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Chemical Compound Review

AC1Q6QTZ     N-[5-(2- carbamimidoylethylcarbamoyl)- 1...

Synonyms: LS-148804, AC1L22HJ, C22H27N9O4, 42073-EP2311808A1, 42073-EP2311829A1
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Disease relevance of Stallimycin

  • Compounds 3a, 3b, and 3c have been synthesized, and the interaction of distamycin A, 2, 3a, 3b, and 3c with calf thymus DNA, poly(dA-dT), poly(dG-dC), poly(dI-dC), pBR322 superhelical plasmid DNA, and, in the case of 3b, T4 coliphage DNA have been studied [1].
  • Distamycin A, which is a minor groove binder that mimics the architectural structure generated by G1P at pac, enhances the specific cut at both bona fide 5'-CTATTGCGG downward arrowC-3' sequences within pacC of SPP1 and SF6 phages [2].
  • Reduction of nitric oxide synthase 2 expression by distamycin A improves survival from endotoxemia [3].
  • Pausing of HIV RT at the polyadenosine tract could be enhanced by either distamycin A or netropsin, (A-T)-rich minor groove binding peptides [4].
  • Antiviral activity of distamycin A against vaccinia virus is the result of inhibition of postreplicative mRNA synthesis [5].

High impact information on Stallimycin

  • To clarify this relationship, the distamycin A-sensitive fragile site FRA16B was isolated by positional cloning and found to be an expanded 33 bp AT-rich minisatellite repeat, p(ATATA TTATATATTATATCTAATAATATATC/ATA)n (consistent with DNA sequence binding preferences of chemicals that induce its cytogenetic expression) [6].
  • Two techniques were especially useful in the mapping: "cloning" 14S + 25S DNA on the plasmid pMB9 to amplify individual R1 fragments, and digesting DNA with R1 in the presence of the antibiotic distamycin A to produce specific partial digestion products [7].
  • Here, we report that bromodeoxyuridine-inducible, distamycin A-insensitive fragile site FRA10B is composed of expanded approximately 42 bp repeats [8].
  • The mobility shift assay was used to study the competition of the minor groove binder distamycin A with either an Antennapedia homeodomain (Antp HD) peptide or derivatives of a fushi tarazu homeodomain (ftz HD) peptide for their AT-rich DNA binding site [9].
  • Distamycin A is a well known polyamide antibiotic that can bind in the minor groove of duplex DNA primarily at AT-rich sequences both as a monomer or as a side-by-side antiparallel dimer [10].

Chemical compound and disease context of Stallimycin


Biological context of Stallimycin


Anatomical context of Stallimycin


Associations of Stallimycin with other chemical compounds


Gene context of Stallimycin

  • Distamycin A or bromodeoxyuridine-inducible fragile site FRA16B is an expanded AT-rich approximately 33 bp repeat; however, the relationship between normal and fragile site alleles is not known [8].
  • However, HMGA1 could not bind alone either to consensus or to modified EREs, and the minor groove binding drug distamycin A failed to prevent the synergism between ER and HMGA1 [31].
  • Instead, we found that the GST-Cdc6 can compete with distamycin A for binding to the DNA molecule [32].
  • Our results demonstrate that reversible MGBs (DAPI, distamycin A, Hoechst 33258, and netropsin) are effective inhibitors of the formation of DNA/TBP complex and that distamycin A is the most potent (0.16 microM inhibits TBP complex formation by 50%) [33].
  • New sulfonated distamycin A derivatives with bFGF complexing activity [34].

Analytical, diagnostic and therapeutic context of Stallimycin


  1. Rational design of substituted tripyrrole peptides that complex with DNA by both selective minor-groove binding and electrostatic interaction with the phosphate backbone. Bruice, T.C., Mei, H.Y., He, G.X., Lopez, V. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  2. Functional analysis of the terminase large subunit, G2P, of Bacillus subtilis bacteriophage SPP1. Gual, A., Camacho, A.G., Alonso, J.C. J. Biol. Chem. (2000) [Pubmed]
  3. Reduction of nitric oxide synthase 2 expression by distamycin A improves survival from endotoxemia. Baron, R.M., Carvajal, I.M., Liu, X., Okabe, R.O., Fredenburgh, L.E., Macias, A.A., Chen, Y.H., Ejima, K., Layne, M.D., Perrella, M.A. J. Immunol. (2004) [Pubmed]
  4. 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]
  5. Antiviral activity of distamycin A against vaccinia virus is the result of inhibition of postreplicative mRNA synthesis. Broyles, S.S., Kremer, M., Knutson, B.A. J. Virol. (2004) [Pubmed]
  6. Human chromosomal fragile site FRA16B is an amplified AT-rich minisatellite repeat. Yu, S., Mangelsdorf, M., Hewett, D., Hobson, L., Baker, E., Eyre, H.J., Lapsys, N., Le Paslier, D., Doggett, N.A., Sutherland, G.R., Richards, R.I. Cell (1997) [Pubmed]
  7. Dictyostelium 17S, 25S, and 5S rDNAs lie within a 38,000 base pair repeated unit. Maizels, N. Cell (1976) [Pubmed]
  8. FRA10B structure reveals common elements in repeat expansion and chromosomal fragile site genesis. Hewett, D.R., Handt, O., Hobson, L., Mangelsdorf, M., Eyre, H.J., Baker, E., Sutherland, G.R., Schuffenhauer, S., Mao, J.I., Richards, R.I. Mol. Cell (1998) [Pubmed]
  9. Distamycin-induced inhibition of homeodomain-DNA complexes. Dorn, A., Affolter, M., Müller, M., Gehring, W.J., Leupin, W. EMBO J. (1992) [Pubmed]
  10. 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]
  11. Tallimustine, an effective antileukemic agent in a severe combined immunodeficient mouse model of adult myelogenous leukemia, induces remissions in a phase I study. Beran, M., Jeha, S., O'Brien, S., Estey, E., Vitek, L., Zurlo, M.G., Rios, M.B., Keating, M., Kantarjian, H. Clin. Cancer Res. (1997) [Pubmed]
  12. PNU-145156E, a novel angiogenesis inhibitor, in patients with solid tumors: a phase I and pharmacokinetic study. Groen, H.J., de Vries, E.G., Wynendaele, W., van der Graaf, W.T., Fokkema, E., Lechuga, M.J., Poggesi, I., Dirix, L.Y., van Oosterom, A.T. Clin. Cancer Res. (2001) [Pubmed]
  13. Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1, 4]benzodiazepine and minor-groove-binding oligopyrrole carriers. Baraldi, P.G., Balboni, G., Cacciari, B., Guiotto, A., Manfredini, S., Romagnoli, R., Spalluto, G., Thurston, D.E., Howard, P.W., Bianchi, N., Rutigliano, C., Mischiati, C., Gambari, R. J. Med. Chem. (1999) [Pubmed]
  14. The use of antibiotics actinomycin D and distamycin A for mapping of phage lambda HindIII fragments. Braga, E.A., Nosikov, V.V., Polyanovsky, O.L. FEBS Lett. (1976) [Pubmed]
  15. Inhibitor studies of phage T4 wild-type and mutant DNA polymerases. III. Distamycin A, actinomycin D, adriamycin, daunomycin and ethidium. Jantschak, J., Schroeder, C. Z. Allg. Mikrobiol. (1980) [Pubmed]
  16. 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]
  17. Distamycin A modulates the sequence specificity of DNA alkylation by duocarmycin A. Sugiyama, H., Lian, C., Isomura, M., Saito, I., Wang, A.H. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  18. An NMR study of [d(CGCGAATTCGCG)]2 containing an interstrand cross-link derived from a distamycin-pyrrole conjugate. Fagan, P.A., Spielmann, H.P., Sigurdsson, S., Rink, S.M., Hopkins, P.B., Wemmer, D.E. Nucleic Acids Res. (1996) [Pubmed]
  19. A theoretical evaluation of the effect of netropsin binding on the reactivity of DNA towards alkylating agents. Zakrzewska, K., Pullman, B. Nucleic Acids Res. (1983) [Pubmed]
  20. Effect of distamycin A on Chinese hamster chromosomes. Prantera, G., Di Castro, M., Marchetti, E., Rocchi, A. Exp. Cell Res. (1977) [Pubmed]
  21. Design, synthesis, DNA binding, and biological evaluation of water-soluble hybrid molecules containing two pyrazole analogues of the alkylating cyclopropylpyrroloindole (CPI) subunit of the antitumor agent CC-1065 and polypyrrole minor groove binders. Baraldi, P.G., Balboni, G., Pavani, M.G., Spalluto, G., Tabrizi, M.A., Clercq, E.D., Balzarini, J., Bando, T., Sugiyama, H., Romagnoli, R. J. Med. Chem. (2001) [Pubmed]
  22. The fragile site (17)(p12): induction by AT-specific DNA-ligands and population cytogenetics. Schmid, M., Feichtinger, W., Deubelbeiss, C., Weller, E. Hum. Genet. (1987) [Pubmed]
  23. Complete deficiency of constitutive heterochromatin on a human chromosome 9. Buys, C.H., Ypma, J.M., Gouw, W.L. Hum. Genet. (1979) [Pubmed]
  24. Demonstration of Y/autosomal translocations using distamycin A. Schmid, M. Hum. Genet. (1979) [Pubmed]
  25. Anti-insulin-like growth factor-I activity of a novel polysulphonated distamycin A derivative in human lung cancer cell lines. de Cupis, A., Ciomei, M., Pirani, P., Ferrera, A., Ardizzoni, A., Favoni, R.E. Br. J. Pharmacol. (1997) [Pubmed]
  26. 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]
  27. Distinct patterns of cell cycle disturbance elicited by compounds interfering with DNA topoisomerase I and II activity. Poot, M., Hiller, K.H., Heimpel, S., Hoehn, H. Exp. Cell Res. (1995) [Pubmed]
  28. 5-Bromodeoxyuridine suppresses position effect variegation of transgenes in HeLa cells. Suzuki, T., Yaginuma, M., Oishi, T., Michishita, E., Ogino, H., Fujii, M., Ayusawa, D. Exp. Cell Res. (2001) [Pubmed]
  29. Synergistic induction of the senescence-associated genes by 5-bromodeoxyuridine and AT-binding ligands in HeLa cells. Suzuki, T., Michishita, E., Ogino, H., Fujii, M., Ayusawa, D. Exp. Cell Res. (2002) [Pubmed]
  30. Comparison of cell-cycle phase perturbations induced by the DNA-minor-groove alkylator tallimustine and by melphalan in the SW626 cell line. Erba, E., Mascellani, E., Pifferi, A., D'Incalci, M. Int. J. Cancer (1995) [Pubmed]
  31. HMGA1 enhances the transcriptional activity and binding of the estrogen receptor to its responsive element. Massaad-Massade, L., Navarro, S., Krummrei, U., Reeves, R., Beaune, P., Barouki, R. Biochemistry (2002) [Pubmed]
  32. Saccharomyces cerevisiae Cdc6 stimulates Abf1 DNA binding activity. Feng, L., Wang, B., Jong, A. J. Biol. Chem. (1998) [Pubmed]
  33. Effects of minor groove binding drugs on the interaction of TATA box binding protein and TFIIA with DNA. Chiang, S.Y., Welch, J., Rauscher, F.J., Beerman, T.A. Biochemistry (1994) [Pubmed]
  34. New sulfonated distamycin A derivatives with bFGF complexing activity. Ciomei, M., Pastori, W., Mariani, M., Sola, F., Grandi, M., Mongelli, N. Biochem. Pharmacol. (1994) [Pubmed]
  35. Interactions of nucleic acids with distamycins. Binding of Dst-3 to d(CGTTTAAACG)2 and d(CGTACGTACG)2. Capobianco, M.L., Colonna, F.P., Forni, A., Garbesi, A., Iotti, S., Moretti, I., Samori, B., Tondelli, L. Nucleic Acids Res. (1991) [Pubmed]
  36. Establishment of L1210 leukemia cells resistant to the distamycin-A derivative (FCE 24517): characterization and cross-resistance studies. Geroni, C., Pesenti, E., Tagliabue, G., Ballinari, D., Mongelli, N., Broggini, M., Erba, E., D'Incalci, M., Spreafico, F., Grandi, M. Int. J. Cancer (1993) [Pubmed]
  37. Concerted DNA recognition and novel site-specific alkylation by duocarmycin A with distamycin A. Yamamoto, K., Sugiyama, H., Kawanishi, S. Biochemistry (1993) [Pubmed]
  38. Longitudinal differentiation of metaphase chromosomes of Indian muntjac as studied by restriction enzyme digestion, in situ hybridization with cloned DNA probes and distamycin A plus DAPI fluorescence staining. Ueda, T., Irie, S., Kato, Y. Chromosoma (1987) [Pubmed]
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