Enterobactin
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| Category | Others |
| Catalog number | BBF-01788 |
| CAS | 28384-96-5 |
| Molecular Weight | 669.55 |
| Molecular Formula | C30H27N3O15 |
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Description
It is produced by the strain of Escherichia coli, Salmonella typhi LT2. Enterobactin is a phenolic iron separation reagent and can be used as a growth accelerator.
Specification
| Synonyms | Enterochelin; tri-(2,3-dihydroxy-N-benzoyl-L-serine)-ester; tri-(N-(2,3-dihydroxybenzoyl)-L-serine)-ester; Enterochellin; N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide); Benzamide, N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy-, [3S-(3R*,7R*,11R*)]- |
| Storage | -20 °C |
| IUPAC Name | N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide |
| Canonical SMILES | C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O |
| InChI | InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1 |
| InChI Key | SERBHKJMVBATSJ-BZSNNMDCSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 1109.1±65.0 °C (Predicted) |
| Melting Point | 202-203 °C |
| Density | 1.72±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Acetone, Dioxane, DMSO, Methanol; Insoluble in Water |
Reference Reading
1. Heavy-Metal Trojan Horse: Enterobactin-Directed Delivery of Platinum(IV) Prodrugs to Escherichia coli
Chuchu Guo, Elizabeth M Nolan J Am Chem Soc. 2022 Jul 20;144(28):12756-12768. doi: 10.1021/jacs.2c03324. Epub 2022 Jul 8.
The global crisis of untreatable microbial infections necessitates the design of new antibiotics. Drug repurposing is a promising strategy for expanding the antibiotic repertoire. In this study, we repurpose the clinically approved anticancer agent cisplatin into a targeted antibiotic by conjugating its Pt(IV) prodrug to enterobactin (Ent), a triscatecholate siderophore employed by Enterobacteriaceae for iron (Fe) acquisition. The l-Ent-Pt(IV) conjugate (l-EP) exhibits antibacterial activity against Escherichia coli K12 and the uropathogenic isolate E. coli CFT073. Similar to cisplatin, l-EP causes a filamentous morphology in E. coli and initiates lysis in lysogenic bacteria. Studies with E. coli mutants defective in Ent transport proteins show that Ent mediates the delivery of l-EP into the E. coli cytoplasm, where reduction of the Pt(IV) prodrug releases the cisplatin warhead, causing growth inhibition and filamentation of E. coli. Substitution of Ent with its enantiomer affords the d-Ent-Pt(IV) conjugate (d-EP), which displays enhanced antibacterial activity, presumably because d-Ent cannot be hydrolyzed by Ent esterases and thus Fe cannot be released from this conjugate. E. coli treated with l/d-EP accumulate ≥10-fold more Pt as compared to cisplatin treatment. By contrast, human embryonic kidney cells (HEK293T) accumulate cisplatin but show negligible Pt uptake after treatment with either conjugate. Overall, this work demonstrates that the attachment of a siderophore repurposes a Pt anticancer agent into a targeted antibiotic that is recognized and transported by siderophore uptake machinery, providing a design strategy for drug repurposing by siderophore modification and heavy-metal "trojan-horse" antibiotics.
2. On the origin of amphi-enterobactin fragments produced by Vibrio campbellii species
Aneta M Jelowicki, Alison Butler J Biol Inorg Chem. 2022 Sep;27(6):565-572. doi: 10.1007/s00775-022-01949-0. Epub 2022 Jul 14.
Amphi-enterobactin is an amphiphilic siderophore isolated from a variety of microbial Vibrio species. Like enterobactin, amphi-enterobactin is a triscatecholate siderophore; however, it is framed on an expanded tetralactone core comprised of four L-Ser residues, of which one L-Ser is appended by a fatty acid and the remaining L-Ser residues are appended by 2,3-dihydroxybenzoate (DHB). Fragments of amphi-enterobactin composed of 2-Ser-1-DHB-FA and 3-Ser-2-DHB-FA have been identified in the supernatant of Vibrio campbellii species. The origin of these fragments has not been determined, although two distinct isomers could exist for 2-Ser-1-DHB-FA and three distinct isomers could exist for 3-Ser-2-DHB-FA. The fragments of amphi-enterobactin could originate from hydrolysis of the amphi-enterobactin macrolactone, or from premature release due to an inefficient biosynthetic pathway. Unique masses in the tandem MS analysis establish that certain fragments isolated from the culture supernatant must originate from hydrolysis of the amphi-enterobactin macrolactone, while others cannot be distinguished from premature release during biosynthesis or hydrolysis of amphi-enterobactin.
3. Hijacking of the Enterobactin Pathway by a Synthetic Catechol Vector Designed for Oxazolidinone Antibiotic Delivery in Pseudomonas aeruginosa
Lucile Moynié, Françoise Hoegy, Stefan Milenkovic, Mathilde Munier, Aurélie Paulen, Véronique Gasser, Aline L Faucon, Nicolas Zill, James H Naismith, Matteo Ceccarelli, Isabelle J Schalk, Gaëtan L A Mislin ACS Infect Dis. 2022 Sep 9;8(9):1894-1904. doi: 10.1021/acsinfecdis.2c00202. Epub 2022 Jul 26.
Enterobactin (ENT) is a tris-catechol siderophore used to acquire iron by multiple bacterial species. These ENT-dependent iron uptake systems have often been considered as potential gates in the bacterial envelope through which one can shuttle antibiotics (Trojan horse strategy). In practice, siderophore analogues containing catechol moieties have shown promise as vectors to which antibiotics may be attached. Bis- and tris-catechol vectors (BCVs and TCVs, respectively) were shown using structural biology and molecular modeling to mimic ENT binding to the outer membrane transporter PfeA in Pseudomonas aeruginosa. TCV but not BCV appears to cross the outer membrane via PfeA when linked to an antibiotic (linezolid). TCV is therefore a promising vector for Trojan horse strategies against P. aeruginosa, confirming the ENT-dependent iron uptake system as a gate to transport antibiotics into P. aeruginosa cells.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
