Abstract
Human serum (HS) and human serum albumin (HSA) were able to hydrolyse the carbamate carbaryl. Carbarylase activity found in HSA was slightly activated by 1 mM Zn2+, Mn2+, Cd2+, Ni2+ and Na+ and by 0.01 mM Pb2+. The organophosphorus compounds paraoxon and O-hexyl O-2,5-dichlorophenyl phosphoramidate, caprylic acid, palmitic acid and the carboxyl ester p-nitrophenyl butyrate inhibited the hydrolysis of carbaryl by HSA, being in the last case a competitive inhibition. Using selective amino acid reagents, we concluded that Cys, Trp, Arg and Tyr seem to play important roles in the carbarylase activity of HSA. In addition, Tyr and Arg seem to be located in the active centre of the enzyme since carbaryl protected the activity from the inhibition. It was concluded that HSA hydrolyses carbaryl by a mechanism similar to that described for rabbit serum albumin based in transient carbamylation of a Tyr residue. The extrapolation of the hydrolysis rate to physiological albumin concentrations suggests that albumin might be playing a critical role in the detoxication of carbaryl.
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Abbreviations
- carbarylase:
-
carbaryl hydrolysing activity;
- DCC:
-
N,N‘-Dicyclohexylcarbodiimide;
- DEPC:
-
Diethyl pyrocarbonate;
- DFP:
-
diisopropyl fluorophosphates;
- DTNB:
-
5,5‘-dithio-bis (2-nitrobenzoic acid);
- HDCP:
-
O-hexyl O-2,5-dichlorophenyl phosphoramidate;
- HS:
-
human serum;m
- HSA:
-
human serum albumin;
- NAI:
-
N-acetylimidazol;
- NBS:
-
N-bromosuccinimide;
- PNG:
-
phenylglyoxal;
- p-NPB:
-
p-nitrophenyl butyrate
References
Casida J, Augustinsson KB (1959a) Enzymic hydrolysis of N.N-dimethylcarbamoul fluoride. Biochem Pharmacol 3:60–67
Casida J, Augustinsson KB (1959b) Reaction of plasma albumin with 1-naphthyl N-methylcarbamate and certain other esters. Biochim Biophys Acta 36:411–426
Chen RF (1967) Removal of fatty acids from serum albumin by charcoal treatment. J Biol Chem 242:173–181
Emerson E (1943) The condensation of aminoantipyrine. II. A new color test for phenolic compounds. J Org Chem 8:417–428
Lotti M (2002) Promotion of organophosphate induced delayed polyneurophathy by certain esterase inhibitors. Toxicology 181–182:245–248
Means GE, Bender M (1975) Acetylation of human serum albumin by p-nitrophenyl acetate. Biochemistry 14:4989–4994
Peters T Jr (1996a) Chemical aspects: albumin in medicine. In: Peters T (eds) All about albumin. Biochemistry, genetics, and medical applications. Academic Press Inc, San Diego, pp 251–284
Peters T Jr (1996b) Ligand binding by albumin. In: Peters T (eds) All about albumin. Biochemistry, genetics, and medical applications. Academic Press Inc, San Diego, pp 79–132
Peters T Jr (1996c) Metabolism: albumin in the body. In: Peters T (eds) All about albumin. Biochemistry, genetics, and medical applications. Academic Press Inc, San Diego, pp 188–250
Sogorb MA (1997) Estudio bioquímico de las actividades hidrolizantes de O-hexil, O-2,5-diclorofenil fosforamidato en suero de pollo y conejo. In: Sogorb MA (PhD Dissertation) Actividades HDCPasa, p-NPBasa y paraoxonasa de albúmina de suero humano. Universidad de Alicante (Alicante, Spain) pp 209–211
Sogorb MA, Vilanova E (2002) Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol Lett 128:215–228
Sogorb MA, Monroy A, Vilanova E (1998) Chicken serum albumin hydrolyzes dichlorophenyl phosphoramidates by a mechanism based in a transient phosphorylation. Chem Res Toxicol 11:1441–1446
Sogorb MA, Sellero I, López-Rivadulla M, Céspedes V, Vilanova E (1999) EDTA-resistant and sensitive phosphotriesterase activities associated with albumin and lipoproteins in rabbit serum. Drug Metab Dispos 27:53–59
Sogorb MA, Carrera V, Benabent M, Vilanova E (2002) Rabbit serum albumin hydrolyzes the carbamate carbaryl. Chem Res Toxicol 15:520–526
World Health Organization (1986) Carbamates: a general Introduction. In: World Health Organization (eds) Environmental health criteria 64. World Health Organization, Geneva
World Health Organization (1994) Carbaryl. In: World Health Organization (eds) Environmental health criteria 153. World Health Organization, Geneva
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Sogorb, M.A., Carrera, V. & Vilanova, E. Hydrolysis of carbaryl by human serum albumin. Arch Toxicol 78, 629–634 (2004). https://doi.org/10.1007/s00204-004-0584-x
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DOI: https://doi.org/10.1007/s00204-004-0584-x