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Chemical Compound Review

Herperetin     N-[5-(2- carbamimidoylethylcarbamoyl)- 1...

Synonyms: Stallimycin, Estalimicina, Stallimicina, Stallimycine, Stallimycinum, ...
 
 
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Disease relevance of Stallimycin

  • Two distinct marker chromosomes, presenting with intercalated C- and distamycin A-Dapi-positive regions, were observed in a metastatic and a primary melanoma [1].
  • Mammalian topoisomerase II activity is modulated by the DNA minor groove binder distamycin in simian virus 40 DNA [2].
  • At proper distamycin concentrations only two endo R.EcoRI sites of phage lambda DNA are available for the restriction enzyme--sRI1 and sRI4 [3].
  • Distamycin-induced inhibition of formation of a nucleoprotein complex between the terminase small subunit G1P and the non-encapsidated end (pacL site) of Bacillus subtilis bacteriophage SPP1 [4].
  • The same unusual conformation that eludes RNase H, thought to be a change in width of minor groove, may also be responsible for the inhibition of HIV RT by minor groove binding drugs such as distamycin and their bis-linked derivatives [5].
 

Psychiatry related information on Stallimycin

  • The DNA minor groove binders SN6999, SN6570, and SN6113, structurally related to netropsin and distamycin, were investigated for sequence-specific interactions with the 154 base pair cDNA fragment of the human tau 40 protein, involved in pathology of Alzheimer's disease [6].
 

High impact information on Stallimycin

  • Distamycin appeared to antagonize the binding of the initiator to the seven 22 bp direct repeats [7].
  • Binding of distamycin induces a cooperative transition of calf thymus DNA to a new form with higher affinity for the drug and altered structural properties [8].
  • The C- and G-positive regions stained with distamycin A-DAPI, which is specific for the centromeric heterochromatin of chromosomes 1, 9, 15p, 16, and Y. DNA extracted from MeWo cells and digested with the restriction enzymes KpnL or Sau3A exhibited marked amplification of a 1.8-kilobase fragment [9].
  • A model for chromatin opening: stimulation of topoisomerase II and restriction enzyme cleavage of chromatin by distamycin [10].
  • Selective titration of A-tracts by the oligopeptide distamycin abolishes this interaction and results in a redistribution of H1 [10].
 

Chemical compound and disease context of Stallimycin

  • Five classic DNA minor groove-binding drugs and a series of bis-linked lexitropsins based on netropsin and distamycin have been screened for their effectiveness in inhibiting transcription by HIV-1 reverse transcriptase (RT) on a poly(rA).oligo(dT) template-primer (TP) [11].
  • These compounds are structurally different from other sulfonic acid containing compounds reported to be potent inhibitors of the human immunodeficiency virus (HIV) in two respects: (1) they are structurally related to the non-toxic minor groove DNA binder distamycin; and (2) a number of them contain the aromatic phosphonic acid group [12].
 

Biological context of Stallimycin

 

Anatomical context of Stallimycin

  • Two fragments of Xenopus borealis DNA 135 and 189 base-pairs long were separately incorporated into nucleosome core particles by reconstitution with chicken erythrocyte histones, and incubated with echinomycin (a bis-intercalating antitumor antibiotic) or distamycin (a minor groove-binding, non-intercalating antibiotic) [17].
  • Specific inhibition of DNA binding to nuclear scaffolds and histone H1 by distamycin. The role of oligo(dA).oligo(dT) tracts [18].
  • A partially purified human HeLa cell DNA helicase is also potently blocked by daunorubicin, distamycin, and teniposide [19].
  • One of the distamycin analogs, 2,2'[4,4'-[[aminocarbonyl]amino]bis[N,4'-di[pyrrole-2-carboxamide- 1,1'-dimethyl]]-6,8 napthalenedisulfonic acid] hexasodium salt (NSC 651016), is shown here to inhibit syncytia formation and cell fusion [20].
  • Expression of distamycin A-inducible rare fragile sites by AT-specific DNA-ligands was examined in lymphoblastoid cell lines derived from heterozygous carriers for the fra(8)(q24), fra(16)(p12), and fra(16)(q22) sites [21].
 

Associations of Stallimycin with other chemical compounds

 

Gene context of Stallimycin

  • The most active of these drugs, MGT-6a, was three orders of magnitude more effective than distamycin and inhibited complexes between E2F1 and the dihydrofolate reductase promoter by 50% at 0.00085 microM [27].
  • Attachment of a slightly modified basic region of a bZIP protein (GCN4) to a distamycin-related tripyrrole provides a bivalent system capable of binding with high affinity to specific DNA sequences [28].
  • Inhibition of in vitro and in vivo HIV replication by a distamycin analogue that interferes with chemokine receptor function: a candidate for chemotherapeutic and microbicidal application [29].
  • Antibody ablation, distamycin inhibition of binding, renaturation and competition experiments, and tissue distribution data all confirmed that the NBP complex contained SATB1 [30].
  • Human fragile site FRA16B DNA excludes nucleosomes in the presence of distamycin [31].
 

Analytical, diagnostic and therapeutic context of Stallimycin

References

  1. In situ hybridization analysis of interstitial C-heterochromatin in marker chromosomes of two human melanomas. Doneda, L., Ginelli, E., Agresti, A., Larizza, L. Cancer Res. (1989) [Pubmed]
  2. Mammalian topoisomerase II activity is modulated by the DNA minor groove binder distamycin in simian virus 40 DNA. Fesen, M., Pommier, Y. J. Biol. Chem. (1989) [Pubmed]
  3. Protection of particular cleavage sites of restriction endonucleases by distamycin A and actinomycin D. Nosikov, V.V., Braga, E.A., Karlishev, A.V., Zhuze, A.L., Polyanovsky, O.L. Nucleic Acids Res. (1976) [Pubmed]
  4. Distamycin-induced inhibition of formation of a nucleoprotein complex between the terminase small subunit G1P and the non-encapsidated end (pacL site) of Bacillus subtilis bacteriophage SPP1. Chai, S., Alsonso, J.C. Nucleic Acids Res. (1996) [Pubmed]
  5. Structure of a DNA analog of the primer for HIV-1 RT second strand synthesis. Han, G.W., Kopka, M.L., Cascio, D., Grzeskowiak, K., Dickerson, R.E. J. Mol. Biol. (1997) [Pubmed]
  6. Down-regulation of H tau 40 protein expression by minor groove binders. Kittler, L., Wollweber, L. Nucleosides Nucleotides Nucleic Acids (2000) [Pubmed]
  7. Conformational changes in a replication origin induced by an initiator protein. Mukherjee, S., Patel, I., Bastia, D. Cell (1985) [Pubmed]
  8. Transmission of allosteric effects in DNA. Hogan, M., Dattagupta, N., Crothers, D.M. Nature (1979) [Pubmed]
  9. Amplified KpnL repetitive DNA sequences in homogeneously staining regions of a human melanoma cell line. Simmons, M.C., Maxwell, J., Haliotis, T., Higgins, M.J., Roder, J.C., White, B.N., Holden, J.J. J. Natl. Cancer Inst. (1984) [Pubmed]
  10. A model for chromatin opening: stimulation of topoisomerase II and restriction enzyme cleavage of chromatin by distamycin. Käs, E., Poljak, L., Adachi, Y., Laemmli, U.K. EMBO J. (1993) [Pubmed]
  11. Linked lexitropsins and the in vitro inhibition of HIV-1 reverse transcriptase RNA-directed DNA polymerization: a novel induced-fit of 3,5 m-pyridyl bisdistamycin to enzyme-associated template-primer. Filipowsky, M.E., Kopka, M.L., Brazil-Zison, M., Lown, J.W., Dickerson, R.E. Biochemistry (1996) [Pubmed]
  12. Novel sulfonated and phosphonated analogs of distamycin which inhibit the replication of HIV. Clanton, D.J., Buckheit, R.W., Terpening, S.J., Kiser, R., Mongelli, N., Borgia, A.L., Schultz, R., Narayanan, V., Bader, J.P., Rice, W.G. Antiviral Res. (1995) [Pubmed]
  13. In vivo topoisomerase II cleavage of the Drosophila histone and satellite III repeats: DNA sequence and structural characteristics. Käs, E., Laemmli, U.K. EMBO J. (1992) [Pubmed]
  14. On the kinetics of distamycin binding to its target sites on duplex DNA. Baliga, R., Crothers, D.M. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  15. A bifurcated hydrogen-bonded conformation in the d(A.T) base pairs of the DNA dodecamer d(CGCAAATTTGCG) and its complex with distamycin. Coll, M., Frederick, C.A., Wang, A.H., Rich, A. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  16. Specific binding of high-mobility-group I (HMGI) protein and histone H1 to the upstream AT-rich region of the murine beta interferon promoter: HMGI protein acts as a potential antirepressor of the promoter. Bonnefoy, E., Bandu, M.T., Doly, J. Mol. Cell. Biol. (1999) [Pubmed]
  17. Interaction of nucleosome core particles with distamycin and echinomycin: analysis of the effect of DNA sequences. Portugal, J., Waring, M.J. Nucleic Acids Res. (1987) [Pubmed]
  18. Specific inhibition of DNA binding to nuclear scaffolds and histone H1 by distamycin. The role of oligo(dA).oligo(dT) tracts. Käs, E., Izaurralde, E., Laemmli, U.K. J. Mol. Biol. (1989) [Pubmed]
  19. Antihelicase action of DNA-binding anticancer agents: relationship to guanosine-cytidine intercalator binding. Bachur, N.R., Johnson, R., Yu, F., Hickey, R., Applegren, N., Malkas, L. Mol. Pharmacol. (1993) [Pubmed]
  20. Small molecule inhibitor of HIV-1 cell fusion blocks chemokine receptor-mediated function. Howard, O.M., Korte, T., Tarasova, N.I., Grimm, M., Turpin, J.A., Rice, W.G., Michejda, C.J., Blumenthal, R., Oppenheim, J.J. J. Leukoc. Biol. (1998) [Pubmed]
  21. Induction of distamycin A-inducible rare fragile sites and increased sister chromatid exchanges at the fragile site. Tsuji, H., Hitomi, A., Takahashi, E., Murata, M., Ikeuchi, T., Yamamoto, K., Tsuji, S., Hori, T. Hum. Genet. (1991) [Pubmed]
  22. Conformational features of distamycin-DNA and netropsin-DNA complexes by Raman spectroscopy. Martin, J.C., Wartell, R.M., O'Shea, D.C. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  23. The A.T-DNA-binding domain of mammalian high mobility group I chromosomal proteins. A novel peptide motif for recognizing DNA structure. Reeves, R., Nissen, M.S. J. Biol. Chem. (1990) [Pubmed]
  24. DNA sequence-specific adenine alkylation by the novel antitumor drug tallimustine (FCE 24517), a benzoyl nitrogen mustard derivative of distamycin. Broggini, M., Coley, H.M., Mongelli, N., Pesenti, E., Wyatt, M.D., Hartley, J.A., D'Incalci, M. Nucleic Acids Res. (1995) [Pubmed]
  25. DNA sequence preferences of several AT-selective minor groove binding ligands. Abu-Daya, A., Brown, P.M., Fox, K.R. Nucleic Acids Res. (1995) [Pubmed]
  26. Use of capillary electrophoresis in the study of ligand-DNA interactions. Hamdan, I.I., Skellern, G.G., Waigh, R.D. Nucleic Acids Res. (1998) [Pubmed]
  27. Targeting E2F1-DNA complexes with microgonotropen DNA binding agents. Chiang, S.Y., Bruice, T.C., Azizkhan, J.C., Gawron, L., Beerman, T.A. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  28. A synthetic miniprotein that binds specific DNA sequences by contacting both the major and the minor groove. Blanco, J.B., Vázquez, M.E., Martinez-Costas, J., Castedo, L., Mascareñas, J.L. Chem. Biol. (2003) [Pubmed]
  29. Inhibition of in vitro and in vivo HIV replication by a distamycin analogue that interferes with chemokine receptor function: a candidate for chemotherapeutic and microbicidal application. Howard, O.M., Oppenheim, J.J., Hollingshead, M.G., Covey, J.M., Bigelow, J., McCormack, J.J., Buckheit, R.W., Clanton, D.J., Turpin, J.A., Rice, W.G. J. Med. Chem. (1998) [Pubmed]
  30. The matrix attachment region-binding protein SATB1 participates in negative regulation of tissue-specific gene expression. Liu, J., Bramblett, D., Zhu, Q., Lozano, M., Kobayashi, R., Ross, S.R., Dudley, J.P. Mol. Cell. Biol. (1997) [Pubmed]
  31. Human fragile site FRA16B DNA excludes nucleosomes in the presence of distamycin. Hsu, Y.Y., Wang, Y.H. J. Biol. Chem. (2002) [Pubmed]
  32. Evidence for structural deformation of the DNA helix by a psoralen diadduct but not by a monoadduct. Shi, Y.B., Griffith, J., Gamper, H., Hearst, J.E. Nucleic Acids Res. (1988) [Pubmed]
  33. Distamycin A complexation with a nucleic acid triple helix. Durand, M., Maurizot, J.C. Biochemistry (1996) [Pubmed]
  34. Differential effects of distamycin analogues on amplification of human gene sequences by polymerase-chain reaction. Passadore, M., Bianchi, N., Feriotto, G., Mischiati, C., Giacomini, P., Piva, R., Gambari, R. Biochem. J. (1995) [Pubmed]
  35. Cytotoxic alpha-halogenoacrylic derivatives of distamycin A and congeners. Beria, I., Baraldi, P.G., Cozzi, P., Caldarelli, M., Geroni, C., Marchini, S., Mongelli, N., Romagnoli, R. J. Med. Chem. (2004) [Pubmed]
  36. Hoechst 33258, distamycin A, and high mobility group protein I (HMG-I) compete for binding to mouse satellite DNA. Radic, M.Z., Saghbini, M., Elton, T.S., Reeves, R., Hamkalo, B.A. Chromosoma (1992) [Pubmed]
 
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