NGP Faculty

Neuroscience Graduate Program (NGP) faculty are committed to mentor students pursuing BS/MS, MS or PhD degrees within their active lab groups that also include postdoctoral fellows, technicians, and undergraduate students. NGP faculty have strong records of funding from NIH, NSF and a variety of private foundations. Their research interests reflect the breadth and depth of the NPG and highlight the many exciting opportunities open to students. Prospective applicants should contact Dr. Kasper Hansen, who serves as the Director of the NGP and welcomes inquiries from interested students.

Chuck Thompson

Professor

Contact

Office
SB 477A
Phone
406-243-4643
Email
charles.thompson@umontana.edu
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Chuck Thompson

Personal Summary

After completing undergraduate studies in chemistry at Rutgers University in New Jersey, Professor Thompson earned a M.S. and Ph.D. under the auspices of Professor T. Roy Fukuto at the University of California, Riverside. He also conducted post-doctoral training under the supervision of Professor E.J. Corey at Harvard University in 1982, and also with Professor Henry Rapoport at the University of California at Berkeley from 1983-1985. Professor Thompson is a medicinal and bioorganic chemist with interests in biologically active compounds.

Visit Dr. Thompson's Web Site

Education

1978 B.S., Chemistry Rutgers University, New Jersey

1980/2 M.S., PhD Organic Chemistry University of California, Riverside (Prof T Roy Fukuto, advisor)

1983-4 Post-doctoral Associate Harvard University, Cambridge, Massachusetts (Prof EJ Corey, advisor)

1983-5 Post-doctoral Associate University of California, Berkeley (Prof H Rapoport, advisor)

1989 Visiting Research Professor Scripps Research Clinic, La Jolla, CA 2005-6 Visiting Research Professor Human Biomolecular Research Institute, SD, CA

Field of Study

General Interests:

Medicinal and bioorganic chemistry, synthesis and investigation of novel probes of enzyme structure and function, protein mass spectrometry & proteomics, enzyme inhibition and binding kinetics, pharmacophore development and computational modeling of proteins, immunoorganic chemistry.

  1. Glutamate Neurotransmitter System:
    My group designs and synthesizes custom-tailored glutamate analogs to study and differentiate the pharmacology of the glutamate neurotransmitter system proteins, in particular, the excitatory amino acid transporters (EAAT), system Xc- (Sxc) and the glutamate vesicular transporter (VGLUT). Research in our group use protein mass spectrometry to solve the vesicle proteome and identify conjugates of neuroproteins that have been modified by custom ligands.
  2. Mechanism of Toxicity of Organophosphate Insecticides:
    The oevrarching goal of this research is to differentiate between toxic and non-toxic mechanisms of action by organophosphorus compounds using an array of chemical, molecular, and biochemical tools and approaches to identify biomarkers of OP toxicity in cells, tissues and organisms.  One of the dominant approaches used in our lab is chemical tags, for example, the use of fluorophores or isotopes to track and validate OP-modified proteins.  Since most OPs modify the essential neurotransmitter hydrolyzing enzyme acetylcholinesterase (AChE) at an essential serine, OP-AChE conjugates correlate strongly with OP mechanism of action. In our most recent approach, we have modified an organophosphate to contain a positron tracer atom (18F) to study the biodistribution and localization of OP in rodents. 
  3. Other Areas of Interest:

a. Immunoorganic chemistry.

b. Synthesis of phosphorus-containing analogs of alpha amino acids and their utility as inhibitors of matrix metalloproteinases.

c. Synthesis and utility of novel protein probes (fluorescent, UV-Vis, spin label, etc.

 

Selected Publications

1.         Gray, A.J., Thompson, C.M., and Fukuto, T.R., 1982 Distribution and excretion of [14CH3S]methamidophos after intravenous administration of a toxic dose and the relationship with anticholinesterase activity. Pesticide Biochemistry and Physiology. 18(1): p. 28.

2.         Thompson, C.M. and Fukuto, T.R., 1982 Mechanism of cholinesterase inhibition by methamidophos. Journal of Agricultural and Food Chemistry. 30(2): p. 282.

3.         Thompson, C.M., Nishioka, T., and Fukuto, T.R., 1983 Determination of the electron impact fragmentation pattern of methamidophos via stable isotope enrichment. Journal of Agricultural and Food Chemistry. 31(4): p. 696.

4.         Thompson, C.M., Castellino, S., and Fukuto, T.R., 1984 A carbon-13 nuclear magnetic resonance study on an organophosphate. Formation and characterization of methamidophos (O,S-dimethyl phosporamidothioate) S-oxide. The Journal of Organic Chemistry. 49(10): p. 1696.

5.         Rapoport, H., Waterhouse, A.L., Thompson, C.M., and O'Connell, J.F., 1986 Synthesis and radiolabeling of heterocyclic food mutagens. Environ Health Perspect. 67: p. 41-45.

6.         Thompson, C.M., 1987 “Remote” dianions-I. Utility of 4-phenylsulfonylbutanoic acid in the mild conversion of aldehydes and ketones to lactones. . Tetrahedron Letters. 28(37): p. 4243-4246

7.         Thompson, C.M. and Docter, S., 1988 Lewis acid promoted photocyclization of arylimines. Studies directed towards the synthesis of pentacyclic natural products. . Tetrahedron Letters. 29(41): p. 5213-5216

8.         Thompson, C.M., Frick, J.A., and Woytowicz, C.E., 1988 “Remote Dianions II. Synthesis of Sulcatole”. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 18(9): p. 889 - 892.

9.         Thompson, C.M., Green, D.L.C., and Kubas, R., 1988 Remote dianions. 3. Novel synthesis of substituted 2-piperidones from imines. The Journal of Organic Chemistry. 53(22): p. 5389.

10.       Thompson, C.M. and Frick, J.A., 1989 Remote dianions. IV. 4-(Phenylsulfonyl)butanoic acid. Preparation, dianion generation, and application to four-carbon chain extension. The Journal of Organic Chemistry. 54(4): p. 890.

11.       Thompson, C.M., Frick, J.A., Natke, B.C., and Hansen, L.K., 1989 Preparation, analysis, and anticholinesterase properties of O,O- dimethyl phosphorothioate isomerides. Chem Res Toxicol. 2(6): p. 386-391.

12.       Thompson, C.M., Frick, J.A., and Green, D.L.C., 1990 Synthesis, configuration, and chemical shift correlations of chiral 1,3,2-oxazaphospholidin-2-ones derived from l-serine. The Journal of Organic Chemistry. 55(1): p. 111.

13.       Green, D.L.C. and Thompson, C.M., 1991 “Remote” dianions 5. Synthesis of δ-coniceine Tetrahedron Letters. 32(38): p. 5051-5054

14.       Ryu, S., Jackson, J.A., and Thompson, C.M., 1991 Methanolysis of phosphoramidates with boron trifluoride-methanol complex. The Journal of Organic Chemistry. 56(16): p. 4999.

15.       Ryu, S.M., Lin, J., and Thompson, C.M., 1991 Comparative anticholinesterase potency of chiral isoparathion methyl. Chem Res Toxicol. 4(5): p. 517-520.

16.       Thompson, C.M. and Green, D.L.C., 1991 Recent advances in dianion chemistry. Tetrahedron. 47(25): p. 4223-4285

17.       Berkman, C.E. and Thompson, C.M., 1992 Synthesis of chiral malathion and isomalathion Tetrahedron Letters. 33(11): p. 1415-1418

18.       Bierer, D.E., O'Connell, J.F., Parquette, J.R., Thompson, C.M., and Rapoport, H., 1992 Regiospecific synthesis of the aminoimidazoquinoxaline (IQx) mutagens from cooked foods. The Journal of Organic Chemistry. 57(5): p. 1390.

19.       Huh, N. and Thompson, C.M., 1992 Chiral, piperidine-based analogues of AF64A and acetylcholine Bioorg Med Chem Lett. 2(12): p. 1551-1554

20.       Jackson, J.A., Berkman, C.E., and Thompson, C.M., 1992 Stereoselective and chemoselective oxidation of phosphorothionates using MMPP Tetrahedron Letters. 33(41): p. 6061-6064

21.       Jackson, J.A., Frick, J.A., and Thompson, C.M., 1992 Synthesis of chiral phosphorus mustards derived from serine Bioorg Med Chem Lett. 2(12): p. 1547-1550

22.       Thompson, C.M., Preparation, Analysis and Toxicity of Phosphorothiolates, in Organophosphates:  Chemistry, Fate and Effects., J.E. Chambers and P.E. Levi, Editors. 1992, Academic Press: San Diego. p. 19-46.

23.       Thompson, C.M., 1992 A Route to 1-Azaspirans Related to Perhydrohistrionicotoxin. Heterocycles. 34(5): p. 979-990

24.       Thompson, C.M., Ryu, S., and Berkman, C.E., 1992 Consequence of phosphorus stereochemistry upon the postinhibitory reaction kinetics of acetylcholinesterase poisoned by phosphorothiolates. Journal of the American Chemical Society. 114(27): p. 10710.

25.       Williams, K. and Thompson, C.M., 1992 Preparation of Oxepan-2-ones (ε-Lactones) via the Dianion of 4-(Phenylsulfonyl)butanoic Acid. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 22(2): p. 239 - 244.

26.       Berkman, C.E., Fernandez, E.J., Thompson, C.M., and Pavkovic, S.F., 1993 Structure of 19-methylstrychninium (S)-{S-[(R)-1,2-di(ethoxycarbonyl)ethyl] O-methyl phosphorodithioate}. Acta Crystallographica Section C. 49(3): p. 554-556.

27.       Berkman, C.E., Quinn, D.A., and Thompson, C.M., 1993 Interaction of acetylcholinesterase with the enantiomers of malaoxon and isomalathion. Chem Res Toxicol. 6(5): p. 724-730.

28.       Berkman, C.E., Ryu, S., Quinn, D.A., and Thompson, C.M., 1993 Kinetics of the postinhibitory reactions of acetylcholinesterase poisoned by chiral isomalathion: a surprising nonreactivation induced by the RP stereoisomers. Chem Res Toxicol. 6(1): p. 28-32.

29.       Berkman, C.E., Thompson, C.M., and Perrin, S.R., 1993 Synthesis, absolute configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers. Chem Res Toxicol. 6(5): p. 718-723.

30.       Thompson, C.M., Suarez, A.I., Lin, J., and Jackson, J.A., 1993 Synthesis of phosphorylated tripeptides representing poisoned acetylcholinesterase Tetrahedron Letters. 34(41): p. 6529-6532

31.       Lin, J. and Thompson, C.M., 1994 The synthesis of biologically relevant 4(5)-phosphono-5(4)-aminoimidazoles using a Pd-catalyzed coupling reaction. Journal of Heterocyclic Chemistry. 31(6): p. 1701-1705.

32.       Green, D.L.C., Kiddle, J.J., and Thompson, C.M., 1995 Stereochemistry of remote dianion addition to imines. Application to the synthesis of (1S, 8aS)-1-hydroxyindolizidine Tetrahedron. 51(10): p. 2865-2874

33.       Huh, N. and Thompson, C.M., 1995 Enantioenriched N-(2-chloroalkyl)-3-acetoxypiperidines as potential cholinotoxic agents. Synthesis and preliminary evidence for spirocyclic aziridinium formation Tetrahedron. 51(21): p. 5935-5950

34.       Kiddle, J.J., Green, D.L.C., and Thompson, C.M., 1995 Synthesis of 5-substituted indolizidines and approaches to 3- and 8-substituted indolizidines from a common intermediate accessed via the remote dianion of 4-PSBA Tetrahedron. 51(10): p. 2851-2864.

35.       Saadeh, H., Thompson, C.M., Fernandez, E., and Pavkovic, S.F., 1995 1-Benzyl-5-methoxycarbonylmethylthio-4-nitroimidazole. Acta Crystallographica Section C. 51(5): p. 950-952.

36.       Jianmongkol, S., Berkman, C.E., Thompson, C.M., and Richardson, R.J., 1996 Relative potencies of the four stereoisomers of isomalathion for inhibition of hen brain acetylcholinesterase and neurotoxic esterase in vitro. Toxicol Appl Pharmacol. 139(2): p. 342-348.

37.       Rodriguez, O.P. and Thompson, C.M., 1996 Synthesis of sterically hindered phosphonamidothiolates and phosphonamidothioates. Phosphorus, Sulfur, and Silicon and the Related Elements. 117(1): p. 101 - 110.

38.       Suarez, A.I., Lin, J., and Thompson, C.M., 1996 Synthesis and pKa evaluation of model phosphonamidic, phosphonamidothioic, and phosphonamidodithioic acids Tetrahedron. 52(17): p. 6117-6124.

39.       Thompson, C.M. and Lin, J., 1996 Synthesis of P-chiral, phosphorothioic acid analogs of N-phospholeucinamide Tetrahedron Letters. 37(50): p. 8979-8982

40.       Thompson, C.M., Suarez, A.I., and Rodriguez, O.P., 1996 Synthesis and 31P chemical shift identification of tripeptide active site models that represent human serum acetylcholinesterase covalently modified at serine by certain organophosphates. Chem Res Toxicol. 9(8): p. 1325-1332.

41.       Hamed, O., Thompson, C., and Henry, P.M., 1997 Stereochemistry of the Wacker Reaction: Modes of Addition of Hydroxide, Methoxide, and Phenyl at High and Low [Cl(-)]. A Study Using Chirality Transfer. J Org Chem. 62(21): p. 7082-7083.

42.       Rodriguez, O.P., Muth, G.W., Berkman, C.E., Kim, K., and Thompson, C.M., 1997 Inhibition of various cholinesterases with the enantiomers of malaoxon. Bull Environ Contam Toxicol. 58(2): p. 171-176.

43.       Bartlett, R.D., Esslinger, C.S., Thompson, C.M., and Bridges, R.J., 1998 Substituted quinolines as inhibitors of L-glutamate transport into synaptic vesicles. Neuropharmacology. 37(7): p. 839-846.

44.       Esslinger, C.S., Koch, H.P., Kavanaugh, M.P., Philips, D.P., Chamberlin, A.R., Thompson, C.M., and Bridges, R.J., 1998 Structural determinants of substrates and inhibitors: probing glutamate transporters with 2,4-methanopyrrolidine-2,4-dicarboxylate. Bioorg Med Chem Lett. 8(21): p. 3101-3106.

45.       Carrigan, C.N., Esslinger, C.S., Bartlett, R.D., Bridges, R.J., and Thompson, C.M., 1999 Quinoline-2,4-dicarboxylic acids: synthesis and evaluation as inhibitors of the glutamate vesicular transport system. Bioorg Med Chem Lett. 9(17): p. 2607-2612.

46.       Hamed, O., Henry, P.M., and Thompson, C., 1999 Palladium(II)-Catalyzed Exchange and Isomerization Reactions. 17. Exchange of Chiral Allyl Alcohols with Hydroxide, Methoxide, and Phenyl at High [Cl-]. Stereochemistry of the Wacker Reaction. The Journal of Organic Chemistry. 64(21): p. 7745.

47.       Jianmongkol, S., Marable, B.R., Berkman, C.E., Talley, T.T., Thompson, C.M., and Richardson, R.J., 1999 Kinetic evidence for different mechanisms of acetylcholinesterase inhibition by (1R)- and (1S)-stereoisomers of isomalathion. Toxicol Appl Pharmacol. 155(1): p. 43-53.

48.       Muth, G.W., Thompson, C.M., and Hill, W.E., 1999 Cleavage of a 23S rRNA pseudoknot by phenanthroline-Cu(II). Nucleic Acids Res. 27(8): p. 1906-1911.

49.       Doorn, J.A., Gage, D.A., Schall, M., Talley, T.T., Thompson, C.M., and Richardson, R.J., 2000 Inhibition of acetylcholinesterase by (1S,3S)-isomalathion proceeds with loss of thiomethyl: kinetic and mass spectral evidence for an unexpected primary leaving group. Chem. Res. Toxicol. 13(12): p. 1313-1320.

50.       Saltmarsh, J.R., Boyd, A.E., Rodriguez, O.P., Radic, Z., Taylor, P., and Thompson, C.M., 2000 Synthesis of fluorescent probes directed to the active site gorge of acetylcholinesterase. Bioorg Med Chem Lett. 10(14): p. 1523-1526.

51.       Denton, T.T., Thompson, C.M., and Cooper, A.J., 2001 Analysis of conformationally restricted alpha-ketoglutarate analogues as substrates of dehydrogenases and aminotransferases. Anal Biochem. 298(2): p. 265-274.

52.       Doorn, J.A., Schall, M., Gage, D.A., Talley, T.T., Thompson, C.M., and Richardson, R.J., 2001 Identification of butyrylcholinesterase adducts after inhibition with isomalathion using mass spectrometry: difference in mechanism between (1R)- and (1S)-stereoisomers. Toxicol Appl Pharmacol. 176(2): p. 73-80.

53.       Doorn, J.A., Talley, T.T., Thompson, C.M., and Richardson, R.J., 2001 Probing the active sites of butyrylcholinesterase and cholesterol esterase with isomalathion: conserved stereoselective inactivation of serine hydrolases structurally related to acetylcholinesterase. Chem Res Toxicol. 14(7): p. 807-813.

54.       Carrigan, C.N., Bartlett, R.D., Esslinger, C.S., Cybulski, K.A., Tongcharoensirikul, P., Bridges, R.J., and Thompson, C.M., 2002 Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport. J Med Chem. 45(11): p. 2260-2276.

55.       Denton, T., Seib, T., Bridges, R., and Thompson, C., 2002 Synthesis and preliminary evaluation of trans-3,4-conformationally-restricted glutamate and pyroglutamate analogues as novel EAAT2 inhibitors. Bioorg Med Chem Lett. 12(21): p. 3209-3213.

56.       George, K.M., Montgomery, M.A., Sandoval, L.E., and Thompson, C.M., 2002 Examination of cross-antigenicity of acetylcholinesterase and butyrylcholinesterase using anti-acetylcholinesterase antibodies. Toxicol Lett. 126(2): p. 99-105.

57.       Trautmann, J., Suarez, A.I., Tongcharoensirikul, P., Muth, G.W., and Thompson, C.M., 2002 A Facile Route to Substituted Dimethoxy Phosphonothionates Using Dimethyl Thiophosphite. Phosphorus, Sulfur & Silicon & the Related Elements. 177(2): p. 471.

58.       Doorn, J.A., Thompson, C.M., Christner, R.B., and Richardson, R.J., 2003 Stereoselective inactivation of Torpedo californica acetylcholinesterase by isomalathion: inhibitory reactions with (1R)- and (1S)-isomers proceed by different mechanisms. Chem Res Toxicol. 16(8): p. 958-965.

59.       George, K.M., Schule, T., Sandoval, L.E., Jennings, L.L., Taylor, P., and Thompson, C.M., 2003 Differentiation between acetylcholinesterase and the organophosphate-inhibited form using antibodies and the correlation of antibody recognition with reactivation mechanism and rate. J Biol Chem. 278(46): p. 45512-45518.

60.       Coughenour, H.D., Spaulding, R.S., and Thompson, C.M., 2004 The synaptic vesicle proteome: a comparative study in membrane protein identification. Proteomics. 4(10): p. 3141-3155.

61.       Tongcharoensirikul, P., Suarez, A.I., Voelker, T., and Thompson, C.M., 2004 Stereoselective addition of dimethyl thiophosphite to imines. J Org Chem. 69(7): p. 2322-2326.

62.       Bunik, V.I., Denton, T.T., Xu, H., Thompson, C.M., Cooper, A.J., and Gibson, G.E., 2005 Phosphonate analogues of alpha-ketoglutarate inhibit the activity of the alpha-ketoglutarate dehydrogenase complex isolated from brain and in cultured cells. Biochemistry. 44(31): p. 10552-10561.

63.       Li, H., Schopfer, L., Spaulding, R., Thompson, C.M., and Lockridge, O., 2005 Identification of organophosphate-reactive proteins by tandem mass spectrometry. Chem Biol Interact. 157-158: p. 383-384.

64.       Lockridge, O., Duysen, E.G., Voelker, T., Thompson, C.M., and Schopfer, L.M., 2005 Life without acetylcholinesterase: the implications of cholinesterase inhibitor toxicity in AChE-knockout mice. Environmental Toxicology and Pharmacology. 19(3): p. 463.

65.       Peeples, E.S., Schopfer, L.M., Duysen, E.G., Spaulding, R., Voelker, T., Thompson, C.M., and Lockridge, O., 2005 Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicol Sci. 83(2): p. 303-312.

66.       Schopfer, L.M., Champion, M.M., Tamblyn, N., Thompson, C.M., and Lockridge, O., 2005 Characteristic mass spectral fragments of the organophosphorus agent FP-biotin and FP-biotinylated peptides from trypsin and bovine albumin (Tyr410). Anal Biochem. 345(1): p. 122-132.

67.       Schopfer, L.M., Voelker, T., Bartels, C.F., Thompson, C.M., and Lockridge, O., 2005 Reaction kinetics of biotinylated organophosphorus toxicant, FP-biotin, with human acetylcholinesterase and human butyrylcholinesterase. Chem Res Toxicol. 18(4): p. 747-754.

68.       Thiagaraj, H.V., Russo, E.B., Burnett, A., Goldstein, E., Thompson, C.M., and Parker, K.K., 2005 Binding properties of dipropyltryptamine at the human 5-HT1a receptor. Pharmacology. 74(4): p. 193-199.

69.       Thompson, C.M., Davis, E., Carrigan, C.N., Cox, H.D., Bridges, R.J., and Gerdes, J.M., 2005 Inhibitors of the glutamate vesicular transporter (VGLUT). Curr Med Chem. 12(18): p. 2041-2056.

70.       Thullbery, M.D., Cox, H.D., Schule, T., Thompson, C.M., and George, K.M., 2005 Differential localization of acetylcholinesterase in neuronal and non-neuronal cells. J Cell Biochem. 96(3): p. 599-610.

71.       Santos, S.S., Gibson, G.E., Cooper, A.J., Denton, T.T., Thompson, C.M., Bunik, V.I., Alves, P.M., and Sonnewald, U., 2006 Inhibitors of the alpha-ketoglutarate dehydrogenase complex alter [1-13C]glucose and [U-13C]glutamate metabolism in cerebellar granule neurons. J Neurosci Res. 83(3): p. 450-458.

72.       Spaulding, R.S., George, K.M., and Thompson, C.M., 2006 Analysis and sequencing of the active-site peptide from native and organophosphate-inactivated acetylcholinesterase by electrospray ionization, quadrupole/time-of-flight (QTOF) mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 830(1): p. 105-113.

73.       Patel, S.A., Nagy, J.O., Bolstad, E.D., Gerdes, J.M., and Thompson, C.M., 2007 Tetrapeptide inhibitors of the glutamate vesicular transporter (VGLUT). Bioorg Med Chem Lett. 17(18): p. 5125-5128.

74.       Cox, H.D., Chao, C.K., Patel, S.A., and Thompson, C.M., 2008 Efficient digestion and mass spectral analysis of vesicular glutamate transporter 1: a recombinant membrane protein expressed in yeast. J Proteome Res. 7(2): p. 570-578.

75.       Cox, H.D. and Thompson, C.M., 2008 Purification and proteomic analysis of synaptic vesicles. Methods Mol Biol. 432: p. 259-274.

76.       Ding, S.J., Carr, J., Carlson, J.E., Tong, L., Xue, W., Li, Y., Schopfer, L.M., Li, B., Nachon, F., Asojo, O., Thompson, C.M., Hinrichs, S.H., Masson, P., and Lockridge, O., 2008 Five tyrosines and two serines in human albumin are labeled by the organophosphorus agent FP-biotin. Chem Res Toxicol. 21(9): p. 1787-1794.

77.       Grigoryan, H., Schopfer, L.M., Thompson, C.M., Terry, A.V., Masson, P., and Lockridge, O., 2008 Mass spectrometry identifies covalent binding of soman, sarin, chlorpyrifos oxon, diisopropyl fluorophosphate, and FP-biotin to tyrosines on tubulin: a potential mechanism of long term toxicity by organophosphorus agents. Chem Biol Interact. 175(1-3): p. 180-186.

78.       Bharate, S.B., Guo, L., Reeves, T.E., Cerasoli, D.M., and Thompson, C.M., 2009 New series of monoquaternary pyridinium oximes: Synthesis and reactivation potency for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase. Bioorg Med Chem Lett. 19(17): p. 5101-5104.

79.       Diaz, P., Phatak, S.S., Xu, J., Fronczek, F.R., Astruc-Diaz, F., Thompson, C.M., Cavasotto, C.N., and Naguib, M., 2009 2,3-Dihydro-1-benzofuran derivatives as a series of potent selective cannabinoid receptor 2 agonists: design, synthesis, and binding mode prediction through ligand-steered modeling. ChemMedChem. 4(10): p. 1615-1629.

80.       Grigoryan, H., Schopfer, L.M., Peeples, E.S., Duysen, E.G., Grigoryan, M., Thompson, C.M., and Lockridge, O., 2009 Mass spectrometry identifies multiple organophosphorylated sites on tubulin. Toxicol Appl Pharmacol. 240(2): p. 149-158.

81.       Guo, L., Thompson, C.M., and Twamley, B., 2009 Diastereomers (R(C),S(P))- and (R(C),R(P))-S-methyl P-(3-azidopropyl)-N-[(1R)-1-phenylethyl]phosphonamidothioate. Acta Crystallogr C. 65(Pt 4): p. o179-182.

82.       Li, B., Schopfer, L.M., Grigoryan, H., Thompson, C.M., Hinrichs, S.H., Masson, P., and Lockridge, O., 2009 Tyrosines of human and mouse transferrin covalently labeled by organophosphorus agents: a new motif for binding to proteins that have no active site serine. Toxicol Sci. 107(1): p. 144-155.

83.       Mullins, J.E., Etoga, J.L., Gajewski, M., Degraw, J.I., and Thompson, C.M., 2009 Unexpected Formation of Highly Functionalized Dihydropyrans via Addition-Cyclization Reactions Between Dimethyl Oxoglutaconate and alpha,beta-Unsaturated Hydrazones. Tetrahedron Lett. 50(20): p. 2298-2300.

84.       Bharate, S.B., Guo, L., Reeves, T.E., Cerasoli, D.M., and Thompson, C.M., 2010 Bisquaternary pyridinium oximes: Comparison of in vitro reactivation potency of compounds bearing aliphatic linkers and heteroaromatic linkers for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase. Bioorg Med Chem. 18(2): p. 787-794.

85.       Bharate, S.B., Prins, J.M., George, K.M., and Thompson, C.M., 2010 Thionate versus Oxon: comparison of stability, uptake, and cell toxicity of ((14)CH(3)O)(2)-labeled methyl parathion and methyl paraoxon with SH-SY5Y cells. J Agric Food Chem. 58(14): p. 8460-8466.

86.       Bharate, S.B. and Thompson, C.M., 2010 Antimicrobial, antimalarial, and antileishmanial activities of mono- and bis-quaternary pyridinium compounds. Chem Biol Drug Des. 76(6): p. 546-551.

87.       Etoga, J.L., Ahmed, S.K., Patel, S., Bridges, R.J., and Thompson, C.M., 2010 Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system x(c)(-) over the vesicular glutamate transporter. Bioorg Med Chem Lett. 20(8): p. 2680-2683.

88.       Guo, L., Suarez, A.I., Braden, M.R., Gerdes, J.M., and Thompson, C.M., 2010 Inhibition of acetylcholinesterase by chromophore-linked fluorophosphonates. Bioorg Med Chem Lett. 20(3): p. 1194-1197.

89.       Guo, L., Suarez, A.I., and Thompson, C.M., 2010 Inactivation of acetylcholinesterase by various fluorophores. J Enzyme Inhib Med Chem. 25(1): p. 116-120.

90.       Prins, J.M., Brooks, D.M., Thompson, C.M., and Lurie, D.I., 2010 Chronic low-level Pb exposure during development decreases the expression of the voltage-dependent anion channel in auditory neurons of the brainstem. NeuroToxicology. 31(6): p. 662-673.

91.       Prins, J.M., George, K.M., and Thompson, C.M., 2010 Paraoxon-induced protein expression changes to SH-SY5Y cells. Chem Res Toxicol. 23(11): p. 1656-1662.

92.       Proskocil, B.J., Bruun, D.A., Thompson, C.M., Fryer, A.D., and Lein, P.J., 2010 Organophosphorus pesticides decrease M2 muscarinic receptor function in guinea pig airway nerves via indirect mechanisms. PLoS ONE. 5(5): p. e10562.

93.       Thompson, C.M., Prins, J.M., and George, K.M., 2010 Mass spectrometric analyses of organophosphate insecticide oxon protein adducts. Environ Health Perspect. 118(1): p. 11-19.

94.       Ye, R., Rhoderick, J.F., Thompson, C.M., and Bridges, R.J., 2010 Functional expression, purification and high sequence coverage mass spectrometric characterization of human excitatory amino acid transporter EAAT2. Protein Expression and Purification. 74(1): p. 49-59.

95.       Ahmed, S.K., Etoga, J.L., Patel, S.A., Bridges, R.J., and Thompson, C.M., 2011 Use of the hydantoin isostere to produce inhibitors showing selectivity toward the vesicular glutamate transporter versus the obligate exchange transporter system x(c)(-). Bioorg Med Chem Lett. 21(14): p. 4358-4362.

96.       Petrov, R.R., Ferrini, M.E., Jaffar, Z., Thompson, C.M., Roberts, K., and Diaz, P., 2011 Design and evaluation of a novel fluorescent CB2 ligand as probe for receptor visualization in immune cells. Bioorg Med Chem Lett. 21: p. 5859–5862.

97.       Calderon-Garciduenas, L., Cross, J.V., Franco-Lira, M., Aragon-Flores, M., Kavanaugh, M., Torres-Jardon, R., Chao, C.-k., Thompson, C., Chang, J., Zhu, H., and D'Angiulli, A., 2013 Brain immune interactions and air pollution: Macrophage inhibitory factor (MIF), Prion cellular protein (PrPC), Interleukin-6 (IL-6), Interleukin 1 receptor antagonist (IL-1Ra), and Interleukin-2 (IL-2) in cerebrospinal fluid and MIF in serum differentiate urban children exposed to severe versus low air pollution. Frontiers in Neuroscience. 7.

98.       Kaleem Ahmed, S., Belabassi, Y., Sankaranarayanan, L., Chao, C.K., Gerdes, J.M., and Thompson, C.M., 2013 Synthesis and anti-acetylcholinesterase properties of novel beta- and gamma-substituted alkoxy organophosphonates. Bioorg Med Chem Lett. 23(7): p. 2048-2051.

99.       Belabassi, Y., Chao, C.K., Holly, R., George, K.M., Nagy, J.O., and Thompson, C.M., 2014 Preparation and characterization of diethoxy- and monoethoxy phosphylated ('aged') serine haptens and use in the production of monoclonal antibodies. Chem Biol Interact.

100.     Carrigan, C.N., Patel, S.A., Cox, H.D., Bolstad, E.S., Gerdes, J.M., Smith, W.E., Bridges, R.J., and Thompson, C.M., 2014 The development of benzo- and naphtho-fused quinoline-2,4-dicarboxylic acids as vesicular glutamate transporter (VGLUT) inhibitors reveals a possible role for neuroactive steroids. Bioorg Med Chem Lett. 24(3): p. 850-854.

101.     Hitt, D.M., Belabassi, Y., Suhy, J., Berkman, C.E., and Thompson, C.M., 2014 Chemoenzymatic resolution of -malathion. Tetrahedron Asymmetry. 25(6-7): p. 529-533.

102.     James, S.L., Ahmed, S.K., Murphy, S., Braden, M.R., Belabassi, Y., VanBrocklin, H.F., Thompson, C.M., and Gerdes, J.M., 2014 A novel fluorine-18 beta-fluoroethoxy organophosphate positron emission tomography imaging tracer targeted to central nervous system acetylcholinesterase. ACS Chem Neurosci. 5(7): p. 519-524.

103.     Prins, J.M., Chao, C.K., Jacobson, S.M., Thompson, C.M., and George, K.M., 2014 Oxidative stress resulting from exposure of a human salivary gland cells to paraoxon: an in vitro model for organophosphate oral exposure. Toxicol In Vitro. 28(5): p. 715-721.

 

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