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Chemical Compound Review

SureCN7740448     1,2-bis(6-methoxy-1H- benzoimidazol-2...

Synonyms: Abbot 36683, KST-1B0921, CTK8D7671, AR-1B5614, A-36683, ...
 
 
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Disease relevance of A-36683

 

High impact information on A-36683

  • (v) The bis-benzimidazole drug Hoechst-33258, which binds in the minor groove of B-DNA, exhibits very little fluorescence in the presence of the ps hairpins but a normal, enhanced emission with the aps oligonucleotides [4].
  • A dimeric bis-benzimidazole molecule has been designed by computer modeling to bind to a DNA sequence via the DNA minor groove that covers a complete turn of B-DNA [5].
  • Hoechst 33258 (bis-benzimidazole) and 5-azacytidine (5-AC) cause decondensation of the pericentric heterochromatin in mouse and aberrations in the sequence of centromere separation apparently by different mechanisms [6].
  • A series of DNA-interactive bis-benzimidazole analogues of Hoechst 33258 was also prepared to explore the potential for anticancer activity mediated for certain of the drugs via bioreductive activation by endogenous NADH or NADPH [7].
  • Alkylation occurs predominantly at the 5'-A or 5'-G termini of mixed sequences, determined largely by the sequence-recognizing properties of the bis-benzimidazole carrier moiety [8].
 

Biological context of A-36683

 

Anatomical context of A-36683

 

Gene context of A-36683

  • The purpose of the present study was to identify the cellular processes and targets affected by treatment with bis-benzimidazole derivatives with chloroalkyl and bromoalkyl moieties (1-4) in the estrogen receptor-negative MDA-MB-231 human breast cancer cells [2].
 

Analytical, diagnostic and therapeutic context of A-36683

References

  1. The efficacy of amantadine and other antiviral compounds against two salmonid viruses in vitro. Hudson, J.B., Graham, E.A., Simpson, M.F. Antiviral Res. (1988) [Pubmed]
  2. Inhibition of DNA topoisomerase I and II, and growth inhibition of MDA-MB-231 human breast cancer cells by bis-benzimidazole derivatives with alkylating moiety. Bielawski, K., Wołczyński, S., Bielawska, A. Polish journal of pharmacology. (2004) [Pubmed]
  3. Modification of the radiation sensitivity of human tumour cells by a bis-benzimidazole derivative. Smith, P.J., Anderson, C.O. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. (1984) [Pubmed]
  4. Parallel stranded DNA. van de Sande, J.H., Ramsing, N.B., Germann, M.W., Elhorst, W., Kalisch, B.W., von Kitzing, E., Pon, R.T., Clegg, R.C., Jovin, T.M. Science (1988) [Pubmed]
  5. Sequence-selective targeting of long stretches of the DNA minor groove by a novel dimeric bis-benzimidazole. Joubert, A., Sun, X.W., Johansson, E., Bailly, C., Mann, J., Neidle, S. Biochemistry (2003) [Pubmed]
  6. 5-Azacytidine- and Hoechst-induced aneuploidy in Indian muntjac. Vig, B.K., Hallett, W.H. Mutat. Res. (2000) [Pubmed]
  7. Bis-benzimidazole anticancer agents: targeting human tumour helicases. Soderlind, K.J., Gorodetsky, B., Singh, A.K., Bachur, N.R., Miller, G.G., Lown, J.W. Anticancer Drug Des. (1999) [Pubmed]
  8. Design, synthesis, DNA sequence preferential alkylation and biological evaluation of N-mustard derivatives of Hoechst 33258 analogues. Gupta, R., Wang, H., Huang, L., Lown, J.W. Anticancer Drug Des. (1995) [Pubmed]
  9. A flow cytometric study of the effect of heat on the kinetics of cell proliferation of Chinese hamster V-79 cells. Ormerod, M.G., Imrie, P.R., Loverock, P., Ter Haar, G. Cell Prolif. (1992) [Pubmed]
  10. Sequence of centromere separation: kinetochore formation in induced laggards and micronuclei. Vig, B.K., Swearngin, S.E. Mutagenesis (1986) [Pubmed]
  11. Plasmodium berghei - infected red cells sorted according to DNA content. Howard, R.J., Battye, F.L. Parasitology (1979) [Pubmed]
  12. DNA minor groove recognition by bis-benzimidazole analogues of Hoechst 33258: insights into structure-DNA affinity relationships assessed by fluorescence titration measurements. Bostock-Smith, C.E., Searle, M.S. Nucleic Acids Res. (1999) [Pubmed]
  13. Bis-benzimidazole dyes, Hoechst 33258 and Hoechst 33342: radioiodination, facile purification and subcellular distribution. Harapanhalli, R.S., Howell, R.W., Rao, D.V. Nucl. Med. Biol. (1994) [Pubmed]
  14. Sequence-specific minor groove binding by bis-benzimidazoles: water molecules in ligand recognition. Bailly, C., Chessari, G., Carrasco, C., Joubert, A., Mann, J., Wilson, W.D., Neidle, S. Nucleic Acids Res. (2003) [Pubmed]
 
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