Inhibition of histamine-N-methyltransferase activity by neuromuscular blocking drugs

Agents and Actions - Tập 17 - Trang 27-31 - 1985
D. G. Harle1,2, B. A. Baldo1,2, M. M. Fisher3
1Kolling Institute of Medical Research, Royal North Shore Hospital, Sydney, Australia
2Department of Medicine, University of Sydney, Australia
3Intensive Therapy Unit, Royal North Shore Hospital, Sydney, Australia

Tóm tắt

On the basis of previous findings that histamine-N-methyltransferase (HMT) activity can be significantly enhanced or inhibited by a number of analogues of histamine and drugs containing dialkylaminoalkyl moieties, we investigated whether the neuromuscular blocking drugs alcuronium,d-tubocurarine, decamethonium, succinylcholine, gallamine and pancuronium each of which contain quaterhary ammonium groups, influence the activity of HMT. Our findings showed that all six drugs significantly inhibited HMT activity in the concentration range 10−7–10−3 M with alcuronium being the most potent inhibitor (I.D.50=2×10−6 M). Activities at these concentrations reveals that alcuronium, pancuronium,d-tubocurarine and gallamine are more potent inhibitors than two of the most potent histamine analogue inhibitors,N τ-methylhistamine and 2-methylhistamine. Alcuronium proved to be of similar potency to the dimaprit analogue, SKF 91488 regarded as one of the most potent HMT inhibitors known. The structurally similar and chemically least complex straight chain neuromuscular blocking compounds, succinylcholine and decamethonium proved to be the least potent inhibitors.

Tài liệu tham khảo

H. Barth, W. Lorenz andI. Niemeyer,Properties and reaction mechanism of gastric histamine methyltransferase, Abstracts 6th Intern. Congress of Pharmacology, Helsinki, 96 (1975). H. Barth, W. Lorenz andI. Niemeyer,Inhibition and activation of histamine methyltransferase by methylated histamines, Hoppe-Seyler's Z. physiol. Chem.354, 1021–1026 (1973). A. Thithapandha andV.H. Cohn,Brain histamine N-methyltransferase purification, mechanism of action and inhibition by drugs, Biochem. Pharmac.27, 263–271 (1978). V.H. Cohn,Inhibition of histamine methylation by antimalarial drugs, Biochem. Pharmac.14, 1686–1688 (1965). H. Barth andW. Lorenz,Structural requirements of imidazole compounds to be inhibitors or activators of histamine methyltransferase: investigation of histamine analogues and H 2-receptor antagonists, Agents and Actions8, 359–365 (1978). M.A. Beaven andR.E. Shaff,New inhibitors of histamine-N-methyltransferase, Biochem. Pharmac.28, 183–188 (1979). K.J. Netter andK. Bodenschatz,Inhibition of histamine-N-methylation by some antihistamines, Biochem. Pharmac.16, 1627–1631 (1967). K.M. Taylor andS.H. Snyder,Histamine methyltransferase: inhibition and potentiation by antihistamines, Molec. Pharmac.8, 300–310 (1972). B.A. Baldo andM.M. Fisher,Substituted ammonium ions as allergenic determinants in drug allergy, Nature, Lond.306, 262–264 (1983). B.A. Baldo andM.M. Fisher,Anaphylaxis to muscle relaxant drugs: cross-reactivity and molecular basis of binding of IgE antibodies detected by radio-immunoassay, Molec. Immun.20, 1393–1400 (1983). B.A. Baldo andM.M. Fisher,Detection of serum IgE antibodies that react with alcuronium and tubocurarine after lifethreatening reactions to muscle relaxant drugs, Anaesth. Intens. Care11, 194–197 (1983). D.G. Harle, B.A. Baldo andM.M. Fisher,Detection of IgE antibodies to suxamethonium after anaphylactoid reactions during anaesthesia, Lanceti, 930–932 (1984). D.G. Harle, B.A. Baldo andM.M. Fisher,Assays for cross-reactivities of, IgE antibodies to the muscle relaxants gallamine, decamethonium and suxamethonium, J. Immunol. Methods78, 293–305 (1985). M. McD. Fisher,Severe histamine mediated reactions to intravenous drugs used in anaesthesia, Anaesth. Intens. Care3, 180–197 (1975). R.E. Shaff andM.A. Beaven,Increased sensitivity of the enzymatic isotopic assay of histamine: measurement of histamine in plasma and serum, Analyt. Biochem.94, 425–430 (1979). M.A. Beaven, A. Robinson-White, N.B. Roderick andG.L. Kauffman,The demonstration of histamine release in clinical conditions: a review of past and present assay procedures, Klin. Wschr.60, 873–881 (1982). K.M. Taylor, S. Krilis andB.A. Baldo,An enzymatic-isotopic microassay for measuring allergic release of histamine from blood and mast cells in vitro, Int. Archs. Allergy appl. Immun.61, 19–27 (1980). S.H. Snyder, R.J. Baldessarini andJ. Axelrod,A sensitive and specific enzymatic isotopic assay for tissue histamine, J. Pharmac. exp. Ther.153, 544–549 (1966). K.M. Taylor andS.H. Snyder,Isotopic microassay of histamine, histidine, histidine decarboxylase and histamine methyltransferase in brain tissue, J. Neurochem.19, 1343–1358 (1972). W. Lorenz, H. Barth, H.E. Karges, A. Schmal, P. Dormann andI. Niemeyer,Problems in the assay of histamine release by gelatin: o-phthaldialdehyde-induced fluorescence, inhibition of histamine methyl-transferase and H 2-receptor antagonism by haemaccel, Agents and Actions4, 324–335 (1974). W. Lorenz andA. Doenicke,Histamine release in clinical conditions, Mt. Sinai J. Med. (NY)45, 357–386 (1978). H. Barth, I. Niemeyer andW. Lorenz,Similar actions of methylated histamines and histamine receptor antagonists on gastric histamine methyltransferase, Agents and Actions3, 173–175 (1973). A. Gustafsson andG.P. Forshell,Studies on the enzymic methylation of histamine, Acta chem. scand.18, 2069–2076 (1964). H. Barth, I. Niemeyer andW. Lorenz,Studies on the mode of action of histamine H 1 - and H 2 -receptor antagonists on gastric histamine methyltransferase, Agents and Actions3, 138–147 (1973). K.M. Taylor,Comparison of the antihistaminic effect of burimamide and mepyramine and their effect on the activity of histamine methyltransferase, Biochem. Pharmac.22, 2775–2776 (1973). W. Lorenz, M. Thermann, K. Messmer, A. Schmal, P. Dormann, J. Kusche, H. Barth, R. Tauber, M. Hutzel, G. Mann andR. Uhlig,Evaluation of histamine elimination curves in plasma and whole blood of several circulatory regions: a method for studying kinetics of histamine release in the whole animal, Agents and Actions4, 336–356 (1974). D.G. Harle, B.A. Baldo andM.M. Fisher,In vitro diagnosis and studies on the mechanism(s) of anaphylactoid reactions to muscle relaxant drugs, Ann. Fr. Anesth, Réanim. (in press) (1985).