Rational design of organophosphorus hydrolase for altered substrate specificities

Chemico-Biological Interactions

Volumn 119-120, Issue , 1999, Pages 211-223

  Di Sioudi, Barbara D ^a   Miller, Charles E ^b   Lai, Kaihua ^c   Grimsley, Janet K ^a   Wild, James R ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^c ADVOCATE CHRIST MEDICAL CENTER   (United States)

Author keywords

Detoxification; Neurotoxin degradation; Organophosphates; Organophosphorus hydrolase; Phosphotriesterase; Protein engineering

Indexed keywords

ACEPHATE; CHEMICAL WARFARE AGENT; DYFLOS; METHYLPHOSPHONOTHIOIC ACID S (2 DIISOPROPYLAMINOETHYL) O ETHYL ESTER; NEUROTOXIN; ORGANOPHOSPHATE INSECTICIDE; ORGANOPHOSPHORUS COMPOUND; ORGANOPHOSPHORUS HYDROLASE; PARATHION; SARIN; SOMAN; UNCLASSIFIED DRUG;

CATALYSIS; CONFERENCE PAPER; DETOXIFICATION; DRUG HYDROLYSIS; ENZYME IMMOBILIZATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; GENETIC ENGINEERING;

ANIMALS; ARYLDIALKYLPHOSPHATASE; DRUG DESIGN; ESTERASES; HUMANS; HYDROLYSIS; PROTEIN ENGINEERING; SUBSTRATE SPECIFICITY;

BACTERIA (MICROORGANISMS); FELIS CATUS;

EID: 0033032010     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(99)00030-7     Document Type: Conference Paper

References (57)

1. Dumas D.P., Durst H.D., Landis W.G., Raushel F.M., Wild J.R. Inactivation of organophosphorus nerve agents by the phosphotriesterase from Pseudomonas diminuta. Arch. Biochem. Biophys. 277:1990;155-159.
2. Chae M.Y., Postula J.F., Raushel F.M. Stereospecific enzymatic hydrolysis of phosphorus-sulfur bonds in chiral organophosphate triesters. Bioorg. Med. Chem. Lett. 4:1994;1473-1478.
3. Lai K., Stolowich N.J., Wild J.R. Characterization of P-S bond hydrolysis in organophosphorothioate pesticides by organophosphorus hydrolase. Arch. Biochem. Biophys. 318:1995;59-64.
4. Kolakowski J.E., DeFrank J.J., Harvey S.P., Szafraniec L.L., Beaudry W.T., Lai K., Wild J.R. Enzymatic hydrolysis of the chemical warfare agent VX and its neurotoxic analogues by organophosphorus hydrolase. Biocatal. Biotransform. 15:1997;297-312.
5. DeFrank J.J., Beaudry W.T., Cheng T.-C., Harvey S.P., Stroup A.N., Szafraniec L.L. Screening of halophilic bacteria and Alteromonas species for organophosphorus hydrolyzing enzyme activity. Chem.-Biol. Interact. 87:1993;141-148.
6. Cheng T.-C., Harvey S.P., Chen G.L. Cloning and expression of a gene encoding a bacterial enzyme for decontamination of organophosphorus nerve agents and nucleotide sequence of the enzyme. Appl. Environ. Microbiol. 62:1996;1636-1641.
7. Hassett C., Richter R.J., Humbert R., Chapline C., Crabb J.W., Omiecinski C.J., Furlong C.E. Characterization of cDNA clones encoding rabbit and human serum paraoxonase: the mature protein retains its signal sequence. Biochemistry. 30:1991;10141-10149.
8. Hoskin F.C.G., Roush A.H. Hydrolysis of nerve gas by squid-type diisopropyl phosphorofluoridate hydrolyzing enzyme on agarose resin. Science. 215:1982;1255-1257.
9. Mulbry W.W., Karns J.S., Kearney P.C., Nelson J.O., McDaniel C.S., Wild J.R. Identification of a plasmid-borne parathion hydrolase gene from Flavobacterium sp. by Southern hybridization with opd from Pseudomonas diminuta. Appl. Environ. Microbiol. 51:1986;926-930.
10. Harper L.L., McDaniel C.S., Miller C.E., Wild J.R. Dissimilar plasmids isolated from Pseudomonas diminuta MG and a Flavobacterium sp. (ATCC 27551) contain identical opd genes. Appl. Environ. Microbiol. 54:1988;2586-2589.
11. Hsich D.P.H., Munnecke D.M. Accelerated microbial degradation of concentrated parathion. Terui G. Fermentation Technology Today: Proceedings of the IVth International Fermentation Symposium, Society of Fermentation Technology, Kyoto, Japan. 1972;551-554.
12. Sethunathan N. Degradation of parathion in flooded acid soils. J. Agric. Food. Chem. 21:1973;602-604.
13. McDaniel C.S., Harper L.L., Wild J.R. Cloning and sequencing of a plasmid-borne gene (opd) encoding a phosphotriesterase. J. Bacteriol. 170:1988;2306-2311.
14. Mulbry W.W., Karns J.S. Parathion hydrolase specified by the Flavobacterium opd gene: relationship between the gene and the protein. J. Bacteriol. 171:1989;6740-6746.
15. Serdar C.M., Murdock D.C., Rohde M.F. Parathion hydrolase gene from Pseudomonas diminuta MG: subcloning, complete nucleotide sequence, and expression of the mature portion of the enzyme in Escherichia coli. Bio/Technology. 7:1989;1151-1155.
16. Dumas D.P., Caldwell S.R., Wild J.R., Raushel F.M. Purification and properties of the phosphotriesterase from Pseudomonas diminuta. J. Biol. Chem. 264:1989;19659-19665.
17. Phillips J.P., Xin J.H., Kirby K., Milne J.C.P., Krell P., Wild J.R. Transfer and expression of an organophosphate insecticide-degrading gene from Pseudomonas in Drosophila melanogaster. Proc. Natl. Acad. Sci. USA. 87:1990;8155-8159.
18. Dave K.I., Lauriano C., Xu B., Wild J.R., Kenerley C.M. Expression of organophosphate hydrolase in the filamentous fungus Gliocladium virens. Appl. Microbiol. Biotechnol. 41:1994;352-358.
19. Steiert J.G., Pogell B.M., Speedie M.K., Laredo J. A gene coding for a membrane-bound hydrolase is expressed as a secreted, soluble enzyme in Streptomyces lividans. Bio/Technology. 7:1989;65-68.
20. Grimsley J.K., Scholtz J.M., Pace C.N., Wild J.R. Organophosphorus hydrolase is a remarkably stable enzyme that unfolds through a homodimeric intermediate. Biochemistry. 36:1997;14366-14374.
21. Benning M.W., Kuo J.M., Raushel F.M., Holden H.M. Three-dimensional structure of phosphotriesterase: an enzyme capable of detoxifying organophosphate nerve agents. Biochemistry. 33:1994;15001-15007.
22. Benning M.W., Kuo J.M., Raushel F.M., Holden H.M. Three-dimensional structure of the binuclear metal center of phosphotriesterase. Biochemistry. 34:1995;7973-7978.
23. Vanhooke J.L., Benning M.M., Raushel F.M., Holden H.M. Three-dimensional structure of the zinc-containing phosphotriesterase with the bound substrate analog diethyl 4-methylbenzylphosphonate. Biochemistry. 35:1996;6020-6025.
24. Hoskin F.C.G., Walker J.E., Dettbarn W.-D., Wild J.R. Hydrolysis of tetriso by an enzyme derived from Pseudomonas diminuta as a model for the detoxication of O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothiolate (VX). Biochem. Pharmacol. 49:1995;711-715.
25. C.E. Miller, Structure/function studies on the signal sequence of organophosphorus hydrolase of Pseudomonas diminuta in Escherichia coli, Ph.D. Dissertation, Texas A&M University, 1992.
26. Sathyamoorthy M., Speedie M.K. Monitoring transport of a recombinant phosphotriesterase in Streptomyces lividans using a pulse-chase system. Appl. Microbiol. Biotechnol. 43:1995;493-507.
27. Richins R.D., Kaneva I., Mulchandani A., Chen W. Biodegradation of organophosphorus pesticides by surface-expressed organophosphorus hydrolase. Nat. Biotechnol. 15:1997;984-987.
28. Omburo G.A., Kuo J.M., Mullins L.S., Raushel F.M. Characterization of the zinc binding site of bacterial phosphotriesterase. J. Biol. Chem. 267:1992;13278-13283.
29. Lai K., Dave K.I., Wild J.R. Bimetallic binding motifs in organophosphorus hydrolase are important for catalysis and structural organization. J. Biol. Chem. 269:1994;16579-16584.
30. Chae M.Y., Omburo G.A., Lindahl P.A., Raushel F.M. Antiferromagnetic coupling in the binuclear metal cluster of manganese-substituted phosphotriesterase. J. Am. Chem. Soc. 115:1993;12173-12174.
31. Chae M.Y., Omburo G.A., Lindahl P.A., Raushel F.M. Utilization of copper as a paramagnetic probe for the binuclear metal center of phosphotriesterase. Arch. Biochem. Biophys. 316:1995;765-772.
32. Hong S.-B., Raushel F.M. Metal-substrate interactions facilitate the catalytic activity of the bacterial phosphotriesterase. Biochemistry. 35:1996;10904-10912.
33. B. diSioudi, Rational enzyme design for enhanced biodegradation of organophosphorus neurotoxins, Ph.D. Dissertation, Texas A&M University, 1998.
34. K. Lai, Modification and characterization of the neurotoxic substrate specificity of organophosphorus hydrolase, Ph.D. Dissertation, Texas A&M University, 1994.
35. J.M. Kuo, Investigations of the active site and metal centers of phosphotriesterase, Ph.D. Dissertation, Texas A&M University, 1995.
36. Watkins L.M., Mahoney H.J., McCulloch J.K., Raushel F.M. Augmented hydrolysis of diisopropyl fluorophosphate in engineered mutants of phosphotriesterase. J. Biol. Chem. 272:1997;25596-25601.
37. Munnecke D.M., Hsieh D.P.H. Microbial decontamination of parathion and p-nitrophenol in aqueous media. Appl. Microbiol. 28:1974;212-217.
38. Yang F., Wild J.R., Russell A.J. Non-aqueous biocatalytic degradation of a nerve gas mimic. Biotechnol. Prog. 11:1995;471-474.
39. LeJeune K.E., Russell A.J. Covalent binding of a nerve agent hydrolyzing enzyme within polyurethane foams. Biotechnol. Bioeng. 51:1996;450-457.
40. Katchalski-Katzir, E., Immobilized enzymes-learning from past successes and failures, Trends in Biotechnology, 11 (1993) 471-478.
41. Munnecke D.M. Properties of an immobilized pesticide-hydrolyzing enzyme. Appl. Environ. Microbiol. 33:1977;503-507.
42. Munnecke D.M. Hydrolysis of organophosphate insecticides by an immobilized enzyme system. Biotechnol. Bioeng. 21:1979;2247-2261.
43. Caldwell S.R., Raushel F.M. Detoxification of organophosphate pesticides using an immobilized phosphotriesterase from Pseudomonas diminuta. Biotechnol. Bioeng. 37:1991;103-109.
44. Caldwell S.R., Raushel F.M. Detoxification of organophosphate pesticides using a nylon based immobilized phosphotriesterase from Pseudomonas diminuta. Appl. Biochem. Biotechnol. 31:1991;59-73.
45. Havens P.L., Rase H.F. Reusable immobilized enzyme/polyurethane sponge for removal and detoxification of localized organophosphate pesticide spills. Ind. Eng. Chem. Res. 32:1993;2254-2258.
46. LeJeune K.E., Mesiano A.J., Bower S.B., Grimsley J.K., Wild J.R., Russell A.J. Dramatically stabilized phosphotriesterase-polymers for nerve agent degradation. Biotechnol. Bioeng. 54:1997;105-114.
47. Rainina E.I., Efremenco E.N., Varfolomeyev S.D. The development of a new biosensor based on recombinant E. coli for the direct detection of organophosphorus neurotoxins. Biosens. Bioelectron. 11:1996;991-1000.
48. Simonian A.L., Rainina E.I., Wild J.R. A new approach for discriminative detection of organophosphate neurotoxins in the presence of other cholinesterase inhibitors. Anal. Lett. 30:1997;2453-2468.
49. Ecobichon D.J. Toxic effects of pesticides. Amdur M.O., Doull J., Klaassen C.D. Casarett and Doull's Toxicology: The Basic Science of Poisons. 1991;565-622 McGraw-Hill, New York.
50. Matsumura F. Toxicology of Insecticides. 1985;Plenum Press, New York.
51. Public Health Impact of Pesticides Used in Agriculture. 1990;World Health Organization, Geneva. 128 pp.
52. Ashani Y., Rothschild N., Segall Y., Levanon D., Raveh L. Prophylaxis against organophosphate poisoning by an enzyme hydrolysing organophosphorus compounds in mice. Life Sci. 49:1991;367-374.
53. E. Kaliste-Korhonen, P. Ylitalo, O. Hänninen and F.M. Raushel, Phosphotriesterase decreases paraoxon toxicity in mice, Toxicology and Applied Pharmacology, 121 (1993) 275-278.
54. Tuovinen K., Kaliste-Korhonen E., Raushel F.M., Hanninen O. Phosphotriesterase - a promising candidate for use in detoxification of organophosphates. Fundam. Appl. Toxicol. 23:1994;578-584.
55. Tuovinen K., Kaliste-Korhonen E., Raushel F.M., Hänninen O. Protection of organophosphate-inactivated esterases with phosphotriesterase. Fundam. Appl. Toxicol. 31:1996;210-217.
56. L. Pei, G. Omburo, W.D. McGuinn, I. Petrikovics, K. Dave, F.M. Raushel, J.R. Wild, J.R. DeLoach, J.L. Way, Encapsulation of phosphotriesterase within murine erythrocytes, Toxicology and Applied Pharmacology, 124 (1994) 296-301.
57. Pei L., Petrikovics I., Way J.L. Antagonism of the lethal effects of paraoxon by carrier erythrocytes containing phosphotriesterase. Fundam. Appl. Toxicol. 28:1995;209-214.