Novel, Orally Effective Cyanide Antidotes

Overview

Journal J Med Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2007 Nov 28

PMID 18038966

Citations 18

Authors

Herbert T Nagasawa

David J W Goon

Daune L Crankshaw

Robert Vince

Steven E Patterson

Affiliations

Soon will be listed here.

Abstract

A series of prodrugs of 3-mercaptopyruvate (3-MP), the substrate for the enzyme 3-mercaptopyruvate/cyanide sulfurtransferase (3-MPST) that converts cyanide to the nontoxic thiocyanate, which are highly effective cyanide antidotes, have been developed. These prodrugs of 3-MP are unique in being not only orally bioavailable, but may be administered up to an hour prior to cyanide as a prophylactic agent and are both rapid- or slow-acting when given parenterally.

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References

Alexander K, Baskin S . The inhibition of cytochrome oxidase by diaminomaleonitrile. Biochim Biophys Acta. 1987; 912(1):41-7. DOI: 10.1016/0167-4838(87)90245-7. View

Roberts J, Nagasawa H, Zera R, Fricke R, Goon D . Prodrugs of L-cysteine as protective agents against acetaminophen-induced hepatotoxicity. 2-(Polyhydroxyalkyl)- and 2-(polyacetoxyalkyl)thiazolidine-4(R)-carboxylic acids. J Med Chem. 1987; 30(10):1891-6. DOI: 10.1021/jm00393a034. View

Hol W, Lijk L, Kalk K . The high resolution three-dimensional structure of bovine liver rhodanese. Fundam Appl Toxicol. 1983; 3(5):370-6. DOI: 10.1016/s0272-0590(83)80007-4. View

Stipanuk M, Dominy Jr J, Lee J, Coloso R . Mammalian cysteine metabolism: new insights into regulation of cysteine metabolism. J Nutr. 2006; 136(6 Suppl):1652S-1659S. DOI: 10.1093/jn/136.6.1652S. View

Megarbane B, Delahaye A, Goldgran-Toledano D, Baud F . Antidotal treatment of cyanide poisoning. J Chin Med Assoc. 2003; 66(4):193-203. View

Huang J, Niknahad H, Khan S, OBrien P . Hepatocyte-catalysed detoxification of cyanide by L- and D-cysteine. Biochem Pharmacol. 1998; 55(12):1983-90. DOI: 10.1016/s0006-2952(98)00072-0. View

Porter D, Baskin S . Specificity studies of 3-Mercaptopyruvate sulfurtransferase. J Biochem Toxicol. 1995; 10(6):287-92. DOI: 10.1002/jbt.2570100602. View

WAY J . Cyanide intoxication and its mechanism of antagonism. Annu Rev Pharmacol Toxicol. 1984; 24:451-81. DOI: 10.1146/annurev.pa.24.040184.002315. View

Crankshaw D, Goon D, Briggs J, DeLong D, Kuskowski M, Patterson S . A novel paradigm for assessing efficacies of potential antidotes against neurotoxins in mice. Toxicol Lett. 2007; 175(1-3):111-7. PMC: 2171362. DOI: 10.1016/j.toxlet.2007.10.001. View

10.

Baskin S, Horowitz A, Nealley E . The antidotal action of sodium nitrite and sodium thiosulfate against cyanide poisoning. J Clin Pharmacol. 1992; 32(4):368-75. DOI: 10.1002/j.1552-4604.1992.tb03849.x. View

11.

Nagahara N, Ito T, Minami M . Mercaptopyruvate sulfurtransferase as a defense against cyanide toxication: molecular properties and mode of detoxification. Histol Histopathol. 1999; 14(4):1277-86. DOI: 10.14670/HH-14.1277. View

12.

DesLauriers C, Burda A, Wahl M . Hydroxocobalamin as a cyanide antidote. Am J Ther. 2006; 13(2):161-5. DOI: 10.1097/01.mjt.0000174349.89671.8c. View

13.

Keim M . Terrorism involving cyanide: the prospect of improving preparedness in the prehospital setting. Prehosp Disaster Med. 2006; 21(2):s56-60. DOI: 10.1017/s1049023x00015910. View

14.

Nagasawa H, Goon D, Muldoon W, Zera R . 2-Substituted thiazolidine-4(R)-carboxylic acids as prodrugs of L-cysteine. Protection of mice against acetaminophen hepatotoxicity. J Med Chem. 1984; 27(5):591-6. DOI: 10.1021/jm00371a006. View

15.

Sylvester M, Sander C . Immunohistochemical localization of rhodanese. Histochem J. 1990; 22(4):197-200. DOI: 10.1007/BF02386005. View