ArticleThe Journal of biological chemistry2010
Structural and biochemical characterization of Mycobacterium tuberculosis CYP142: evidence for multiple cholesterol 27-hydroxylase activities in a human pathogen.
Article in The Journal of biological chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 54 papers.
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Who cites it
54 citing papers in PubMed, 109 citations in OpenAlex.
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- Updates on Mechanisms of Cytochrome P450 Catalysis of Complex Steroid Oxidations.International journal of molecular sciences · 2024Review
- Structure Based Discovery of Inhibitors of CYP125 and CYP142 from Mycobacterium tuberculosis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Improved 2α-Hydroxylation Efficiency of Steroids by CYP154C2 Using Structure-Guided Rational Design.Applied and environmental microbiology · 2023Article
- Evolutionary pathways for deep-sea adaptation in marine planktonicFrontiers in microbiology · 2023Article
- Roles of cysteine in the structure and metabolic function ofRSC advances · 2022Article
- Genome-wide association studies of global Mycobacterium tuberculosis resistance to 13 antimicrobials in 10,228 genomes identify new resistance mechanisms.PLoS biology · 2022Article
- Enzymatic β-Oxidation of the Cholesterol Side Chain inACS infectious diseases · 2021Article
- ATP-dependent hydroxylation of an unactivated primary carbon with water.Nature communications · 2020Article
- The Sterol Carrier Hydroxypropyl-β-Cyclodextrin Enhances the Metabolism of Phytosterols by Mycobacterium neoaurum.Applied and environmental microbiology · 2020Article
- IpdE1-IpdE2 Is a Heterotetrameric Acyl Coenzyme A Dehydrogenase That Is Widely Distributed in Steroid-Degrading Bacteria.Biochemistry · 2020Article
- Evaluation of Luminogenic Substrates as Probe Substrates for Bacterial Cytochrome P450 Enzymes: Application toSLAS discovery : advancing life sciences R & D · 2019Article
- Cytochrome P450 Monooxygenase CYP139 Family Involved in the Synthesis of Secondary Metabolites in 824 Mycobacterial Species.International journal of molecular sciences · 2019Article
- Function, essentiality, and expression of cytochrome P450 enzymes and their cognate redox partners in Mycobacterium tuberculosis: are they drug targets?Applied microbiology and biotechnology · 2019Review
- Comprehensive Comparative Analysis of Cholesterol Catabolic Genes/Proteins in Mycobacterial Species.International journal of molecular sciences · 2019Article
- Novel insights into P450 BM3 interactions with FDA-approved antifungal azole drugs.Scientific reports · 2019Article
- Modeling Host-Pathogen Interaction to Elucidate the Metabolic Drug Response of IntracellularFrontiers in cellular and infection microbiology · 2019Article
- Electron transfer ferredoxins with unusual cluster binding motifs support secondary metabolism in many bacteria.Chemical science · 2018Article
- Linking cytochrome P450 enzymes from Mycobacterium tuberculosis to their cognate ferredoxin partners.Applied microbiology and biotechnology · 2018Article
- Structural and catalytic properties of the peroxygenase P450 enzyme CYP152K6 from Bacillus methanolicus.Journal of inorganic biochemistry · 2018Article
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Authors and funding
9 authors at 3 institutions in 3 countries.
Funding
Abstract
The Mycobacterium tuberculosis cytochrome P450 enzyme CYP142 is encoded in a large gene cluster involved in metabolism of host cholesterol. CYP142 was expressed and purified as a soluble, low spin P450 hemoprotein. CYP142 binds tightly to cholesterol and its oxidized derivative cholest-4-en-3-one, with extensive shift of the heme iron to the high spin state. High affinity for azole antibiotics was demonstrated, highlighting their therapeutic potential. CYP142 catalyzes either 27-hydroxylation of cholesterol/cholest-4-en-3-one or generates 5-cholestenoic acid/cholest-4-en-3-one-27-oic acid from these substrates by successive sterol oxidations, with the catalytic outcome dependent on the redox partner system used. The CYP142 crystal structure was solved to 1.6 Å, revealing a similar active site organization to the cholesterol-metabolizing M. tuberculosis CYP125, but having a near-identical organization of distal pocket residues to the branched fatty acid oxidizing M. tuberculosis CYP124. The cholesterol oxidizing activity of CYP142 provides an explanation for previous findings that ΔCYP125 strains of Mycobacterium bovis and M. bovis BCG cannot grow on cholesterol, because these strains have a defective CYP142 gene. CYP142 is revealed as a cholesterol 27-oxidase with likely roles in host response modulation and cholesterol metabolism.
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