Characterization of Pyrethroid Hydrolysis by the Human Liver Carboxylesterases HCE-1 and HCE-2

Overview

Journal Arch Biochem Biophys

Publisher Elsevier

Specialties Biochemistry
Biophysics

Date 2005 Dec 20

PMID 16359636

Citations 35

Authors

Kosuke Nishi

Huazhang Huang

Shizuo G Kamita

In-Hae Kim

Christophe Morisseau

Bruce D Hammock

Affiliations

Soon will be listed here.

Abstract

Carboxylesterases hydrolyze a large array of endogenous and exogenous ester-containing compounds, including pyrethroid insecticides. Herein, we report the specific activities and kinetic parameters of human carboxylesterase (hCE)-1 and hCE-2 using authentic pyrethroids and pyrethroid-like, fluorescent surrogates. Both hCE-1 and hCE-2 hydrolyzed type I and II pyrethroids with strong stereoselectivity. For example, the trans-isomers of permethrin and cypermethrin were hydrolyzed much faster than corresponding cis-counterparts by both enzymes. Kinetic values of hCE-1 and hCE-2 were determined using cypermethrin and 11 stereoisomers of the pyrethroid-like, fluorescent surrogates. K(m) values for the authentic pyrethroids and fluorescent surrogates were in general lower than those for other ester-containing substrates of hCEs. The pyrethroid-like, fluorescent surrogates were hydrolyzed at rates similar to the authentic pyrethroids by both enzymes, suggesting the potential of these compounds as tools for high throughput screening of esterases that hydrolyze pyrethroids.

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References

Bencharit S, Morton C, Hyatt J, Kuhn P, Danks M, Potter P . Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition. Chem Biol. 2003; 10(4):341-9. DOI: 10.1016/s1074-5521(03)00071-1. View

Bradford M . A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976; 72:248-54. DOI: 10.1016/0003-2697(76)90527-3. View

Humerickhouse R, Lohrbach K, Li L, Bosron W, Dolan M . Characterization of CPT-11 hydrolysis by human liver carboxylesterase isoforms hCE-1 and hCE-2. Cancer Res. 2000; 60(5):1189-92. View

Elliott M, Janes N, Pulman D, Gaughan L, Unai T, Casida J . Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin. J Agric Food Chem. 1976; 24(2):270-6. DOI: 10.1021/jf60204a007. View

Butte W, Kemper K . A spectrophotometric assay for pyrethroid-cleaving enzymes in human serum. Toxicol Lett. 1999; 107(1-3):49-53. DOI: 10.1016/s0378-4274(99)00030-2. View

Kang K, Jones P, Huang H, Zhang R, Mostovich L, Wheelock C . Evaluation of alpha-cyano ethers as fluorescent substrates for assay of cytochrome P450 enzyme activity. Anal Biochem. 2005; 344(2):183-92. PMC: 1450254. DOI: 10.1016/j.ab.2005.06.032. View

Institoris L, Undeger U, Siroki O, Nehez M, Desi I . Comparison of detection sensitivity of immuno- and genotoxicological effects of subacute cypermethrin and permethrin exposure in rats. Toxicology. 1999; 137(1):47-55. DOI: 10.1016/s0300-483x(99)00081-5. View

Bencharit S, Morton C, Xue Y, Potter P, Redinbo M . Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol. 2003; 10(5):349-56. DOI: 10.1038/nsb919. View

Leng G, Lewalter J, Rohrig B, Idel H . The influence of individual susceptibility in pyrethroid exposure. Toxicol Lett. 1999; 107(1-3):123-30. DOI: 10.1016/s0378-4274(99)00039-9. View

10.

Senter P, Beam K, Mixan B, Wahl A . Identification and activities of human carboxylesterases for the activation of CPT-11, a clinically approved anticancer drug. Bioconjug Chem. 2001; 12(6):1074-80. DOI: 10.1021/bc0155420. View

11.

Ljungquist A, AUGUSTINSSON K . Purification and properties of two carboxylesterases from rat-liver microsomes. Eur J Biochem. 1971; 23(2):303-13. DOI: 10.1111/j.1432-1033.1971.tb01622.x. View

12.

Wheelock C, Severson T, Hammock B . Synthesis of new carboxylesterase inhibitors and evaluation of potency and water solubility. Chem Res Toxicol. 2001; 14(12):1563-72. DOI: 10.1021/tx015508+. View

13.

Morton C, Potter P . Comparison of Escherichia coli, Saccharomyces cerevisiae, Pichia pastoris, Spodoptera frugiperda, and COS7 cells for recombinant gene expression. Application to a rabbit liver carboxylesterase. Mol Biotechnol. 2001; 16(3):193-202. DOI: 10.1385/MB:16:3:193. View

14.

Shan G, Hammock B . Development of sensitive esterase assays based on alpha-cyano-containing esters. Anal Biochem. 2001; 299(1):54-62. DOI: 10.1006/abio.2001.5388. View

15.

Abernathy C, Casida J . Pyrethroid insecticides: esterase cleavage in relation to selective toxicity. Science. 1973; 179(4079):1235-6. DOI: 10.1126/science.179.4079.1235. View

16.

Wheelock C, Wheelock A, Zhang R, Stok J, Morisseau C, Le Valley S . Evaluation of alpha-cyanoesters as fluorescent substrates for examining interindividual variation in general and pyrethroid-selective esterases in human liver microsomes. Anal Biochem. 2003; 315(2):208-22. DOI: 10.1016/s0003-2697(03)00002-2. View

17.

Gaughan L, Unai T, Casida J . Permethrin metabolism in rats. J Agric Food Chem. 1976; 25(1):9-17. DOI: 10.1021/jf60209a005. View

18.

Huang H, Fleming C, Nishi K, Redinbo M, Hammock B . Stereoselective hydrolysis of pyrethroid-like fluorescent substrates by human and other mammalian liver carboxylesterases. Chem Res Toxicol. 2005; 18(9):1371-7. PMC: 1444893. DOI: 10.1021/tx050072+. View

19.

Pindel E, Kedishvili N, Abraham T, Brzezinski M, Zhang J, Dean R . Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin. J Biol Chem. 1997; 272(23):14769-75. DOI: 10.1074/jbc.272.23.14769. View

20.

Brzezinski M, Abraham T, Stone C, Dean R, Bosron W . Purification and characterization of a human liver cocaine carboxylesterase that catalyzes the production of benzoylecgonine and the formation of cocaethylene from alcohol and cocaine. Biochem Pharmacol. 1994; 48(9):1747-55. DOI: 10.1016/0006-2952(94)90461-8. View