Abstract
Commercial hexane was concentrated by distillation. The distillation residue (0.43 ml/l original solvent) contains material which inhibits human serum cholinesterase (ChE) “in vitro” with a slight effect on acetylcholinesterase. Phosphorus was detected equivalent to 0.33 μmol monophosphorus compound/litre original solvent. The inhibition was progressive with the enzyme-inhibitor preincubation time. A partial reactivation of the inhibited enzyme was obtained by treatment with hydroxylamine and 2-PAM. The results are coherent with a covalent inactivation by more than one inhibitor which acylate (probably phosphorylate) ChE, although it seems likely that a reversible but unstable inhibitor could also be present in the hexane residue. The results are discussed in the context of the known neurotoxic effects ofn-hexane and some organophosphorus esters.
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References
Abou-Donia MB (1981) Organophosphorus ester-induced delayed neurotoxicity. Ann Rev Pharmacol Toxicol 21:511–548
Abou-Donia MB, Makkawy HAM, Graham DG (1982) The relative neurotoxicity of n-hexane, methyl n-butylketone, 2,5-hexanediol and 2,5-hexanedione following oral or intraperitoneal administration in hens. Toxicol Appl Pharmacol 62:369–389
Allen N, Mendell JR, Billmaier DJ, Fontaine RE, O'Neil J (1975) Toxic polyneuropathy due to methyl n-butylketone. Arch Neurol 32:209–218
Bartolucci GB, De Rosa E, Cocheo V, Manno M, De Zanche I, Negrin P, Fardin P (1978) Polineuropatia nell'industria calzaturiera: Contributo sperimentale, etiologico e clinico. Securitas 63:187–206
Bermejillo M (1971) Intoxicación laboral por el triortocresilfosfato. Rev Medicina y Seguridad en el Trabajo 77:49–58
Capellini A, Chiappino G, Zurlo N (1968) Osservazioni cliniche e sperimentali sulle polineuriti considette da tricresilfosfati. La Medicina del Lavoro 59:721–759
Cavalleri A, Cosi V (1978) Polyneuritis incidence in shoe factory workers: cases report and etiological considerations. Arch Environ Health 33:192–197
Cavalleri A, Cosi V (1979) Polyneuropathies in shoe factories workers. In: Manzo L (ed) Adv Neurotoxicol. Pergamon Press, Amsterdam, pp 193–200
Crepet M, Gaffuri E, Picotti G (1968) La patologia da tri-aril-fosfati nell'industria calzaturiera. Lavoro Umano 20:443–447
Desantis M (1978) Neuropatia da collanti: Inquadramento epidemiologico arisultati preliminari di intossicazioni sperimentali. Securitas 63:207–219
Egan G, Spencer P, Schaumburg H, Murray K, Bischoff M, Scala R (1980)n-Hexane “free” hexane mixture fails to produce nervous system damage. Neurotoxicology 1:515–524
Ellman GL, Courtney KD, Andres V Jr, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7:88–91
Gonzalez EG, Downey JA (1972) Polyneuropathy in a glue sniffer. Arch Phys Med 53:333–337
Herskowitz A, Ishii N, Schaumburg HH (1971)n-Hexane neuropathy. A syndrome occurring as a result of industrial exposure. N Engl J Med 285:82–85
Hornby WE, Goldstein L (1976) Immobilization of enzymes on nylon. In: Mosbach K (ed) Methods in enzymology, vol XLIV. Academic Press, New York, pp 118–134
Johnson MK (1969) The delayed neurotoxic effect of some organophosphorus compounds. Identification of phosphorylation site as an esterase. Biochem J 114:711–717
Johnson MK (1980) Organophosphate neuropathy. Progress in understanding. In: Manzo L (ed) Adv Neurotoxicol. Pergamon Press, Amsterdam, pp 223–235
Karczmar AG, Usdin E, Wills JH (1970) Anticholinesterase agents. In: Karczmar AG (ed) Int Encyclop Pharmacol Therap, Section 13. Pergamon Press, Amsterdam
Kurita H (1967) Experimental studies on the effects ofn-hexane in albino rats. Jpn J Ind Health 9:672–677
Main AR (1976) Structure and inhibition of cholinesterases. In: Goldberg AM, Hanin I (eds) Biology of cholinergic function. Raven Press, New York, pp 239–268
Marcuello D (1973) Parálisis del calzado. II Asamblea Anual de la Sociedad Española de Medicina y Seguridad del Trabajo. Zaragoza, Spain
Mazzella di Bosco M (1964) Su alcuni casi di intossicazione professionale da triortocresilfosfato. Lavoro Umano 16:267–275
Navarro R (1970) Toxicidad de colas y disolventes en la industria del calzado. Caucho 244:29–32
Navarro R (1973) Adhesivos para el calzado. II. Anticolinesterasas fosforados y fenoles enn-hexanos yn-heptanos industriales. Caucho 281:15–23
Paulson GW, Waylonis GW (1976) Polyneuropathy due ton-hexane. Arch Int Med 136:880–882
Perbellini L, De Grandis D, Semenzato F, Rizzuto N, Simonati A (1978) An experimental study on the neurotoxicity ofn-hexane metabolites: hexanol-1 and hexanol-2. Toxicol Appl Pharmacol 46:421–427
Perbellini L, Brugnone F, Pavan I (1980) Identification of the metabolites ofn-hexane, cyclohexane and their isomers in men's urine. Toxicol Appl Pharmacol 53:220–229
Rizzuto N, Terzian H, Galiazzo-Rizzuto S (1977) Toxic polyneuropathies in Italy due to leather cement poisoning in shoe industries. A light and electron microscopy study. J Neurol Sci 31:343–354
Saida K, Mendell JR, Weiss H (1976) Peripheral nerve changes induced by methyl n-butyl ketone and potentiation by methyl ethyl ketone. J Neuropathol Exp Neurol 35:207–225
Schaumburg HH, Spencer PS (1976) Central and peripheral nervous system degeneration produced by puren-hexane: an experimental study. Brain 99:183–192
Segel IH (1975) Enzyme kinetics: Behaviour and analysis of rapid equilibrium and steady-state enzyme systems. Wiley-Interscience
Spencer PS, Schaumburg HH (1975) Experimental neuropathy produced by 2,5-hexanedione. A mayor metabolite of the neurotoxic industrial solvent methyl n-butyl ketone. J Neurol Neurosurg Psych 38:771–775
Spencer PS, Schaumburg HH, Sabri MF, Veronise B (1980) The enlarging view of hexacarbon neuropathy. CRC Crit Rev Toxicol 7:279–336
Staff Report (1976) The Environmental Protection Agency and the regulation of pesticides. Staff Report to the Subcommitee on Administrative Practices and Procedures of the Commitee on the Judiciary of the United States Senate. US Govern Printing Office, Washington, DC, pp 32–34
Takeuchi Y, Ono Y, Hisanaga N (1981) An experimental study on the combined effects of n-hexane and toluene on the peripheral nerve of rat. Br J Ind Med 38:14–19
Towfighi J, Gonatas MK, Pleasure D, Cooper HS, McCree L (1976) Glue sniffer's neuropathy. Neurology 26:238–243
Usdin E, Chase C (1970) Reaction of cholinesterases with substrates and reactivators. In: Karczmar AG (ed) Anticholinesterases agents. Int Encyclop Pharmacol Therap, Section 13, vol 1. Pergamon Press, Amsterdam, pp 47–354
Vigliani EC (1968) Osservazioni cliniche su 47 casi di polineuriti motorie manifestatesi in operai lavoranti con mastici e collanti. Lavoro Umano 20:448–449
Vilanova E, Gómez B, Santiago JM (1978a) Determinación de compuestos orgánicos de fósforo con posible toxicidad y detección de actividad anticolinesterásica en muestras obtenidas a partir de caucho natural. An Quim 74:1259–1262
Vilanova E, Gómez B, Vicedo JL, Santiago JM (1978b) Actividad anticolinesterásica de fracciones aisladas mediante métodos cromatográficos a partir de muestras de caucho natural. An Quim 74:1263–1266
Vilanova E (1981) Revisión sobre las neuropatías del calzado y su posible relación con inhibidores de colinesterasas. Prevention 77:15–22
Xintaras C, Burg JR, Tanaka S, Lee ST, Johnson BL, Cottrill CA, Bender J (1978) NIOSH Health Survey of Velsicol Pesticide Workers: Occupational exposure to leptophos and other chemicals. US Govern Printing Office, Washington DC
Yamamura Y (1969) n-Hexane polyneuropathy. Folia Psychiatr Neurol Jpn 23:45–47
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This work was partly supported by “Asociación para la Prevención de Accidentes”, Echaide, 6, San Sebastián, Spain
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Vilanova, E., Vicedo, J.L. Serum cholinesterase inhibitors in the commercial hexane impurities. Arch Toxicol 53, 59–69 (1983). https://doi.org/10.1007/BF01460002
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DOI: https://doi.org/10.1007/BF01460002