Colibactin is a genotoxic metabolite produced by Escherichia coli and other Enterobacteriaceae ("enteric bacteria") believed to cause mutations leading to colorectal cancer and the progression of colorectal cancer.[1][2][3][4] Colibactin is a polyketide peptide that can form interstrand crosslinks in DNA.[2] Colibactin is only produced by bacterial strains containing a polyketide synthase genomic island (pks)[1] or clb biosynthetic gene cluster.[4] About 20% of humans are colonized with E. coli that harbor the pks island.[5]
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IUPAC name
2-[6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl]-N-[[4-[2-[4-[2-[[2-[6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl]acetyl]amino]acetyl]-1,3-thiazol-2-yl]-2-oxoacetyl]-1,3-thiazol-2-yl]methyl]acetamide
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3D model (JSmol)
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ChEBI |
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PubChem CID
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Properties | |
C37H38N8O7S2 | |
Molar mass | 770.88 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Colibactin forms DNA inter-strand cross-links by alkylation of adenine moieties on opposing DNA strands.[4] It induces lytic development in certain bacteria that contain prophages.[6]