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MedKoo Cat#: 534910 | Name: Staphyloferrin A

Description:

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

Staphyloferrin A is a siderophore used by Staphylococcus bacteria for ferric iron retrieval. The binding affinity of ironcomplexed staphyloferrin A to the HtsA receptor has been demonstrated to be in the low nM range. Importantly, this highly selective association between S. aureus and staphyloferrin A can be exploited to deliver attached therapeutic and imaging agents to bacteria in vivo for treatment and localization of infections.

Chemical Structure

Staphyloferrin A
Staphyloferrin A
CAS#127902-98-1

Theoretical Analysis

MedKoo Cat#: 534910

Name: Staphyloferrin A

CAS#: 127902-98-1

Chemical Formula: C17H24N2O14

Exact Mass: 480.1228

Molecular Weight: 480.38

Elemental Analysis: C, 42.51; H, 5.04; N, 5.83; O, 46.63

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
Staphyloferrin A
IUPAC/Chemical Name
Butanedioic acid, 2,2'-((1-carboxy-1,4-butanediyl)bis(imino(2-oxo-2,1-ethanediyl)))bis(2-hydroxy-
InChi Key
VJSIXUQLTJCRCS-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H24N2O14/c20-9(4-16(32,14(28)29)6-11(22)23)18-3-1-2-8(13(26)27)19-10(21)5-17(33,15(30)31)7-12(24)25/h8,32-33H,1-7H2,(H,18,20)(H,19,21)(H,22,23)(H,24,25)(H,26,27)(H,28,29)(H,30,31)
SMILES Code
O=C(C(NC(CC(CC(O)=O)(O)C(O)=O)=O)CCCNC(CC(CC(O)=O)(O)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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 480.38 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: Milner SJ, Seve A, Snelling AM, Thomas GH, Kerr KG, Routledge A, Duhme-Klair AK. Staphyloferrin A as siderophore-component in fluoroquinolone-based Trojan horse antibiotics. Org Biomol Chem. 2013 Jun 7;11(21):3461-8. doi: 10.1039/c3ob40162f. Epub 2013 Apr 11. PMID: 23575952. 2: Laakso HA, Marolda CL, Pinter TB, Stillman MJ, Heinrichs DE. A Heme- responsive Regulator Controls Synthesis of Staphyloferrin B in Staphylococcus aureus. J Biol Chem. 2016 Jan 1;291(1):29-40. doi: 10.1074/jbc.M115.696625. Epub 2015 Nov 3. PMID: 26534960; PMCID: PMC4697164. 3: Konetschny-Rapp S, Jung G, Meiwes J, Zähner H. Staphyloferrin A: a structurally new siderophore from staphylococci. Eur J Biochem. 1990 Jul 20;191(1):65-74. doi: 10.1111/j.1432-1033.1990.tb19094.x. PMID: 2379505. 4: Pandey RK, Jarvis GG, Low PS. Chemical synthesis of staphyloferrin A and its application for Staphylococcus aureus detection. Org Biomol Chem. 2014 Mar 21;12(11):1707-10. doi: 10.1039/c3ob41230j. PMID: 24500249. 5: Nakaminami H, Chen C, Truong-Bolduc QC, Kim ES, Wang Y, Hooper DC. Efflux Transporter of Siderophore Staphyloferrin A in Staphylococcus aureus Contributes to Bacterial Fitness in Abscesses and Epithelial Cells. Infect Immun. 2017 Jul 19;85(8):e00358-17. doi: 10.1128/IAI.00358-17. PMID: 28559406; PMCID: PMC5520428. 6: Beasley FC, Vinés ED, Grigg JC, Zheng Q, Liu S, Lajoie GA, Murphy ME, Heinrichs DE. Characterization of staphyloferrin A biosynthetic and transport mutants in Staphylococcus aureus. Mol Microbiol. 2009 May;72(4):947-63. doi: 10.1111/j.1365-2958.2009.06698.x. Epub 2009 Apr 14. PMID: 19400778. 7: Sheldon JR, Marolda CL, Heinrichs DE. TCA cycle activity in Staphylococcus aureus is essential for iron-regulated synthesis of staphyloferrin A, but not staphyloferrin B: the benefit of a second citrate synthase. Mol Microbiol. 2014 May;92(4):824-39. doi: 10.1111/mmi.12593. Epub 2014 Apr 15. PMID: 24666349. 8: Cooper JD, Hannauer M, Marolda CL, Briere LA, Heinrichs DE. Identification of a positively charged platform in Staphylococcus aureus HtsA that is essential for ferric staphyloferrin A transport. Biochemistry. 2014 Aug 12;53(31):5060-9. doi: 10.1021/bi500729h. Epub 2014 Jul 28. PMID: 25050909. 9: Beasley FC, Marolda CL, Cheung J, Buac S, Heinrichs DE. Staphylococcus aureus transporters Hts, Sir, and Sst capture iron liberated from human transferrin by Staphyloferrin A, Staphyloferrin B, and catecholamine stress hormones, respectively, and contribute to virulence. Infect Immun. 2011 Jun;79(6):2345-55. doi: 10.1128/IAI.00117-11. Epub 2011 Mar 14. PMID: 21402762; PMCID: PMC3125851. 10: Meiwes J, Fiedler HP, Haag H, Zähner H, Konetschny-Rapp S, Jung G. Isolation and characterization of staphyloferrin A, a compound with siderophore activity from Staphylococcus hyicus DSM 20459. FEMS Microbiol Lett. 1990 Jan 15;55(1-2):201-5. doi: 10.1111/j.1574-6968.1990.tb13863.x. PMID: 2139423. 11: Haag H, Fiedler HP, Meiwes J, Drechsel H, Jung G, Zähner H. Isolation and biological characterization of staphyloferrin B, a compound with siderophore activity from staphylococci. FEMS Microbiol Lett. 1994 Jan 15;115(2-3):125-30. doi: 10.1111/j.1574-6968.1994.tb06626.x. PMID: 8138126. 12: Drechsel H, Winkelmann G. The configuration of the chiral carbon atoms in staphyloferrin A and analysis of the transport properties in Staphylococcus aureus. Biometals. 2005 Feb;18(1):75-81. doi: 10.1007/s10534-004-5774-8. PMID: 15865412. 13: Cotton JL, Tao J, Balibar CJ. Identification and characterization of the Staphylococcus aureus gene cluster coding for staphyloferrin A. Biochemistry. 2009 Feb 10;48(5):1025-35. doi: 10.1021/bi801844c. PMID: 19138128. 14: Grigg JC, Cheung J, Heinrichs DE, Murphy ME. Specificity of Staphyloferrin B recognition by the SirA receptor from Staphylococcus aureus. J Biol Chem. 2010 Nov 5;285(45):34579-88. doi: 10.1074/jbc.M110.172924. Epub 2010 Sep 1. PMID: 20810662; PMCID: PMC2966073. 15: Cheung J, Beasley FC, Liu S, Lajoie GA, Heinrichs DE. Molecular characterization of staphyloferrin B biosynthesis in Staphylococcus aureus. Mol Microbiol. 2009 Nov;74(3):594-608. doi: 10.1111/j.1365-2958.2009.06880.x. Epub 2009 Sep 22. PMID: 19775248. 16: Grigg JC, Cooper JD, Cheung J, Heinrichs DE, Murphy ME. The Staphylococcus aureus siderophore receptor HtsA undergoes localized conformational changes to enclose staphyloferrin A in an arginine-rich binding pocket. J Biol Chem. 2010 Apr 9;285(15):11162-71. doi: 10.1074/jbc.M109.097865. Epub 2010 Feb 10. PMID: 20147287; PMCID: PMC2856993. 17: Hannauer M, Sheldon JR, Heinrichs DE. Involvement of major facilitator superfamily proteins SfaA and SbnD in staphyloferrin secretion in Staphylococcus aureus. FEBS Lett. 2015 Mar 12;589(6):730-7. doi: 10.1016/j.febslet.2015.02.002. Epub 2015 Feb 11. PMID: 25680529. 18: Kobylarz MJ, Grigg JC, Liu Y, Lee MS, Heinrichs DE, Murphy ME. Deciphering the Substrate Specificity of SbnA, the Enzyme Catalyzing the First Step in Staphyloferrin B Biosynthesis. Biochemistry. 2016 Feb 16;55(6):927-39. doi: 10.1021/acs.biochem.5b01045. Epub 2016 Feb 3. PMID: 26794841; PMCID: PMC5084695. 19: Beasley FC, Cheung J, Heinrichs DE. Mutation of L-2,3-diaminopropionic acid synthase genes blocks staphyloferrin B synthesis in Staphylococcus aureus. BMC Microbiol. 2011 Sep 9;11:199. doi: 10.1186/1471-2180-11-199. PMID: 21906287; PMCID: PMC3179956. 20: Perry WJ, Spraggins JM, Sheldon JR, Grunenwald CM, Heinrichs DE, Cassat JE, Skaar EP, Caprioli RM. Staphylococcus aureus exhibits heterogeneous siderophore production within the vertebrate host. Proc Natl Acad Sci U S A. 2019 Oct 29;116(44):21980-21982. doi: 10.1073/pnas.1913991116. Epub 2019 Oct 14. PMID: 31611408; PMCID: PMC6825271.