Synthesis and evaluation of novel analogues of vitamin B6 as reactivators of tabun and paraoxon inhibited acetylcholinesterase

Chemico-Biological Interactions

Volumn 187, Issue 1-3, 2010, Pages 234-237

  Gašo Sokač, Dajana ^a   Katalinić, Maja ^b   Kovarik, Zrinka ^b   Bušić, Valentina ^a   Kovač, Spomenka ^a  

^a JOSIP JURAJ STROSSMAYER UNIVERSITY OF OSIJEK   (Croatia)

^b INSTITUTE FOR MEDICAL RESEARCH AND OCCUPATIONAL HEALTH   (Croatia)

Author keywords

Acetylcholinesterase; Paraoxon; Pyridoxal oxime; Reactivation; Tabun

Indexed keywords

1 (4' CHLOROPHENACYL) 3 HYDROXY 4 HYDROXYIMINOMETHYL 5 HYDROXYMETHYL 2 METHYLPYRIDINIUM BROMIDE; 1 (4' FLUOROPHENACYL) 3 HYDROXY 4 HYDROXYIMINOMETHYL 5 HYDROXYMETHYL 2 METHYLPYRIDINIUM BROMIDE; 1 PHENACYL 3 HYDROXY 4 HYDROXYIMINOMETHYL 5 HYDROXYMETHYL 2 METHYLPYRIDINIUM BROMIDE; 3 HYDROXY 4 HYDROXYIMINOMETHYL 5 HYDROXYMETHYL 2 METHYL 1 (4' METHOXYPHENACYL)PYRIDINIUM BROMIDE; 3 HYDROXY 4 HYDROXYIMINOMETHYL 5 HYDROXYMETHYL 2 METHYL 1 (4' METHYLPHENACYL)PYRIDINIUM BROMIDE; ACETYLCHOLINESTERASE; OXIME DERIVATIVE; PARAOXON; PYRIDOXAL OXIME; PYRIDOXINE DERIVATIVE; TABUN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME REACTIVATION; ERYTHROCYTE; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; STRUCTURE ANALYSIS;

EID: 77955519218     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.02.004     Document Type: Article

References (16)

1. Somani S.M., Romano J.A. Chemical Warfare Agents: Toxicity at Low levels 2001, CRS Press LLC, Boca Raton, Florida.
2. Bajgar J. Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Adv. Clin. Chem. 2004, 38:151-216.
3. Gray A.P. Design and structure-activity relationships of antidotes to organophosphorus anticholinesterase agents. Drug Metab. Rev. 1984, 15:557-589.
4. Dawson R.M. Review of oximes available for the treatment of nerve agent poisoning. J. Appl. Toxicol. 1994, 14:317-331.
5. Primožič I., Odžak R., Tomić S., Simeon-Rudolf V., Reiner E. Pyridinium, imidazolium, and quinucludinium oximes: synthesis, interaction with native and phosphylated cholinesterases, and antidotes against organophosphorus compounds. J. Med. Chem. Def. 2004, 2:1-29.
6. Rudolf S., Reiner E., Škrinjarić-Špoljar M., Radić B., Lucić A., Primožić I., Tomić S. Quinuclidinium-imidazolium compounds: synthesis, mode of interaction with acetylcholinesterase and effect upon soman intoxicated mice. Arch. Toxicol. 1998, 72:289-295.
7. Škrinjarić-Špoljar M., Burger N., Lovrić J. Inhibition of acetylcholinesterase by three new pyridinium compounds and their effect on phosphonylation of the enzyme. J. Enzyme Inhib. 1999, 14:331-341.
8. Kovarik Z., Čalić M., Šinko G., Bosak A., Berend S., Lucić Vrdoljak A., Radić B. Oxime: reactivators of phosphorylated acetylcholinesterase and antidotes in therapy against tabun poisoning. Chem. Biol. Interact. 2008, 175:173-179.
9. Kovarik Z., Čalić M., Bosak A., Šinko G., Jelić D. In vitro evaluation of aldoxime interactions with human acetylcholinesterase. Croat. Chem. Acta 2008, 81(1):47-57.
10. Jukić M., Hergold-Brundić A., Cetina M., Nagl A., Vorkapić-Furač J. Synthesis and structures of the novel pyridoxal oxime derivatives. Struct. Chem. 2003, 14:597-604.
11. Čalić M., Lucić A., Vrdoljak Radić B., Jelić D., Jun D., Kuča K., Kovarik Z. In vitro and in vivo evaluation of pyridinium oximes: mode of interaction with acetylcholinesterase, effect on tabun- and soman-poisoned mice and their cytotoxicity. Toxicology 2006, 219:85-96.
12. Ellman G.L., Courtney K.D., Andres V., Featherstone R.M. New and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7:88-95.
13. Milatović D., Vorkapić-Furač J., Škrinjarić-Špoljarić M., Reiner E. Synthesis of three pyridoxal oxime derivatives and their reactivating potency against phosphylated acetylcholinesterase. Acta Pharm. Jugoslav. 1989, 39:281-287.
14. Bevandić Z., Deljac A., Maksimović M., Bošković B., Binenfeld Z. Methylthio analogues of PAM-2, TMB-4 and obidoxime as antidotes in organophosphate poisonings. Acta Pharm. Jugoslav. 1985, 35:213-218.
15. Bregovec I., Maksimović M., Deljac V., Binenfeld Z. Reactivators of phosphorylated and phosphonylated acetylcholinesterase. Dicarbamoyl substituted pyridinium monooximes. Acta Pharm. Jugoslav. 1983, 33:177-182.
16. Odžak R., Čalić M., Hrenar T., Primožič I., Kovarik Z. Evaluation of monoquaternary pyridinium oximes potency to reactivate tabun-inhibited human acetylcholinesterase. Toxicology 2007, 233:85-96.