Медико-биологический
информационный портал
для специалистов
 
Medline.ru

СОДЕРЖАНИЕ ЖУРНАЛА:
Физико-химическая биология

Клиническая медицина

Профилактическая медицина

Медико-биологические науки


АРХИВ:

Фундаментальные исследования

Организация здравохраниения

История медицины и биологии



Последние публикации

Поиск публикаций

Articles

Архив :  2000 г.  2001 г.  2002 г. 
               2003 г.  2004 г.  2005 г. 
               2006 г.  2007 г.  2008 г. 
               2009 г.  2010 г.  2011 г. 
               2012 г.  2013 г.  2014 г. 
               2015 г.  2016 г.  2017 г. 
               2018 г.  2019 г.  2020 г.  2021 г.  2022 г.  2023 г. 

Редакционная информация:
        Опубликовать статью
        Наша статистика


 РЕДАКЦИЯ:
Главный редактор

Заместители главного редактора

Члены редколлегии
Специализированные редколлегии


 УЧРЕДИТЕЛИ:
Институт теоретической и экспериментальной биофизики Российской академии наук.

ООО "ИЦ КОМКОН".




Адрес редакции и реквизиты

199406, Санкт-Петербург, ул.Гаванская, д. 49, корп.2

ISSN 1999-6314

Российская поисковая система
Искать: 


«
Vol. 24, Art. 22 (pp. 305-324)    |    2023       
»

Toxicokinetic approaches to the development of effective and safe cyanide antidotes. experimental and theoretical aspects
Gladkikh V.D.

Federal State Unitary Enterprise Scientific and Production Center «Pharmzaschita» Federal Medical and Biological Agency



Brief summary

Based on the analysis of literature data, the article characterizes multiple biotransformation pathways of endogenous cyanide, discusses toxicokinetic approaches to the development of cyanide antidotes. Attention is focused on the shortcomings of modern antidotes and promising directions for improving antidote prevention and treatment of acute cyanide poisoning are considered. The role of potential cyanide antidotes, effective and safe for intramuscular, inhalation and oral delivery, is claimed primarily by chemical compounds mediating anti-cyanide activity by stimulating the main mechanisms of detoxification of endogenous cyanide: sulfangene, cobinamide, ketoglutaric acid derivatives.


Key words

tidotes; detoxification; cobinamide; poisoning; toxicokinetics; sulfangene; cyanides; α-ketoglutaric acid





(The article in PDF format. For preview need Adobe Acrobat Reader)



Open article in new window

Reference list

1. Marrs  T.C. The choice of cyanide antidotes. Clinical and Experimental Toxicology of Cyanides. 1987; 383-401.


2. Gunasekar P.G., Borowitz J.L., Turek J.J., et al.  Endogenous generation of cyanide in neuronal tissue: Involvement of a peroxidase system. J. Neurosci. Res.2000; 61: 570-575.


3. Cipollone R., Visca P. Is there evidence that cyanide can act as a neuromodulator IUBMB Life. 2007; 59: 187-189.


4. Chen K.K., Rose C.L.  Nitrite and thiosulfate therapy in cyanide poisoning. J. Am. Med. Assoc. 1952; 149 (2): 113-119.


5. Chen K., Rose C., Clowes G. Comparative values of several antidotes in cyanide poisoning. Amer. J. Med. Sci. 1934; 188: 767-781.


6. Hall  A.H., Saiers J., Baud F. Which cyanide antidote? Crit. Rev. Toxicol. 2009; 39: 541-552.


7. Zilker T.  Medical management of incidents with chemical warfare agents. Toxicology. 2005; 214: 221-231.


8. Baselt R.C. Disposition of Toxic Drugs and Chemicals in Man. 11th edn. - Seal Beach, CA: Biomedical Publications, 2011.


9. Pluta R.M., Oldfield E.H., Bakhtian K.D., et al. Safety and feasibility of long-term intravenous sodium nitrite infsion in healthy volunteers. PLoS One. 2011; 6(1): 14504.


10. Zverev M.I. Otravlenie cianidami. - M.: Medicina, 1983.


11. Paulet G., Le Bars R. Resuscitation after death by cyanide poisoning (study in the dog). J. Physiologie. 1959; 51: 547-548.


12. Mushett C.W., Kelley K.L., Boxer G.E., et al. Antidotal efficacy of vitamin B12a (hydroxo-cobalamin) in experimental cyanide poisoning. Proc. Soc. Exp. Biol. Med. 1952; 81: 234-237.


13. Marrs T.C. Dicobalt edetate (Kelocyanor) van Heijst (eds.) IPCS/CEC Evaluation of Antidotes Series. Vol. 2: Antidotes for Poisoning by Cyanide. -Cambridge: Cambridge University Press, 1993.


14. Baud F. Cyanide: critical issues in diagnosis and treatment. Human Exp. Toxicol. 2007; 26: 191-201.


15. Isom G.E., Borowitz J.L., Mukhdpadhyay S. Enzymes involved in cyanide metabolism. Comprehensive Toxicology. Vol. 3: Biotransformation, 2nd edn. - Oxford: Elsevier Science, 2010.


16. Johnson J.D., Conroy W.G., Isom G.E. Alteration of cytosolic calcium levels in PC12 cells by potassium cyanide. Toxicol. Appl. Pharmacol. 1987; 88: 217-224.


17. Aminlari M., Malekhussein A., Akrami F., Ebrahimnejad A. Cyanide-metabolizing enzyme rhodanese in human tissues: Comparison with domestic animals. Comp. Clin. Pathol. 2007; 16: 47-51.


18. Way J.L, Cannon E., Leung P., et al. Antagonism of cyanide intoxication with rhodanese encapsulated resealed erythrocytes. Adv. Biosci. 1991; 81: 207-211.


19. Wing D.A., Patel H.C., Baskin S.I. The effect of picrylsulfonic acid on in vitro conversion of cyanide to thiocyanate by 3-mercaptopyruvate sulfurtransferase and rhodanese. Toxicol. in Vitro. 1992; 6: 597-603.


20. Borowitz J.L., Kanthasamy A., Isom G.E. Toxicodynamics of Cyanide // Chemical Warfare Agents. San Diego: Academic Press, 1992.


21. Szczepkowski T.W., Wood J.L. The cystathionase rhodanese system. Biochim. Biophys. Acta. 1967; 139: 469-478.


22. Cavallini D., DeMarco C., Mondovi B. The cleavage of cystine by cystathionase and the transulfuration of hypotaurine. Enzymologia. 1960; 22: 161-165.


23. Jarabak R., Westley J. Localization of the sulfur-cyanolysis site of serum albumin to subdomain 3-AB. J. Biochem. Toxicol. 1991; 6: 65-70.


24. Dzombak D.A., Ghosh R.S., Young T.C. Physical-chemical properties and reactivity of cyanide in water and soil. Cyanide in Water and Soil. New York: Taylor & Francis, 2006.


25. Moore S.J., Norris J.C., Ho I.K., Hume A.S. The efficacy of α-ketoglutaric acid in the antagonism of cyanide intoxication. Toxicol. Appl. Pharmacol. 1986; 82: 40-44.


26. Porter D.W., Baskin S.I. The effect of three α-keto acids on 3-mercaptopyruvate sulfurtransferase activity. Biochem. Molec. Toxicol. 1996; 11: 45-50.


27. Isom G.E., Johnson J.D. Sulfur donors in cyanide intoxication. Clinical and Experimental Toxicology of Cyanides. Bristol: Wright, 1987.


28. Nagasawa H.T., Goon D.J., Crankshaw D.L. Novel, orally effective cyanide antidotes. J. Med. Chem. 2007; 50 (26): 6462-6464.


29. Brenner M., Lim J.G., Lee J., et al. Sulfanegen sodium treatment in a rabbit model of sub-lethal cyanide toxicity. Toxicol. Appl. Pharmacol. 2010; 248: 269-276.


30. Belani K.G., Singh H., Beebe D.S., et al. Cyanide toxicity in juvenile pigs and its reversal by a new prodrug, sulfanegen sodium. Anesth. Analg. 2012; 114(5): 956-961.


31. Clemedson C.J., Hultman H.I., Sörbo B. The antidote effect of some sulfur compounds and rhodanese in experimental cyanide poisoning. Acta Physiol. Scand. 1954; 32: 245-251.


32. Petrikovics I., Cannon E.P., McGuinn W.D., et al. Cyanide antagonism with carrier erythrocytes and organic thiosulfonates. Appl. Toxicol. 1995; 24: 86-93.


33. Petrikovics I., Budal M., Baskin S.I., et al. Characterization of liposomal vesicles encapsulating rhodanese for cyanide antagonism. Drug. Deliv. 2009; 16: 312-319.


34. Baskin S.I., Porter D.W., Rockwood G.A., et al. In vitro and in vivo comparison of sulfur donors as antidotes to acute cyanide intoxication. J. Appl. Toxicol. 1999; 19(3): 173-182.


35. Chan A., Balasubramanian M., Blackledge W., et al. Cobinamide is superior to other treatments in a mouse model of cyanide poisoning. Clin. Toxicol. (Phila). 2010; 48: 709-717.


36. Hayward G.C., Hill H.A., Pratt J.M., et al. The chemistry of vitamin B12. Part IV: The thermodynamic trans effect. J. Chem. Soc.1965; 12: 6485-6493.


37. Broderick K.E., Potluri P., Zhuang S., et al. Cyanide detoxification by the cobalamin precursor cobinamide. Exp. Biol. Med. 2006; 231: 641-649.


38. Brenner M., Kim J.G., Mahon S.B., et al. Intramuscular cobinamide sulfite in a rabbit model of sublethal cyanide toxicity. Emerg. Med. 2009; 55: 352-362.


39. Chan A., Crankshaw D.L., Monteil A., et al. The combination of cobinamide and sulfanegen is highly effective in mouse models of cyanide poisoning. Clin. Toxicol. (Phila). 2011; 49: 366-373.


40. Patent SShA ? 5674904, kl. 514/574. - Opyblik. 07.10.1997.


41. Schwartz C., Morgan R.L., Way L.M. et al. Antagonism of cyanide intoxication with sodium pyruvate. Toxicol. Appl. Pharmacol. 1979; 50: 437-441.


42. Hume A.S., Moore S J., Hume A.T. Effects of alpha-ketoglutaric acid on the distribution of cyanide and acidosis associated with cyanide intoxication. Toxicologist. 1996; 3: 98.


43. Bhattacharya R., Tulsawani R.K. In vitro and in vivo evaluation of various carbonyl compounds against cyanide toxicity with particular reference to alpha-ketoglutaric acid. Drug. Chem. Toxicol. 2008; 31: 149-161.


44. Norris J.C., Utley W.A., Hume A.S. Mechanism of antagonising cyanide induced lethality by α-ketoglutarate acid. Toxicology. 1990; 9: 3-9.


45. Bhattacharya R., Satpute R.M., Hariharakrishnan J., et al. Acute toxicity of some synthetic cyanogens in rats and their response to oral treatment with alpha-ketoglutarate. Food. Chem. Toxicol. 2009; 47: 2314-2320.


46. Bhattacharya R., Lakshmana Rao P.V., Vijayaraghavan R. In vitro and in vivo attenuation of experimental cyanide poisoning by α-ketoglutarate. Toxicol. Lett. 2002; 128: 185-195.


47. Kravzov J., Ríos C, Altagracia M., Jiménez D. Comparison of cobalt edetate and alpha-ketoglutarate as antidotes against cyanide intoxication in mice. Proc. West. Pharmacol. Soc. 1994; 37: 43-44.


48.Hariharakrishnan J., Satpute R.M., Bhattacharya R. Cyanide-induced changes in the levels of neurotransmitters in discrete brain regions of rats and their response to oral treatment with α-ketoglutarate. Indian J. Exp. Biol. 2010; 48: 731-736.


49.Hariharakrishnan J., Satpute R.M., Prasad G.B., Bhattacharya R. Oxidative stress mediated cytotoxicity of cyanide in LLC-MK2 cells and its attenuation by Alpha-ketoglutarate and N acetyl cysteine. Toxicol. Lett. 2009; 185: 132-141.


50. Satpute R.M., Hariharakrishnan J., Bhattacharya R. Effect of alpha-ketoglutarate and N acetyl cysteine on cyanide-induced oxidative stress mediated cell death in PC12 cells. Toxicol. Ind. Health. 2010; 26: 297-308.


51.Satpute R.M., Hariharakrishnan J., Lomash V., et al. Oxidative stress and tissue pathology caused by subacute exposure to ammonium acetate in rats and their response to treatments with alpha-ketoglutarate and N acetyl cysteine. Toxicol. Ind. Health. 2012.


52. Rockwood G.A., Duniho S.M., Briscoe C.M. Toxicity in rhesus monkeys following administration of the 8-aminoquinoline 8-[(4-amino 1-methylbuthyl) amino]-5-(1-hexyloxy)-6-methoxy 4-methylquinoline (WR242511). J. Med. Toxicol. 2000; 4 (3): 157-166.


53. Marino M.T., Urquhart M.R., Sperry M.L. Pharmacokinetics and kinetic-dynamic modeling of aminophenones as methaemoglobin forms. J. Pharm. Pharmacol. 1997; 49(3): 282-287.


54. Nicholls P., Soulimane T. The mixed valence state of the oxidase binuclear centre: How thermos thermaphilus cytochrome Ba3 differs from classical Aa3 in the aerobic steady state and when inhibited by cyanide. Biochim. Biophys. Acta. 2004; 1655: 381-387.


55. Bhattacharya R., Vijayaraghavan R. Promising role of α-ketoglutarate in protecting the lethal effects of cyanide. Hum. Exp. Toxicol. 2002; 21: 297-303.


56. Dulaney M.D., Brumley M., Willis J.T., Hume S. Protection against cyanide toxicity by oral alpha-ketoglutaric acid. Vet. Hum. Toxicol. 1991: 33: 571-575.


57. Bhattacharya R., Niranjan L. Protective efficacy of various carbonyl compounds and their metabolites, and nutrients against acute toxicity of some cyanogens in rats: biochemical and physiological studies. Interdisciplinary Toxicology 2017; 10(1): 1-10.


58. Tulsawani R.K., Kumar D., Bhattacharya R. Effect of pretreatment of α-ketoglutarate on cyanide-induced toxicity and alterations in various physiological variables in rodents. Biomed. Environ. Sci. 2007; 20: 56-63.


59. Mittal G., Singh T., Kumar N., et al. Radiolabeling and dose fixation study of oral alpha-ketoglutarate as a cyanide antidote in healthy human volunteers. Clin. Toxicol. 2010; 48: 509-515.


60. Mathangi D.C., Shyamala R., Vijayshree R., et al. Effect of alpha-ketoglutarate on neurobehavioral, neurochemical and oxidative changes caused by sub-chronic cyanide poisoning in rats. Neurochem. Res.2011; 36: 540-548.


61. Tulsawani R.K., Debnath M., Pant S.C., et al. Effect of sub-acute oral cyanide administration in rats: Protective efficacy of α-ketoglutarate and sodium thiosulfate. Chem. Biol. Inter. 2005; 156: 1-12.


62. Patra D. Serum kinetics study of α-ketoglutarate in Wistar rats following single oral administration. A project report. Jai Research Foundation, Valsad, India to DRDE, Gwalior.- Personal communication (Study No. 1573). 2005; 1: 27.


63.Patent RU2553275. Smeshannie kobalt(II)ovie soli ketokarbonovih i merkaptokarbonovih kislot ili ih gidrati ili ih solvati, sposob ih polycheniya i primenenie v kachestve antidotov cianidov / V.U. Kovtyn, U.A. Davidovich, V.D. Gladkih i dr.- Opybl. 10.06.2015.


64. Balandin N.V., Kovtyn V.U., Gladkih V.D. i dr. Doklinicheskaya ocenka innovacionnogo lechebno-profilakticheskogo antidota cianidov na osnove smeshannoi kobaltovoi (II) soli merkaptoyksysnoi i pirovinogradnoi kislot. Sovremennie problemi nayki i obrazovaniya. 2014;  3: 521.


65 Balandin N.V., Kovtyn V.U., Gladkih V.D. i dr. K voprosy farmakokinetiki lekarstvennoi formi potencialnogo lechebno-profilakticheskogo antidota cianidov na osnove smeshannoi kobaltovoi (2 +) soli merkaptoyksysnoi i pirovinogradnoi kislot. Fyndamentalnie Issledovaniya. 2014; 9(5): 1023-1026.


66. Davidovich U.A., Vershinina G.V., Gladkih V.D. i dr. Eksperimentalnaya ocenka vozmojnosti sozdaniya profilakticheskogo antidota monooksida ygleroda i cianidov na osnove metallokompleksnih soedinenii s psevdopeptidnimi ligandami. Medlain.ry. 2019; 20: 71-80.


67. Vershinina G.V., Gladkih V.D., Balandin N.V. i dr. K voprosy razrabotki kombinirovannogo antidota monooksida ygleroda i cianidov na osnove digidrata diacetata kobaltovogo (II) kompleksa N-merkaptoacetil -L -arginina //Sbornik statei po materialam XXY-oi mejdynarodnoi naychno-prakticheskoi konferencii «Nayka Rossii: Celi i zadachi». 2021; Ch.1.:16-19.





Свидетельство о регистрации сетевого электронного научного издания N 077 от 29.11.2006
Журнал основан 16 ноября 2000г.
Выдано Министерством РФ по делам печати, телерадиовещания и средств массовых коммуникаций
(c) Перепечатка материалов сайта Medline.Ru возможна только с письменного разрешения редакции

Размещение рекламы

Rambler's Top100