Evidence map›Paper›PMID 32527463›Full record

ReviewBioorganic & medicinal chemistry letters2020

Structure and bioactivity of colibactin.

Kevin M Wernke, Mengzhao Xue, Alina Tirla, Chung Sub Kim, Jason M Crawford, Seth B Herzon

Open access · greenAbstract readReview
In one paragraph

Review in Bioorganic & medicinal chemistry letters, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.

0numbers the graph read from it
0cells of the map it votes in
42citing papers in PubMed
3.5field-weighted citation impact, top 6% 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

42 citing papers in PubMed, 69 citations in OpenAlex.

  1. Article
  2. Review
  3. Article
  4. The Role of Selected Bacteria in Breast Cancer Initiation and Development.International journal of molecular sciences · 2026
    Review
  5. Article
  6. Article
  7. Article
  8. Review
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Current understandings of colibactin regulation.Microbiology (Reading, England) · 2024
    Review
  19. The synthesis of the novelFrontiers in microbiology · 2024
    Review
  20. Article
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 1 institution in 1 country.

Kevin M WernkeDepartment of Chemistry, Yale University, New Haven, CT 06520, United States.
Mengzhao XueDepartment of Chemistry, Yale University, New Haven, CT 06520, United States.
Alina TirlaDepartment of Chemistry, Yale University, New Haven, CT 06520, United States.
Chung Sub KimDepartment of Chemistry, Yale University, New Haven, CT 06520, United States; Chemical Biology Institute, Yale University, West Haven, CT 06516, United States.
Jason M CrawfordDepartment of Chemistry, Yale University, New Haven, CT 06520, United States; Chemical Biology Institute, Yale University, West Haven, CT 06516, United States; Department of Microbial Pathogenesis, Yale School of Medicine, New Haven, CT 06536, United States.
Seth B HerzonDepartment of Chemistry, Yale University, New Haven, CT 06520, United States; Department of Pharmacology, Yale School of Medicine, New Haven, CT 06520, United States. Electronic address: seth.herzon@yale.edu.
Yale University · US

Funding

Yale Clinical and Translational Science Award (U Component)UL1TR001863 · NCATS · YALE UNIVERSITY · PI John H. Krystal, LUCILA OHNO-MACHADO · 2016 to 2026
$102.9M
Predoc Training at the Interface Chemistry and BiologyT32GM067543 · NIGMS · YALE UNIVERSITY · PI CRAWFORD, JASON MICHAEL · 2003 to 2022
$7.4M
Structural and functional studies of colibactinR01CA215553 · NCI · YALE UNIVERSITY · PI Seth B. Herzon, Christian Jobin · 2018 to 2026
$5.5M
NCATS NIH HHS UL1 TR001863NCI NIH HHS R01 CA215553NIGMS NIH HHS T32 GM067543
6 · The paper itself

Abstract

Colibactin is a secondary metabolite produced by certain strains of bacteria found in the human gut. The presence of colibactin-producing bacteria has been correlated to colorectal cancer in humans. Colibactin was first discovered in 2006, but because it is produced in small quantities and is unstable, it has yet to be isolated from bacterial cultures. Here we summarize advances in the field since ~2017 that have led to the identification of the structure of colibactin as a heterodimer containing two DNA-reactive electrophilic cyclopropane residues. Colibactin has been shown to form interstrand cross-links by alkylation of adenine residues on opposing strands of DNA. The structure of colibactin contains two thiazole rings separated by a two-carbon linker that is thought to exist as an α-aminoketone following completion of the biosynthetic pathway. However, synthetic studies have now established that this α-aminoketone is unstable toward aerobic oxidation; the resulting oxidation products are in turn unstable toward nucleophilic cleavage under mild conditions. These data provide a simple molecular-level explanation for colibactin's instability and potentially also explain the observation that cell-to-cell contact is required for genotoxic effects.

Indexed as

Escherichia coli ProteinsPeptidesPolyketidesAnimalsHumansMolecular StructurecolibactinEscherichia coli ProteinsPeptidesPolyketidesColibactinGenotoxinMicrobiome

Identifiers

PMID32527463
PMCPMC7309967
OpenAlexW3026356621

What OpenQuestion holds

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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.