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Chemical Compound Review

Echinomycin     N-[3,11,13,16,24,26- hexamethyl-27...

Synonyms: Levomycin, Echinomycin A, Quinomycin A, GNF-PF-1958, LS-161, ...
 
 
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Disease relevance of NSC 526417

 

High impact information on NSC 526417

  • This method reveals that echinomycin has a binding site size of four base pairs [6].
  • Unstable Hoogsteen base pairs adjacent to echinomycin binding sites within a DNA duplex [7].
  • In an effort to find evidence for Hoogsteen base-pairing at quinoxaline-binding sites in solution, chemical "footprinting" (differential cleavage reactivity) of echinomycin bound to DNA restriction fragments was examined [8].
  • Both 1 and 2 were found to exhibit exceptional cytotoxic activity (IC(50) = 200 and 400 pM, respectively, L1210 cell line) comparable to echinomycin and one analogue, which bears the luzopeptin chromophore, was also found to be a potent cytotoxic agent [9].
  • We have studied the binding of echinomycin to DNA fragments containing GC-rich regions flanked by blocks of alternating AT by DNase I footprinting and diethylpyrocarbonate modification [10].
 

Chemical compound and disease context of NSC 526417

  • For quinomycin C the highest binding constant was found with Micrococcus lysodeikticus DNA, and its pattern of specificity among natural DNA species was broadly similar to that of echinomycin, although the binding constants were 2--6 times as large [11].
  • The short-term effects on restenosis and thrombosis of echinomycin-eluting stents topcoated with a hydrophobic heparin-containing polymer [12].
  • Streptomyces echinatus A8331 cultured on a maltose minimal salts medium normally produces a single antibiotic, echinomycin (quinomycin A), containing two quinoxaline-2-carbonyl chromophores [13].
  • Newly modified-echinomycin such as S-methylated sulfonium perchlorate of echinomycin (1), monosulfoxide (2), disulfoxid (3) and sulfone (4) have been prepared and evaluated for in vitro biological activities of cytotoxicity against P388, B16 and SNU-16 as well as in vivo antitumor activity against murine leukemia P388 and melanoma B16 [14].
 

Biological context of NSC 526417

 

Anatomical context of NSC 526417

  • When nucleosome cores reconstituted from chicken erythrocyte histones and a 160 bp DNA molecule are exposed to echinomycin, a bis-intercalating antitumour antibiotic, the DNA appears to rotate with respect to the histone octamer by about half a turn [19].
  • Echinomycin suppresses the pyrogenic effects of endotoxin and interleukin-1 beta in human endothelial cells and peripheral blood mononuclear cells [20].
  • A phase II trial of echinomycin in metastatic cervix carcinoma [21].
  • Molecular signaling cascade in DNA bisintercalator, echinomycin-induced apoptosis of HT-29 cells: evidence of the apoptotic process via activation of the cytochrome c-ERK-caspase-3 pathway [22].
  • PD98059 treatment or overexpression of kinase-inactive ERK did not alter the echinomycin-induced cytochrome c release into the cytosol, but did diminish the activation of procaspase-3 [22].
 

Associations of NSC 526417 with other chemical compounds

  • Moreover, a 12-base-pair segment of alternating A-T DNA, which is 6 base pairs away from the nearest strong echinomycin-binding site, is also hyperreactive to diethyl pyrocarbonate in the presence of echinomycin [8].
  • Interaction of nucleosome core particles with distamycin and echinomycin: analysis of the effect of DNA sequences [23].
  • In the case of echinomycin only one purine 2-amino group is required for remarkably strong binding to the asymmetric TpDAP.TpA dinucleotide step, but the CpDAP.TpI step (which also contains only a single purine-2 amino group) does not afford a binding site [24].
  • Further experiments were performed with echinomycin at pH 5.5 and 4.6 to facilitate the protonation of cytosine required for formation of Hoogsteen GC base pairs [25].
  • There are intermolecular hydrogen bonds between each of the Ala NH and the AN3 protons of the TpA binding site, analogous to those observed between Ala NH and GN3 in the crystal structures of the CpG-specific complexes of echinomycin and triostin A with DNA [26].
 

Gene context of NSC 526417

  • These observations demonstrate that echinomycin protects endothelial cells and PBMC from the pyrogenic effect of LPS and IL-1 beta [20].
  • Echinomycin also reduced LPS-induced secretion of IL-1 beta and IL-6 by human PBMC (IC50 = 10 +/- 2 and 3 +/- 0.5 nM respectively) [20].
  • It seems that certain sequences, mainly runs of A or runs of T, switch from a nuclease-resistant to a nuclease-sensitive form when echinomycin binds nearby [3].
  • Taken together, these results indicate that cytochrome c release, and the activation of ERK and caspase-3 in the final apoptosis pathway are all relevant factors in echinomycin-induced apoptosis [22].
 

Analytical, diagnostic and therapeutic context of NSC 526417

  • Atomic force microscopy study of the structural effects induced by echinomycin binding to DNA [27].
  • The DNase I footprinting titration studies greatly refined the existing knowledge of the DNA-binding characteristics of echinomycin, as they revealed five general types of concentration-dependent behavior at single-bond resolution [28].
  • Hydrophobic heparinized polymer was then topcoated onto stent over echinomycin/PU layer by dipping to improve hemocompatibility [12].
  • The objective of this trial was to determine the efficacy of echinomycin (1.2 mg/m2) administered on a weekly times four schedule in the treatment of patients with recurrent or progressive central nervous malignancies despite adequate radiotherapy [29].
  • For instance, against Bacillus anthracis strains, kakadumycin A has minimum inhibitory concentrations of 0.2-0.3 microg x ml(-1) in contrast to echinomycin at 1.0-1.2 microg x ml(-1) [30].

References

  1. Intermolecular cross-linking of DNA through bifunctional intercalation of an antitumor antibiotic, luzopeptin A (BBM-928A). Huang, C.H., Mirabelli, C.K., Mong, S., Crooke, S.T. Cancer Res. (1983) [Pubmed]
  2. Functional cross-talk between fatty acid synthesis and nonribosomal peptide synthesis in quinoxaline antibiotic-producing streptomycetes. Schmoock, G., Pfennig, F., Jewiarz, J., Schlumbohm, W., Laubinger, W., Schauwecker, F., Keller, U. J. Biol. Chem. (2005) [Pubmed]
  3. Sequence-specific binding of echinomycin to DNA: evidence for conformational changes affecting flanking sequences. Low, C.M., Drew, H.R., Waring, M.J. Nucleic Acids Res. (1984) [Pubmed]
  4. Binding of quinoline analogues of echinomycin to deoxyribonucleic acid. Role of the chromophores. Fox, K.R., Gauvreau, D., Goodwin, D.C., Waring, M.J. Biochem. J. (1980) [Pubmed]
  5. Phase II study of echinomycin in the treatment of renal cell carcinoma ECOG study E2885. Chang, A.Y., Tu, Z.N., Bryan, G.T., Kirkwood, J.M., Oken, M.M., Trump, D.L. Investigational new drugs. (1994) [Pubmed]
  6. Echinomycin binding sites on DNA. Van Dyke, M.M., Dervan, P.B. Science (1984) [Pubmed]
  7. Unstable Hoogsteen base pairs adjacent to echinomycin binding sites within a DNA duplex. Gilbert, D.E., van der Marel, G.A., van Boom, J.H., Feigon, J. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  8. Hoogsteen base pairs proximal and distal to echinomycin binding sites on DNA. Mendel, D., Dervan, P.B. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  9. Total syntheses of thiocoraline and BE-22179 and assessment of their DNA binding and biological properties. Boger, D.L., Ichikawa, S., Tse, W.C., Hedrick, M.P., Jin, Q. J. Am. Chem. Soc. (2001) [Pubmed]
  10. Echinomycin binding to alternating AT. Fox, K.R., Marks, J.N., Waterloh, K. Nucleic Acids Res. (1991) [Pubmed]
  11. Bifunctional intercalation and sequence specificity in the binding of quinomycin and triostin antibiotics to deoxyribonucleic acid. Lee, J.S., Waring, M.J. Biochem. J. (1978) [Pubmed]
  12. The short-term effects on restenosis and thrombosis of echinomycin-eluting stents topcoated with a hydrophobic heparin-containing polymer. Lee, Y.K., Hyung Park, J., Tae Moon, H., Yun Lee, D., Han Yun, J., Byun, Y. Biomaterials (2007) [Pubmed]
  13. Directed biosynthesis of novel derivatives of echinomycin by Streptomyces echinatus. I. Effect of exogenous analogues of quinoxaline-2-carboxylic acid on the fermentation. Gauvreau, D., Waring, M.J. Can. J. Microbiol. (1984) [Pubmed]
  14. A new antitumor agent: methyl sulfonium perchlorate of echinomycin. Park, Y.S., Kim, Y.H., Kim, S.K., Choi, S.J. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  15. Echinomycin-induced hypersensitivity to osmium tetroxide of DNA fragments incapable of forming Hoogsteen base pairs. McLean, M.J., Seela, F., Waring, M.J. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  16. Footprinting reveals that nogalamycin and actinomycin shuffle between DNA binding sites. Fox, K.R., Waring, M.J. Nucleic Acids Res. (1986) [Pubmed]
  17. Kinetic evidence that echinomycin migrates between potential DNA binding sites. Fox, K.R., Waring, M.J. Nucleic Acids Res. (1985) [Pubmed]
  18. Localized chemical reactivity in DNA associated with the sequence-specific bisintercalation of echinomycin. Bailly, C., Gentle, D., Hamy, F., Purcell, M., Waring, M.J. Biochem. J. (1994) [Pubmed]
  19. Echinomycin and distamycin induce rotation of nucleosome core DNA. Low, C.M., Drew, H.R., Waring, M.J. Nucleic Acids Res. (1986) [Pubmed]
  20. Echinomycin suppresses the pyrogenic effects of endotoxin and interleukin-1 beta in human endothelial cells and peripheral blood mononuclear cells. Herbert, J.M., Lalé, A., Pereillo, J.M., Derocq, J.M., Casellas, P. Thromb. Haemost. (1996) [Pubmed]
  21. A phase II trial of echinomycin in metastatic cervix carcinoma. Hakes, T., Markman, M., Phillips, M. Investigational new drugs. (1990) [Pubmed]
  22. Molecular signaling cascade in DNA bisintercalator, echinomycin-induced apoptosis of HT-29 cells: evidence of the apoptotic process via activation of the cytochrome c-ERK-caspase-3 pathway. Park, J.Y., Ryang, Y.S., Shim, K.Y., Lee, J.I., Kim, H.S., Kim, Y.H., Kim, S.K. Int. J. Biochem. Cell Biol. (2006) [Pubmed]
  23. 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]
  24. Footprinting of echinomycin and actinomycin D on DNA molecules asymmetrically substituted with inosine and/or 2,6-diaminopurine. Jennewein, S., Waring, M.J. Nucleic Acids Res. (1997) [Pubmed]
  25. Diethyl pyrocarbonate can detect a modified DNA structure induced by the binding of quinoxaline antibiotics. Portugal, J., Fox, K.R., McLean, M.J., Richenberg, J.L., Waring, M.J. Nucleic Acids Res. (1988) [Pubmed]
  26. Solution structure of a complex between [N-MeCys3,N-MeCys7]TANDEM and [d(GATATC)]2. Addess, K.J., Sinsheimer, J.S., Feigon, J. Biochemistry (1993) [Pubmed]
  27. Atomic force microscopy study of the structural effects induced by echinomycin binding to DNA. Tseng, Y.D., Ge, H., Wang, X., Edwardson, J.M., Waring, M.J., Fitzgerald, W.J., Henderson, R.M. J. Mol. Biol. (2005) [Pubmed]
  28. Footprinting titration studies on the binding of echinomycin to DNA incapable of forming Hoogsteen base pairs. Sayers, E.W., Waring, M.J. Biochemistry (1993) [Pubmed]
  29. Phase II evaluation of echinomycin (NSC-526417) in patients with central nervous system malignancies. A Southwest Oncology Group study. Taylor, S.A., Crowley, J., Townsend, J., Vogel, F.S., Eyre, H., Braun, J.J., Goodwin, J.W. J. Neurooncol. (1993) [Pubmed]
  30. Kakadumycins, novel antibiotics from Streptomyces sp NRRL 30566, an endophyte of Grevillea pteridifolia. Castillo, U., Harper, J.K., Strobel, G.A., Sears, J., Alesi, K., Ford, E., Lin, J., Hunter, M., Maranta, M., Ge, H., Yaver, D., Jensen, J.B., Porter, H., Robison, R., Millar, D., Hess, W.M., Condron, M., Teplow, D. FEMS Microbiol. Lett. (2003) [Pubmed]
 
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