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Chemical Compound Review

Ethidium     5-ethyl-6-phenyl- phenanthridine-3,8-diamine

Synonyms: Novidium, homidium, UPCMLD-DP076, CHEMBL48166, SureCN27609, ...
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Disease relevance of ETHIDIUM BROMIDE

  • CD4+ or CD8+ cells from clinically asymptomatic HIV-1 carriers contain a significantly elevated percentage of cells endowed with enhanced HE --> Eth conversion and/or reduced DiOC6(3) uptake as compared with normal controls [1].
  • One of these proteins, EmrE, is an Escherichia coli protein, which has been cloned based on its ability to confer resistance to ethidium and methyl viologen and which has been extensively characterized [2].
  • We have investigated internal motion of DNA in bacteriophages by measuring fluorescence anisotropy decays of intercalated ethidium [3].
  • A set of covalently closed circular duplex simian virus 40 DNA preparations of varying superhelical densities was prepared by closure of nicked duplex DNA with polynucleotide ligase in the presence of varying amounts of ethidium [4].
  • Interestingly, in the presence of an inwardly directed ethidium concentration gradient in ATP-depleted cells of Lactococcus lactis, the ABC multidrug transporter LmrA mediated the reverse transport (or uptake) of ethidium with an apparent K(t) of 2.0 microm [5].

Psychiatry related information on ETHIDIUM BROMIDE


High impact information on ETHIDIUM BROMIDE

  • Ethidium intercalation in 0.9 M NaCl both removes the negative superhelical turns and dissociates the four histones from the DNA [7].
  • Cytofluorometrically purified cells with reduced mitochondrial transmembrane potential are initially incapable of oxidizing hydroethidine (HE) into ethidium [8].
  • PV IgG and complement also resulted in significant cytotoxicity to cell membranes as assessed using an ethidium bromide-fluorescein diacetate assay [9].
  • The entire coding region of the dystrophin mRNA was amplified in 10 sections by reverse transcription and nested polymerase chain reaction, and the products were directly visualised on acrylamide minigels with ethidium staining [10].
  • To monitor the simultaneous binding of Pf and Et to QacR, as well as to determine the effects on the binding affinity of one drug when the other drug is prebound, a novel application of near-ultraviolet circular dichroism (UVCD) was developed [11].

Chemical compound and disease context of ETHIDIUM BROMIDE


Biological context of ETHIDIUM BROMIDE

  • In contrast to the "Caltech systems," these conjugates contain ethidium tightly incorporated (as a base pair surrogate) into the DNA base stack, opposite to an abasic site analog [17].
  • This was confirmed by the observation that ethidium homodimer incorporation (a measure of plasma membrane integrity) into endothelial cells was increased by angiostatin in a manner similar to that seen with tumor necrosis factor- (TNF-) and transforming growth factor-beta1 (TGF-beta1), both of which induce apoptosis in endothelial cells [18].
  • Control experiments involving rotenone, an inhibitor of the respiratory chain complex I, indicate that the reactive oxygen species responsible for HE --> Eth conversion is generated during mitochondrial electron transport [1].
  • Following transfection of FITC-labeled oligonucleotides and ethidium monoazide-labeled plasmid DNA, cellular uptake and intracellular localization of nucleic acids were examined by laser scanning confocal microscopy [19].
  • The magnitude of the quantum yield enhancement and the shifts of excitation and emission maxima of bound ethidium suggest that its binding site is within a hydrophobic domain with limited accessibility to the aqueous phase [20].

Anatomical context of ETHIDIUM BROMIDE

  • Recent experiments on photoaffinity labeling of mitochondria with monoazide ethidium, which is an anisotropic inhibitor, showed that the inhibitor specifically binds to a hydrophobic protein of the membranes [21].
  • P2X(7) function was measured by ATP-induced fluxes of Rb(+), Ba(2+), and ethidium(+) into various lymphocyte subsets and was decreased to values of approximately 25% of normal [22].
  • Both ATP-induced ethidium+ uptake and ATP-induced shedding of L-selectin (CD62L) were nearly absent in monocytes from four subjects homozygous for Glu496Ala confirming that this polymorphism impairs P2X7 function [23].
  • Additional studies characterized P2z receptor regulation of Ca2+ influx, depolarization, ethidium uptake, and fura-2 loss in native BAC1.2F5 macrophages [24].
  • Because previous work has shown that radioisotope release from parasites may be nonspecific, separate experiments were performed to determine the cytotoxicity of LAK cells against antibody-coated trophozoites by using ethidium bromide-acridine orange staining to assess effector cell damage [25].

Associations of ETHIDIUM BROMIDE with other chemical compounds

  • X-ray crystallographic visualization of drug-nucleic acid intercalative binding: structure of an ethidium-dinucleoside monophosphate crystalline complex, Ethidium: 5-iodouridylyl (3'-5') adenosine [26].
  • RANKL-induced apoptosis was further confirmed using calcein AM/ethidium homodimer-1 dye and cleavage of poly(ADP-ribose) polymerase (PARP), procaspase 3, and procaspase 9; benzyloxycarbonyl-VAD, the pancaspase inhibitor, suppressed the PARP cleavage [27].
  • Homogenates of the aortas were incubated with various substrates for superoxide-producing enzymes, and superoxide production was assessed by fluorogenic oxidation of dihydroethidium to ethidium [28].
  • Upon dilution of the proteoliposomes in ammonium-free medium, a pH gradient was formed that drove transport of ethidium and methyl viologen into the proteoliposome [29].
  • Similar to LmrA, MsbA interacted with photoactivatable substrate [3H]azidopine, displayed a daunomycin, vinblastine, and Hoechst 33342-stimulated vanadate-sensitive ATPase activity, and mediated the transport of ethidium from cells and Hoechst 33342 in proteoliposomes containing purified and functionally reconstituted protein [30].

Gene context of ETHIDIUM BROMIDE

  • A good correlation was found, except for a recB mutant and for an ethidium-sensitive strain, both able to produce as much recA protein as the wild type but 100-fold more sensitive to the drug [31].
  • Subsequently, the cells were double-labeled with markers of injury (either Ethidium Homodimer-1 for cellular injury or MitoTracker dye for functional mitochondria) or oxidant stress (5-[and 6]-chloromethyl-2',7'-dicholorodihydrofluorescein diacetate) and antibodies specific for the chemoattractants IL-8 or thioredoxin [32].
  • N-Ethylmaleimide was shown to inhibit qacC-mediated ethidium export [33].
  • A gene coding for a small 110-amino acid membrane protein (emrE or mvrC) has been previously identified and cloned and shown to render Escherichia coli cells resistant to methyl viologen and to ethidium [29].
  • Furthermore, it was shown that ethidium binds to both RNA and DNA when it enters CCCP-treated wild-type E. coli cells, whereas it binds mainly to DNA when it enters Ebs and acrA cells in exponential growth [34].

Analytical, diagnostic and therapeutic context of ETHIDIUM BROMIDE


  1. Mitochondrial dysfunctions in circulating T lymphocytes from human immunodeficiency virus-1 carriers. Macho, A., Castedo, M., Marchetti, P., Aguilar, J.J., Decaudin, D., Zamzami, N., Girard, P.M., Uriel, J., Kroemer, G. Blood (1995) [Pubmed]
  2. Functional analysis of novel multidrug transporters from human pathogens. Ninio, S., Rotem, D., Schuldiner, S. J. Biol. Chem. (2001) [Pubmed]
  3. Internal motion of DNA in bacteriophages. Ashikawa, I., Furuno, T., Kinosita, K., Ikegami, A., Takahashi, H., Akutsu, H. J. Biol. Chem. (1984) [Pubmed]
  4. The effect of superhelicity on the interaction of histone f1 with closed circular duplex DNA. Vogel, T., Singer, M.F. J. Biol. Chem. (1976) [Pubmed]
  5. Reversible transport by the ATP-binding cassette multidrug export pump LmrA: ATP synthesis at the expense of downhill ethidium uptake. Balakrishnan, L., Venter, H., Shilling, R.A., van Veen, H.W. J. Biol. Chem. (2004) [Pubmed]
  6. Ethidium cooperativity in the formation of complexes with CpG. Day, M., Trowbridge, C.G. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  7. Isolation, characterization, and structure of the folded interphase genome of Drosophila melanogaster. Benyajati, C., Worcel, A. Cell (1976) [Pubmed]
  8. Sequential reduction of mitochondrial transmembrane potential and generation of reactive oxygen species in early programmed cell death. Zamzami, N., Marchetti, P., Castedo, M., Decaudin, D., Macho, A., Hirsch, T., Susin, S.A., Petit, P.X., Mignotte, B., Kroemer, G. J. Exp. Med. (1995) [Pubmed]
  9. Complement fixation by pemphigus antibody. V. Assembly of the membrane attack complex on cultured human keratinocytes. Xia, P., Jordon, R.E., Geoghegan, W.D. J. Clin. Invest. (1988) [Pubmed]
  10. Direct diagnosis of carriers of Duchenne and Becker muscular dystrophy by amplification of lymphocyte RNA. Roberts, R.G., Bentley, D.R., Barby, T.F., Manners, E., Bobrow, M. Lancet (1990) [Pubmed]
  11. Structural mechanism of the simultaneous binding of two drugs to a multidrug-binding protein. Schumacher, M.A., Miller, M.C., Brennan, R.G. EMBO J. (2004) [Pubmed]
  12. Efflux-mediated antiseptic resistance gene qacA from Staphylococcus aureus: common ancestry with tetracycline- and sugar-transport proteins. Rouch, D.A., Cram, D.S., DiBerardino, D., Littlejohn, T.G., Skurray, R.A. Mol. Microbiol. (1990) [Pubmed]
  13. A helicase assay based on the displacement of fluorescent, nucleic acid-binding ligands. Eggleston, A.K., Rahim, N.A., Kowalczykowski, S.C. Nucleic Acids Res. (1996) [Pubmed]
  14. Infection by Mycobacterium tuberculosis promotes human alveolar macrophage apoptosis. Keane, J., Balcewicz-Sablinska, M.K., Remold, H.G., Chupp, G.L., Meek, B.B., Fenton, M.J., Kornfeld, H. Infect. Immun. (1997) [Pubmed]
  15. Human lymphoblastoid cell lines derived from individuals without lymphoproliferative disease contain the same latent forms of Epstein-Barr virus DNA as those found in tumor cells. Kaschka-Dierich, C., Falk, L., Bjursell, G., Adams, A., Lindahl, T. Int. J. Cancer (1977) [Pubmed]
  16. NorM, a putative multidrug efflux protein, of Vibrio parahaemolyticus and its homolog in Escherichia coli. Morita, Y., Kodama, K., Shiota, S., Mine, T., Kataoka, A., Mizushima, T., Tsuchiya, T. Antimicrob. Agents Chemother. (1998) [Pubmed]
  17. Base pair motions control the rates and distance dependencies of reductive and oxidative DNA charge transfer. Valis, L., Wang, Q., Raytchev, M., Buchvarov, I., Wagenknecht, H.A., Fiebig, T. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  18. Multiple forms of angiostatin induce apoptosis in endothelial cells. Lucas, R., Holmgren, L., Garcia, I., Jimenez, B., Mandriota, S.J., Borlat, F., Sim, B.K., Wu, Z., Grau, G.E., Shing, Y., Soff, G.A., Bouck, N., Pepper, M.S. Blood (1998) [Pubmed]
  19. Targeted gene transfer to hepatocellular carcinoma cells in vitro using a novel monoclonal antibody-based gene delivery system. Mohr, L., Schauer, J.I., Boutin, R.H., Moradpour, D., Wands, J.R. Hepatology (1999) [Pubmed]
  20. Interaction of noncompetitive inhibitors with the acetylcholine receptor. The site specificity and spectroscopic properties of ethidium binding. Herz, J.M., Johnson, D.A., Taylor, P. J. Biol. Chem. (1987) [Pubmed]
  21. Purified hydrophobic proteins, chargerins, are essential for energy transduction in oxidative phosphorylation. Higuti, T., Takigawa, M., Kotera, Y., Oka, H., Uchida, J., Arakaki, R., Fujita, T., Ogawa, T. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  22. An Ile-568 to Asn polymorphism prevents normal trafficking and function of the human P2X7 receptor. Wiley, J.S., Dao-Ung, L.P., Li, C., Shemon, A.N., Gu, B.J., Smart, M.L., Fuller, S.J., Barden, J.A., Petrou, S., Sluyter, R. J. Biol. Chem. (2003) [Pubmed]
  23. Glu496 to Ala polymorphism in the P2X7 receptor impairs ATP-induced IL-1 beta release from human monocytes. Sluyter, R., Shemon, A.N., Wiley, J.S. J. Immunol. (2004) [Pubmed]
  24. Differential activation of cation channels and non-selective pores by macrophage P2z purinergic receptors expressed in Xenopus oocytes. Nuttle, L.C., Dubyak, G.R. J. Biol. Chem. (1994) [Pubmed]
  25. Assessment of human natural killer and lymphokine-activated killer cell cytotoxicity against Toxoplasma gondii trophozoites and brain cysts. Dannemann, B.R., Morris, V.A., Araujo, F.G., Remington, J.S. J. Immunol. (1989) [Pubmed]
  26. X-ray crystallographic visualization of drug-nucleic acid intercalative binding: structure of an ethidium-dinucleoside monophosphate crystalline complex, Ethidium: 5-iodouridylyl (3'-5') adenosine. Tsai, C.C., Jain, S.C., Sobell, H.M. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  27. Evidence that receptor activator of nuclear factor (NF)-kappaB ligand can suppress cell proliferation and induce apoptosis through activation of a NF-kappaB-independent and TRAF6-dependent mechanism. Bharti, A.C., Takada, Y., Shishodia, S., Aggarwal, B.B. J. Biol. Chem. (2004) [Pubmed]
  28. Endothelial dysfunction in rat adjuvant-induced arthritis: vascular superoxide production by NAD(P)H oxidase and uncoupled endothelial nitric oxide synthase. Haruna, Y., Morita, Y., Komai, N., Yada, T., Sakuta, T., Tomita, N., Fox, D.A., Kashihara, N. Arthritis Rheum. (2006) [Pubmed]
  29. EmrE, an Escherichia coli 12-kDa multidrug transporter, exchanges toxic cations and H+ and is soluble in organic solvents. Yerushalmi, H., Lebendiker, M., Schuldiner, S. J. Biol. Chem. (1995) [Pubmed]
  30. The ATP binding cassette multidrug transporter LmrA and lipid transporter MsbA have overlapping substrate specificities. Reuter, G., Janvilisri, T., Venter, H., Shahi, S., Balakrishnan, L., van Veen, H.W. J. Biol. Chem. (2003) [Pubmed]
  31. Survival and induction of recA protein in mitomycin C-treated Escherichia coli rec, lex, or uvr strains. Giacomoni, P.U. J. Biol. Chem. (1983) [Pubmed]
  32. Oxidant-injured airway epithelial cells upregulate thioredoxin but do not produce interleukin-8. Oslund, K.L., Miller, L.A., Usachenko, J.L., Tyler, N.K., Wu, R., Hyde, D.M. Am. J. Respir. Cell Mol. Biol. (2004) [Pubmed]
  33. Molecular characterization of the staphylococcal multidrug resistance export protein QacC. Paulsen, I.T., Brown, M.H., Dunstan, S.J., Skurray, R.A. J. Bacteriol. (1995) [Pubmed]
  34. Effect of mutation, electric membrane potential, and metabolic inhibitors on the accessibility of nucleic acids to ethidium bromide in Escherichia coli cells. Lambert, B., Le Pecq, J.B. Biochemistry (1984) [Pubmed]
  35. Twist constraints on linker DNA in the 30-nm chromatin fiber: implications for nucleosome phasing. Yao, J., Lowary, P.T., Widom, J. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  36. Purification of closed circular lambda deoxyribonucleic acid and its sedimentation properties as a function of Sodium chloride concentration and ethidium binding. Hinton, D.M., Bode, V.C. J. Biol. Chem. (1975) [Pubmed]
  37. Pathogenesis of mucous cell metaplasia in a murine asthma model. Reader, J.R., Tepper, J.S., Schelegle, E.S., Aldrich, M.C., Putney, L.F., Pfeiffer, J.W., Hyde, D.M. Am. J. Pathol. (2003) [Pubmed]
  38. Electrophoretic analysis of covalently closed SV40 DNA: Boltzmann distributions of DNA species. DeLeys, R.J., Jackson, D.A. Nucleic Acids Res. (1976) [Pubmed]
  39. The binding of polyamines and of ethidium bromide to tRNA. Sakai, T.T., Torget, R., I, J., Freda, C.E., Cohen, S.S. Nucleic Acids Res. (1975) [Pubmed]
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