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Chemical Compound Review

Pibenzimol     4-[5-[6-(4-methylpiperazin-1- yl)-1H...

Synonyms: Pibenzimol HCl, HOECHST-33258, Hoechst33258, HOECHST 33258, Hoe-33258, ...
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Disease relevance of NSC322921


High impact information on NSC322921

  • Structure/activity relationships suggest that, although the tripyrrole/polyamine functional group of L2 may be largely responsible for its inhibition of TF complexes in cell-free assays, its bisbenzimidazole moiety appears to impart improved cellular uptake and activity [5].
  • An X-ray crystallographic study of a complex with the DNA dodecanucleotide sequence d(CGCGAATTCGCG) shows the compound bound in the A/T minor groove region of a B-DNA duplex and that the head-to-head bisbenzimidazole motif hydrogen-bonds to the edges of all four consecutive A:T base pairs [6].
  • The 1064-nm emission from a pulsed Nd:YVO4 laser was used to excite the visible mitochondrial specific dye MitoTracker Orange CM-H2TMRos or a Cy3-labeled antibody by two-photon excitation, and the UV absorbing DNA dyes DAPI and the bisbenzimidazole BBI-342 by three-photon excitation, in a shared aperture SNOM using uncoated fiber tips [7].
  • These factors coupled with the affinity of pibenzimol for pancreatic tissue led us to conduct a phase I-II trial of pibenzimol hydrochloride in patients with advanced pancreatic cancer [8].
  • The interaction of the bisbenzimidazole dye 33258 Hoechst with DNA and chromatin is characterized by changes in absorption, fluorescence, and circular dichroism measurements [9].

Biological context of NSC322921


Associations of NSC322921 with other chemical compounds


Gene context of NSC322921

  • The use of AGTP solution results in stability of measurable DNA in cell lysates for periods of at least 10 weeks (permitting batching of samples and retrospective measurement) and stability of fluorescence for at least 20 h after the addition of bisbenzimidazole making the timing of fluorescence measurement less critical [17].

Analytical, diagnostic and therapeutic context of NSC322921

  • Fluorochrome 33,258 H, a bisbenzimidazole, was employed for demonstrating Chlamydiae in cell cultures, and proved to be particularly suitable for illustrating the unique intracellular reproduction processes of these organisms [18].


  1. Phase II study of pibenzimol in pancreatic cancer. A Southwest Oncology Group study. Kraut, E.H., Fleming, T., Segal, M., Neidhart, J.A., Behrens, B.C., MacDonald, J. Investigational new drugs. (1991) [Pubmed]
  2. Transcriptional regulation of differentiation, selective toxicity and ATGCAAAT binding of bisbenzimidazole derivatives in human melanoma cells. Wong, S.S., Sturm, R.A., Michel, J., Zhang, X.M., Danoy, P.A., McGregor, K., Jacobs, J.J., Kaushal, A., Dong, Y., Dunn, I.S. Biochem. Pharmacol. (1994) [Pubmed]
  3. Structure-activity relationship studies of a bisbenzimidazole-based, Zn(2+)-dependent inhibitor of HCV NS3 serine protease. Yeung, K.S., Meanwell, N.A., Qiu, Z., Hernandez, D., Zhang, S., McPhee, F., Weinheimer, S., Clark, J.M., Janc, J.W. Bioorg. Med. Chem. Lett. (2001) [Pubmed]
  4. DNA ligand Hoechst-33342 enhances UV induced cytotoxicity in human glioma cell lines. Singh, S., Dwarakanath, B.S., Mathew, T.L. J. Photochem. Photobiol. B, Biol. (2004) [Pubmed]
  5. Inhibition of transcription factor-DNA complexes and gene expression by a microgonotropen. White, C.M., Satz, A.L., Bruice, T.C., Beerman, T.A. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  6. A new class of symmetric bisbenzimidazole-based DNA minor groove-binding agents showing antitumor activity. Mann, J., Baron, A., Opoku-Boahen, Y., Johansson, E., Parkinson, G., Kelland, L.R., Neidle, S. J. Med. Chem. (2001) [Pubmed]
  7. Picosecond multiphoton scanning near-field optical microscopy. Jenei, A., Kirsch, A.K., Subramaniam, V., Arndt-Jovin, D.J., Jovin, T.M. Biophys. J. (1999) [Pubmed]
  8. Phase I-II study of pibenzimol hydrochloride (NSC 322921) in advanced pancreatic carcinoma. Patel, S.R., Kvols, L.K., Rubin, J., O'Connell, M.J., Edmonson, J.H., Ames, M.M., Kovach, J.S. Investigational new drugs. (1991) [Pubmed]
  9. Optical studies of the interaction of 33258 Hoechst with DNA, chromatin, and metaphase chromosomes. Latt, S.A., Wohlleb, J.C. Chromosoma (1975) [Pubmed]
  10. DNA minor groove targeted alkylating agents based on bisbenzimidazole carriers: synthesis, cytotoxicity and sequence-specificity of DNA alkylation. Smaill, J.B., Fan, J.Y., Denny, W.A. Anticancer Drug Des. (1998) [Pubmed]
  11. Flow cytometric analysis of cell cycle-dependent changes in cell thiol level by combining a new laser dye with Hoechst 33342. Poot, M., Kavanagh, T.J., Kang, H.C., Haugland, R.P., Rabinovitch, P.S. Cytometry. (1991) [Pubmed]
  12. Mutations induced by some DNA minor groove binding alkylators in AS52 Chinese hamster cells. Wu, X.C., Marcinkowski, K., Turner, P.M., Ferguson, L.R. Mutat. Res. (2000) [Pubmed]
  13. High-performance liquid chromatographic assay and preclinical pharmacological studies of pibenzimol (bisbenzimidazole). Ames, M.M., Miller, K.J., Moertel, D.M. J. Chromatogr. (1985) [Pubmed]
  14. Multivariate chromosome analysis and complete karyotyping using dual labeling and fluorescence digital imaging microscopy. Arndt-Jovin, D.J., Jovin, T.M. Cytometry. (1990) [Pubmed]
  15. Pulse radiolysis of the DNA-binding bisbenzimidazole derivatives Hoechst 33258 and 33342 in aqueous solutions. Adhikary, A., Bothe, E., Jain, V., Von Sonntag, C. Int. J. Radiat. Biol. (2000) [Pubmed]
  16. Stability of pibenzimol hydrochloride in commonly used infusion solutions and after filtration. Toledo, M.M., Cadwallader, D.E., Trissel, L.A., Flora, K.P. American journal of hospital pharmacy. (1989) [Pubmed]
  17. Estimation of cellular DNA content in cell lysates suitable for RNA isolation. Rymaszewski, Z., Abplanalp, W.A., Cohen, R.M., Chomczynski, P. Anal. Biochem. (1990) [Pubmed]
  18. Optical demonstration of Chlamydiae in cell cultures by means of fluorochrome 33,258 H. Rolly, H., Schachner, B. Infection (1979) [Pubmed]
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