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Chemical Compound Review

Congocidine     N-(2-carbamimidoylethyl)-4- [[4-[2...

Synonyms: CHEMBL553984, NSC-3067, NSC3067, SureCN10408939, NSC-275885, ...
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Disease relevance of Congocidine


High impact information on Congocidine

  • The conformation and dynamics of the d(CGCGAATTCGCG) duplex, its analogs containing mismatched base pairs and helix interruptions, and its complexes with actinomycin and Netropsin, bound separately and simultaneously, have been investigated by nuclear magnetic resonance spectroscopy in aqueous solution [5].
  • Our results demonstrate that the TOP1 poison 5PTB binds differentially to and alters the structures of the two duplexes, in contrast to netropsin and DAPI, which bind with similar affinities to the two duplexes and do not significantly alter their structures [6].
  • Netropsin specifically enhances RNA polymerase II termination at terminator sites in vitro [7].
  • In this system, the basal level of termination by RNA polymerase II at the gastrin gene terminator is specifically enhanced by netropsin, an (A + T)-rich minor groove-binding peptide [7].
  • J. Breslauer [(1984) Proc. Natl. Acad. Sci. USA 84, 4359-4363] for both A.T and C.G sequences on the complexation of netropsin to the minor groove of DNAs [8].

Chemical compound and disease context of Congocidine


Biological context of Congocidine


Anatomical context of Congocidine


Associations of Congocidine with other chemical compounds

  • Map of distamycin, netropsin, and actinomycin binding sites on heterogeneous DNA: DNA cleavage-inhibition patterns with methidiumpropyl-EDTA.Fe(II) [22].
  • The base specificity that makes netropsin bind preferentially to runs of four or more A X T base pairs is provided not by hydrogen bonding but by close van der Waals contacts between adenine C-2 hydrogens and CH groups on the pyrrole rings of the drug molecule [23].
  • However, the yeast and human mutant enzymes differed in their responses to the minor groove binding ligand netropsin and to saintopin, a DNA intercalator that targets both DNA topoisomerase I and II [24].
  • We also detect intermolecular NOEs between the guanidino CH2 protons at one end of netropsin and adenosine H2 proton of the two flanking A3 X T6 base pairs of the octanucleotide duplex [25].
  • The inhibitory effect of the polypeptide antibiotics netropsin and distamycin A on DNA dependent nucleic acid synthesis has been shown to be related to the base composition of the template DNA [26].

Gene context of Congocidine

  • The results demonstrate that BLM and WRN proteins exhibit similar sensitivity profiles to these DNA-binding ligands and are most potently inhibited by the structurally related minor groove binders distamycin A and netropsin (K(i) </=1 microM) [27].
  • Hydroxyl radicals, generated by allowing an iron (II).EDTA complex to react with hydrogen peroxide, have been employed to cleave the 160-base pair tyrT DNA fragment in the presence and absence of the minor groove-binding antibiotics netropsin and distamycin A [28].
  • The properties of the duplex block polymer d(C15A15) - d(T15G15) were examined by thermal denaturation and nuclease susceptibility studies in the absence and presence of drugs (actinomycin and netropsin) which bind specifically to only one end of the block polymer [29].
  • The following results have been obtained: 1) Netropsin groove binding is accompanied by a large exothermic enthalpy of 9.2 kcal/mol of drug bound at 25 degrees C. This indicates that a large negative binding enthalpy may be a necessary but not a sufficient criterion for drug intercalation [30].
  • The binding sites of Hoechst 33258, netropsin and distamycin on three DNA restriction fragments from plasmid pBR322 were compared by footprinting with methidiumpropyl-EDTA X Fe(II) [MPE X Fe(II)] [31].

Analytical, diagnostic and therapeutic context of Congocidine

  • Circular dichroism spectroscopy demonstrates that netropsin can bind to the triple helical structure [32].
  • The titration viscometric investigation of the multi-mode interaction of netropsin (Nt) with (A.T) clusters of NaDNA12 and NH4DNA10 has been extended to different temperatures [33].
  • Satellite DNA's were isolated using preparativeCsCl - netropsin gradient centrifugation and were characterised by density and homogeneity in native and in reassociated state [17].
  • We have prepared this molecule in a relaxed form by simple ligation and in a positively supercoiled form by ligation in the presence of netropsin [34].
  • Capillary zone electrophoresis (CZE) and affinity capillary electrophoresis (ACE) were applied to study the interaction between netropsin and a 14mer double-stranded DNA (dsDNA) [35].


  1. Mutagenicity and pausing of HIV reverse transcriptase during HIV plus-strand DNA synthesis. Ji, J., Hoffmann, J.S., Loeb, L. Nucleic Acids Res. (1994) [Pubmed]
  2. Evidence in Escherichia coli that N3-methyladenine lesions and cytotoxicity induced by a minor groove binding methyl sulfonate ester can be modulated in vivo by netropsin. Shah, D., Gold, B. Biochemistry (2003) [Pubmed]
  3. Influence of drug binding on DNA hydration: acoustic and densimetric characterizations of netropsin binding to the poly(dAdT).poly(dAdT) and poly(dA).poly(dT) duplexes and the poly(dT).poly(dA).poly(dT) triplex at 25 degrees C. Chalikian, T.V., Plum, G.E., Sarvazyan, A.P., Breslauer, K.J. Biochemistry (1994) [Pubmed]
  4. Effect of netropsin on the derepression of enzymes during growth and sporulation of Bacillus subtilis. Keilman, G.R., Brutis, K., Tanimoto, B., Doi, R.H. J. Bacteriol. (1976) [Pubmed]
  5. DNA conformation, dynamics, and interactions in solution. Patel, D.J., Pardi, A., Itakura, K. Science (1982) [Pubmed]
  6. A terbenzimidazole that preferentially binds and conformationally alters structurally distinct DNA duplex domains: a potential mechanism for topoisomerase I poisoning. Pilch, D.S., Xu, Z., Sun, Q., LaVoie, E.J., Liu, L.F., Breslauer, K.J. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  7. Netropsin specifically enhances RNA polymerase II termination at terminator sites in vitro. Ueno, A., Baek, K., Jeon, C., Agarwal, K. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  8. Theoretical considerations on the "spine of hydration" in the minor groove of d(CGCGAATTCGCG).d(GCGCTTAAGCGC): Monte Carlo computer simulation. Subramanian, P.S., Ravishanker, G., Beveridge, D.L. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  9. Effect of netropsin, distamycin A and chromomycin A3 on the binding and cleavage reaction of DNA gyrase. Simon, H., Wittig, B., Zimmer, C. FEBS Lett. (1994) [Pubmed]
  10. Stimulation of the onset of sporulation of Clostridium perfringens type A by netropsin and distamycin. Ryu, S., Labbe, R.G. Curr. Microbiol. (1992) [Pubmed]
  11. Synthesis and antiviral activity of three pyrazole analogues of distamycin A. Ding, L., Grehn, L., De Clercq, E., Andrei, G., Snoeck, R., Balzarini, J., Fransson, B., Ragnarsson, U. Acta Chem. Scand. (1994) [Pubmed]
  12. Mutual interaction between adjacent dG . dC actinomycin binding sites and dA . dT netropsin binding sites on the self-complementary d(C-G-C-G-A-A-T-T-C-G-C-G) duplex in solution. Patel, D.J., Kozlowski, S.A., Rice, J.A., Broka, C., Itakura, K. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  13. The compatibility of netropsin and actinomycin binding to natural deoxyribonucleic acid. Wartell, R.M., Larson, J.E., Wells, R.D. J. Biol. Chem. (1975) [Pubmed]
  14. Influence of nucleotide sequence on dA.dT-specific binding of Netropsin to double stranded DNA. Zimmer, C., Marck, C., Schneider, C., Guschlbauer, W. Nucleic Acids Res. (1979) [Pubmed]
  15. Protection of (dA.dT) cluster regions in the DNAase I cleavage of DNA by specific interaction with netropsin. Zimmer, C., Luck, G., Nüske, R. Nucleic Acids Res. (1980) [Pubmed]
  16. The effect of several nucleic acid binding drugs on the cleavage of d(GGAATTCC) and pBR 322 by the Eco RI restriction endonuclease. Goppelt, M., Langowski, J., Pingoud, A., Haupt, W., Urbanke, C., Mayer, H., Maass, G. Nucleic Acids Res. (1981) [Pubmed]
  17. Identification and separation of components of calf thymus DNA using a CsC1-netropsin density gradient. Votavová, H., Sponar, J. Nucleic Acids Res. (1975) [Pubmed]
  18. Effects of netropsin on yeast mitochondria. Criddle, R.S., Short, L. Biochem. Biophys. Res. Commun. (1976) [Pubmed]
  19. Novel aromatic urea derivatives with DNA-binding ability. Fukutomi, R., Kagechika, H., Hashimoto, Y., Shudo, K. Chem. Pharm. Bull. (1996) [Pubmed]
  20. Thermodynamics of drug-DNA interactions. Marky, L.A., Snyder, J.G., Remeta, D.P., Breslauer, K.J. J. Biomol. Struct. Dyn. (1983) [Pubmed]
  21. The antiviral activity of the combinations of netropsin derivatives with modified nucleosides and phosphonoacetic acid as estimated in the model of herpesvirus type 1 in a vero cell culture. Andronova, V.L., Grokhovsky, S.L., Surovaya, A.N., Gursky, G.V., Galegov, G.A. Dokl. Biochem. Biophys. (2005) [Pubmed]
  22. Map of distamycin, netropsin, and actinomycin binding sites on heterogeneous DNA: DNA cleavage-inhibition patterns with methidiumpropyl-EDTA.Fe(II). Van Dyke, M.W., Hertzberg, R.P., Dervan, P.B. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  23. The molecular origin of DNA-drug specificity in netropsin and distamycin. Kopka, M.L., Yoon, C., Goodsell, D., Pjura, P., Dickerson, R.E. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  24. A camptothecin-resistant DNA topoisomerase I mutant exhibits altered sensitivities to other DNA topoisomerase poisons. Knab, A.M., Fertala, J., Bjornsti, M.A. J. Biol. Chem. (1995) [Pubmed]
  25. Sequence-dependent recognition of DNA duplexes. Netropsin complexation to the AATT site of the d(G-G-A-A-T-T-C-C) duplex in aqueous solution. Patel, D.J., Shapiro, L. J. Biol. Chem. (1986) [Pubmed]
  26. (dA-dT) dependent inactivation of the DNA template properties by interaction with netropsin and distamycin A. Wähnert, U., Zimmer, O., Luck, G., Pitra, O. Nucleic Acids Res. (1975) [Pubmed]
  27. Potent inhibition of werner and bloom helicases by DNA minor groove binding drugs. Brosh, R.M., Karow, J.K., White, E.J., Shaw, N.D., Hickson, I.D., Bohr, V.A. Nucleic Acids Res. (2000) [Pubmed]
  28. Hydroxyl radical footprinting of the sequence-selective binding of netropsin and distamycin to DNA. Portugal, J., Waring, M.J. FEBS Lett. (1987) [Pubmed]
  29. Transmission of stability (telestability) in deoxyribonucleic acid. Physical and enzymatic studies on the duplex block polymer d(C15A15) - d(T15G15). Burd, J.F., Wartell, R.M., Dodgson, J.B., Wells, R.D. J. Biol. Chem. (1975) [Pubmed]
  30. Calorimetric and spectroscopic investigation of drug-DNA interactions. I. The binding of netropsin to poly d(AT). Marky, L.A., Blumenfeld, K.S., Breslauer, K.J. Nucleic Acids Res. (1983) [Pubmed]
  31. Molecular recognition of B-DNA by Hoechst 33258. Harshman, K.D., Dervan, P.B. Nucleic Acids Res. (1985) [Pubmed]
  32. Binding of netropsin to a DNA triple helix. Durand, M., Thuong, N.T., Maurizot, J.C. J. Biol. Chem. (1992) [Pubmed]
  33. Temperature mediated variation of DNA secondary structure in (A.T) clusters; evidence by use of the oligopeptide netropsin as a structural probe. Reinert, K.E., Geller, D., Stutter, E. Nucleic Acids Res. (1981) [Pubmed]
  34. No braiding of Holliday junctions in positively supercoiled DNA molecules. Sun, W., Mao, C., Iwasaki, H., Kemper, B., Seeman, N.C. J. Mol. Biol. (1999) [Pubmed]
  35. Interaction between netropsin and double-stranded DNA in capillary zone electrophoresis and affinity capillary electrophoresis. He, X., Li, D., Liang, A., Lin, B. Journal of chromatography. A. (2002) [Pubmed]
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