Evidence map›Paper›PMID 28396419›Full record

ArticleProceedings of the National Academy of Sciences of the United States of America2017

Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids.

Amy A Rand, Bogdan Barnych, Christophe Morisseau, Tomas Cajka, Kin Sing Stephen Lee, Dipak Panigrahy, Bruce D Hammock

Open access · bronzeAbstract read
In one paragraph

Article in Proceedings of the National Academy of Sciences of the United States of America, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 49 papers.

0numbers the graph read from it
0cells of the map it votes in
49citing papers in PubMed
5.2field-weighted citation impact, top 4% 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

49 citing papers in PubMed, 72 citations in OpenAlex.

  1. Article
  2. Article
  3. Unusual and atypical cyclooxygenase reactions.The Journal of biological chemistry · 2026
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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

7 authors at 3 institutions in 1 country.

Amy A RandDepartment of Entomology and Nematology, University of California, Davis, CA 95616.ORCID 0000-0003-4465-4930
Bogdan BarnychDepartment of Entomology and Nematology, University of California, Davis, CA 95616.
Christophe MorisseauDepartment of Entomology and Nematology, University of California, Davis, CA 95616.
Tomas CajkaWest Coast Metabolomics Center, UC Davis Genome Center, University of California, Davis, CA 95616.
Kin Sing Stephen LeeDepartment of Entomology and Nematology, University of California, Davis, CA 95616.
Dipak PanigrahyCenter for Vascular Biology Research, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, MA 02115.
Bruce D HammockDepartment of Entomology and Nematology, University of California, Davis, CA 95616; bdhammock@ucdavis.edu.ORCID 0000-0003-1408-8317
UC Davis Comprehensive Cancer CenterBeth Israel Deaconess Medical Center · USUniversity of California, Davis · US

Funding

Workshop on Environmental Technology Transfer and EntrepreneurshipP42ES004699 · NIEHS · UNIVERSITY OF CALIFORNIA DAVIS · PI HAMMOCK, BRUCE D · 1987 to 2021
$50.1M
West Coast Central Comprehensive Metabolomics Resource Core (WC3MRC)U24DK097154 · NIDDK · UNIVERSITY OF CALIFORNIA AT DAVIS · PI FIEHN, OLIVER · 2012 to 2017
$9.9M
HYDROLYTIC ENZYMES IN THE METABOLISM OF TOXINSR01ES002710 · NIEHS · UNIVERSITY OF CALIFORNIA DAVIS · PI HAMMOCK, BRUCE D · 1985 to 2018
$4.0M
Training Program in Oncogenic Signals and Chromosome BiologyT32CA108459 · NCI · UNIVERSITY OF CALIFORNIA AT DAVIS · PI HEYER, WOLF-DIETRICH · 2006 to 2020
$3.6M
Identifying the receptors of environmentally sensitive epoxy-eicosanoids with AMSR00ES024806 · NIEHS · MICHIGAN STATE UNIVERSITY · PI LEE, KIN SING STEPHEN · 2017 to 2019
$727k
NCI NIH HHS T32 CA108459NIDDK NIH HHS U24 DK097154NIEHS NIH HHS P42 ES004699NIEHS NIH HHS R00 ES024806NIEHS NIH HHS R01 ES002710
6 · The paper itself

Abstract

Arachidonic acid (ARA) is metabolized by cyclooxygenase (COX) and cytochrome P450 to produce proangiogenic metabolites. Specifically, epoxyeicosatrienoic acids (EETs) produced from the P450 pathway are angiogenic, inducing cancer tumor growth. A previous study showed that inhibiting soluble epoxide hydrolase (sEH) increased EET concentration and mildly promoted tumor growth. However, inhibiting both sEH and COX led to a dramatic decrease in tumor growth, suggesting that the contribution of EETs to angiogenesis and subsequent tumor growth may be attributed to downstream metabolites formed by COX. This study explores the fate of EETs with COX, the angiogenic activity of the primary metabolites formed, and their subsequent hydrolysis by sEH and microsomal EH. Three EET regioisomers were found to be substrates for COX, based on oxygen consumption and product formation. EET substrate preference for both COX-1 and COX-2 were estimated as 8,9-EET > 5,6-EET > 11,12-EET, whereas 14,15-EET was inactive. The structure of two major products formed from 8,9-EET in this COX pathway were confirmed by chemical synthesis:

Indexed as

8,11,14-Eicosatrienoic AcidAngiogenesis Inducing AgentsArachidonic AcidCyclooxygenase 1Cyclooxygenase 2Humans11,12-epoxy-5,8,14-eicosatrienoic acid14,15-epoxy-5,8,11-eicosatrienoic acid5,6-epoxy-8,11,14-eicosatrienoic acid8,11,14-Eicosatrienoic Acid8,9-epoxyeicosatrienoic acidAngiogenesis Inducing AgentsArachidonic AcidCyclooxygenase 1Cyclooxygenase 2angiogenesiscyclooxygenaseepoxyeicosatrienoic acidsmetabolismomega-6 fatty acids

Identifiers

PMID28396419
PMCPMC5410821
OpenAlexW2606516348

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.