Liver prenylated methylated protein methyl esterase is an organophosphate-sensitive enzyme

Journal of Biochemical and Molecular Toxicology

Volumn 19, Issue 5, 2005, Pages 347-357

  Lamango, Nazarius S ^a  

^a FLORIDA A AND M UNIVERSITY   (United States)

Author keywords

Carboxylesterase; Farnesylcysteine; Methylation; Mipafox; Organophosphate; Paraoxon; Prenylation

Indexed keywords

BENZOYLGLYCYLFARNESYLCYSTEINE; BENZOYLGLYCYLFARNESYLCYSTEINE METHYL ESTER; CHOLINESTERASE; ESTERASE; G PROTEIN COUPLED RECEPTOR; GUANINE NUCLEOTIDE BINDING PROTEIN; LAMIN; MECYSTEINE; MIPAFOX; ORGANOPHOSPHATE PESTICIDE; PARAOXON; PARATHION; PRENYLATED METHYLATED PROTEIN METHYL ESTERASE; RAS PROTEIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; APOPTOSIS; ARTICLE; BRAIN; CALCULATION; CELL DIFFERENTIATION; CELL PROLIFERATION; ELECTROSPRAY MASS SPECTROMETRY; ELUTION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; GEL FILTRATION CHROMATOGRAPHY; HYDROLYSIS; IC 50; LIVER; MALE; MOLECULAR WEIGHT; NERVE CELL DEGENERATION; NEUROTOXICITY; NONHUMAN; PARKINSONISM; PRENYLATION; PROTEIN METABOLISM; PROTEIN METHYLATION; PROTEIN MODIFICATION; RAT; RAT STRAIN; RETINA DEGENERATION; SIGNAL TRANSDUCTION; TIME;

ANIMALS; BRAIN; CARBOXYLIC ESTER HYDROLASES; CHROMATOGRAPHY, GEL; ENZYME INHIBITORS; HYDROLYSIS; LIVER; MALE; ORGANOPHOSPHORUS COMPOUNDS; RATS; RATS, SPRAGUE-DAWLEY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

ANIMALIA; EUKARYOTA;

EID: 27844576132     PISSN: 10956670     EISSN: None     Source Type: Journal    
DOI: 10.1002/jbt.20100     Document Type: Article

References (60)

1. Khosravi-Far R, Cox AD, Kato K, Der CJ. Protein prenylation: Key to Ras function and cancer intervention? Cell Growth Differ 1992;3(7):461-469.
2. Lutz RJ, McLain TM, Sinensky M. Feedback inhibition of polyisoprenyl pyrophosphate synthesis from mevalonate in vitro. Implications for protein prenylation. J Biol Chem 1992;267(12):7983-7986.
3. Dolence JM, Poulter CD. A mechanism for posttranslational modifications of proteins by yeast protein farnesyltransferase. Proc Natl Acad Sci USA 1995;92(11):5008-5011.
4. Ma YT, Gilbert BA, Rando RR. Farnesylcysteine analogs to probe role of prenylated protein methyltransferase. Methods Enzymol 1995;250:226-234.
5. Morris AJ, Malbon CC. Physiological regulation of G protein-linked signaling. Physiol Rev 1999;79(4): 1373-1430.
6. Khwaja A, O'Connolly J, Hendry BM. Prenylation inhibitors in renal disease. Lancet 2000;355(9205):741-744.
7. Ehrhardt A, Ehrhardt GR, Guo X, Schrader JW. Ras and relatives-job sharing and networking keep an old family together. Exp Hematol 2002;30(10):1089-1106.
8. Shields JM, Pruitt K, McFall A, Shaub A, Der CJ. Understanding Ras: 'it ain't over 'til it's over'. Trends Cell Biol 2000;10(4):147-154.
9. Yalovsky S, Rodr Guez-Concepcion M, Gruissem W. Lipid modifications of proteins-slipping in and out of membranes. Trends Plant Sci 1999;4(11):439-445.
10. Roskoski R Jr. Protein prenylation: A pivotal post-translational process. Biochem Biophys Res Commun 2003;303(l):1-7.
11. Ghomashchi F, Zhang X, Liu L, Gelb MH. Binding of prenylated and polybasic peptides to membranes: Affinities and intervesicle exchange. Biochemistry 1995;34(37):11910-11918.
12. Chavrier P, Parton RG, Hauri HP, Simons K, Zerial M. Localization of low molecular weight GTP binding proteins to exocytic and endocytic compartments. Cell 1990;62(2):317-329.
13. Myung CS, Yasuda H, Liu WW, Harden TK, Garrison JC. Role of isoprenoid lipids on the heterotrimeric G protein gamma subunit in determining effector activation. J Biol Chem 1999;274(23):16595-16603.
14. Dietrich A, Brazil D, Jensen ON, Meister M, Schrader M, Moomaw JF, Mann M, Illenberger D, Gierschik P. Isoprenylation of the G protein gamma subunit is both necessary and sufficient for beta gamma dimer-mediated stimulation of phospholipase C. Biochemistry 1996;35(48):15174-15182.
15. Iniguez-Lluhi JA, Simon MI, Robishaw JD, Gilman AG. G protein beta gamma subunits synthesized in Sf9 cells. Functional characterization and the significance of prenylation of gamma. J Biol Chem 1992;267(32):23409-23417.
16. Hayes JS, Lawler OA, Walsh MT, Kinsella BT. The prostacyclin receptor is isoprenylated. Isoprenylation is required for efficient receptor-effector coupling. J Biol Chem 1999;274(34):23707-23718.
17. Pumiglia KM, LeVine H, Haske T, Habib T, Jove R, Decker SJ. A direct interaction between G-protein beta gamma subunits and the Raf-1 protein kinase. J Biol Chem 1995;270(24):14251-14254.
18. De Waard M, Liu H, Walker D, Scott VE, Gurnett CA, Campbell KP. Direct binding of G-protein betagamma complex to voltage-dependent calcium channels. Nature 1997;385(6615):446-450.
19. + channel. Proc Natl Acad Sci USA 1988;85(16):5814-5818.
20. Volker C, Miller RA, McCleary WR, Rao A, Poenie M, Backer JM, Stock JB. Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction. J Biol Chem 1991;266(32):21515-21522.
21. Stephenson RC, Clarke S. Identification of a C-terminal protein carboxyl methyltransferase in rat liver membranes utilizing a synthetic farnesyl cysteine-containing peptide substrate. J Biol Chem 1990;265(27):16248-16254.
22. Perez-Sala D, Gilbert BA, Tan EW, Rando RR. Prenylated protein methyltransferases do not distinguish between farnesylated and geranylgeranylated substrates. Biochem J 1992;284(Pt 3):835-840.
23. Klein Z, Ben-Baruch G, Marciano D, Solomon R, Altaras M, Kloog Y. Characterization of the prenylated protein methyltransferase in human endometrial carcinoma. Biochim Biophys Acta 1994;1226(3):330-336.
24. Ding J, Lu DJ, Perez-Sala D, Ma YT, Maddox JF, Gilbert BA, Badwey JA, Rando RR. Farnesyl-L-cysteine analogs can inhibit or initiate superoxide release by human neutrophils. J Biol Chem 1994;269(24):16837-16844.
25. Marom M, Haklai R, Ben-Baruch G, Marciano D, Egozi Y, Kloog Y. Selective inhibition of Ras-dependent cell growth by farnesylthiosalisylic acid. J Biol Chem 1995;270(38):22263-22270.
26. Scheer A, Gierschik P. S-prenylated cysteine analogues inhibit receptor-mediated G protein activation in native human granulocyte and reconstituted bovine retinal rod outer segment membranes. Biochemistry 1995;34(15):4952-4961.
27. Huzoor A, Wang W, Kornhauser R, Volker C, Stock JB. Protein prenylcysteine analog inhibits agonist-receptor-mediated signal transduction in human platelets. Proc Natl Acad Sci USA 1993;90(3):868-872.
28. Ma YT, Shi YQ, Lim YH, McGrail SH, Ware JA, Rando RR. Mechanistic studies on human platelet isoprenylated protein methyltransferase: Farnesylcysteine analogs block platelet aggregation without inhibiting the methyltransferase. Biochemistry 1994;33(18):5414-5420.
29. Regazzi R, Sasaki T, Takahashi K, Jonas JC, Volker C, Stock JB, Takai Y, Wollheim CB. Prenylcysteine analogs mimicking the C-terminus of GTP-binding proteins stimulate exocytosis from permeabilized HIT-T15 cells: Comparison with the effect of Rab3AL peptide. Biochim Biophys Acta 1995;1268(3):269-278.
30. Capdevila A, Decha-Umphai W, Song KH, Borchardt RT, Wagner C. Pancreatic exocrine secretion is blocked by inhibitors of methylation. Arch Biochem Biophys 1997;345(1):47-55.
31. 2+ entry into cells by farnesylcysteine analogs. Mol Pharmacol 1996;50(6):1495-1501.
32. Perez-Sala D, Gilbert BA, Rando RR, Canada FJ. Analogs of farnesylcysteine induce apoptosis in HL-60 cells. FEBS Lett 1998;426(3):319-324.
33. Bergo MO, Leung GK, Ambroziak P, Otto JC, Casey PJ, Gomes AQ, Seabra MC, Young SG. Isoprenylcysteine carboxyl methyltransferase deficiency in mice. J Biol Chem 2001;276(8):5841-5845.
34. Lamango NS, Charlton CG. Farnesyl-L-cysteine analogs block SAM-induced Parkinson's disease-like symptoms in rats. Pharmacol Biochem Behav 2000;66(4):841-849.
35. Lamango NS, Ayuk-Takem LT, Nesby R, Zhao WQ, Charlton CG. Inhibition mechanism of S-adenosylmethionine-induced movement deficits by prenylcysteine analogs. Pharmacol Biochem Behav 2003;76(3-4):433-442.
36. Charlton CG, Crowell B Jr. Striatal dopamine depletion, tremors, and hypokinesia following the intracranial injection of S-adenosylmethionine: A possible role of hypermethylation in parkinsonism. Mol Chem Neuropathol 1995;26(3):269-284.
37. Fournier A, Couvineau A, Laburthe M. Synthesis of a hydrophilic affinity matrix for the purification of vasoactive intestinal peptide receptor. Anal Biochem 1993;212(2):305-310.
38. Chiu VK, Silletti J, Dinsell V, Wiener H, Loukeris K, Ou G, Philips MR, Pillinger MH. Carboxyl methylation of Ras regulates membrane targeting and effector engagement. J Biol Chem 2004;279(8):7346-7352.
39. Philips MR, Pillinger MH, Staud R, Volker C, Rosenfeld MG, Weissmann G, Stock JB. Carboxyl methylation of Ras-related proteins during signal transduction in neutrophils. Science 1993;259(5097):977-980.
40. Dai Q, Choy E, Chiu V, Romano J, Slivka SR, Steitz SA, Michaelis S, Philips MR. Mammalian prenylcysteine carboxyl methyltransferase is in the endoplasmic reticulum. J Biol Chem 1998;273(24):15030-15034.
41. Buckner FS, Eastman RT, Nepomuceno-Silva JL, Speelmon EC, Myler PJ, Van Voorhis WC, Yokoyama K. Cloning, heterologous expression, and substrate specificities of protein farnesyltransferases from Trypanosoma cruzi and Leishmania major. Mol Biochem Parasitol 2002;122(2):181-188.
42. Gosser YQ, Nomanbhoy TK, Aghazadeh B, Manor D, Combs C, Cerione RA, Rosen MK. C-terminal binding domain of Rho GDP-dissociation inhibitor directs N-terminal inhibitory peptide to GTPases. Nature 1997;387(6635):814-819.
43. Dietrich A, Scheer A, Illenberger D, Kloog Y, Henis YI, Gierschik P. Studies on G-protein alpha.betagamma heterotrimer formation reveal a putative S-prenyl-binding site in the alpha subunit. Biochem J 2003;376(Pt 2): 449-456.
44. Magee AI, Seabra MC. Are prenyl groups on proteins sticky fingers or greasy handles? Biochem J 2003;376(Pt 2):e3-e4.
45. Anderson JL, Frase H, Michaelis S, Hrycyna CA. Purification, functional reconstitution, and characterization of the Saccharomyces cerevisiae isoprenylcysteine carboxylmethyltransferase Ste14p. J Biol Chem 2005;280(8): 7336-7345.
46. Volker C, Lane P, Kwee C, Johnson M, Stock J. A single activity carboxyl methylates both farnesyl and geranylgeranyl cysteine residues. FEBS Lett 1991;295(1-3):189-194.
47. Bhatt MH, Elias MA, Mankodi AK. Acute and reversible parkinsonism due to organophosphate pesticide intoxication: Five cases. Neurology 1999;52(7):1467-1471.
48. Muller-Vahl KR, Kolbe H, Dengler R. Transient severe parkinsonism after acute organophosphate poisoning. J Neurol Neurosurg Psychiatry 1999;66(2):253-254.
49. Shahar E, Andraws J. Extra-pyramidal parkinsonism complicating organophosphate insecticide poisoning. Eur J Paediatr Neurol 2001;5(6):261-264.
50. Glynn P. Neural development and neurodegeneration: Two faces of neuropathy target esterase. Prog Neurobiol 2000;61(1):61-74.
51. Atkins J, Glynn P. Membrane association of and critical residues in the catalytic domain of human neuropathy target esterase. J Biol Chem 2000;275(32):24477-24483.
52. Lush MJ, Li Y, Read DJ, Willis AC, Glynn P. Neuropathy target esterase and a homologous Drosophila neurodegeneration-associated mutant protein contain a novel domain conserved from bacteria to man. Biochem J 1998;332(Pt 1):1-4.
53. Pope CN, Padilla SS. Chromatographic characterization of neurotoxic esterase. Biochem Pharmacol 1989;38(1):181-188.
54. Kretzschmar D, Hasan G, Sharma S, Heisenberg M, Benzer S. The Swiss cheese mutant causes glial hyperwrapping and brain degeneration in Drosophila. J Neurosci 1997;17(19):7425-7432.
55. Lamango NS, Nesby RA, Charlton CG. Quantification of S- adenosylmethionine-induced tremors: A possible tremor model for Parkinson's disease. Pharmacol Biochem Behav 2000;65(3):523-529.
56. Benmoyal-Segal L, Vander T, Shifman S, Bryk B, Ebstein RP, Marcus EL, Stessman J, Darvasi A, Herishanu Y, Friedman A and others. Acetylcholinesterase/ paraoxonase interactions increase the risk of insecticide-induced Parkinson's disease. Faseb J 2005;19(3):452-454.
57. Akhmedova SN, Yakimovsky AK, Schwartz EI. Paraoxonase 1 Met-Leu 54 polymorphism is associated with Parkinson's disease. J Neurol Sci 2001;184(2):179-182.
58. Kondo I, Yamamoto M. Genetic polymorphism of paraoxonase 1 (PON1) and susceptibility to Parkinson's disease. Brain Res 1998;806(2):271-273.
59. van Tienhoven M, Atkins J, Li Y, Glynn P. Human neuropathy target esterase catalyzes hydrolysis of membrane lipids. J Biol Chem 2002;277(23):20942-20948.
60. von Bohlen und Halbach O, Schober A, Krieglstein K. Genes, proteins, and neurotoxins involved in Parkinson's disease. Prog Neurobiol 2004;73(3):151-177.