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Macrocyclic colibactins

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Matters Arising to this article was published on 21 September 2020

The Original Article was published on 16 September 2019

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Fig. 1: Structures of precolibactin-969 (1), colibactin-645 (2) and other structures discussed in this manuscript.

References

  1. Arthur, J. C. et al. Intestinal inflammation targets cancer-inducing activity of the microbiota. Science 338, 120–123 (2012).

    Article  CAS  Google Scholar 

  2. Li, Z.-R. et al. Macrocyclic colibactin induces DNA double-strand breaks via copper-mediated oxidative cleavage. Nat. Chem. 11, 880–889 (2019).

    Article  CAS  Google Scholar 

  3. Nougayrède, J.-P. et al. Escherichia coli induces DNA double-strand breaks in eukaryotic cells. Science 313, 848–851 (2006).

    Article  Google Scholar 

  4. Bossuet-Greif, N. et al. The colibactin genotoxin generates DNA interstrand crosslinks in infected cells. MBio 9, e02393–02317 (2018).

    Article  CAS  Google Scholar 

  5. Colis, L. C. et al. The cytotoxicity of (–)-lomaiviticin A arises from induction of double-strand breaks in DNA. Nat. Chem. 6, 504–510 (2014).

    Article  CAS  Google Scholar 

  6. Healy, A. R., Nikolayevskiy, H., Patel, J. R., Crawford, J. M. & Herzon, S. B. A mechanistic model for colibactin-induced genotoxicity. J. Am. Chem. Soc. 138, 15563–15570 (2016).

    Article  CAS  Google Scholar 

  7. Xue, M. et al. Structure elucidation of colibactin. Preprint at https://doi.org/10.1101/574053 (2019).

  8. Jiang, Y. et al. The reactivity of an unusual amidase may explain colibactin’s DNA crosslinking activity. Preprint at https://doi.org/10.1101/567248 (2019).

  9. Vizcaino, M. I. & Crawford, J. M. The colibactin warhead crosslinks DNA. Nat. Chem. 7, 411–417 (2015).

    Article  CAS  Google Scholar 

  10. Bossuet-Greif, N. et al. Escherichia coli ClbS is a colibactin resistance protein. Mol. Microbiol. 99, 897–908 (2016).

    Article  CAS  Google Scholar 

  11. Tripathi, P. et al. ClbS is a cyclopropane hydrolase that confers colibactin resistance. J. Am. Chem. Soc. 139, 17719–17722 (2017).

    Article  CAS  Google Scholar 

  12. Shine, E. E. et al. Model colibactins exhibit human cell genotoxicity in the absence of host bacteria. ACS Chem. Biol. 13, 3286–3293 (2018).

    Article  CAS  Google Scholar 

  13. Xue, M., Shine, E., Wang, W., Crawford, J. M. & Herzon, S. B. Characterization of natural colibactin–nucleobase adducts by tandem mass spectrometry and isotopic labeling. Support for DNA alkylation by cyclopropane ring opening. Biochemistry 57, 6391–6394 (2018).

    Article  CAS  Google Scholar 

  14. Wilson, M. R. et al. The human gut bacterial genotoxin colibactin alkylates DNA. Science 363, eaar7785 (2019).

    Article  CAS  Google Scholar 

  15. Clauson, C., Schärer, O. D. & Niedernhofer, L. Advances in understanding the complex mechanisms of DNA interstrand crosslink repair. Cold Spring Harbor Perspect. Biol. 5, a012732 (2013).

    Article  Google Scholar 

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Acknowledgements

Financial support from the National Institutes of Health (R01CA215553) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Yale University, New Haven, CT, USA

    Seth B. Herzon

  2. Department of Pharmacology, Yale School of Medicine, New Haven, CT, USA

    Seth B. Herzon

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  1. Seth B. Herzon
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S.B.H. wrote the manuscript.

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Correspondence to Seth B. Herzon.

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Herzon, S.B. Macrocyclic colibactins. Nat. Chem. 12, 1005–1006 (2020). https://doi.org/10.1038/s41557-020-00551-8

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