Human erythrocyte but not brain acetylcholinesterase hydrolyses heroin to morphine

Clinical and Experimental Pharmacology and Physiology

Volumn 26, Issue 8, 1999, Pages 596-600

  Salmon, Asher Y ^a   Goren, Zafrir ^b   Avissar, Yaniv ^b   Soreq, Hermona ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b Analytical Laboratory   (Israel)

Author keywords

6 monoacetylmorphine; Acetylcholinesterase; Brain; Butyrylcholinesterase; Erythrocytes; Heroin; Morphine; Opiates

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE; DIAMORPHINE; ISO OMPA; MORPHINE; MORPHINE 6 ACETATE;

BLOOD BRAIN BARRIER; CARBOXY TERMINAL SEQUENCE; CATALYSIS; DRUG DEGRADATION; DRUG HYDROLYSIS; ENZYME ACTIVITY; ENZYME INHIBITION; ERYTHROCYTE MEMBRANE; HUMAN; HUMAN CELL; HYDROLYSIS; IMMOBILIZED CELL; SHORT SURVEY;

ACETYLCHOLINESTERASE; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ERYTHROCYTES; HEROIN; HUMANS; ISOENZYMES; MORPHINE; MORPHINE DERIVATIVES;

EID: 0032770793     PISSN: 03051870     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1440-1681.1999.03090.x     Document Type: Short Survey

References (24)

1. Inturrisi CE, Max MB, Foley KM, Schultz M, Shin S-U, Houde RW. The pharmacokinetics of heroin in patients with chronic pain. New Engl. J. Med. 1984; 310: 1213-17.
2. Boerner V, Abbot S, Roe RL. The metabolism of morphine and heroin in man. Drug Metab. Rev. 1975; 4: 39-73.
3. Lockridge O, Mattershaw-Jackson N, Eckerson HW, LaDu BN. Hydrolysis of diacetylmorphine (heroin) by human serum cholinesterase. J. Pharmacol. Exp. Ther. 1980; 215; 1-8.
4. Kamendulis LM, Brezezinski MR, Pindel EV, Bosron WF, Dean RA. Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases. J. Pharmacol. Exp. Ther. 1996; 279: 713-17.
5. Smith DA, Cole WJ. Identification of an arylesterase as the enzyme hydrolysing diacetylmorphine (heroin) in human plasma. Biochem. Pharmacol. 1976; 25: 367-70.
6. Owen JA, Nakatsu K. Diacetylmorphine (heroin) hydrolases in human blood. Can. J. Physiol. Pharmacol. 1983; 61: 870-5.
7. Ben Aziz-Aloya R, Scidman S, Timberg R, Sternfeld M, Zakut II, Soreq H. Expression of a human acetylcholinesterase promoter-reporter construct in developing neuromuscular junctions of Xenupus embryos. Proc. Natl Acad. Sci. USA 1993; 90: 2471-5.
8. Inturrisi CE, Schultz M, Shin S, Umans JG, Angel C, Simon EJ. Evidence from opiate binding studies that heroin acts through its metabolites. Life Sci. 1983; 33: 773-6.
9. Barrett DA, Dyssegaard AL, Shaw PN. The effect of temperature and pH on the deacylation of diamorphine in aqueous solution and in human plasma. J. Pharm. Pharmacol. 1992; 44: 606-8.
10. Liao J, Mortensen V, Norgaard-Pedersen B, Koch C, Brodbeck U. Monoclonal antibodies against brain acetylcholinesterase which recognize the subunits bearing the Hydrophobic anchor. Eur. J. Biochem. 1993; 215: 33-40.
11. Ellman GL, Courtney D, Anders V Jr, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961; 7: 88-95.
12. Schwarz M, Loewenstein-Lichtenstein Y, Glick D, Liao J, Norgaard-Pedersen B, Soreq H. Successive organophosphate inhibition and oxime reaction reveals distinct responses of recombinant human cholinesterase variants. Mol. Brain Res. 1995; 31: 101-10.
13. Loewenstein-Lichtenstein Y, Schwarz M, Click D, Soreq H. Genetic predisposition to adverse consequences of anti-cholinesterases in 'atypical' BCHE carriers. Nature Med. 1995; 1: 1082-5.
14. Martin WR, Fraser HF. A comparative study of physiological and subjective effects of heroin and morphine administered intravenously in post-addicts. J. Pharmacol. Exp. Ther. 1961; 133: 388-99.
15. Nakamura G, Thornton JI, Noguchi TT. Kinetics of heroin deacylation in aqueous alkaline solution and in human serum and whole blood. J. Chromatogr. 1975; 110: 81-9.
16. Neville LF, Gnatt A, Loewenstein Y, Seidman S, Ehrlich G, Soreq H. Intramolecular relationships in cholinesterases revealed by oocyte expression of site-directed and natural variants of human BCHE. EMBO J. 1992; 11: 1641-9.
17. Soreq H, Ben-Aziz R, Prody CA et al. Molecular cloning and construction of the coding region for human acetylcholinesterase reveals a G + C-rich attenuating structure. Proc. Natl Acad. Sci. USA 1990; 87: 9688-92.
18. Sussman JL, Hard M, Frolow F et al. Atomic structure of acetylcholinesterase from Torpedo californica: A prototype acetylcholine binding protein. Science 1991; 253: 872-9.
19. Taylor P, Radic Z. The cholinesterases: From genes to proteins. Ann. Rev. Pharmacol. Toxicol. 1994, 34: 281-320.
20. Shafferman A, Velan B, Ordentlich A. et al. Substrate inhibition of acetylcholineslerase: Residues affecting signal transduction from the surface to the catalytic center. EMBO J. 1992; 11: 3651-8.
21. Cauet G, Friboulet A, Thomas D. Horse serum butyrylcholinesterase kinetics: A molecular mechanism based on inhibition studies with dalensylaminoethyltrimethylammonium. Biochem. Cell. Biol. 1987; 65: 529-35.
22. Eriksson H, Agustinsson KB. A mechanistic model for butyrylcholinesterase. Biochim. Biophys. Acta 1979; 567: 161-73.
23. Getley SJ. Activities of the enantiomers of cocaine and some related compounds as substrates and inhibitors of plasma butyrylcholinesterase. Biochem. Pharmacol. 1991; 41: 1249-54.
24. Haas R, Adams EW, Rosenberry MA, Rosenberry TL. Substrate-selective inhibition and peripheral site labeling of acetylcholinesterase by platinum (terpyridine) chloride. In: Shafferman A, Velan B (eds). Multidisciplinary Approaches to Cholinesterase Functions. Plenum Press, New York. 1992; 131-9.