N-methyl-N-formylhydrazine: A toxic and mutagenic inhibitor of the intestinal diamine oxidase

@article{Biegski2005NmethylNformylhydrazineAT,
  title={N-methyl-N-formylhydrazine: A toxic and mutagenic inhibitor of the intestinal diamine oxidase},
  author={T. Biegński and Ralf Braun and J{\"u}rgen Kusche},
  journal={Agents and Actions},
  year={2005},
  volume={14},
  pages={351-355}
}
N-methyl-N-formylhydrazine is the first active intermediate of the poison gyromitrin of the mushroom: false morel. This compound is a non-competitive inhibitor of human intestinal diamine oxidase (ID50=1.6×10−5 mol/l). This concentration corresponds to less than 5g of wet weight of mushroom/l. The diamine oxidases from 5 other sources are inhibited in a similar manner. Semicarbazide and aminoguanidine are 10-respectively 1000-fold more potent inhibitors of the human intestinal diamine oxidase… 
View on Springer
ncbi.nlm.nih.gov
5 Citations
Highly Influential Citations
1
Background Citations
2

Figures from this paper

5 Citations

Citation Type

Citation Type

Early alterations of rat intestinal diamine oxidase activity by azoxymethane, an intestinal carcinogen
TLDR
Some mutagenic hydrazino compounds are also diamine oxidase inhibitors, and this interrelationship was studied for the intestinal carcinogen azoxymethane, which was a very weak inhibitor of rat intestinal diamine oxidation activity.
Histamine receptor activation by unsaturated (allyl and propargyl) homologs of histamine
TLDR
Three new homologs of histamine have the ability to stimulate H1- and H2-histamine receptors andbeta-adrenoreceptors in vitro and are histamine-like, pharmacologically and physically.
Histamine reduces the deamination of putrescinein vitro—but alsoin vivo?
TLDR
The diamine oxidase catalysed deamination of putrescine was reducedin vitro by histamine at concentrations occurring in the gut and a decrease of intestinal diamine oxidation activity was observed which, however, did not depend on histamine but probably on an unspecific irritation of the gut.
An amyotrophic lateral sclerosis hot spot in the French Alps associated with genotoxic fungi
Hypothesis: Etiologic and Molecular Mechanistic Leads for Sporadic Neurodegenerative Diseases Based on Experience With Western Pacific ALS/PDC
TLDR
Exposure to naturally occurring and manmade sources of nitrosamines and hydrazines in association with sporadic forms of ALS (with or without frontotemporal degeneration), progressive supranuclear palsy, and Alzheimer disease is explored.

References

SHOWING 1-10 OF 37 REFERENCES
On the mutagenicity of metabolites derived from the mushroom poison gyromitrin.
The importance of human intestinal diamine oxidase in the oxidation of histamine and/or putrescine.
Histamine, naturally methylated histamine and putrescine are good substrates for human intestinal diamine oxidase, N-Methyl-N-formylhydrazine, the constituent of the mashroom poison-gyromitrin is an…
Inhibition of diamine oxidase in vivo by hydrazine derivatives.
Time-dependent inhibition of diamine oxidase by carbonyl-group reagents and urea.
TLDR
By applying a new theory for time-dependent inhibition, the inhibition of diamine oxidase by aminoguanidine and phenylhydrazine is adequately accounted for and the compounds used are acting solely as carbonyl group reagents.
Distribution and properties of human intestinal diamine oxidase and its relevance for the histamine catabolism.
In vitro inhibition of rat intestinal histamine-metabolizing enzymes.
Oxidative deamination of biogenic amines by intestinal amine oxidases: histamine is specifically inactivated by diamine oxidase.
TLDR
It was concluded that in dog small intestine (as well as in rabbit small intestine) only diamine oxidase was capable of inactivating histamine by oxidative deamination.
Über die Wirkung von optisch aktiven Hydraziden auf die Diamin‐oxydase. 14. Mitteilung über Amin‐oxydasen
TLDR
Some conclusions about the optical configuration of the reactive site of DO have been drawn and the possible relationship between the low efficiency of the D-amino acid isomers as inhibitors and their low toxicity has been discussed.
Diamine oxydase in rabbit small intestine: Separation from a soluble monoamine oxidase, properties and pathophysiological significance in intestinal ischemia
TLDR
In rabbits the small intestine was damaged severely by inducing total intestinal ischemia, which occurs as mesenteric infarction also in human subjects and is accompanied by histamine release, which supported the hypothesis on a protective role of intestinal diamine oxidase against histamine.
Influence of isonicotinic acid hydrazide (INH) and 1-isonicotinyl-2-isopropyl hydrazide (IIH) on bacterial and mammalian enzymes
Isonikotinsäure-hydrazid (INH) und 1-Isonikotinyl-2-isopropyl-hydrazin (IIH) hemmen Diaminoxydase und Guanidindeamidinase vonMycobacterium smegmatis und verhalten sich in dieser Hinsicht gleich wie…
...
1
2
3
4
...