Azure B, a metabolite of methylene blue, is a high-potency, reversible inhibitor of monoamine oxidase

Toxicology and Applied Pharmacology

Volumn 258, Issue 3, 2012, Pages 403-409

  Petzer, Anél ^a   Harvey, Brian H ^a   Wegener, Gregers ^b   Petzer, Jacobus P ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

^b AARHUS UNIVERSITY HOSPITAL   (Denmark)

Author keywords

Antidepressant; Azure B; Inhibition; Methylene blue; Monoamine oxidase; Reversible

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; AZURE B; DRUG METABOLITE; METHYLENE BLUE; MONOAMINE OXIDASE INHIBITOR; RECOMBINANT HUMAN MONOAMINE OXIDASE A; RECOMBINANT HUMAN MONOAMINE OXIDASE B; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; IC 50; NONHUMAN;

AZURE STAINS; HUMANS; INHIBITORY CONCENTRATION 50; METHYLENE BLUE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; TIME FACTORS;

ANIMALIA;

EID: 84855972241     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2011.12.005     Document Type: Article

References (36)

1. Aeschlimann C., Cerny T., Küpfer A. Inhibition of monoamine oxidase activity and prevention of ifosfamide encephalopathy by methylene blue. Drug. Metab. Dispos. 1996, 24:1336-1339.
2. Alda M., MacQueen G.M., McKinnon M., Garnham J., MacLellan S., Hajek T., O'Donovan C., Sokolenko M. Methylene blue for residual symptoms and for cognitive dysfunction in bipolar disorder: results of a double-blind trial. Eur. Neuropsychopharmacol. 2011, 21(Suppl. 3):S417.
3. Blass N., Fung D. Dyed but not dead - methylene blue overdose. Anesthesiology 1976, 45:458-459.
4. Bonneau R., Faure J., Joussot-Dubien J. Purification des colorants thiaziniques, azur A, azur B, azur C, par une méthode de partage. Talanta 1967, 14:121-122.
5. Buchholz K., Schirmer R.H., Eubel J.K., Akoachere M.B., Dandekar T., Becker K., Gromer S. Interactions of methylene blue with human disulfide reductases and their orthologues from Plasmodium falciparum. Antimicrob. Agents Chemother. 2008, 52:183-191.
6. i values for inhibitors of enzyme activity and ligand binding. Nucleic Acids Res. 2009, 37:W441-W445.
7. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22:3099-3108.
8. I values for tight binding inhibitors from dose-response plots. Bioorg. Med. Chem. Lett. 1995, 5:1947-1952.
9. Culo F., Sabolović D., Somogyi L., Marusić M., Berbiguier N., Galey L. Anti-tumoral and anti-inflammatory effects of biological stains. Agents Actions. 1991, 34:424-428.
10. Deutsch S.I., Rosse R.B., Schwartz B.L., Fay-McCarthy M., Rosenberg P.B., Fearing K. Methylene blue adjuvant therapy of schizophrenia. Clin. Neuropharmacol. 1997, 20:357-363.
11. DiSanto A.R., Wagner J.G. Pharmacokinetics of highly ionized drugs. II. Methylene blue absorption, metabolism, and excretion in man and dog after oral administration. J. Pharm. Sci. 1972, 61:1086-1090.
12. Eroǧlu L., Caǧlayan B. Anxiolytic and antidepressant properties of methylene blue in animal models. Pharmacol. Res. 1997, 36:381-385.
13. Gillman P.K. A review of serotonin toxicity data: implications for the mechanisms of antidepressant drug action. Biol. Psychiatry 2006, 59:1046-1051.
14. Harris J.E., Peters A. Experiments on vital staining with methylene blue. Quart. J. Microb. Sci. 1953, 26:113-124.
15. Harvey B.H., Duvenhage I., Viljoen F., Scheepers N., Malan S.F., Wegener G., Brink C.B., Petzer J.P. Role of monoamine oxidase, nitric oxide synthase and regional brain monoamines in the antidepressant-like effects of methylene blue and selected structural analogues. Biochem. Pharmacol. 2010, 80:1580-1591.
16. Lewis R.J. Sax's Dangerous Properties of Industrial Chemicals, vol. 2 1992, Van Nostrand Reinhold, New York. eight ed.
17. Morrison J.F. Kinetics of reversible inhibition of enzyme catalysed reactions by tight-binding inhibitors. Biochim. Biophys. Acta 1968, 185:269-286.
18. Narsapur S.L., Naylor G.J. Methylene blue. A possible treatment for manic depressive psychosis. J. Affect. Disord. 1983, 5:155-161.
19. Naylor G.J., Martin B., Hopwood S.E., Watson Y. A two-year double-blind crossover trial of the prophylactic effect of methylene blue in manic-depressive psychosis. Biol. Psychiatry 1986, 21:915-920.
20. Naylor G.J., Smith A.H., Connelly P. A controlled trial of methylene blue in severe depressive illness. Biol. Psychiatry 1987, 22:657-659.
21. Osterhoudt K.C., Penning T.M. Drug toxicity and poisoning. Goodman and Gilman's The Pharmacological Basis of Therapeutics 2011, 86. McGraw Hill Publishers, New York. twelfth ed. L.L. Brunton, B.A. Chabner, B.C. Knollmann (Eds.).
22. Oz M., Lorke D.E., Petroianu G.A. Methylene blue and Alzheimer's disease. Biochem. Pharmacol. 2009, 78:927-932.
23. Oz M., Lorke D.E., Hasan M., Petroianu G.A. Cellular and molecular actions of methylene blue in the nervous system. Med. Res. Rev. 2011, 31:93-117.
24. Peter C., Hongwan D., Küpfer A., Lauterburg B.H. Pharmacokinetics and organ distribution of intravenous and oral methylene blue. Eur. J. Clin. Pharmacol. 2000, 56:247-250.
25. Ramsay R.R., Dunford C., Gillman P.K. Methylene blue and serotonin toxicity: inhibition of monoamine oxidase A (MAO A) confirms a theoretical prediction. Br. J. Pharmacol. 2007, 152:946-951.
26. Schirmer R.H., Adler H., Pickhardt M., Mandelkow E. Lest we forget you - methylene blue. Neurobiol. Aging 2011, 32:2325.e7-2325.e16.
27. Stanford S.C., Stanford B.J., Gillman P.K. Risk of severe serotonin toxicity following co-administration of methylene blue and serotonin reuptake inhibitors: an update on a case report of post-operative delirium. J. Psychopharmacol. 2010, 24:1433-1438.
28. Strydom B., Malan S.F., Castagnoli N., Bergh J.J., Petzer J.P. Inhibition of monoamine oxidase by 8-benzyloxycaffeine analogues. Bioorg. Med. Chem. 2010, 18:1018-1028.
29. Strydom B., Bergh J.J., Petzer J.P. 8-Aryl- and alkyloxycaffeine analogues as inhibitors of monoamine oxidase. Eur. J. Med. Chem. 2011, 46:3474-4385.
30. Taniguchi S., Suzuki N., Masuda M., Hisanaga S., Iwatsubo T., Goedert M., Hasegawa M. Inhibition of heparin-induced tau filament formation by phenothiazines, polyphenols, and porphyrins. J. Biol. Chem. 2005, 280:7614-7623.
31. Volke V., Wegener G., Vasar E., Rosenberg R. Methylene blue inhibits hippocampal nitric oxide synthase activity in vivo. Brain Res. 1999, 826:303-305.
32. Wagner S.J., Skripchenko A., Robinette D., Foley J.W., Cincotta L. Factors affecting virus photoinactivation by a series of phenothiazine dyes. Photochem. Photobiol. 1998, 67:343-349.
33. Wang J., Harris J., Mousseau D.D., Edmondson D.E. Mutagenic probes of the role of Ser209 on the cavity shaping loop of human monoamine oxidase A. FEBS J. 2009, 276:4569-4581.
34. Warth A., Goeppert B., Bopp C., Schirmacher P., Flechtenmacher C., Burhenne J. Turquoise to dark green organs at autopsy. Virchows Arch. 2009, 454:341-344.
35. Wegener G., Volke V., Rosenberg R. Endogenous nitric oxide decreases hippocampal levels of serotonin and dopamine in vivo. Brit. J. Pharmacol. 2000, 130:575-580.
36. Wegener G., Volke V., Bandpey Z., Rosenberg R. Nitric oxide modulates lithium-induced conditioned taste aversion. Behav. Brain Res. 2001, 118:195-200.