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MedKoo Cat#: 461915 | Name: Schizokinen

Description:

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

Schizokinen is a citrate-containing dihydroxamate and a siderophore produced by Bacillus megaterium and Anabaena sp.

Chemical Structure

Schizokinen
Schizokinen
CAS#35418-52-1

Theoretical Analysis

MedKoo Cat#: 461915

Name: Schizokinen

CAS#: 35418-52-1

Chemical Formula: C16H28N4O9

Exact Mass: 420.1856

Molecular Weight: 420.41

Elemental Analysis: C, 45.71; H, 6.71; N, 13.33; O, 34.25

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 #
No Data
Synonym
Schizokinen;
IUPAC/Chemical Name
2-hydroxy-4-((3-(N-hydroxyacetamido)propyl)amino)-2-(2-((3-(N-hydroxyacetamido)propyl)amino)-2-oxoethyl)-4-oxobutanoic acid
InChi Key
YILWWVUXGMGOAM-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H28N4O9/c1-11(21)19(28)7-3-5-17-13(23)9-16(27,15(25)26)10-14(24)18-6-4-8-20(29)12(2)22/h27-29H,3-10H2,1-2H3,(H,17,23)(H,18,24)(H,25,26)
SMILES Code
O=C(O)C(O)(CC(NCCCN(C(C)=O)O)=O)CC(NCCCN(C(C)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 420.41 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: Rudolf M, Stevanovic M, Kranzler C, Pernil R, Keren N, Schleiff E. Multiplicity and specificity of siderophore uptake in the cyanobacterium Anabaena sp. PCC 7120. Plant Mol Biol. 2016 Sep;92(1-2):57-69. doi: 10.1007/s11103-016-0495-2. Epub 2016 Jun 20. PubMed PMID: 27325117. 2: Lammers PJ, Sanders-Loehr J. Active transport of ferric schizokinen in Anabaena sp. J Bacteriol. 1982 Jul;151(1):288-94. PubMed PMID: 6806241; PubMed Central PMCID: PMC220240. 3: Storey EP, Boghozian R, Little JL, Lowman DW, Chakraborty R. Characterization of 'Schizokinen'; a dihydroxamate-type siderophore produced by Rhizobium leguminosarum IARI 917. Biometals. 2006 Dec;19(6):637-49. Epub 2006 Jun 7. PubMed PMID: 16758117. 4: Nicolaisen K, Moslavac S, Samborski A, Valdebenito M, Hantke K, Maldener I, Muro-Pastor AM, Flores E, Schleiff E. Alr0397 is an outer membrane transporter for the siderophore schizokinen in Anabaena sp. strain PCC 7120. J Bacteriol. 2008 Nov;190(22):7500-7. doi: 10.1128/JB.01062-08. Epub 2008 Sep 19. PubMed PMID: 18805987; PubMed Central PMCID: PMC2576664. 5: Fadeev EA, Luo M, Groves JT. Synthesis, structure, and molecular dynamics of gallium complexes of schizokinen and the amphiphilic siderophore acinetoferrin. J Am Chem Soc. 2004 Sep 29;126(38):12065-75. PubMed PMID: 15382941. 6: Goldman SJ, Lammers PJ, Berman MS, Sanders-Loehr J. Siderophore-mediated iron uptake in different strains of Anabaena sp. J Bacteriol. 1983 Dec;156(3):1144-50. PubMed PMID: 6227608; PubMed Central PMCID: PMC217960. 7: Cuív PO, Keogh D, Clarke P, O'Connell M. FoxB of Pseudomonas aeruginosa functions in the utilization of the xenosiderophores ferrichrome, ferrioxamine B, and schizokinen: evidence for transport redundancy at the inner membrane. J Bacteriol. 2007 Jan;189(1):284-7. Epub 2006 Oct 20. PubMed PMID: 17056746; PubMed Central PMCID: PMC1797220. 8: Byers BR, Powell MV, Lankford CE. Iron-chelating hydroxamic acid (schizokinen) active in initiation of cell division in Bacillus megaterium. J Bacteriol. 1967 Jan;93(1):286-94. PubMed PMID: 4960152; PubMed Central PMCID: PMC315000. 9: Cuív PO, Clarke P, O'Connell M. Identification and characterization of an iron-regulated gene, chtA, required for the utilization of the xenosiderophores aerobactin, rhizobactin 1021 and schizokinen by Pseudomonas aeruginosa. Microbiology. 2006 Apr;152(Pt 4):945-54. PubMed PMID: 16549659. 10: Mullis KB, Pollack JR, Neilands JB. Structure of schizokinen, an iron-transport compound from Bacillus megaterium. Biochemistry. 1971 Dec 21;10(26):4894-8. PubMed PMID: 4332462. 11: Arceneaux JL, Lankford CE. A schizokinen (siderochrome) auxotroph of Bacillus megaterium induced with N-methyl-N'-nitro-N-nitrosoguanidine. Biochem Biophys Res Commun. 1966 Aug 12;24(3):370-5. PubMed PMID: 4961150. 12: Clarke SE, Stuart J, Sanders-Loehr J. Induction of siderophore activity in Anabaena spp. and its moderation of copper toxicity. Appl Environ Microbiol. 1987 May;53(5):917-22. PubMed PMID: 2955743; PubMed Central PMCID: PMC203786. 13: Akers HA. Isolation of the siderophore schizokinen from soil of rice fields. Appl Environ Microbiol. 1983 May;45(5):1704-6. PubMed PMID: 16346301; PubMed Central PMCID: PMC242521. 14: Seidman P, Chan EC. Growth of Arthrobacter citreus in a chemically-defined medium and its requirement for chelating agents with schizokinen activity. J Gen Microbiol. 1969 Nov;58(3):v. PubMed PMID: 5365937. 15: Lankford CE, Walker JR, Reeves JB, Nabbut NH, Byers BR, Jones RJ. Inoculum-dependent division lag of Bacillus cultures and its relation to an endogenous factor(s) ("schizokinen"). J Bacteriol. 1966 Mar;91(3):1070-9. PubMed PMID: 4956330; PubMed Central PMCID: PMC315998. 16: Haydon AH, Davis WB, Arceneaux JE, Byers BR. Hydroxamate recognition during iron transport from hydroxamate-ion chelates. J Bacteriol. 1973 Sep;115(3):912-8. PubMed PMID: 4199516; PubMed Central PMCID: PMC246336. 17: Arceneaux JE, Davis WB, Downer DN, Haydon AH, Byers BR. Fate of labeled hydroxamates during iron transport from hydroxamate-ion chelates. J Bacteriol. 1973 Sep;115(3):919-27. PubMed PMID: 4199517; PubMed Central PMCID: PMC246337. 18: Davis WB, Byers BR. Active transport of iron in Bacillus megaterium: role of secondary hydroxamic acids. J Bacteriol. 1971 Aug;107(2):491-8. PubMed PMID: 5000305; PubMed Central PMCID: PMC246951. 19: Miethke M, Pierik AJ, Peuckert F, Seubert A, Marahiel MA. Identification and characterization of a novel-type ferric siderophore reductase from a gram-positive extremophile. J Biol Chem. 2011 Jan 21;286(3):2245-60. doi: 10.1074/jbc.M110.192468. Epub 2010 Nov 4. PubMed PMID: 21051545; PubMed Central PMCID: PMC3023520. 20: Sonier MB, Weger HG. Plasma membrane ferric reductase activity of iron-limited algal cells is inhibited by ferric chelators. Biometals. 2010 Dec;23(6):1029-42. doi: 10.1007/s10534-010-9348-7. Epub 2010 May 29. PubMed PMID: 20508972.

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