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Chemical Compound Review

THIOCHOLINE     trimethyl-(1- sulfanylethyl)azanium

Synonyms: AC1L1Z59, 625-00-3, trimethyl(1-sulfanylethyl)azanium, N,N,N-trimethyl-1-sulfanylethanaminium
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Disease relevance of THIOCHOLINE

  • In confirmation of earlier light microscopic findings by the highly specific copper thiocholine method, there was nearly a total disappearance of AChE from the ganglion; no myelinated or unmyelinated axons with AChE-stained axolemmas were found, and only occasional traces of AChE staining were noted at dendritic and perikaryonal plasma membranes [1].
  • The cutaneous nodules obtained from seven patients with von Recklinghausen's neurofibromatosis were investigated by electron microscopy, and ultrastructural localization of acetylcholinesterase activity was demonstrated in the nerve fibers of this tumor for the first time using Karnovsky's thiocholine method [2].

Psychiatry related information on THIOCHOLINE

  • REM sleep deprivation induced a significant decrease of 16% in the membrane-bound Achase activity (nmol thiocholine formed min-1 mg protein-1) in the 100,000 g pellet enzyme preparation (home-cage group 152.1 +/- 5.7, large platform group 152.7 +/- 24.9 and REM sleep-deprived group 127.9 +/- 13.8) [3].

High impact information on THIOCHOLINE

  • Before the infusion of fixative, one of the enzymes was selectively, irreversibly inactivated in vivo, as confirmed by light microscope (LM) examination of sections of the stellate ganglion stained by the more specific copper thiocholine method [4].
  • During the ensuing 72 hr, the regenerating enzyme became detectable by the copper thiocholine histochemical method in the somata of essentially all ganglion cells and in the neuropil [5].
  • This study presents the ultrastructural localization of AChE activity in human thymus cells, using the indirect thiocholine method [6].
  • This study presents the ultrastructural transport and fate of this substance in the megakaryocytes of mouse bone marrow, using Tranum-Jensen and Behnke's adaptation of the indirect thiocholine method [7].
  • This investigation was possible because the nucleus pulvinaris of the thalamus, the main source of subcortical projections to the prestriate cortex, displays positive reactivity after thiocholine incubation during the last three quarters of gestation, while neighboring thalamic nuclei that project to the adjacent neocortical areas are unstained [8].

Biological context of THIOCHOLINE

  • [2-(Trimethylammonium)-ethyl]-methanethiosulfonate (MTSET), which attaches thiocholine to binding site Cys, also acted as an irreversible antagonist when tethered at alphaY93C, alphaN94C, or gammaE57C [9].
  • The immobilized AChE could catalyze the hydrolysis of acetylthiocholine with a K(M)app value of 177 microM to form thiocholine, which was then oxidized to produce detectable signal in a linear range of 1.0-500 microM and fast response [10].
  • Substrate specificities were studied using p-nitrophenyl esters (acetate, propionate and butyrate) and corresponding thiocholine esters as substrates [11].
  • The assay may be used for monitoring the kinetics of enzymatic activities in microscale reaction mixtures, providing a linear determination of the thiocholine produced over a period of at least 30 h at room temperature [12].
  • Although similarity of the N-terminal amino acid sequence of the enzyme with an internal sequence of ChEs is weak, its catalytic activity towards thiocholine esters, and its affinity for positively charged ligands supports the contention that this enzyme may belong to the ChE family [13].

Anatomical context of THIOCHOLINE


Associations of THIOCHOLINE with other chemical compounds

  • In addition to its channel-blocking action, Eco (50 microM) had a weak agonist effect: it is suggested that this may be attributable to thiocholine produced by hydrolysis of Eco [19].
  • The reactions, followed by measuring substrate-dependent thiocholine oxidation [Guo and Ziegler, Anal Biochem 198: 143-148, 1991], were carried out in the presence of 2 mM 1-benzylimidazole to minimize potential interference from reactions other than those catalyzed by isoforms of the flavin-containing monooxygenase (FMO) [20].
  • In this paper, micron long DNA templates stretched on aminosilane- and hexamethyldisilazane-modified silicon surfaces are used to assemble 3.5 nm gold nanoparticles passivated with cationic thiocholine [21].
  • The selenoxide oxidized GSH and thiocholine at rate constants of 1.2 x 10(2) and 7.2 x 10(2) M-1 s-1, respectively at pH 7.4, 37 degrees C. n-Octylamine stimulated the oxidation of the ring-opened metabolites of ebselen catalyzed by pig and guinea pig liver microsomes but it had essentially no effect on these activities in rat liver microsomes [22].
  • The loss of thiocholine in deproteinized aliquots of the reaction medium is measured colorimetrically with the thiol reagent, DTNB [5,5'-dithiobis(2-nitrobenzoate)] [23].

Gene context of THIOCHOLINE


Analytical, diagnostic and therapeutic context of THIOCHOLINE


  1. Electron microscope localization of acetylcholinesterase and butyrylcholinesterase in the superior cervical ganglion of the cat. II. Preganglionically denervated ganglion. Davis, R., Koelle, G.B. J. Cell Biol. (1981) [Pubmed]
  2. Study on the ultrastructure and acetylcholinesterase activity in von Recklinghausen's neurofibromatosis. Kamata, Y. Acta Pathol. Jpn. (1978) [Pubmed]
  3. Rapid eye movement (REM) sleep deprivation reduces rat frontal cortex acetylcholinesterase (EC activity. Camarini, R., Benedito, M.A. Braz. J. Med. Biol. Res. (1997) [Pubmed]
  4. Electron microscope localization of acetylcholinesterase and butyrylcholinesterase in the superior cervical ganglion of the cat. I. Normal ganglion. Davis, R., Koelle, G.B. J. Cell Biol. (1978) [Pubmed]
  5. Identification of the probable site of synthesis of butyrylcholinesterase in the superior cervical and ciliary ganglia of the cat. Uchida, E., Koelle, G.B. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  6. Acetylcholinesterase in human thymus cells. Topilko, A., Caillou, B. Blood (1985) [Pubmed]
  7. Mouse megakaryocytes secrete acetylcholinesterase. Paulus, J.M., Maigne, J., Keyhani, E. Blood (1981) [Pubmed]
  8. Development of prestriate visual projections in the monkey and human fetal cerebrum revealed by transient cholinesterase staining. Kostovic, I., Rakic, P. J. Neurosci. (1984) [Pubmed]
  9. Mapping the agonist binding site of the nicotinic acetylcholine receptor. Orientation requirements for activation by covalent agonist. Sullivan, D.A., Cohen, J.B. J. Biol. Chem. (2000) [Pubmed]
  10. Binding of acetylcholinesterase to multiwall carbon nanotube-cross-linked chitosan composite for flow-injection amperometric detection of an organophosphorous insecticide. Kandimalla, V.B., Ju, H. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  11. Solubilization, molecular forms, purification and substrate specificity of two acetylcholinesterases in the medicinal leech (Hirudo medicinalis). Talesa, V., Grauso, M., Giovannini, E., Rosi, G., Toutant, J.P. Biochem. J. (1995) [Pubmed]
  12. A microfluorometric assay for cholinesterases, suitable for multiple kinetic determinations of picomoles of released thiocholine. Parvari, R., Pecht, I., Soreq, H. Anal. Biochem. (1983) [Pubmed]
  13. Purification, molecular characterization and catalytic properties of a Pseudomonas fluorescens enzyme having cholinesterase-like activity. Rochu, D., Rothlisberger, C., Taupin, C., Renault, F., Gagnon, J., Masson, P. Biochim. Biophys. Acta (1998) [Pubmed]
  14. Vasoactive intestinal polypeptide (VIP)-like immunoreactivity in the nerves of human axillary sweat glands. Vaalasti, A., Tainio, H., Rechardt, L. J. Invest. Dermatol. (1985) [Pubmed]
  15. Prenatal development of nucleus basalis complex and related fiber systems in man: a histochemical study. Kostović, I. Neuroscience (1986) [Pubmed]
  16. Hydrolysis of ester- and amide-type drugs by the purified isoenzymes of nonspecific carboxylesterase from rat liver. Mentlein, R., Heymann, E. Biochem. Pharmacol. (1984) [Pubmed]
  17. On the intrinsic innervation of normal rat liver. Histochemical and scanning electron microscopical studies. Skaaring, P., Bierring, F. Cell Tissue Res. (1976) [Pubmed]
  18. Ultrastructure of acetylcholinesterase synthesizing neurons in the neostriatum. Kaiya, H., Kreutzberg, G.W., Namba, M. Brain Res. (1980) [Pubmed]
  19. Effects of organophosphorus anticholinesterases on nicotinic receptor ion channels at adult mouse muscle endplates. Tattersall, J.E. Br. J. Pharmacol. (1990) [Pubmed]
  20. Use of thiocarbamides as selective substrate probes for isoforms of flavin-containing monooxygenases. Guo, W.X., Poulsen, L.L., Ziegler, D.M. Biochem. Pharmacol. (1992) [Pubmed]
  21. Gold nanoparticle decoration of DNA on silicon. Braun, G., Inagaki, K., Estabrook, R.A., Wood, D.K., Levy, E., Cleland, A.N., Strouse, G.F., Reich, N.O. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  22. The oxidation of ebselen metabolites to thiol oxidants catalyzed by liver microsomes and perfused rat liver. Akerboom, T.P., Sies, H., Ziegler, D.M. Arch. Biochem. Biophys. (1995) [Pubmed]
  23. Estimation of flavin-containing monooxygenase activities in crude tissue preparations by thiourea-dependent oxidation of thiocholine. Guo, W.X., Ziegler, D.M. Anal. Biochem. (1991) [Pubmed]
  24. Acetylcholinesterase and butyrylcholinesterase activities in human thyroid cancer cells. Topilko, A., Caillou, B. Cancer (1988) [Pubmed]
  25. Specificity and orientation of trigonal carboxyl esters and tetrahedral alkylphosphonyl esters in cholinesterases. Hosea, N.A., Berman, H.A., Taylor, P. Biochemistry (1995) [Pubmed]
  26. Expression of a single dimeric membrane-bound acetylcholinesterase in Parascaris equorum. Talesa, V., Romani, R., Grauso, M., Rosi, G., Giovannini, E. Parasitology (1997) [Pubmed]
  27. Comparative inhibition of enzymes of human erythrocytes and plasma in vitro by agricultural chemicals. Dowla, H.A., Panemangalore, M., Byers, M.E. Arch. Environ. Contam. Toxicol. (1996) [Pubmed]
  28. Host-donor interactions in healing of human split-thickness skin grafts onto nude mice: in situ hybridization, immunohistochemical, and histochemical studies. Plenat, F., Vignaud, J.M., Guerret-Stocker, S., Hartmann, D., Duprez, K., Duprez, A. Transplantation (1992) [Pubmed]
  29. The fine structural localization of acetylcholinesterase in the muscle spindle of the rat. Schober, R., Thomas, E. Cell Tissue Res. (1978) [Pubmed]
  30. Autonomic neurons supplying the rat eye and the intraorbital distribution of vasoactive intestinal polypeptide (VIP)-like immunoreactivity. Kuwayama, Y., Grimes, P.A., Ponte, B., Stone, R.A. Exp. Eye Res. (1987) [Pubmed]
  31. Histochemical localization of cholinesterase activity in the dental epithelium of guinea pig teeth. Jayawardena, C.K., Takano, Y. Anat. Embryol. (2004) [Pubmed]
  32. The comparative analysis of the myenteric plexus in pigeon and hen. Kuder, T., Nowak, E., Szczurkowski, A., Kuchinka, J. Anatomia, histologia, embryologia. (2003) [Pubmed]
  33. A method for acetylcholinesterase staining of brain sections previously processed for receptor autoradiography. Lim, M.M., Hammock, E.A., Young, L.J. Biotechnic & histochemistry : official publication of the Biological Stain Commission. (2004) [Pubmed]
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