IUPAC/Chemical Name
N,N',N''-((3S,7S,11S)-2,6,10- trioxo-1,5,9-trioxacyclododecane- 3,7,11-triyl)tris(2,3-dihydroxybenzamide)
InChi Key
SERBHKJMVBATSJ-BZSNNMDCSA-N
InChi Code
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
SMILES Code
O=C1OC[C@H](NC(C2=CC=CC(O)=C2O)=O)C(OC[C@H](NC(C3=CC=CC(O)=C3O)=O)C(OC[C@@H]1NC(C4=CC=CC(O)=C4O)=O)=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
669.55
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Raymond KN, Dertz EA, Kim SS. Enterobactin: an archetype for microbial iron
transport. Proc Natl Acad Sci U S A. 2003 Apr 1;100(7):3584-8. doi:
10.1073/pnas.0630018100. Epub 2003 Mar 24. PMID: 12655062; PMCID: PMC152965.
2: Klebba PE. Three paradoxes of ferric enterobactin uptake. Front Biosci. 2003
Sep 1;8:s1422-36. doi: 10.2741/1233. PMID: 12957833.
3: Zou Z, Robinson JI, Steinberg LK, Henderson JP. Uropathogenic Escherichia
coli wield enterobactin-derived catabolites as siderophores. bioRxiv
[Preprint]. 2023 Jul 25:2023.07.25.550588. doi: 10.1101/2023.07.25.550588.
Update in: J Biol Chem. 2024 Jan;300(1):105554. doi: 10.1016/j.jbc.2023.105554.
PMID: 37546885; PMCID: PMC10402112.
4: Jelowicki AM, Butler A. On the origin of amphi-enterobactin fragments
produced by Vibrio campbellii species. J Biol Inorg Chem. 2022
Sep;27(6):565-572. doi: 10.1007/s00775-022-01949-0. Epub 2022 Jul 14. PMID:
35834122; PMCID: PMC9470620.
5: Peralta DR, Farizano JV, Bulacio Gil N, Corbalán NS, Pomares MF, Vincent PA,
Adler C. Less is more: Enterobactin concentration dependency in copper tolerance
and toxicity. Front Mol Biosci. 2022 Aug 16;9:961917. doi:
10.3389/fmolb.2022.961917. PMID: 36052165; PMCID: PMC9426971.
6: Zou Z, Robinson JI, Steinberg LK, Henderson JP. Uropathogenic Escherichia
coli wield enterobactin-derived catabolites as siderophores. J Biol Chem. 2024
Jan;300(1):105554. doi: 10.1016/j.jbc.2023.105554. Epub 2023 Dec 10. PMID:
38072063; PMCID: PMC10788543.
7: Peralta DR, Adler C, Corbalán NS, Paz García EC, Pomares MF, Vincent PA.
Enterobactin as Part of the Oxidative Stress Response Repertoire. PLoS One. 2016
Jun 16;11(6):e0157799. doi: 10.1371/journal.pone.0157799. PMID: 27310257; PMCID:
PMC4911079.
8: Baramov T, Schmid B, Ryu H, Jeong J, Keijzer K, von Eckardstein L, Baik MH,
Süssmuth RD. How Many O-Donor Groups in Enterobactin Does It Take to Bind a
Metal Cation? Chemistry. 2019 May 17;25(28):6955-6962. doi:
10.1002/chem.201900453. Epub 2019 Apr 10. PMID: 30816591.
9: Sikora AL, Cahill SM, Blanchard JS. Enterobactin synthetase-catalyzed
formation of P(1),P(3)-diadenosine-5'-tetraphosphate. Biochemistry. 2009 Nov
24;48(46):10827-9. doi: 10.1021/bi901680m. PMID: 19852513; PMCID: PMC2783875.
10: Guo C, Nolan EM. Heavy-Metal Trojan Horse: Enterobactin-Directed Delivery of
Platinum(IV) Prodrugs to Escherichia coli. J Am Chem Soc. 2022 Jul
20;144(28):12756-12768. doi: 10.1021/jacs.2c03324. Epub 2022 Jul 8. PMID:
35803281; PMCID: PMC9347114.
