Passive diffusion of acetylcholinesterase oxime reactivators through the blood-brain barrier: Influence of molecular structure

Toxicology in Vitro

Volumn 24, Issue 6, 2010, Pages 1838-1844

  Karasova, Jana Zdarova ^a   Pohanka, Miroslav ^b   Musilek, Kamil ^a   Zemek, Filip ^a   Kuca, Kamil ^a,b  

^a UNIVERSITY OF DEFENCE   (Czech Republic)

^b UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

Acetylcholinesterase; Blood brain barrier; CNS penetration; HPLC; Immobilized artificial membrane; Reactivator

Indexed keywords

4 METHYLANILINE; ATENOLOL; CAFFEINE; CEFUROXIME; CHLORPROMAZINE; CHOLINESTERASE REACTIVATOR; CIMETIDINE; CORTICOSTERONE; DESIPRAMINE; ENALAPRIL; ESTRADIOL; HYDROCORTISONE; IBUPROFEN; IMIPRAMINE; LOMEFLOXACIN; LOPERAMIDE; NADOLOL; PIROXICAM; PROGESTERONE; PROMAZINE; PROPRANOLOL; TESTOSTERONE;

ARTICLE; ARTIFICIAL MEMBRANE; BLOOD BRAIN BARRIER; CENTRAL NERVOUS SYSTEM; CONTROLLED STUDY; DRUG PENETRATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MOLECULAR WEIGHT; PASSIVE TRANSPORT; PREDICTION; SCREENING TEST; VALIDITY;

BIOLOGICAL MARKERS; BIOLOGICAL TRANSPORT; BLOOD-BRAIN BARRIER; CHOLINESTERASE REACTIVATORS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIFFUSION; MEMBRANES, ARTIFICIAL; MOLECULAR STRUCTURE; OXIMES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956174483     PISSN: 08872333     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tiv.2010.05.009     Document Type: Article

References (31)

1. Bajgar J. Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment. Advances in Clinical Chemistry 2004, 38:151-216.
2. Bajgar J., Jakl A., Hrdina V. The influence of obidoxime on acetylcholinesterase activity in different parts of the mouse brain following isopropylmethyl phosphonofluoridate intoxication. European Journal of Pharmacology 1972, 19:199-202.
3. Bajgar J., Kuca K., Jun D., Bartosova L., Fusek J. Cholinesterase reactivators: the fate and effects in the organism poisoned with organophosphates/nerve agents. Current Drug Metabolism 2007, 8:803-809.
4. Balali-Mood M., Balali-Mood K. Neurotoxic disorders of organophosphorus compounds and their managements. Archives of Iranian Medicine 2008, 11:65-89.
5. Berend S., Vrdoljak A.L., Radić B., Kuca K. New bispyridinium oximes: in vitro and in vivo evaluation of their biological efficiency in soman and tabun poisoning. Chemico-Biological Interactions 2008, 175(2008):413-416.
6. Cassel G., Karlsson L., Waara L., Ang K.W., Göransson-Nyberg A. Pharmacokinetics and effects of HI 6 in blood and brain of soman-intoxicated rats: a microdialysis study. European Journal of Pharmacology 1997, 332:43-52.
7. Chen Y., Zhu Q.J., Pan J., Yang Y., Wu X.P. A prediction model for blood-brain barrier permeation and analysis on its parameter biologically. Computer Methods and Programs in Biomedicine 2009, 95:280-287.
8. Clark D.E. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 2. Prediction of blood-brain barrier penetration. Journal of Pharmaceutical Sciences 1999, 88:815-821.
9. Gyenge M., Kalasz H., Petroianu G.A., Laufer R., Kuca K., Tekes K. Measurement of K-27, an oxime-type cholinesterase reactivator by high-performance liquid chromatography with electrochemical detection from different biological samples. Journal of Chromatography A 2007, 1161:146-151.
10. Kalász H., Szöko E., Tábi T., Petroianu G.A., Lorke D.E., Omar A., Alafifi S., Jasem A., Tekesz K. Analysis of pralidoxime in serum, brain and CSF of rats. Medicinal Chemistry 2009, 5:237-241.
11. Karasova J.Z., Kassa J., Jung Y.S., Musilek K., Pohanka M., Kuca K. Effect of several new and currently available oxime cholinesterase reactivators on tabun-intoxicated rats. International Journal of Molecular Sciences 2008, 9:2243-2252.
12. Karasova J.Z., Kassa J., Musilek K., Pohanka M., Novotny L., Kuca K. Effect of seven newly synthesized and currently available oxime cholinesterase reactivators on cyclosarin-intoxicated rats. International Journal of Molecular Sciences 2009, 10:3065-3075.
13. Karasova J.Z., Bajgar J., Jun D., Pavlikova R., Kuca K. Time-course changes of acetylcholinesterase activity in blood and some tissues in rats after intoxication by Russian VX. Neurotoxicity Research 2009, 16:356-360.
14. Karasova, J.Z., Stodulka, P., Pohanka, M., Kuca, K., in press. In vitro screening of blood-brain barrier penetration of monoquaternary acetylcholinesterase reactivators. Analytical Letters. doi: doi:10.1080/00032710903502082.
15. Karasova J.Z., Stodulka P., Kuca K. In vitro screening of blood-brain barrier penetration of clinically used acetylcholinesterase reactivators. Journal of Applied Biomedicine 2010, 8:35-40.
16. Lanevskij K., Japertas P., Didziapetris R., Petrauskas A. Ionization-specific prediction of blood-brain permeability. Journal of Pharmaceutical Sciences 2009, 98:122-134.
17. Ligtenstein D.A., Kosen S.P. Kinetic profile in blood and brain of the cholinesterase reactivating oxime HI-6 after intravenous administration to the rat. Toxicology and Applied Pharmacology 1983, 71:177-183.
18. Lorke D.E., Hasan M.Y., Nurulain S.M., Sheen R., Kuca K., Petroianu G.A. Entry of two new asymmetric bispyridinium oximes (K-27 and K-48) into the rat brain: comparison with obidoxime. Journal of Applied Toxicology 2007, 27:482-490.
19. Lorke D.E., Kalasz H., Petroianu G.A., Tekes K. Entry of oximes into the brain: a review. Current Medicinal Chemistry 2008, 15:743-753.
20. Marrs T.C., Rice P., Vale J.A. The role of oximes in the treatment of nerve agent poisoning in civilian casualties. Toxicological Reviews 2006, 25:297-323.
21. Palm K., Luthman K., Ungell A.L., Strandlung G., Beigi F., Lundahl P. Evaluation of dynamic polar molecular surface area as predictor of drug absorption: comparison with other computational and experimental predictors. Journal of Medicinal Chemistry 1998, 41:5382-5392.
22. Petroianu G.A., Lorke D.E., Hasan M.Y., Adem A., Sheen R., Nurulain S.M., Kalasz H. Paraoxon has only a minimal effect on pralidoxime brain concentration in rats. Journal of Applied Toxicology 2007, 27:350-357.
23. Reiner E., Radić Z., Simeon-Rudolf V. Mechanisms of organophosphate toxicity and detoxication with emphasis on studies in Croatia. Arhiv za Higijenu Rada i Toksikologiju 2007, 58:329-338.
24. Sakurada K., Matsubara K., Shimizu K., Shiono H., Seto Y., Tsuge K., Yoshino M., Sakai I., Mukoyama H., Takatori T. Pralidoxime iodide (2-pAM) penetrates across the blood-brain barrier. Neurochemical Research 2003, 28:1401-1407.
25. Terasaki T., Ohtsuki S. Brain-to-blood transporters for endogenous substrates and xenobiotics at the blood-brain barrier: an overview of biology and methodology. Neurotherapeutics 2005, 2:63-72.
26. Tsukita S., Furuse M., Itoh M. Multifunctional strance in tight junctions. Nature Reviews Molecular Cell Biology 2001, 2:285-293.
27. Turksen K., Troy T.C. Barriers built on claudins. Journal of Cell Science 2004, 117:2435-2447.
28. van Helden H.P., Busker R.W., Melchers B.P., Bruijnzeel P.L. Pharmacological effects of oximes: how relevant are they?. Archives of Toxicology 1996, 70:779-786.
29. Yanagisawa N., Morita H., Nakajima T. Sarin experiences in Japan: acute toxicity and long-term effects. Journal of the Neurological Sciences 2006, 249:76-85.
30. Yoon H.C., Kim S.J., Shin B.S., Lee K.C., Yoo S.D. Rapid screening of blood-brain barrier penetration of drugs using the immobilized artificial membrane phosphatidylcholine column chromatography. Journal of Biomolecular Screening 2006, 11:13-20.
31. Zhu C., Juany L., Chen T.M., Hwang K.K. A comparative study of artificial membrane permeability assay for high throughput profiling of drug absorption potential. European Journal of Medicinal Chemistry 2002, 37:399-407.