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Photoactivated Colibactin Probes Induce Cellular DNA Damage
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.ORCID-id: 0000-0002-9500-4535
Umeå universitet, Medicinska fakulteten, Institutionen för integrativ medicinsk biologi (IMB).
Umeå universitet, Medicinska fakulteten, Institutionen för medicinsk kemi och biofysik.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Vise andre og tillknytning
2019 (engelsk)Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, nr 5, s. 1417-1421Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2019. Vol. 58, nr 5, s. 1417-1421
Emneord [en]
click chemistry, colibactin, DNA damage, microbiome, photochemistry
HSV kategori
Identifikatorer
URN: urn:nbn:se:umu:diva-156892DOI: 10.1002/anie.201812326ISI: 000458826100026PubMedID: 30506956OAI: oai:DiVA.org:umu-156892DiVA, id: diva2:1295208
Tilgjengelig fra: 2019-03-11 Laget: 2019-03-11 Sist oppdatert: 2019-03-11bibliografisk kontrollert

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