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MedKoo Cat#: 591260 | Name: Aerobactin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aerobactin is a bacterial iron chelating agent (siderophore) found in E. coli. It is a virulence factor enabling E. coli to sequester iron in iron-poor environments such as the urinary tract. Aerobactin is biosynthesized by the oxidation of lysine, catalyzed by the enzyme aerobactin synthase, which is then coupled to citric acid. The gene for this enzyme is found in the aerobactin operon, which is roughly 8 kilobases long and contains 5 or more genes in total. Yersinia pestis contains genes relating to aerobactin, but they have been inactivated by a frameshift mutation, thus Y. pestis is no longer able to synthesize aerobactin.

Chemical Structure

Aerobactin
CAS#26198-65-2

Theoretical Analysis

MedKoo Cat#: 591260

Name: Aerobactin

CAS#: 26198-65-2

Chemical Formula: C22H36N4O13

Exact Mass: 564.2279

Molecular Weight: 564.55

Elemental Analysis: C, 46.81; H, 6.43; N, 9.92; O, 36.84

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Aerobactin;
IUPAC/Chemical Name
3,9,15,21-Tetraazatricosane-8,12,16-tricarboxylic acid, 3,12,21-trihydroxy-2,10,14,22-tetraoxo-, (S-(R*,R*))-
InChi Key
KDHHWXGBNUCREU-HOTGVXAUSA-N
InChi Code
InChI=1S/C22H36N4O13/c1-13(27)25(38)9-5-3-7-15(19(31)32)23-17(29)11-22(37,21(35)36)12-18(30)24-16(20(33)34)8-4-6-10-26(39)14(2)28/h15-16,37-39H,3-12H2,1-2H3,(H,23,29)(H,24,30)(H,31,32)(H,33,34)(H,35,36)/t15-,16-/m0/s1
SMILES Code
CC(N(O)CCCC[C@@H](C(O)=O)NC(CC(C(O)=O)(O)CC(N[C@H](C(O)=O)CCCCN(O)C(C)=O)=O)=O)=O
Appearance
Solid powder
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
>2 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 564.55 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.

Recalculate based on batch purity %
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: Delgado-Iribarren A, Martinez-Suarez J, Baquero F, Perez-Diaz JC, Martinez JL. Aerobactin-producing multi-resistance plasmids. J Antimicrob Chemother. 1987 Apr;19(4):552-3. doi: 10.1093/jac/19.4.552. PMID: 3294780. 2: Kaspersen H, Franklin-Alming FV, Hetland MAK, Bernhoff E, Löhr IH, Jiwakanon J, Urdahl AM, Leangapichart T, Sunde M. Highly conserved composite transposon harbouring aerobactin iuc3 in Klebsiella pneumoniae from pigs. Microb Genom. 2023 Feb;9(2):mgen000960. doi: 10.1099/mgen.0.000960. PMID: 36820818; PMCID: PMC9997749. 3: Russo TA, Gulick AM. Aerobactin Synthesis Proteins as Antivirulence Targets in Hypervirulent Klebsiella pneumoniae. ACS Infect Dis. 2019 Jul 12;5(7):1052-1054. doi: 10.1021/acsinfecdis.9b00117. Epub 2019 Apr 29. PMID: 31032610; PMCID: PMC6625901. 4: Williams P, Smith MA, Stevenson P, Griffiths E, Tomas JM. Novel aerobactin receptor in Klebsiella pneumoniae. J Gen Microbiol. 1989 Dec;135(12):3173-81. doi: 10.1099/00221287-135-12-3173. PMID: 2534599. 5: Li C, Pan D, Li M, Wang Y, Song L, Yu D, Zuo Y, Wang K, Liu Y, Wei Z, Lu Z, Zhu L, Shen X. Aerobactin-Mediated Iron Acquisition Enhances Biofilm Formation, Oxidative Stress Resistance, and Virulence of Yersinia pseudotuberculosis. Front Microbiol. 2021 Jul 15;12:699913. doi: 10.3389/fmicb.2021.699913. PMID: 34335534; PMCID: PMC8319957. 6: Genuini M, Bidet P, Benoist JF, Schlemmer D, Lemaitre C, Birgy A, Bonacorsi S. ShiF acts as an auxiliary factor of aerobactin secretion in meningitis Escherichia coli strain S88. BMC Microbiol. 2019 Dec 17;19(1):298. doi: 10.1186/s12866-019-1677-2. PMID: 31847813; PMCID: PMC6918656. 7: Li G, Sun S, Zhao ZY, Sun Y. The pathogenicity of rmpA or aerobactin- positive Klebsiella pneumoniae in infected mice. J Int Med Res. 2019 Sep;47(9):4344-4352. doi: 10.1177/0300060519863544. Epub 2019 Jul 21. PMID: 31328596; PMCID: PMC6753543. 8: Choi O, Cho J, Kang B, Lee Y, Kim J. Negatively Regulated Aerobactin and Desferrioxamine E by Fur in Pantoea ananatis Are Required for Full Siderophore Production and Antibacterial Activity, but Not for Virulence. Appl Environ Microbiol. 2022 Mar 22;88(6):e0240521. doi: 10.1128/aem.02405-21. Epub 2022 Feb 2. PMID: 35108090; PMCID: PMC8939360. 9: de Lorenzo V, Martinez JL. Aerobactin production as a virulence factor: a reevaluation. Eur J Clin Microbiol Infect Dis. 1988 Oct;7(5):621-9. doi: 10.1007/BF01964239. PMID: 2973985. 10: Russo TA, Olson R, MacDonald U, Beanan J, Davidson BA. Aerobactin, but not yersiniabactin, salmochelin, or enterobactin, enables the growth/survival of hypervirulent (hypermucoviscous) Klebsiella pneumoniae ex vivo and in vivo. Infect Immun. 2015 Aug;83(8):3325-33. doi: 10.1128/IAI.00430-15. Epub 2015 Jun 8. PMID: 26056379; PMCID: PMC4496593. 11: Shankar C, Basu S, Lal B, Shanmugam S, Vasudevan K, Mathur P, Ramaiah S, Anbarasu A, Veeraraghavan B. Aerobactin Seems To Be a Promising Marker Compared With Unstable RmpA2 for the Identification of Hypervirulent Carbapenem-Resistant Klebsiella pneumoniae: In Silico and In Vitro Evidence. Front Cell Infect Microbiol. 2021 Sep 13;11:709681. doi: 10.3389/fcimb.2021.709681. PMID: 34589442; PMCID: PMC8473682. 12: Johnson JR, Moseley SL, Roberts PL, Stamm WE. Aerobactin and other virulence factor genes among strains of Escherichia coli causing urosepsis: association with patient characteristics. Infect Immun. 1988 Feb;56(2):405-12. doi: 10.1128/iai.56.2.405-412.1988. PMID: 2892793; PMCID: PMC259296. 13: Lawlor KM, Payne SM. Aerobactin genes in Shigella spp. J Bacteriol. 1984 Oct;160(1):266-72. doi: 10.1128/jb.160.1.266-272.1984. PMID: 6090419; PMCID: PMC214711. 14: Mydy LS, Bailey DC, Patel KD, Rice MR, Gulick AM. The Siderophore Synthetase IucA of the Aerobactin Biosynthetic Pathway Uses an Ordered Mechanism. Biochemistry. 2020 Jun 16;59(23):2143-2153. doi: 10.1021/acs.biochem.0c00250. Epub 2020 Jun 1. PMID: 32432457; PMCID: PMC7325057. 15: Bailey DC, Alexander E, Rice MR, Drake EJ, Mydy LS, Aldrich CC, Gulick AM. Structural and functional delineation of aerobactin biosynthesis in hypervirulent Klebsiella pneumoniae. J Biol Chem. 2018 May 18;293(20):7841-7852. doi: 10.1074/jbc.RA118.002798. Epub 2018 Apr 4. PMID: 29618511; PMCID: PMC5961048. 16: Neilands JB. Mechanism and regulation of synthesis of aerobactin in Escherichia coli K12 (pColV-K30). Can J Microbiol. 1992 Jul;38(7):728-33. doi: 10.1139/m92-119. PMID: 1393837. 17: de Lorenzo V, Bindereif A, Paw BH, Neilands JB. Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12. J Bacteriol. 1986 Feb;165(2):570-8. doi: 10.1128/jb.165.2.570-578.1986. PMID: 2935523; PMCID: PMC214457. 18: Vokes SA, Reeves SA, Torres AG, Payne SM. The aerobactin iron transport system genes in Shigella flexneri are present within a pathogenicity island. Mol Microbiol. 1999 Jul;33(1):63-73. doi: 10.1046/j.1365-2958.1999.01448.x. PMID: 10411724. 19: Ling J, Pan H, Gao Q, Xiong L, Zhou Y, Zhang D, Gao S, Liu X. Aerobactin synthesis genes iucA and iucC contribute to the pathogenicity of avian pathogenic Escherichia coli O2 strain E058. PLoS One. 2013;8(2):e57794. doi: 10.1371/journal.pone.0057794. Epub 2013 Feb 27. PMID: 23460907; PMCID: PMC3584046. 20: Buyer JS, de Lorenzo V, Neilands JB. Production of the siderophore aerobactin by a halophilic pseudomonad. Appl Environ Microbiol. 1991 Aug;57(8):2246-50. doi: 10.1128/aem.57.8.2246-2250.1991. PMID: 1768095; PMCID: PMC183558.