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Chemical Compound Review

TMANO     N,N-dimethylmethanamine oxide

Synonyms: Triox, TMAO, TMAe, TMA-oxide, AG-D-40837, ...
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Disease relevance of trimethyl-oxido-azanium


Psychiatry related information on trimethyl-oxido-azanium


High impact information on trimethyl-oxido-azanium

  • The trimethylamine N-oxide (TMAO) reductase of Escherichia coli is a soluble periplasmic molybdoenzyme [1].
  • The most intriguing observation is that translocation of the TMAO reductase across the cytoplasmic membrane is independent of the SecY, SecE, SecA and SecB proteins [1].
  • These results strongly suggest that the translocation of the molybdoenzyme TMAO reductase into the periplasm uses a mechanism fundamentally different from general protein translocation [1].
  • The export of the TMAO reductase is driven mainly by the proton motive force, whereas sodium azide exhibits a limited effect on the export [1].
  • Expression of the tor operon is positively controlled by the TorS/TorR phosphorelay system in response to TMAO availability and negatively regulated by apocytochrome TorC [7].

Chemical compound and disease context of trimethyl-oxido-azanium


Biological context of trimethyl-oxido-azanium

  • ApoTorC negative autoregulation and TMAO induction are thus mediated by the same sensor protein [7].
  • TMAO does not act by causing a chemical dephosphorylation of phosphorylated tau, but it acts to overcome the functional deficit caused by phosphorylation [6].
  • This property was exploited in the performance of miniMu replicon-mediated in vivo cloning of the promoter region of gene(s) positively regulated by TMAO [13].
  • The second open reading frame, torA, was identified as the structural gene for TMAO reductase [13].
  • The effect of insulin concentration, agitation, pH, ionic strength, anions, seeding, and addition of 1-anilinonaphthalene-8-sulfonic acid (ANS), urea, TMAO, sucrose, and ThT on the kinetics of fibrillation was investigated [14].

Anatomical context of trimethyl-oxido-azanium

  • Addition of the osmolyte trimethylamine-oxide (TMAO) and the ketolide antibiotic telithromycin (HMR3647) to the reconstitution stimulates its efficiency up to 100-fold yielding a substantially improved system for the in vitro analysis of mutant ribosomes [15].
  • The natural osmolyte trimethylamine N-oxide (TMAO) restores the ability of mutant tau to promote microtubule assembly [16].
  • Treatment of pigs with BAL containing hepatocytes resulted in an improvement of survival, the plasma concentrations of choline and TMAO being decreased in three out of five animals [17].
  • Detergent treatments were examined for their efficacy in purifying trimethylamine-N-oxide (TMAO) demethylase activity from fish muscle microsomes [18].
  • Addition of urea (urea/TMAO, 2:1) did not overcome the detrimental effects of TMAO in the mitochondria of either species [19].

Associations of trimethyl-oxido-azanium with other chemical compounds

  • We then studied the effects of organic solvent dimethyl sulfoxide (DMSO), cellular osmolytes glycerol, and trimethylamine N-oxide (TMAO) on aggregate formation and cell death [20].
  • The frdR mutant was also derepressed for nitrate control of the trimethylamine-N-oxide reductase and alcohol dehydrogenase enzymes [21].
  • Stopped-flow methods, monitoring intrinsic tyrosine fluorescence and far-UV circular dichroism, have been used to measure folding and unfolding kinetics as a function of guanidinium hydrochloride (GdnHCl) and monomer concentrations, in 0 and 1 M TMAO [22].
  • The concentrations of choline and TMAO increased from the beginning to the end in animals treated with the BAL containing alginate beads without hepatocytes [17].
  • RESULTS: The patient's urinalyses showed an augmented TMA (12.64+/-0.95 mg/l) and TMAO (88.42+/-0.82 mg/l) excretion 6 h after the overload test representing an oxidation capacity of 84.6%, consistent with a heterozygosis condition [23].

Gene context of trimethyl-oxido-azanium

  • We confirmed this genetically and biochemically using a strain in which phage MudII 1734 carrying lacZ was inserted into torA, the structural gene for inducible trimethylamine-N-oxide reductase [24].
  • Co-immunoadsorption experiments indicate that in TMAO each of these and the coactivator SRC-1 are found complexed with AF1 [25].
  • The chemical chaperone trimethylamine-N-oxide (TMAO) also reversed the GFP-PDS-mediated ER collapse and vesiculation, suggesting that exposed hydrophobic stretches of misfolded or aggregated GFP-PDS may contribute to ER retention [26].
  • Significantly, the binding of TBP was modulated by induced folding of the TAD with TMAO [27].
  • Surprisingly, TorR autoregulation is TMAO independent and still occurs in a torS mutant [28].

Analytical, diagnostic and therapeutic context of trimethyl-oxido-azanium

  • PKA-phosphorylated tau (2.7 mol phosphates/mol) does not promote tubulin assembly as judged by spectrophotometric and atomic force microscopy measurements, unless trimethylamine N-oxide (TMAO), a natural occurring osmolyte, is included in these assays [6].
  • We show here that in buffers containing the natural osmolyte trimethylamine N-oxide (TMAO), recombinant AF1 folds into more a compact structure, as evidenced by altered fluorescence emission, circular dichroism spectra, and ultracentrifugal analysis [25].
  • Ultracentrifugation studies indicate that AF1/tau1 exists as a monomer in aqueous solution and that the presence of TMAO does not lead to oligomerization or aggregation [25].
  • The equilibrium constant of folding (K(fold)) at 37 degrees C for the P protein was determined to be 0.0071 +/- 0.0005 using a two-state folding model to describe the TMAO titration data [29].
  • Levels were significantly increased after reperfusion (control 0.02 +/- 0.03 micromol/mL, TX24 1.13 +/- 0.22, and TX42 1.89 +/- 0.38, P < 0.001), and correlated with cold ischemia time (r= 0.96) and TMAO (r= 0.94) [30].


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  2. Molecular analysis of the trimethylamine N-oxide (TMAO) reductase respiratory system from a Shewanella species. Dos Santos, J.P., Iobbi-Nivol, C., Couillault, C., Giordano, G., Méjean, V. J. Mol. Biol. (1998) [Pubmed]
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  15. Osmolytes stimulate the reconstitution of functional 50S ribosomes from in vitro transcripts of Escherichia coli 23S rRNA. Semrad, K., Green, R. RNA (2002) [Pubmed]
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  29. Linked folding and anion binding of the Bacillus subtilis ribonuclease P protein. Henkels, C.H., Kurz, J.C., Fierke, C.A., Oas, T.G. Biochemistry (2001) [Pubmed]
  30. H-NMR-based metabolic signatures of mild and severe ischemia/reperfusion injury in rat kidney transplants. Serkova, N., Fuller, T.F., Klawitter, J., Freise, C.E., Niemann, C.U. Kidney Int. (2005) [Pubmed]
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