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Literature summary for 1.14.18.1 extracted from

  • Radhakrishnan, S.K.; Shimmon, R.G.; Conn, C.; Baker, A.T.
    Inhibitory kinetics of azachalcones and their oximes on mushroom tyrosinase a facile solid-state synthesis (2016), Chem. Biodivers., 13, 531-538 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(1E,2E)-3-(2,4-dimethoxyphenyl)-N-hydroxy-1-(pyridin-2-yl)prop-2-en-1-imine 52.5% inhibition at 50 mM Agaricus bisporus
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one 59.2% inhibition at 50 mM Agaricus bisporus
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-3-yl)prop-2-en-1-one 55.9% inhibition at 50 mM Agaricus bisporus
(2E)-1-(2-hydroxyphenyl)-3-(pyridin-4-yl)prop-2-en-1-one 48.9% inhibition at 50 mM Agaricus bisporus
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-2-yl)prop-2-en-1-one 49.5% inhibition at 50 mM Agaricus bisporus
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-3-yl)prop-2-en-1-one 59.2% inhibition at 50 mM Agaricus bisporus
(2E)-1-(3-hydroxynaphthalen-2-yl)-3-(pyridin-4-yl)prop-2-en-1-one 42.7% inhibition at 50 mM Agaricus bisporus
(2E)-3-(2,4-dimethoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one 12.3% inhibition at 50 mM Agaricus bisporus
(2E)-3-[4-(dimethylamino)phenyl]-1-(pyridin-2-yl)prop-2-en-1-one 16.9% inhibition at 50 mM Agaricus bisporus
2-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]phenol 77.5% inhibition at 50 mM, reversible competitive inhibition Agaricus bisporus
2-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]phenol 80.6% inhibition at 50 mM, reversible competitive inhibition Agaricus bisporus
2-[(1E,2E)-N-hydroxy-3-(pyridin-4-yl)prop-2-enimidoyl]phenol 69.8% inhibition at 50 mM Agaricus bisporus
3-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]naphthalen-2-ol 58.2% inhibition at 50 mM Agaricus bisporus
3-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]naphthalen-2-ol 62.6% inhibition at 50 mM Agaricus bisporus
3-[(1E,2E)-N-hydroxy-3-(pyridin-4-yl)prop-2-enimidoyl]naphthalen-2-ol 57.5% inhibition at 50 mM Agaricus bisporus
4-[(1E,3E)-3-(hydroxyimino)-3-(pyridin-2-yl)prop-1-en-1-yl]-N,N-dimethylaniline 50.6% inhibition at 50 mM Agaricus bisporus
kojic acid 42.8% inhibition at 50 mM, competitive inhibition Agaricus bisporus
additional information inhibitory kinetics of azachalcones and their oximes on mushroom tyrosinase, solid-state-based mechanochemical synthesis process, and analysis of the inhibition mechanism, overview. The 2'-OH group substituted on ring A is an important design element in achieving enhanced tyrosinase inhibition. The presence of a pyridinyl skeleton results in an improved tyrosinase effect. The pyridinyl N-atom of substituted azachalcone derivatives can possibly get protonated at physiological pH or might be available to coordinate the Cu-atoms existing in the tyrosinase active site Agaricus bisporus

Metals/Ions

Metals/Ions Comment Organism Structure
Cu2+ a copper-containing enzyme Agaricus bisporus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2 L-dopa + O2 Agaricus bisporus
-
2 dopaquinone + 2 H2O
-
?

Organism

Organism UniProt Comment Textmining
Agaricus bisporus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
commercial preparation
-
Agaricus bisporus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2 L-dopa + O2
-
Agaricus bisporus 2 dopaquinone + 2 H2O
-
?

Synonyms

Synonyms Comment Organism
mushroom tyrosinase
-
Agaricus bisporus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
additional information inhibition kinetics Agaricus bisporus
0.0025
-
2-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]phenol pH 6.8, 30°C Agaricus bisporus
0.0051
-
2-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]phenol pH 6.8, 30°C Agaricus bisporus
0.0088
-
kojic acid pH 6.8, 30°C Agaricus bisporus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0127
-
pH 6.8, 30°C Agaricus bisporus 2-[(1E,2E)-N-hydroxy-3-(pyridin-3-yl)prop-2-enimidoyl]phenol
0.0153
-
pH 6.8, 30°C Agaricus bisporus 2-[(1E,2E)-N-hydroxy-3-(pyridin-2-yl)prop-2-enimidoyl]phenol
0.0373
-
pH 6.8, 30°C Agaricus bisporus kojic acid