Evidence map›Paper›PMID 26833565›Full record

ArticleThe Journal of biological chemistry2016

Cholesterol Analogs with Degradation-resistant Alkyl Side Chains Are Effective Mycobacterium tuberculosis Growth Inhibitors.

Daniel J Frank, Yan Zhao, Siew Hoon Wong, Debashree Basudhar, James J De Voss, Paul R Ortiz de Montellano

Open access · hybridAbstract read
In one paragraph

Article in The Journal of biological chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing papers in PubMed
1.7field-weighted citation impact, top 16% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

9 citing papers in PubMed, 22 citations in OpenAlex.

  1. Structure-Function Analysis ofInternational journal of molecular sciences · 2025
    Article
  2. Article
  3. Article
  4. Enzymatic synthesis of fluorinated compounds.Applied microbiology and biotechnology · 2021
    Review
  5. Article
  6. The first report on theSaudi journal of biological sciences · 2019
    Article
  7. Review
  8. Review
  9. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors at 2 institutions in 2 countries.

Daniel J FrankFrom the Department of Pharmaceutical Chemistry, University of California, San Francisco, California 94158-2517 and.
Yan ZhaoFrom the Department of Pharmaceutical Chemistry, University of California, San Francisco, California 94158-2517 and.
Siew Hoon Wongthe School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia.
Debashree BasudharFrom the Department of Pharmaceutical Chemistry, University of California, San Francisco, California 94158-2517 and.
James J De Vossthe School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane 4072, Australia.
Paul R Ortiz de MontellanoFrom the Department of Pharmaceutical Chemistry, University of California, San Francisco, California 94158-2517 and ortiz@cgl.ucsf.edu.
University of California, San Francisco · USUniversity of Queensland · AU

Funding

Oxygen Sensors and P450 Monooxygenases in Mycobacertium tuberculosisR01AI074824 · NIAID · UNIVERSITY OF CALIFORNIA, SAN FRANCISCO · PI ORTIZ DE MONTELLANO, PAUL R · 2007 to 2016
$4.3M
NIAID NIH HHS AI074824NIAID NIH HHS R01 AI074824
6 · The paper itself

Abstract

Cholest-4-en-3-one, whether added exogenously or generated intracellularly from cholesterol, inhibits the growth ofMycobacterium tuberculosiswhen CYP125A1 and CYP142A1, the cytochrome P450 enzymes that initiate degradation of the sterol side chain, are disabled. Here we demonstrate that a 16-hydroxy derivative of cholesterol, which was previously reported to inhibit growth ofM. tuberculosis, acts by preventing the oxidation of the sterol side chain even in the presence of the relevant cytochrome P450 enzymes. The finding that (25R)-cholest-5-en-3β,16β,26-triol (1) (and its 3-keto metabolite) inhibit growth suggests that cholesterol analogs with non-degradable side chains represent a novel class of anti-mycobacterial agents. In accord with this, two cholesterol analogs with truncated, fluorinated side chains have been synthesized and shown to similarly block the growth in culture ofM. tuberculosis.

Indexed as

Antitubercular AgentsBacterial ProteinsCholestenonesCholesterolCytochrome P-450 Enzyme SystemMycobacterium tuberculosisAntitubercular AgentsBacterial ProteinsCholestenonesCholesterolcytochrome P-450 CYP12A1 (house fly)Cytochrome P-450 Enzyme Systemcholesterol metabolismcytochrome P450dehydrogenaseenzyme inhibitorMycobacterium tuberculosis

Identifiers

PMID26833565
PMCPMC4817165
OpenAlexW2277293961

What OpenQuestion holds

Textmetadata
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.