MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 534871 | Name: Myxochelin A
Featured

Description:

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

Myxochelin A is a catechole siderophore isolated from angiococcus disciformis. It is active against Gram-positive bacteria, including B. cereus, S. aureus, and M. luteus, but not Gram-negative bacteria or fungi in an agar diffusion assay when used at a concentration of 80 µg/disc. Myxochelin A inhibits 5-lipoxygenase (5-LO) activity with an IC50 value of 1.9 µM for the recombinant human enzyme.2 It is cytotoxic to 26-L5 colon cancer cells when used at a concentration of 3 µg/ml.

Chemical Structure

Myxochelin A
Myxochelin A
CAS#120243-02-9

Theoretical Analysis

MedKoo Cat#: 534871

Name: Myxochelin A

CAS#: 120243-02-9

Chemical Formula: C20H24N2O7

Exact Mass: 404.1584

Molecular Weight: 404.42

Elemental Analysis: C, 59.40; H, 5.98; N, 6.93; O, 27.69

Price and Availability

Size Price Availability Quantity
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Myxochelin A
IUPAC/Chemical Name
Benzamide, N,N'-(1-(hydroxymethyl)-1,5-pentanediyl)bis(2,3-dihydroxy-
InChi Key
WNBVGSNESTZACV-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H24N2O7/c23-11-12(22-20(29)14-7-4-9-16(25)18(14)27)5-1-2-10-21-19(28)13-6-3-8-15(24)17(13)26/h3-4,6-9,12,23-27H,1-2,5,10-11H2,(H,21,28)(H,22,29)
SMILES Code
OCC(NC(C1=CC=CC(O)=C1O)=O)CCCCNC(C2=CC=CC(O)=C2O)=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 404.42 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: Sester A, Winand L, Pace S, Hiller W, Werz O, Nett M. Myxochelin- and Pseudochelin-Derived Lipoxygenase Inhibitors from a Genetically Engineered Myxococcus xanthus Strain. J Nat Prod. 2019 Sep 27;82(9):2544-2549. doi: 10.1021/acs.jnatprod.9b00403. Epub 2019 Aug 29. PMID: 31465225. 2: Schieferdecker S, König S, Pace S, Werz O, Nett M. Myxochelin-Inspired 5-Lipoxygenase Inhibitors: Synthesis and Biological Evaluation. ChemMedChem. 2017 Jan 5;12(1):23-27. doi: 10.1002/cmdc.201600536. Epub 2016 Nov 29. PMID: 27875023. 3: Kunze B, Bedorf N, Kohl W, Höfle G, Reichenbach H. Myxochelin A, a new iron- chelating compound from Angiococcus disciformis (Myxobacterales). Production, isolation, physico-chemical and biological properties. J Antibiot (Tokyo). 1989 Jan;42(1):14-7. doi: 10.7164/antibiotics.42.14. PMID: 2493439. 4: Korp J, Winand L, Sester A, Nett M. Engineering Pseudochelin Production in Myxococcus xanthus. Appl Environ Microbiol. 2018 Oct 30;84(22):e01789-18. doi: 10.1128/AEM.01789-18. PMID: 30217842; PMCID: PMC6210110. 5: Korp J, König S, Schieferdecker S, Dahse HM, König GM, Werz O, Nett M. Harnessing Enzymatic Promiscuity in Myxochelin Biosynthesis for the Production of 5-Lipoxygenase Inhibitors. Chembiochem. 2015 Nov;16(17):2445-50. doi: 10.1002/cbic.201500446. Epub 2015 Oct 13. PMID: 26416255. 6: Komaki H, Ichikawa N, Hosoyama A, Fujita N, Igarashi Y. Draft Genome Sequence of Nonomuraea sp. TP-A0861, a Producer of Myxochelin A. Genome Announc. 2015 Dec 10;3(6):e01430-15. doi: 10.1128/genomeA.01430-15. PMID: 26659677; PMCID: PMC4675942. 7: Li Y, Weissman KJ, Müller R. Myxochelin biosynthesis: direct evidence for two- and four-electron reduction of a carrier protein-bound thioester. J Am Chem Soc. 2008 Jun 18;130(24):7554-5. doi: 10.1021/ja8025278. Epub 2008 May 23. PMID: 18498160. 8: Miyanaga S, Obata T, Onaka H, Fujita T, Saito N, Sakurai H, Saiki I, Furumai T, Igarashi Y. Absolute configuration and antitumor activity of myxochelin A produced by Nonomuraea pusilla TP-A0861. J Antibiot (Tokyo). 2006 Nov;59(11):698-703. doi: 10.1038/ja.2006.93. PMID: 17256468. 9: Silakowski B, Kunze B, Nordsiek G, Blöcker H, Höfle G, Müller R. The myxochelin iron transport regulon of the myxobacterium Stigmatella aurantiaca Sg a15. Eur J Biochem. 2000 Nov;267(21):6476-85. doi: 10.1046/j.1432-1327.2000.01740.x. PMID: 11029592. 10: Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y. Synthesis and evaluation of myxochelin analogues as antimetastatic agents. Bioorg Med Chem. 2009 Apr 1;17(7):2724-32. doi: 10.1016/j.bmc.2009.02.040. Epub 2009 Feb 25. PMID: 19282185. 11: Gaitatzis N, Kunze B, Müller R. In vitro reconstitution of the myxochelin biosynthetic machinery of Stigmatella aurantiaca Sg a15: Biochemical characterization of a reductive release mechanism from nonribosomal peptide synthetases. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11136-41. doi: 10.1073/pnas.201167098. Epub 2001 Sep 18. PMID: 11562468; PMCID: PMC58696. 12: Bitok JK, Lemetre C, Ternei MA, Brady SF. Identification of biosynthetic gene clusters from metagenomic libraries using PPTase complementation in a Streptomyces host. FEMS Microbiol Lett. 2017 Sep 1;364(16):fnx155. doi: 10.1093/femsle/fnx155. PMID: 28817927; PMCID: PMC5827622. 13: Schieferdecker S, König S, Koeberle A, Dahse HM, Werz O, Nett M. Myxochelins target human 5-lipoxygenase. J Nat Prod. 2015 Feb 27;78(2):335-8. doi: 10.1021/np500909b. Epub 2015 Feb 16. PMID: 25686392. 14: Gaitatzis N, Kunze B, Müller R. Novel insights into siderophore formation in myxobacteria. Chembiochem. 2005 Feb;6(2):365-74. doi: 10.1002/cbic.200400206. PMID: 15678426. 15: Bäumler AJ, Norris TL, Lasco T, Voight W, Reissbrodt R, Rabsch W, Heffron F. IroN, a novel outer membrane siderophore receptor characteristic of Salmonella enterica. J Bacteriol. 1998 Mar;180(6):1446-53. PMID: 9515912; PMCID: PMC107043. 16: Findlay BL. The Chemical Ecology of Predatory Soil Bacteria. ACS Chem Biol. 2016 Jun 17;11(6):1502-10. doi: 10.1021/acschembio.6b00176. Epub 2016 Apr 14. PMID: 27035738. 17: Mullowney MW, McClure RA, Robey MT, Kelleher NL, Thomson RJ. Natural products from thioester reductase containing biosynthetic pathways. Nat Prod Rep. 2018 Sep 19;35(9):847-878. doi: 10.1039/c8np00013a. PMID: 29916519; PMCID: PMC6146020. 18: Izzat S, Rachid S, Ajdidi A, El-Nakady YA, Liu XX, Ye BC, Müller R. The ROK like protein of Myxococcus xanthus DK1622 acts as a pleiotropic transcriptional regulator for secondary metabolism. J Biotechnol. 2020 Mar 10;311:25-34. doi: 10.1016/j.jbiotec.2020.02.005. Epub 2020 Feb 11. PMID: 32057784.