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Photoactivated Colibactin Probes Induce Cellular DNA Damage
Umeå University, Faculty of Science and Technology, Department of Chemistry.ORCID iD: 0000-0002-9500-4535
Umeå University, Faculty of Medicine, Department of Integrative Medical Biology (IMB).
Umeå University, Faculty of Medicine, Department of Medical Biochemistry and Biophysics.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 5, p. 1417-1421Article in journal (Refereed) Published
Abstract [en]

Colibactin is a small molecule produced by certain bacterial species of the human microbiota that harbour the pks genomic island. Pks(+) bacteria induce a genotoxic phenotype in eukaryotic cells and have been linked with colorectal cancer progression. Colibactin is produced in a benign, prodrug form which, prior to export, is enzymatically matured by the producing bacteria to its active form. Although the complete structure of colibactin has not been determined, key structural features have been described including an electrophilic cyclopropane motif, which is believed to alkylate DNA. To investigate the influence of the putative "warhead" and the prodrug strategy on genotoxicity, a series of photolabile colibactin probes were prepared that upon irradiation induced a pks(+) like phenotype in HeLa cells. Furthermore, results from DNA cross-linking and imaging studies of clickable analogues enforce the hypothesis that colibactin effects its genotoxicity by directly targeting DNA.

Place, publisher, year, edition, pages
2019. Vol. 58, no 5, p. 1417-1421
Keywords [en]
click chemistry, colibactin, DNA damage, microbiome, photochemistry
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:umu:diva-156892DOI: 10.1002/anie.201812326ISI: 000458826100026PubMedID: 30506956OAI: oai:DiVA.org:umu-156892DiVA, id: diva2:1295208
Available from: 2019-03-11 Created: 2019-03-11 Last updated: 2019-03-11Bibliographically approved

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Moodie, Lindon W. K.Hubert, MadlenZhou, XinAlbers, Michael FranzLundmark, RichardWanrooij, SjoerdHedberg, Christian

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Moodie, Lindon W. K.Hubert, MadlenZhou, XinAlbers, Michael FranzLundmark, RichardWanrooij, SjoerdHedberg, Christian
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Department of ChemistryDepartment of Integrative Medical Biology (IMB)Department of Medical Biochemistry and Biophysics
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Angewandte Chemie International Edition
Biochemistry and Molecular Biology

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