772
Views
3
CrossRef citations to date
0
Altmetric
Research Article

Thioesters for the in vitro evaluation of agents to image brain cholinesterases

, , , , &
Pages 447-455 | Received 31 Oct 2011, Accepted 29 Nov 2011, Published online: 11 Jan 2012

References

  • Davies P, Maloney AJ. Selective loss of central cholinergic neurons in Alzheimer’s disease. Lancet 1976;2:1403.
  • Bartus RT,Dean RL 3rd, Beer B, Lippa AS. The cholinergic hypothesis of geriatric memory dysfunction. Science 1982;217:408–414.
  • Whitehouse PJ, Price DL, Struble RG, Clark AW, Coyle JT, Delon MR. Alzheimer’s disease and senile dementia: loss of neurons in the basal forebrain. Science 1982;215:1237–1239.
  • Nizri E, Hamra-Amitay Y, Sicsic C, Lavon I, Brenner T. Anti-inflammatory properties of cholinergic up-regulation: A new role for acetylcholinesterase inhibitors. Neuropharmacology 2006;50:540–547.
  • Darvesh S, Leblanc AM, Macdonald IR, Reid GA, Bhan V, Macaulay RJ et al. Butyrylcholinesterase activity in multiple sclerosis neuropathology. Chem Biol Interact 2010;187:425–431.
  • Barbosa M, Rios O, Velásquez M, Villalobos J, Ehrmanns J. Acetylcholinesterase and butyrylcholinesterase histochemical activities and tumor cell growth in several brain tumors. Surg Neurol 2001;55:106–112.
  • Silver A. (1974). The biology of cholinesterases. Amsterdam, The Netherlands: Elsevier.
  • Friede RL. Enzyme histochemical studies of senile plaques. J Neuropathol Exp Neurol 1965;24:477–491.
  • Geula C, Mesulam M. Special properties of cholinesterases in the cerebral cortex of Alzheimer’s disease. Brain Res 1989;498:185–189.
  • Carson KA, Geula C, Mesulam MM. Electron microscopic localization of cholinesterase activity in Alzheimer brain tissue. Brain Res 1991;540:204–208.
  • Morán MA, Mufson EJ, Gómez-Ramos P. Colocalization of cholinesterases with beta amyloid protein in aged and Alzheimer’s brains. Acta Neuropathol 1993;85:362–369.
  • Gómez-Ramos P, Bouras C, Morán MA. Ultrastructural localization of butyrylcholinesterase on neurofibrillary degeneration sites in the brains of aged and Alzheimer’s disease patients. Brain Res 1994;640:17–24.
  • Mesulam MM, Geula C. Butyrylcholinesterase reactivity differentiates the amyloid plaques of aging from those of dementia. Ann Neurol 1994;36:722–727.
  • Geula C, Mesulam MM. Cholinesterases and the pathology of Alzheimer disease. Alzheimer Dis Assoc Disord 1995;9 Suppl 2:23–28.
  • Guillozet AL, Smiley JF, Mash DC, Mesulam MM. Butyrylcholinesterase in the life cycle of amyloid plaques. Ann Neurol 1997;42:909–918.
  • Darvesh S, Reid GA, Martin E. Biochemical and histochemical comparison of cholinesterases in normal and Alzheimer brain tissues. Curr Alzheimer Res 2010;7:386–400.
  • Irie T, Fukushi K, Akimoto Y, Tamagami H, Nozaki T. Design and evaluation of radioactive acetylcholine analogs for mapping brain acetylcholinesterase (AchE) in vivo. Nucl Med Biol 1994;21:801–808.
  • Kilbourn MR, Snyder SE, Sherman PS, Kuhl DE. In vivo studies of acetylcholinesterase activity using a labeled substrate, N-[11C]methylpiperdin-4-yl propionate ([11C]PMP). Synapse 1996;22:123–131.
  • Kilbourn MR, Nguyen TB, Snyder SE, Sherman P. N-[11C]methylpiperidine esters as acetylcholinesterase substrates: an in vivo structure-reactivity study. Nucl Med Biol 1998;25:755–760.
  • Snyder SE, Tluczek L, Jewett DM, Nguyen TB, Kuhl DE, Kilbourn MR. Synthesis of 1-[11C]methylpiperidin-4-yl propionate ([11C]PMP) for in vivo measurements of acetylcholinesterase activity. Nucl Med Biol 1998;25:751–754.
  • Irie T, Fukushi K, Namba H, Iyo M, Tamagami H, Nagatsuka S et al. Brain acetylcholinesterase activity: validation of a PET tracer in a rat model of Alzheimer’s disease. J Nucl Med 1996;37:649–655.
  • Snyder SE, Gunupudi N, Sherman PS, Butch ER, Skaddan MB, Kilbourn MR et al. Radiolabeled cholinesterase substrates: in vitro methods for determining structure-activity relationships and identification of a positron emission tomography radiopharmaceutical for in vivo measurement of butyrylcholinesterase activity. J Cereb Blood Flow Metab 2001;21:132–143.
  • Kuhl DE, Koeppe RA, Snyder SE, Minoshima S, Frey KA, Kilbourn MR. In vivo butyrylcholinesterase activity is not increased in Alzheimer’s disease synapses. Ann Neurol 2006;59:13–20.
  • Macdonald IR, Reid GA, Joy EE, Pottie IR, Matte G, Burrell S, Mawko G, Martin E, Darvesh S. Synthesis and preliminary evaluation of piperidinyl and pyrrolidinyl iodobenzoates as imaging agents for butyrylcholinesterase. Mol Imaging Biol 2010. doi: 10.1007/s11307-010-0448-0.
  • Kikuchi T, Fukushi K, Ikota N, Ueda T., Nagatsuka S., Arano Y, Irie T. Synthesis of piperidinyl and pyrrolidinyl butyrates for potential In Vivo measurement of cerebral butyrylcholinesterase activity. J Labelled Comp Rad 2001;44:31–41.
  • Ellman GL, Courtney KD, Andres V Jr,Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
  • Pottie IR, Higgins EA, Blackman RA, Macdonald IR, Martin E, Darvesh S. Cysteine thioesters as myelin proteolipid protein analogues to examine the role of butyrylcholinesterase in myelin decompaction. ACS Chem Neurosci 2011;2:151–159.
  • Masson P, Froment MT, Gillon E, Nachon F, Lockridge O, Schopfer LM. Hydrolysis of oxo- and thio-esters by human butyrylcholinesterase. Biochim Biophys Acta 2007;1774:16–34.
  • Karnovsky MJ, Roots L. A “Direct-coloring” thiocholine method for cholinesterases. J Histochem Cytochem 1964;12:219–221.
  • Barrera H, Lyle RE. Piperidine derivatives with a sulfur-containing function in the 4-position. J Org Chem 1962;27:641–643.
  • Darvesh S, Kumar R, Roberts S, Walsh R, Martin E. Butyrylcholinesterase-Mediated enhancement of the enzymatic activity of trypsin. Cell Mol Neurobiol 2001;21:285–296.
  • Spartan’06 Program. (2006). Irvine, CA: Wavefunction Inc.
  • Darvesh S, Grantham DL, Hopkins DA. Distribution of butyrylcholinesterase in the human amygdala and hippocampal formation. J Comp Neurol 1998;393:374–390.
  • Meanwell NA, Hewawasam P, Thomas JA, Wright JJ, Russell JW, Gamberdella M et al. Inhibitors of blood platelet cAMP phosphodiesterase. 4. Structural variation of the side-chain terminus of water-soluble 1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one derivatives. J Med Chem 1993;36:3251–3264.
  • Darvesh S, McDonald RS, Darvesh KV, Mataija D, Mothana S, Cook H et al. On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases. Bioorg Med Chem 2006;14:4586–4599.
  • Darvesh S, Hopkins DA. Differential distribution of butyrylcholinesterase and acetylcholinesterase in the human thalamus. J Comp Neurol 2003;463:25–43.
  • Darvesh S, Walsh R, Kumar R, Caines A, Roberts S, Magee D et al. Inhibition of human cholinesterases by drugs used to treat Alzheimer disease. Alzheimer Dis Assoc Disord 2003;17:117–126.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.