Autor: Frömmel, J.; Končitíková, R.; Kopečný, D.; Soural, M.; Šebela, M.
Název práce v češtině: Oxidace pyrazolových a i midazolových aldehydů rostlinnými aldehyd dehydrogenázami z rodiny 2 a 10
Název práce v angličtině: Oxidation of imidazole- and pyrazole-derived aldehydes by plant aldehyde dehydrogenases from the family 2 and 10
Studentská publikace: ne
Klíčová slova v češtině: Aldehyd dehydrogenáza, aminoaldehyd dehydrogenáza, pyrazol, isoenzym, imidazol, substrát
Klíčová slova v angličtině: Aldehyde dehydrogenase; aminoaldehyde dehydrogenase, imidazole; isoenzyme; pyrazole; substrate
Abstrakt česky: Série imidazo- a pyrazol- karbaldehydů a jejich alkyl-, allyl-, benzyl-, fenyl-, pyrimidinyl- a thienyl-derivátů byly testovány jako možné substráty rostlinných ALDH2 a ALDH10. Imidazol představuje stavební blok histidinu, histaminu a některých alkoloidů. Také se objevuje v syntetických farmaceutikách jako jsou např. antifungální látky. Přírodní deriváty pyrazolu jsou vzácné ale heterocyklus je často obsažen v syntetických léčivech a pesticidech. Cílem práce bylo vyhodnotit zda příslušné deriváty jsou oxidované enzymy, což by mohlo podpořit jejich roli coby detoxikačních vychytávačů aldehydů.
Abstrakt anglicky: Plant cytosolic aldehyde dehydrogenases from family 2 (ALDH2s, EC 1.2.1.3) are non-specific enzymes and participate
for example in the metabolism of acetaldehyde or biosynthesis of phenylpropanoids. Plant aminoaldehyde
dehydrogenases (AMADHs, ALDH10 family, EC 1.2.1.19) are broadly specific and play an important role
in polyamine degradation or production of osmoprotectants. We have tested imidazole and pyrazole carbaldehydes
and their alkyl-, allyl-, benzyl-, phenyl-, pyrimidinyl- or thienyl-derivatives as possible substrates of plant
ALDH2 and ALDH10 enzymes. Imidazole represents a building block of histidine, histamine as well as certain
alkaloids. It also appears in synthetic pharmaceuticals such as imidazole antifungals. Biological compounds containing
pyrazole are rare (e.g. pyrazole-1-alanine and pyrazofurin antibiotics) but the ring is often found as a
constituent of many synthetic drugs and pesticides. The aim was to evaluate whether aldehyde compounds based
on azole heterocycles are oxidized by the enzymes, which would further support their expected role as detoxifying
aldehyde scavengers. The analyzed imidazole and pyrazole carbaldehydes were only slowly converted by
ALDH10s but well oxidized by cytosolic maize ALDH2 isoforms (particularly by ALDH2C1). In the latter case,
the respective Km values were in the range of 10–2000μmoll−1; the kcat values appeared mostly between 0.1 and
1.0 s−1. The carbaldehyde group at the position 4 of imidazole was oxidized faster than that at the position 2.
Such a difference was not observed for pyrazole carbaldehydes. Aldehydes with an aromatic substituent on their
heterocyclic ring were oxidized faster than those with an aliphatic substituent. The most efficient of the tested
substrates were comparable to benzaldehyde and p-anisaldehyde known as the best aromatic aldehyde substrates
of plant cytosolic ALDH2s in vitro.
Jazyk v originále: angličtina
Název časopisu: Chem Biol Interact.
Rok: 2019
Svazek (ročník): 304
Číslo časopisu v rámci uvedeného svazku: –
Strana od-do: 154-157
Impact factor: 3.296
Q1: ne

ISSN časopisu: 0009-2797
Vydavatel: Elsevier
Způsob financování: LO1204, IGA_PrF_2017_016
DOI: 10.1016/j.cbi.2019.02.008