Literature DB >> 31395743

Structure elucidation of colibactin and its DNA cross-links.

Mengzhao Xue1, Chung Sub Kim1,2, Alan R Healy1,2, Kevin M Wernke1, Zhixun Wang1, Madeline C Frischling1, Emilee E Shine2,3, Weiwei Wang4,5, Seth B Herzon6,7, Jason M Crawford6,2,3.   

Abstract

Colibactin is a complex secondary metabolite produced by some genotoxic gut Escherichia coli strains. The presence of colibactin-producing bacteria correlates with the frequency and severity of colorectal cancer in humans. However, because colibactin has not been isolated or structurally characterized, studying the physiological effects of colibactin-producing bacteria in the human gut has been difficult. We used a combination of genetics, isotope labeling, tandem mass spectrometry, and chemical synthesis to deduce the structure of colibactin. Our structural assignment accounts for all known biosynthetic and cell biology data and suggests roles for the final unaccounted enzymes in the colibactin gene cluster.
Copyright © 2019 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works.

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Year:  2019        PMID： 31395743      PMCID： PMC6820679          DOI： 10.1126/science.aax2685

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  42 in total

1.  Escherichia coli induces DNA damage in vivo and triggers genomic instability in mammalian cells.

Authors:  Gabriel Cuevas-Ramos; Claude R Petit; Ingrid Marcq; Michèle Boury; Eric Oswald; Jean-Philippe Nougayrède
Journal:  Proc Natl Acad Sci U S A       Date:  2010-06-07       Impact factor: 11.205

Review 2.  Colibactin: understanding an elusive gut bacterial genotoxin.

Authors:  Emily P Balskus
Journal:  Nat Prod Rep       Date:  2015-11       Impact factor: 13.423

3.  The human gut bacterial genotoxin colibactin alkylates DNA.

Authors:  Matthew R Wilson; Yindi Jiang; Peter W Villalta; Alessia Stornetta; Paul D Boudreau; Andrea Carrá; Caitlin A Brennan; Eunyoung Chun; Lizzie Ngo; Leona D Samson; Bevin P Engelward; Wendy S Garrett; Silvia Balbo; Emily P Balskus
Journal:  Science       Date:  2019-02-15       Impact factor: 47.728

Review 4.  The Enterobacterial Genotoxins: Cytolethal Distending Toxin and Colibactin.

Authors:  Frederic Taieb; Claude Petit; Jean-Philippe Nougayrède; Eric Oswald
Journal:  EcoSal Plus       Date:  2016-07

Review 5.  Molecular Basis of Gut Microbiome-Associated Colorectal Cancer: A Synthetic Perspective.

Authors:  Alan R Healy; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2017-10-12       Impact factor: 15.419

6.  Characterization of Polyketide Synthase Machinery from the pks Island Facilitates Isolation of a Candidate Precolibactin.

Authors:  Li Zha; Matthew R Wilson; Carolyn A Brotherton; Emily P Balskus
Journal:  ACS Chem Biol       Date:  2016-03-01       Impact factor: 5.100

7.  Convergent and Modular Synthesis of Candidate Precolibactins. Structural Revision of Precolibactin A.

Authors:  Alan R Healy; Maria I Vizcaino; Jason M Crawford; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2016-04-12       Impact factor: 15.419

8.  Characterization of Natural Colibactin-Nucleobase Adducts by Tandem Mass Spectrometry and Isotopic Labeling. Support for DNA Alkylation by Cyclopropane Ring Opening.

Authors:  Mengzhao Xue; Emilee Shine; Weiwei Wang; Jason M Crawford; Seth B Herzon
Journal:  Biochemistry       Date:  2018-10-31       Impact factor: 3.162

9.  The colibactin warhead crosslinks DNA.

Authors:  Maria I Vizcaino; Jason M Crawford
Journal:  Nat Chem       Date:  2015-04-06       Impact factor: 24.427

10.  Colibactin assembly line enzymes use S-adenosylmethionine to build a cyclopropane ring.

Authors:  Li Zha; Yindi Jiang; Matthew T Henke; Matthew R Wilson; Jennifer X Wang; Neil L Kelleher; Emily P Balskus
Journal:  Nat Chem Biol       Date:  2017-08-07       Impact factor: 15.040
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  58 in total

Review 1.  Structure and bioactivity of colibactin.

Authors:  Kevin M Wernke; Mengzhao Xue; Alina Tirla; Chung Sub Kim; Jason M Crawford; Seth B Herzon
Journal:  Bioorg Med Chem Lett       Date:  2020-05-23       Impact factor: 2.823

2.  Sulfamethoxazole drug stress upregulates antioxidant immunomodulatory metabolites in Escherichia coli.

Authors:  Hyun Bong Park; Zheng Wei; Joonseok Oh; Hao Xu; Chung Sub Kim; Rurun Wang; Thomas P Wyche; Grazia Piizzi; Richard A Flavell; Jason M Crawford
Journal:  Nat Microbiol       Date:  2020-07-27       Impact factor: 17.745

Review 3.  Signaling Natural Products from Human Pathogenic Bacteria.

Authors:  Zhijuan Hu; Wenjun Zhang
Journal:  ACS Infect Dis       Date:  2019-10-30       Impact factor: 5.084

Review 4.  Oral and intestinal bacterial exotoxins: Potential linked to carcinogenesis.

Authors:  Matthew Silbergleit; Adrian A Vasquez; Carol J Miller; Jun Sun; Ikuko Kato
Journal:  Prog Mol Biol Transl Sci       Date:  2020-04-09       Impact factor: 3.622

5.  A mutational signature that can be made by a bacterium arises in human colon cancer.

Authors:  Ye Yang; Christian Jobin
Journal:  Nature       Date:  2020-04       Impact factor: 49.962

Review 6.  Employing chemical synthesis to study the structure and function of colibactin, a "dark matter" metabolite.

Authors:  Peyton C Williams; Kevin M Wernke; Alina Tirla; Seth B Herzon
Journal:  Nat Prod Rep       Date:  2020-11-18       Impact factor: 13.423

7.  Mutational signature in colorectal cancer caused by genotoxic pks+ E. coli.

Authors:  Cayetano Pleguezuelos-Manzano; Jens Puschhof; Axel Rosendahl Huber; Arne van Hoeck; Henry M Wood; Jason Nomburg; Carino Gurjao; Freek Manders; Guillaume Dalmasso; Paul B Stege; Fernanda L Paganelli; Maarten H Geurts; Joep Beumer; Tomohiro Mizutani; Yi Miao; Reinier van der Linden; Stefan van der Elst; K Christopher Garcia; Janetta Top; Rob J L Willems; Marios Giannakis; Richard Bonnet; Phil Quirke; Matthew Meyerson; Edwin Cuppen; Ruben van Boxtel; Hans Clevers
Journal:  Nature       Date:  2020-02-27       Impact factor: 49.962

Review 8.  The manifold roles of microbial ribosomal peptide-based natural products in physiology and ecology.

Authors:  Yanyan Li; Sylvie Rebuffat
Journal:  J Biol Chem       Date:  2019-11-29       Impact factor: 5.157

9.  Spatiochemically Profiling Microbial Interactions with Membrane Scaffolded Desorption Electrospray Ionization-Ion Mobility-Imaging Mass Spectrometry and Unsupervised Segmentation.

Authors:  Berkley M Ellis; Caleb N Fischer; Leroy B Martin; Brian O Bachmann; John A McLean
Journal:  Anal Chem       Date:  2019-10-24       Impact factor: 6.986

10.  Cellular Stress Upregulates Indole Signaling Metabolites in Escherichia coli.

Authors:  Chung Sub Kim; Jhe-Hao Li; Brenden Barco; Hyun Bong Park; Alexandra Gatsios; Ashiti Damania; Rurun Wang; Thomas P Wyche; Grazia Piizzi; Nicole K Clay; Jason M Crawford
Journal:  Cell Chem Biol       Date:  2020-04-02       Impact factor: 8.116
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