Uncoupling of mitochondrial and bacterial respiration by β-nitrostyrenes and benzol malononitriles

Bovell, Carlton R.; Packer, Lester; Schonbaum, Gregory R.

doi:10.1016/0003-9861(64)90489-8

Cited by 14 publications

(2 citation statements)

References 22 publications

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“…Its chemical relatives are biologically active as uncouplers of mitochondrial and bacterial respiration' 3 ', others have been used as cytotoxic agents against tumors' 4 ' or synthesised for use as pesticides' 5 ', fungicides' 6 ' and insecticides' 7 '. It causes, besides heavy lachrymation, widespread reflectory changes in the respiratory tract' 8 '.…”

Section: Benzylidenmalononitril-derivate Ah Substrate Und Inhibitorenmentioning

confidence: 99%

Benzylidenemalononitrile Derivatives as Substrates and Inhibitors of a New NAD(P)H Dehydrogenase of Erythrocytes. Purification and Crystallisation of Two Forms of the Enzyme

Ueberschär¹,

Kille²,

Laule³

et al. 1979

Hoppe-Seyler´s Zeitschrift für physiologische Chemie

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Using the powerful lachrymator (2-chlorobenzylidene)malononitrile as electron acceptor, two types of NAD(P)H dehydrogenases have been isolated from human blood. Crystallisation of the homogenous enzymes was performed in 50% polyethylene glycol solution.The enzymes (average molecular weight 18000) are composed of only one polypeptide chain and have a very similar amino acid composition.B-side stereospecificity was determined with respect to the cofactor by gas chromatographymass spectrometry for the reductase. Besides (2-chlorobenzylidene)malononitrile, 2,6-dichloroindophenol, methylene blue, 4-benzoquinone, FMN and FAD are also reduced using NADH or NADPH as hydrogen donor with the rates decreasing in the given order. Reduction of methemoglobin is observed only upon addition of methylene blue, FMN or FAD as carriers. (2-Chlorobenzylidene)malononitrile reduction is inhibited by most of the compounds known to be decouplers of oxidative phosphorylation. Benzylidenmalononitril-Derivate ah Substrate und Inhibitoren einer neuen NAD(P)H-Dehydrogenase aus Erythrozyten: Reinigung und Kristallisation von zwei EnzymformenZusammenfassung: Zwei Typen von NAD(P)HDehydrogenasen konnten bei Verwendung des starken Tränenerregers (2-Chlorbenzyliden)-malononitril als Elektronen-Acceptor aus menschlichem Blut isoliert werden. Die homogenen Enzyme wurden aus SOproz. Polyethylenglycol-Lö-sung kristallisiert.Die Enzyme (mittleres Molekulargewicht 18000) haben nur eine Polypeptidkette; ihre Aminosäu-renzusammensetzung ist sehr ähnlich. Die Reduktase hat bezüglich des Cofaktors B-Seiten-Stereospezifität, wie mit Hilfe der Gaschromatographie-Massenspektrometrie bestimmt wurde. Außer (2-Chlorbenzyliden)malononitril

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Section: Benzylidenmalononitril-derivate Ah Substrate Und Inhibitorenmentioning

confidence: 99%

Benzylidenemalononitrile Derivatives as Substrates and Inhibitors of a New NAD(P)H Dehydrogenase of Erythrocytes. Purification and Crystallisation of Two Forms of the Enzyme

Ueberschär¹,

Kille²,

Laule³

et al. 1979

Hoppe-Seyler´s Zeitschrift für physiologische Chemie

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“…128 Other 2-substituted benzylidenemalononitriles, especially the 2-nitro derivative 21, are relatively effective irritants. 127 The R Rs 21, R, = Rj = H; R = N02…”

Section: B Toxicity and Analysismentioning

confidence: 99%

Properties and reactions of ylidenemalononitriles

Freeman¹

1980

Chem. Rev.

310

150

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Electrochemical Studies of Some Activated Olefinic Double Bonds in Nonaqueous Medium

El‐Maghraby

1999

Electroanalysis

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Redox characteristics of some activated ole®nic double bonds as in malonitriles in nonaqueous acetonitrile at gold, platinum and glassy carbon electrodes have been extensively studied. They are oxidized in a single irreversible one-electron process followed by deprotonation to form the dimer. On the other hand, the reduction occurs in two-electron process to give the corresponding dianion which abstracts protons to saturate the bond. The effect of substituents present on the phenyl ring on the E 1a2 values has also been studied.

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Uncoupling of mitochondrial and bacterial respiration by β-nitrostyrenes and benzol malononitriles

Cited by 14 publications

References 22 publications

Benzylidenemalononitrile Derivatives as Substrates and Inhibitors of a New NAD(P)H Dehydrogenase of Erythrocytes. Purification and Crystallisation of Two Forms of the Enzyme

Benzylidenemalononitrile Derivatives as Substrates and Inhibitors of a New NAD(P)H Dehydrogenase of Erythrocytes. Purification and Crystallisation of Two Forms of the Enzyme

Properties and reactions of ylidenemalononitriles

Electrochemical Studies of Some Activated Olefinic Double Bonds in Nonaqueous Medium

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