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Structure and bioactivity of colibactin.
Kevin M Wernke1, Mengzhao Xue1, Alina Tirla1
1Department of Chemistry, Yale University, New Haven, CT 06520, United States.
Bioorganic & Medicinal Chemistry Letters
|June 13, 2020
Summary
Colibactin, a gut bacteria metabolite linked to colorectal cancer, has had its structure identified. This discovery explains its instability and genotoxicity, advancing cancer research.
Area of Science:
- Microbiology
- Organic Chemistry
- Cancer Research
Background:
- Colibactin is a bacterial metabolite found in the human gut.
- Its presence is associated with colorectal cancer.
- Colibactin's instability and low production have hindered its isolation and study.
Purpose of the Study:
- To identify the chemical structure of colibactin.
- To understand the molecular basis of colibactin's instability.
- To elucidate the mechanism of colibactin's genotoxic effects.
Main Methods:
- Recent advances in chemical synthesis and structural analysis.
- Investigating the stability of synthetic colibactin intermediates.
- Studying DNA alkylation by colibactin.
Main Results:
- Colibactin identified as a heterodimer with DNA-reactive cyclopropane residues.
- Colibactin forms interstrand DNA cross-links by alkylating adenine.
- The α-aminoketone precursor is unstable to oxidation and cleavage, explaining colibactin's instability.
Conclusions:
- The structure of colibactin has been elucidated.
- Molecular instability is linked to its chemical structure.
- This provides a basis for understanding its role in colorectal cancer development.
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