Chemistry:Colibactin
From HandWiki
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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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| 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). | |
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Tracking categories (test):
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]
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]
References
- ↑ 1.0 1.1 Arthur JC (2020). "Microbiota and colorectal cancer: colibactin makes its mark". Nature Reviews Gastroenterology & Hepatology 17 (6): 317–318. doi:10.1038/s41575-020-0303-y. PMID 32317778.
- ↑ 2.0 2.1 "Isolation of New Colibactin Metabolites from Wild-Type Escherichia coli and In Situ Trapping of a Mature Colibactin Derivative". Journal of the American Chemical Society 143 (14): 5526–5533. 2021. doi:10.1021/jacs.1c01495. PMID 33787233.
- ↑ "The microbiome, cancer, and cancer therapy". Nature Medicine 25 (3): 377–388. 2019. doi:10.1038/s41591-019-0377-7. PMID 30842679.
- ↑ 4.0 4.1 4.2 "Structure and bioactivity of colibactin". Bioorganic & Medicinal Chemistry Letters 30 (15): 127280. 2020. doi:10.1016/j.bmcl.2020.127280. PMID 32527463.
- ↑ "Colibactin: understanding an elusive gut bacterial genotoxin". Natural Product Reports 32 (11): 1534–40. 2015. doi:10.1039/c5np00091b. PMID 26390983.
- ↑ Silpe, Justin E.; Wong, Joel W. H.; Owen, Siân V.; Baym, Michael; Balskus, Emily P. (2022-02-23). "The bacterial toxin colibactin triggers prophage induction" (in en). Nature 603 (7900): 315–320. doi:10.1038/s41586-022-04444-3. ISSN 1476-4687. PMID 35197633. Bibcode: 2022Natur.603..315S.
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