Enzymatic mechanisms and toxicological significance of hydrogen cyanide liberation from various organothiocyanates and organonitriles in mice and houseflies

Ohkawa, Hideo; Ohkawa, Reiko; Yamamoto, Ichiro; Casida, John E.

doi:10.1016/0048-3575(72)90011-9

Cited by 89 publications

(21 citation statements)

References 20 publications

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“…Acetonitrile causes nervous disruption in mammals (Ahmed et al, 1992) and may have affected the bees either directly or through its metabolites, which include hydrogen cyanide (Ohkawa et al, 1972). In our study, dietary acetonitrile also accelerated the impact of imidacloprid on feeding rate.…”

Section: The Dose-response Relationship In Bumble Beesmentioning

confidence: 83%

Differential sensitivity of honey bees and bumble bees to a dietary insecticide (imidacloprid)

Cresswell

Page

Uygun

et al. 2012

Zoology

141

104

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Section: The Dose-response Relationship In Bumble Beesmentioning

confidence: 83%

Differential sensitivity of honey bees and bumble bees to a dietary insecticide (imidacloprid)

Cresswell

Page

Uygun

et al. 2012

Zoology

141

104

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“…Originally described as producing cyanide, a mercaptan, and GSSG from organic thiocyanates (66,67), the stoichiometry of the reaction is now known to be that of equation 5 (54); subsequent nonenzymatic disulfide exchange would lead to the formation of GSH + CH&HaCN + CHaCHtSSG + HCN (5) the free mercaptan and GSSG. This reaction is catalyzed by each of the glutathione transferases (Table VIII) and with the same distribution on purification that is observed with "nitrate ester reductase" activity (59).…”

Section: William B Jakobymentioning

confidence: 99%

The Glutathione S ‐Transferases: A Group of Multifunctional Detoxification Proteins

Jakoby¹

1978

Advances in Enzymology - And Related Areas of Molecular Biology

346

102

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“…They proposed that cyanide liberation from nitriles results from cytochrome P450-mediated hydroxylation of the carbon atom alpha (a) to the cyano (C=N) group to form a cyanohydrin intermediate, which rapidly decomposes to liberate cyanide and the corresponding carbonyl compound (7). Subsequent studies have confirmed the role of hepatic cytochrome P450 enzymes in the release of cyanide from various nitriles following the administration of these substances to laboratory animals .…”

Section: Acute Lethality Of Nitrilesmentioning

confidence: 90%

Designing Safer Nitriles

DeVito

1996

ACS Symposium Series

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Nitriles represent an important class of chemical substances that have broad commercial utility. A comprehensive search and review of the literature to identify studies pertaining to toxic effects caused by nitriles revealed that certain nitriles are acutely toxic (lethal) or may produce osteolathyrism. A retrospective analysis of these studies, particularly those that describe toxic mechanisms and provide structure-activity relationship data, enabled an understanding of why certain nitriles are highly toxic while others are not. From this understanding, structural modifications that reduce toxicity became apparent. This paper describes how safer (less toxic) nitriles can be designed. Chemists who design nitriles will find this paper useful for designing safer, commercially efficacious nitriles. The general approach and strategy described herein for the design of safer nitriles can be used for the design of safer substances belonging to other chemical classes as well.The design of a safer substance begins with the concomitant consideration of structural features that are needed for commercial usefulness along with any toxicological effects that are caused by such features. In addition, the toxic effects that can be caused by other structural features intended to be present in a planned substance needs to be considered as well.Chemists developing a particular type or class of substance for a specific purpose (e.g., dye, surfactant) are aware of the structural features that are necessary for use function, and will design substances such that they contain these structural features. In many instances, however, chemists are probably not aware of the toxic effects associated with the structural

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Enzymatic mechanisms and toxicological significance of hydrogen cyanide liberation from various organothiocyanates and organonitriles in mice and houseflies

Cited by 89 publications

References 20 publications

Differential sensitivity of honey bees and bumble bees to a dietary insecticide (imidacloprid)

Differential sensitivity of honey bees and bumble bees to a dietary insecticide (imidacloprid)

The Glutathione S ‐Transferases: A Group of Multifunctional Detoxification Proteins

Designing Safer Nitriles

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