crystal structure of the A-tract DNA dodecamer d(CGCAAATTTGCG) complexed with the minor-groove-binding drug Hoechst 33258, European Journal of Biochemistry, Volume 222, (Issue 3), June 1994, 721-726.
G. Evripidis, G.J. Sharman, et al., Sequence-dependent variation in DNA minor groove width dictates orientational preference of Hoechst 33258 in A-tract recognition: solution NMR structure of the 2:1 complex with d(CTTTTGCAAAAG)2, Nucleic Acids Research, Volume 28, (Issue 3), February 2000, Pages 728-235.
A. Fede, M. Billeter, et al., Determination of the NMR solution structure of the Hoechst 33258-d(GTGGAATTCCAC)2 complex and comparison with the X-ray crystal structure, Structure, Volume 1, (Issue 3), November 1993, Pages 177-186.
A. Fede, A. Labhardt, et al., Dynamics and binding mode of Hoechst 33258 to d(GTGGAATTCCAC)2 in the 1:1 solution complex as determined by two-dimensional proton NMR, Biochemistry, Volume 30, (Issue 48), December 1991, Pages 11377-11388.
J.A. Parkinson, J. Barber, et al., Minor-groove recognition of the self-complementary duplex d(CGCGAATTCGCG)2 by Hoechst 33258: A high-field NMR study, Biochemistry, Volume 29, (Issue 44), November 1990, Pages 10181-10190.
J.A Parkinson, S.E. Ebrahimi, et al., Molecular design of DNA-directed ligands with specific interactions: Solution NMR studies of the interaction of a m-hydroxy analog of Hoechst 33258 with d(CGCGAATTCGCG)2, Biochemistry, Volume 33, (Issue 28), July 1994, Pages 8442-8452.
M.S. Searle, K.J. Embrey, Sequence-specific interaction of Hoechst 33258 with the minor groove of an adenine-tract DNA duplex studied in solution by proton NMR spectroscopy, Nucleic Acids Research, Volume 18, (Issue 13), July 1990, Pages 3753-3762.
A. Abu-Daya, P.M. Brown, et al., DNA sequence preferences of several AT-selective minor groove binding ligands, Nucleic Acids Research, Volume 23, (Issue 17), September 1995, Pages 3385-3392.
A. Adhikary, V. Buschmann, et al., Ensemble and single-molecule fluorescence spectroscopic study of the binding modes of the bis-benzimidazole derivative Hoechst 33258 with DNA, Nucleic Acids Research, Volume 31, (Issue 8), April 2003, Pages 2178-2186.
P. Colson, C. Bailly, et al., Electric linear dichroism as a new tool to study sequence preference in drug binding to DNA, Biophysical Chemistry, Volume 58, (Issue 1-2), January 1996, Pages 125-140.
F.G. Loontiens, P. Regenfuss, et al., Binding characteristics of Hoechst 33258 with calf thymus DNA, poly[d(A-T)] and d(CCGGAATTCCGG): multiple stoichiometries and determination of tight binding with a wide spectrum of site affinities, Biochemistry, Volume 29, (Issue 38), September 1990, Pages 9029-9039.
K. Utsuno, Y. Maeda, et al., How and how much can Hoechst 33258 cause unwinding in a DNA duplex? Chemical and Pharmaceutical Bulletin, Volume 47, (Issue 10), October 1999, Pages 1363-1368.
D.-K. Chang, S.-K. Cheng, et al., Molecular mechanics calculations on the complexes between analogs of Hoechst 33258 and d(CGCGAATTCGCG)2: Influence of bulky group substitution on base pair preference of DNA minor groove binders, Canadian Journal of Chemistry, Volume 73, (Issue 6), 1995, Pages 878-884.
R. Kakkar, R. Garg, et al., Towards understanding the molecular recognition process in Hoechst-DNA complexes, Journal of Molecular Structure (Theochem), Volume 584, (Issue 1-3), April 2002, Pages 37-44.
S.Y. Breusegem, R.M. Clegg, et al., Base-sequence specificity of Hoechst 33258 and DAPI binding to five (A/T)4 DNA sites with kinetic evidence for more than one high-affinity Hoechst 33258-AATT complex, Journal of Molecular Biology, Volume 315, (Issue 5), February 2002, Pages 1049-1061.
H. Wang, C.A. Laughton, Molecular modelling methods for prediction of sequence selectivity in DNA recognition, Methods, Volume 42, (Issue 2), June 2007, Pages 196-203.
F. Rosu, V. Gabelica, et al., Determination of affinity, stoichiometry and sequence selectivity of minor groove bindercomplexes with oligo-deoxynucleotides by electrospray ionization mass spectrometry, Nucleic Acids Research, Volume 30, (Issue 16), August 2002, Pages e82.
F. Han, N. Taulier, et al., Association of the minor groove binding drug Hoechst 33258 with d(CGCGAATTCGCG)2: Volumetric, calorimetric, and spectroscopic characterizations, Biochemistry, Volume 44, (Issue 28), June 2005, Pages 9785-9794.
H.R. Drew, R.E. Dickerson, Structure of a B-DNA dodecamer. III. Geometry of hydration, Journal of Molecular Biology, Volume 151, (Issue 3), September 1981, Pages 535- 556.
X. Shui, L. McFail-Isom, et al., The B-DNA dodecamer at high resolution reveals a spine of water on sodium, Biochemistry, Volume 37, (Issue 23), May 1998, Pages 8341-8355.
C. Bailly, G. Chessari, et al., Sequence-specific minor groove binding by bis-benzimidazoles: Water molecules in ligand recognition, Nucleic Acids Research, Volume 31, (Issue 5), March 2003, Pages 1514-1524.
A.A. Wood, C. Nunn, et al., Variability in DNA minor groove width recognised by ligand binding: the crystal structure of a bis-benzimidazole compound bound to the DNA duplex d(CGCGAATTCGCG)2, Nucleic Acids Research, Volume 23, (Issue 81), September 1995, Pages 3678-3684.
G.R. Clark, C.J. Squire, et al., Designer DNA-binding drugs: The crystal structure of a m-hydroxy analog of Hoechst 33258 bound to d(CGCGAATTCGCG)2, Nucleic Acids Research, Volume 24, (Issue 24), Demember 1996, Pages 4882-4889.
J.R. Kiser, R.W. Monk, et al., Hydration Changes in the Association of Hoechst 33258 with DNA, Biochemistry, Volume 44, (Issue 51), December 2005, Pages 16988-16997.
Anuradha, M.S. Alam, et al., Osmolyte changes the binding affinity and mode of interaction of minor groove binder Hoechst 33258 with calf thymus DNA, Chemical and Pharmaceutical Bulletin, Volume 58, (Issue 11), November 2010, Pages 1447-1454.
P.O. Vardevanyan, A.P. Antonyan, et al., Influence of Ionic Strength on Hoechst 33258 Binding with DNA, Journal of Biomolecular Structure and Dynamics, Volume 25, (Issue 6), June 2008, Pages 641-646.
J.F. Constant, P. Laûgaa, et al., Heterodimeric molecules including nucleic acid bases and 9-aminoacridine. Spectroscopic studies, conformations, and interactions with DNA, Biochemistry, Volume 27, (Issue 11), May 1988, Pages 3997-4003.
R.F. Steiner, H. Sternberg, The interaction of Hoechst 33258 with natural and biosynthetic nucleic acids, Archives in Biochemistry and Biophysics, Volume 197, (Issue 2), October 1979, Pages 580-588.
S.A. Streltsov, A.L. Zhuze, Hoechst 33258-poly(dG-dC)•poly(dG-dC) complexes of three types, Journal of Biomolecular Structure and Dynamics, Volume 26, (Issue 1), August 2008, Pages 99-113.
G. Singhal, M.R. Rajeswari, Molecular aspects of the interaction of Hoechst-33258 with GC-rich promoter region of c-met, DNA and Cell Biology, Volume 29, (Issue 2), February 2010, Pages 91-100.
S. Maiti, N.K. Chaudhury, et al., Hoechst 33258 binds to G-quadruplex in the promoter region of human c-myc, Biochemical and Biophysical Research Communications, Volume 310, (Issue 2), October 2003, Pages 505-512.
R. Sinha, M. Hossain, et al., Interaction of small molecules with Double stranded RNA: Spectroscopic, viscometric, and calorimetric study of Hoechst and proflavine binding to polyCG structures, DNA and Cell Biology, Volume 28, (Issue 4), April 2009, Pages 209-219.
Z.A. Sands, C.A. Laughton, Molecular dynamics simulations of DNA using the Generalized Born Solvation Model: Quantitative comparisons with explicit solvation results, Journal of Physical Chemisrty B, Volume 108, (Issue 28), June 2004, Pages 10113-10119.
E. Gavathiotis, G.J. Sharman, et al., Sequence-dependent variation in DNA minor groove width dictates orientational preference of Hoechst 33258 in A-tract recognition: Solution NMR structure of the 2:1 complex with d(CTTTTGCAAAAG)2, Nucleic Acids Research, Volume 28, (Issue 3), February 2000, Pages 728-735.
S.A. Harris, E. Gavathiotis, et al., Cooperativity in drug-DNA recognition: A Molecular Dynamics study, Journal of the American Chemical Society, Volume 123, (Issue 50), December 2001, Pages 12658-12663.
N.N. Degtyareva, B.D. Wallace, et al., Hydration changes accompanying the binding of minor groove ligands with DNA, Biophysical Journal, Volume 92, (Issue 3), February 2007, Pages 959-965.
A.L. Mikheikin, A.L. Zhuze, et al., Molecular modelling of ligand-DNA minor groove binding: role of ligand-water interactions, Journal of Biomolecular Structure and Dynamics, Volume 19, (Issue 1), August 2001, Pages 175-178.
F.A. Tanious, D. Hamelberg, et al., DNA sequence dependent monomer-dimer binding modulation of asymmetric benzimidazole derivatives, Journal of the American Chemical Society, Volume 126, (Issue 1), January 2004, Pages 143-153.
M. Rahimian, Y. Miao, et al., Influence of DNA Structure on Adjacent Site Cooperative Binding, Journal of Physical Chemistry B, Volume 112, (Issue 29), June 2008, Pages 8770-8778.
Y. Bathini, E.K. Rao, et al., Molecular recognition between ligands and nucleic acids: Novel pyridine- and benzoxazole- containing agents related to Hoechst 33258 that exhibit altered DNA sequence specificity deduced from footprinting analysis and spectroscopic studies, Chemical Research in Toxicology, Volume 3, (Issue 3), May 1990, Pages 268-280.
E.K. Rao, J.W. Lown, Molecular recognition between ligands and nucleic acids: DNA binding characteristics of analogues of Hoechst 33258 designed to exhibit altered base and sequence recognition, Chemical Research in Toxicology, Volume 4, (Issue 6), November 1991, Pages 661-669.
M.P. Singh, T. Joseph, et al., Synthesis and sequence-specific DNA binding of a topoisomerase inhibitory analog of Hoechst 33258 designed for altered base and sequence recognition, Chemical Research in Toxicology, Volume 5, (Issue 5), September 1992, Pages 597-607.
R.F. Martin, S. Broadhurst, et al., In vitro studies with methylproamine: A potent new radioprotector, Cancer Research, Volume 64, (Issue 3), February 2004, Pages 1067-1070.
M. Singh, V. Tandon, Synthesis and biological activity of novel inhibitors of topoisomerase I: 2-Aryl-substituted 2-bis-1H-benzimidazoles, European Journal of Medicinal Chemistry, Volume 46, (Issue 2), February 2011, Pages 659-669.
C.J. Squire, L.J. Baker, et al., Structures of m-iodoHoechst-DNA complexes in crystals with reduced solvent content: Implications for minor groove binding drug design, Nucleic Acids Research, Volume 28, (Issue 5), March 2000, Pages 1252-1258.
T.C. Karagiannis, P.N. Lobachevsky, et al., DNA targeted UVA photosensitization: Characterization of an extremely photopotent iodinated minor groove binding DNA ligand, Journal of Photochemistry and Photobiology B: Biology, Volume 83, (Issue 3), June 2006, Pages 195-204.
K. Bielawski, A. Bielawska, et al., Synthesis, DNA binding, topoisomerase inhibition and cytotoxic properties of 2-chloroethylnitrosourea derivatives of Hoechst 33258, Biological and Pharmaceutical Bulletin, Volume 28, (Issue 6), June 2005, Pages 1004-1009.
K. Bielawski, A. Bielawska, et al., Synthesis, DNA-binding activity and cytotoxicity of carbamate derivatives of Hoechst 33258 in breast cancer MCF-7 cells, Biological and Pharmaceutical Bulletin, Volume 25, (Issue 7), July 2002, Pages 916-919.
K. Wiederholt, S.B. Rajur, et al., Oligonucleotides tethering Hoechst 33258 derivatives: Effect of the conjugation site on duplex stabilization and fluorescence properties, Bioconjugate Chemistry, Volume 8, (Issue 2), March 1997, Pages 119-126.
A.K. Jain, S.K. Gupta, et al., Evaluation of electronic effect of phenyl ring substituents on the DNA minor groove binding properties of novel bis and terbenzimidazoles: Synthesis and spectroscopic studies of ligand-DNA interaction, Oligonucleotides, Volume 19, (Issue 4), December 2009, Pages 329-340.
S.Y. Breusegem, S.E. Sadat-Ebrahimi, et al., Increased stability and lifetime of the complex formed between DNA and meta-phenyl-substituted Hoechst dyes as studied by fluorescence titrations and stopped-flow kinetics, Journal of Molecular Biology, Volume 308, (Issue 4), May 2001, Pages 649-663.
U. Tawar, A.K. Jain, et al., Influence of phenyl ring disubstitution on bisbenzimidazole and terbenzimidazole cytotoxicity: Synthesis and biological evaluation as radioprotectors, Journal of Medicinal Chemistry, Volume 46, (Issue 18), August 2003, Pages 3785-3792.
K. Chen, S.J. Adelstein, et al., Molecular modeling of the interaction of iodinated Hoechst analogs with DNA: Implications for new radiopharmaceutical design, Journal of Molecular Structure (Theochem), Volume 711, (Issue 1-3), December 2004, Pages 49-56.
A. Narita, S. Sando, et al., Sensing of nucleic acid sequences using unmodified nucleic acid as a probe, Nucleic Acids Symposium Series, Volume 51, (Issue 1), November 2007, Pages 281-282.
S. Sando, A. Narita, et al., Light-up Hoechst–DNA aptamer pair: Generation of an aptamer-selective fluorophore from a conventional DNA-staining dye, ChemBioChem, Volume 8, (Issue 15), October 2007, Pages 1795-1803.
N.P. Bazhulina, A.M. Nikitin, et al., Binding of Hoechst 33258 and its derivatives to DNA, Journal of Biomolecular Structure Dynamics, Volume 26, (Issue 6), June 2009, Pages 701-718.
S. Sando, A. Narita, et al., Transcription monitoring using fused RNA with a dye-binding light-up aptamer as a tag: a blue fluorescent RNA, Chemical Communications, (Issue 33), 2008, Pages 3858-3860.
S.E. Sadat Ebrahimi, A.N. Wilton, et al., Unique binding site for bis-benzimidazoles on transfer RNA, Chemical Communications, (Issue 4), 1997, Pages 385-386.
K.V. Popov, E.I. Egorova, et al., Dimeric Bis-benzimidazole Hoechst 33258-related dyes as novel at-specific dna-binding fluorochromes for human and plant cytogenetics, Biochemistry (Moscow) Supplement Series A: Memberane and cell Biology, Volume 2, (Issue 3), January 2008, Pages 203-209.
C. Behrens, N. Harrit, et al., Synthesis of a Hoechst 32258 analogue amino acid building block for direct incorporation of a fluorescent, high-affinity DNA binding motif into peptides, Bioconjugate Chemistry, Volume 12, (Issue 6), November 2001, Pages 1021-1027.
J. Bunkenborg, C. Behrens, et al., NMR characterization of the DNA binding properties of a novel Hoechst 33258 analogue peptide building block, Bioconjugate Chemistry, Volume 13, (Issue 5), September 2002, Pages 927-936.
C.E. Bostock-Smith, S.A. Harris, et al., Induced fit DNA recognition by a minor groove binding analogue of Hoechst 33258: Fluctuations in DNA A tract structure investigated by NMR and molecular dynamics simulations, Nucleic Acids Research, Volume 29, (Issue 3), November 2000, Pages 693-702.
S.Alper, Ö. T. Arpaci, et al., Some new bi- and ter-benzimidazole derivatives as topoisomerase I inhibitors, IL Farmaco, Volume 58, (Issue 7), July 2003, Pages 497-507.
G.R. Clark, D.W. Boykin, et al., Structure of bis-amidinium derivative of Hoechst 33258 complexed to dodecanucleotide d(CGCGAATTCGCG)2: The role of hydrogen bonding in minor groove drug-DNA recognition, Nucleic Acids Research, Volume 25, (Issue 8), April 1997, Pages1510-1515.
A. Czarny, D.W. Boykin, et al., Analysis of van der Waals and electrostatic contributions in the interactions of minor groove binding benzimidazoles with DNA, Journal of the American Chemical Society, Volume 117, (Issue 16), April 1995, Pages 4716-4717.
J. Mann, A. Baron, et al., A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity, Journal of Medicinal Chemistry, Volume 44, (Issue 2), January 2001, Pages 138-144.
S. Neidle, J. Mann, et al., Symmetric bis-benzimidazoles: New sequence-selective DNA-binding molecules, Chemical Communications, (Issue 10), 1999, Pages 929-930.
A. Seaton, C. Higgins, et al., Mechanistic and anti-proliferative studies of two novel, biologically active bis-benzimidazoles, European Journal of Cancer, Volume 39, (Issue 17), November 2003, Pages 2548-2555.
S. Bhattacharya, P. Chaudhuri, Metal-ion-mediated tuning of duplex DNA binding by bis(2-(2-pyridyl)-1H-benzimidazole, Chemistry – An Asian Journal, Volume 2, (Issue 5), May 2007, Pages 648-655.
P. Chaudhuri, B. Ganguly, et al., An experimental and computational analysis on the differential role of the positional isomers of symmetric bis-2-(pyridyl)-1H-benzimidazoles as DNA binding agents, Journal of Organic Chemistry, Volume 72, (Issue 6), March 2007, Pages 1912-1923.
A.L. Satz, T.C. Bruice, Recognition in the minor groove of double-stranded DNA by microgonotropens, Accounts of Chemical Research, Volume 35, (Issue 2), February 2002, Pages 86-95.
A.L. Satz, C.M. White, et al., Double-stranded DNA binding characteristics and subcellular distribution of a minor groove binding diphenyl ether bisbenzimidazole, Biochemistry, Volume 40, (Issue 21), May 2001, Pages 6465-6474.
A.L. Satz, T.C. Bruice, Recognition of nine base pairs in the minor groove of DNA by a tripyrrole peptide-Hoechst conjugate, Journal of the American Chemical Society, Volume 123, (Issue 11), March 2001, Pages 2469-2477.
S.A. Streltsov, A.V. Gromyko, et al., The Hoechst 33258 covalent dimer covers a total turn of the double-stranded DNA, Journal of Biomolecular Structure and Dynamics, Volume 24, (Issue 3), December 2006, Pages 285-302.
A.V. Gromyko, S.A. Streltsov, et al., A DNA-Specific Dimeric Bisbenzimidazole, Russian Journal of Bioorganic Chemistry, Volume 30, (Issue 4), March 2004, Pages 400–401.
A.V. Gromyko, K.V. Popov, et al., DNA sequence-specific ligands: XII. Synthesis and cytological studies of dimeric Hoechst 33258 molecules, Russian Journal of Bioorganic Chemistry, Volume 31, (Issue 4), November 2005, Pages 344-351.
A.V. Gromyko, V.I. Salyanov, et al., DNA Sequence-Specific Ligands: XIII. new dimeric Hoechst 33258 molecules, inhibitors of HIV-1 Integrase in vitro, Russian Journal of Bioorganic Chemistry, Volume 33, (Issue 6), November 2007, Pages 569-578.
O.Y. Susova, A.A. Ivanov, et al., Minor groove dimeric bisbenzimidazoles inhibit in vitro DNA Binding to eukaryotic DNA topoisomerase I, Biochemistry (Moscow), Volume 75, (Issue 6), June 2010, Pages 695-701.
A.Joubert, X.W. Sun, et al., Sequence-selective targeting of long stretches of the DNA minor groove by a novel dimeric bis-benzimidazole, Biochemistry, Volume 42, (Issue 20), May 2003, Pages 5984-5992.
P.M. Reddy, R. Dexter, et al., DNA sequence recognition in the minor groove by hairpin pyrrole polyamide-Hoechst 33258 analogue conjugate, Bioorganic & Medicinal Chemistry Letters, Volume 14, (Issue 14), July 2004, Pages 3803-3807.
P.M. Reddy, J.W. Toprowski, et al., Recognition of a 10 base pair sequence of DNA and stereochemical control of the binding affinity of chiral hairpin polyamide-Hoechst 33258 conjugates, Bioorganic & Medicinal Chemistry Letters, Volume 15, (Issue 24), December 2005, Pages 5531-5536.
B. Willis, D.P. Arya, Recognition of B-DNA by neomycin-Hoechst 33258 conjugates, Biochemistry, Volume 45, (Issue 34), August 2006, Pages 10217-10232.
B. Willis, D.P. Arya, Triple recognition of B-DNA, Bioorganic and Medicinal Chemistry Letters, Volume 19, (Issue 17), September 2009, Pages 4974-4979.
B. Willis, D.P. Arya, Triple recognition of B-DNA by a neomycin-Hoechst 33258-pyrene conjugate, Biochemistry, Volume 49, (Issue 3), January 2010, Pages 452-469.
N.V. Lyubimova, P.G. Coultas, et al., In vivo radioprotection of mouse brain endothelial cells by Hoechst 33342, The British Journal of Radiology, Volume 74, (Issue 877), January 2001, Pages 77-82.
P.J. Smith, C.O. Anderson, Modification of the radiation sensitivity of human tumor cells by a bis-benzimidazole derivative, International Journal of Radiation Biology and Related Studies in Physics, Chemistry and Medicine, Volume 46, (Issue 4), October 1984, Pages 331-344.
S.P. Singh, V.R. Jayanth, et al., Radioprotective effects of DNA ligands Hoechst-33342 and 33258 in whole body irradiated mice, Indian Journal of Experimental Biology, Volume 36, (Issue 4), April 1998, Pages 375-384.
A. Adhikary, E. Bothe, et al., Inhibition of radiation-induced DNA strand breaks by Hoechst 33258: OH-radical scavenging and DNA radical quenching, Radioprotection, Volume 32, 1997, Pages C1-89-C1-90.
A. Adhikary, E. Bothe, et al., DNA radioprotection by the bisbenzimidazole derivative Hoechst 33258: model studies at the nucleotide level, Radiation Research, Volume 148, (Issue 5), November 1997, Pages 493-494.
L. Denison, A. Haigh, et al., DNA ligands as radioprotectors: molecular studies with Hoechst 33342 and Hoechst 33258, International Journal of Radiation Biology, Volume 61, (Issue 1), January 1992, Pages 69-81.
H. Mohan, A. Adhikary, et al., Quenching of nucleotide derived radicals by bisbenzimidazole derivative Hoechst-33258 in aqueous solution, Proceedings of Indian Academy of Sciences (Chemical Science), Volume 112, (Issue 4), August 2000, Pages 487-496.
J.S. Adhikari, D. Khaitan, et al., Heterogeneity in the radiosensitizing effects of the DNA ligand hoechst-33342 in human tumor cell lines, Journal of Cancer Research and Therapeutics, Volume 1, (Issue 3), July-September 2005, Pages 151-161.
R.F. Martin, S. Broadhurst, et al., Radioprotection by DNA ligands, British Journal of Cancer, Volume 74, July 1996, Pages S99-S101.
R. Kakkar, R. Garg, et al., Theoretical study on the mechanism of radioprotection by Hoechst 33258 derivatives, Journal of Molecular. Structure (Theochem), Volume 668, (Issue 2-3), January 2004, Pages 287-294.
R.F. Martin, M. Pardee, Preparation of carrier free 125I-iodoHoechst 33258. The International Journal of Applied Radiation and Isotopes, Volume 36, (Issue 9), September 1985, Pages 745-747.
R.F. Martin, M. Pardee, et al., Synthesis and characterization of 2-iodo-4[5”-(4”’-methylpiperazin-1”’-yl”’)-2”,5’bi-1H-benzimidazole-2’-yl]phenol (iodoHoechst 33258) and 2,5-disubstituted benzimidazole model compounds, Australian Journal of Chemistry, Volume 39, (Issue 2), 1986, Pages 373-381.
R.F. Martin, D.P. Kelly, et al., Comparative studies of UV-induced DNA cleavage by structural isomers of an iodinated DNA ligand, International Journal of Radiation Oncology, Biology, Physics, Volume 29, (Issue 3), June 1994, Pages 549-553.
R.F. Martin, D.P Kelly, et al., Comparative studies of UV-induced DNA cleavaged by analogs of iodoHoechst 33258, International Journal of Radiation Biology, Volume 66, (Issue 5), November 1994, Pages 517-521.
U. Tawar, S. Bansal, et al., Nuclear condensation and free radical scavenging: A dual mechanism of bisbenzimidazoles to modulate radiation damage to DNA, Molecular and Cellular Biochemistry, Volume 305, (Issue 1-2), November 2007, Pages 221-233.
R. Kakkar, Suruchi, et al., QSAR studies on the mechanism of radioprotection by Hoechst 33258 analogues, Journal of Molecular Structure (Theochem), Volume 714, (Issue 1), January 2005, Pages 35-42.
T.A. Beerman, M.M. McHugh, et al., Effects of analogs of the DNA minor groove binder Hoechst 33258 on topoisomerase II and I mediated activities, Biochimica et Biophysica Acta, Volume 1131, (Issue 1), May 1992, Pages 53-61.
Q. Sun, B. Gatto, et al., Structure-activity of topoisomerase I poisons related to Hoechst 33342, Bioorganic and Medicinal Chemistry Letters, Volume 4, (Issue 24), December 1994, Pages 2871-2876.
A.Y. Chen, C. Yu, et al., A new mammalian DNA topoisomerase I poison Hoechst 33342: Cytotoxicity and drug resistance in human cell cultures, Proceedings of the National Academy of Sciences of the United States of America, Volume 90, (Issue 17), September 1993, Pages 8131-8135.
Q.A. Khan, D.S. Pilch, Topoisomerase I-mediated DNA cleavage induced by the minor groove-directed binding of bibenzimidazoles to a distal site, Journal of Molecular Biology, Volume 365, (Issue 3), January 2007, Pages 561-569.
M. Caserta, A. Amadei, et al., In vitro preferential topoisomerization of bent DNA, Nucleic Acids Research, Volume 17, (Issue 21), December 1989, Pages 8463-8474.
S. Krogh, U.H. Mortensen, et al., Eukaryotic topoisomerase I-DNA interaction is stabilized by helix curvature, Nucleic Acids Research, Volume 19, (Issue 6), March 1991, Pages 1235-1241.
S.B. Mekapati, C. Hansch, Comparative QSAR studies on bibenzimidazoles and terbenzimidazoles inhibiting topoisomerase I, Bioorganic and Medicinal Chemistry, Volume 9, (Issue 11), November 2001, Pages 2885-2893.
D. Winkler, Modelling topoisomerase I inhibition by minor groove binders, Bioorganic and Medicinal Chemistry, Volume 19, (Issue 4), February 2011, Pages 1450-1457.
Refbacks
- There are currently no refbacks.
Please send any question about this web site to info@praiseworthyprize.com
Copyright © 2005-2024 Praise Worthy Prize
