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Literature summary for 1.14.15.6 extracted from

  • Sheets, J.J.; Vickery, L.E.
    Active site-directed inhibitors of cytochrome P-450scc. Structural and mechanistic implications of a side chain-substituted series of amino-steroids (1983), J. Biol. Chem., 258, 11446-11452.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(20R,S)-20-amino-5-pregnen-3beta-ol 20-amine derivative, amine is attached closer to the D-ring than in the 22-amine, very weak inhibitor, 0.1 mM causes less than 20% inhibition Bos taurus
17beta-amino-5-androsten-3beta-ol 17-amine derivative, amine is attached closer to the D-ring than in the 22-amine, very weak inhibitor, 0.1 mM causes less than 20% inhibition Bos taurus
22-Amino-23,24-bisnor-5-cholen-3beta-ol 22-amine derivative, same steroid ring structure as cholesterol, competitive inhibitor with respect to cholesterol, 50% reversible inhibition at 0.0001 mM, reversible cooperative binding Bos taurus
22-amino-23,24-bisnor-5alpha-cholen-3beta-ol 50% inhibition at 0.003 mM Bos taurus
23-Amino-24-nor-5-cholen-3beta-ol 23-amine derivative, same steroid ring structure as cholesterol, competitive inhibitor with respect to cholesterol, 50% inhibition at 0.0001 mM, reversible cooperative binding Bos taurus
24-Amino-5-cholen-3beta-ol 24-amine derivative, amine attached in greater distance from steroid ring, same steroid ring structure as cholesterol, causes a progressive decrease in inhibitory potency, 50% inhibition at 0.0023 mM, reversible noncooperative binding Bos taurus
25-Amino-26,27-bisnor-5-cholesten-3beta-ol 25-amine derivative, amine attached in greater distance from steroid ring, causes a progressive decrease in inhibitory potency, 50% inhibition at more than 0.1 mM Bos taurus
additional information cholesterol analogues have shortened side chain and primary amine group, tested in presence of 0.07 mM cholesterol; steroid ring is suggested to bind to the substrate site on the enzyme and the amine is coordinated to the heme iron Bos taurus

Localization

Localization Comment Organism GeneOntology No. Textmining
mitochondrial inner membrane
-
Bos taurus 5743
-

Organism

Organism UniProt Comment Textmining
Bos taurus
-
-
-

Purification (Commentary)

Purification (Comment) Organism
-
Bos taurus

Source Tissue

Source Tissue Comment Organism Textmining
adrenal cortex
-
Bos taurus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
cholesterol + reduced adrenodoxin + O2
-
Bos taurus pregnenolone + 4-methylpentanal + oxidized adrenodoxin + H2O
-
?

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
-
Bos taurus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.2
-
assay at Bos taurus

Cofactor

Cofactor Comment Organism Structure
adrenodoxin
-
Bos taurus
NADPH
-
Bos taurus