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Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives.

Šeršeň F, Gregáň F, Peško M, Dvoranová D, Kráľová K, Matkovičová Z, Gregáň J, Donovalová J - Molecules (2015)

Bottom Line: IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect.EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II.Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Bratislava 842 15, Slovakia. sersen@fns.uniba.sk.

ABSTRACT
Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

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Effect of N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]thiophene-2-carbohydrazonoyl chloride on fluorescence of chloroplast amino acids. Compound 3e was added to spinach chloroplasts to a final concentration of 0, 10, 20, 30, 40, 60, 80 μmol/dm3 (from top to bottom).
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Figure 2: Effect of N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]thiophene-2-carbohydrazonoyl chloride on fluorescence of chloroplast amino acids. Compound 3e was added to spinach chloroplasts to a final concentration of 0, 10, 20, 30, 40, 60, 80 μmol/dm3 (from top to bottom).

Mentions: We speculated that the mechanism of inhibitory action of the studied compounds may involve their interaction with proteins present in the photosynthetic reaction centers. To test our hypothesis, we analyzed the effect of studied compounds on the fluorescence of aromatic amino acids present in spinach chloroplasts. Quenching of the fluorescence was observed when compound 3e was added to spinach chloroplasts (Figure 2). A similar effect was observed with other tested compounds (data not shown).


Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives.

Šeršeň F, Gregáň F, Peško M, Dvoranová D, Kráľová K, Matkovičová Z, Gregáň J, Donovalová J - Molecules (2015)

Effect of N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]thiophene-2-carbohydrazonoyl chloride on fluorescence of chloroplast amino acids. Compound 3e was added to spinach chloroplasts to a final concentration of 0, 10, 20, 30, 40, 60, 80 μmol/dm3 (from top to bottom).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4759945&req=5

Figure 2: Effect of N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]thiophene-2-carbohydrazonoyl chloride on fluorescence of chloroplast amino acids. Compound 3e was added to spinach chloroplasts to a final concentration of 0, 10, 20, 30, 40, 60, 80 μmol/dm3 (from top to bottom).
Mentions: We speculated that the mechanism of inhibitory action of the studied compounds may involve their interaction with proteins present in the photosynthetic reaction centers. To test our hypothesis, we analyzed the effect of studied compounds on the fluorescence of aromatic amino acids present in spinach chloroplasts. Quenching of the fluorescence was observed when compound 3e was added to spinach chloroplasts (Figure 2). A similar effect was observed with other tested compounds (data not shown).

Bottom Line: IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect.EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II.Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Bratislava 842 15, Slovakia. sersen@fns.uniba.sk.

ABSTRACT
Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

Show MeSH