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MedKoo Cat#: 591266 | Name: Aeruginosin B

Description:

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

Aeruginosin B is a biochemical.

Chemical Structure

Aeruginosin B
CAS#6508-65-2

Theoretical Analysis

MedKoo Cat#: 591266

Name: Aeruginosin B

CAS#: 6508-65-2

Chemical Formula: C14H11N3O5S

Exact Mass: 333.0419

Molecular Weight: 333.32

Elemental Analysis: C, 50.45; H, 3.33; N, 12.61; O, 24.00; S, 9.62

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
Aeruginosin B;
IUPAC/Chemical Name
Phenazinium, 7-amino-1-carboxy-5-methyl-3-sulfo-, inner salt
InChi Key
NBUSANFLZHRAMZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H11N3O5S/c1-17-11-4-7(15)2-3-10(11)16-13-9(14(18)19)5-8(6-12(13)17)23(20,21)22/h2-6,15H,1H3,(H2,18,19,20,21,22)
SMILES Code
O=S(C1=CC2=C(C(C(O)=O)=C1)N=C3C=CC(N)=CC3=[N+]2C)([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 333.32 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: Anas ARJ, Mori A, Tone M, Naruse C, Nakajima A, Asukabe H, Takaya Y, Imanishi SY, Nishizawa T, Shirai M, Harada KI. FVIIa-sTF and Thrombin Inhibitory Activities of Compounds Isolated from Microcystis aeruginosa K-139. Mar Drugs. 2017 Aug 30;15(9). pii: E275. doi: 10.3390/md15090275. PubMed PMID: 28867804; PubMed Central PMCID: PMC5618414. 2: Anas AR, Nakajima A, Naruse C, Tone M, Asukabe H, Harada K. Determination of FVIIa-sTF Inhibitors in Toxic Microcystis Cyanobacteria by LC-MS Technique. Mar Drugs. 2015 Dec 30;14(1):7. doi: 10.3390/md14010007. PubMed PMID: 26729138; PubMed Central PMCID: PMC4728504. 3: Qiu X, Xu C, Chen X. Crystallographic analysis of a cupin superfamily enzyme from Microcystis aeruginosa involved in aeruginosin biosynthesis. Acta Crystallogr F Struct Biol Commun. 2015 Dec;71(Pt 12):1511-5. doi: 10.1107/S2053230X15021937. Epub 2015 Nov 27. PubMed PMID: 26625293; PubMed Central PMCID: PMC4666479. 4: Ding R, Xu C, Chen X, Bao M, Qiu X. Cloning, expression, purification, crystallization and preliminary X-ray diffraction analysis of AerF from Microcystis aeruginosa, a putative reductase participating in aeruginosin biosynthesis. Acta Crystallogr F Struct Biol Commun. 2015 Apr;71(Pt 4):466-70. doi: 10.1107/S2053230X15005063. Epub 2015 Mar 21. PubMed PMID: 25849511; PubMed Central PMCID: PMC4388185. 5: Dailler D, Danoun G, Baudoin O. A general and scalable synthesis of aeruginosin marine natural products based on two strategic C(sp³)-H activation reactions. Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4919-22. doi: 10.1002/anie.201500066. Epub 2015 Feb 25. PubMed PMID: 25712875. 6: Kapuścik A, Hrouzek P, Kuzma M, Bártová S, Novák P, Jokela J, Pflüger M, Eger A, Hundsberger H, Kopecký J. Novel Aeruginosin-865 from Nostoc sp. as a potent anti-inflammatory agent. Chembiochem. 2013 Nov 25;14(17):2329-37. doi: 10.1002/cbic.201300246. Epub 2013 Oct 2. PubMed PMID: 24123716. 7: Trost BM, Kaneko T, Andersen NG, Tappertzhofen C, Fahr B. Total synthesis of aeruginosin 98B. J Am Chem Soc. 2012 Nov 21;134(46):18944-7. doi: 10.1021/ja309947n. Epub 2012 Nov 12. PubMed PMID: 23116136; PubMed Central PMCID: PMC3551629. 8: Ferranti P, Nasi A, Bruno M, Basile A, Serpe L, Gallo P. A peptidomic approach for monitoring and characterising peptide cyanotoxins produced in Italian lakes by matrix-assisted laser desorption/ionisation and quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2011 May 15;25(9):1173-83. doi: 10.1002/rcm.4973. PubMed PMID: 21488115. 9: Rounge TB, Rohrlack T, Nederbragt AJ, Kristensen T, Jakobsen KS. A genome-wide analysis of nonribosomal peptide synthetase gene clusters and their peptides in a Planktothrix rubescens strain. BMC Genomics. 2009 Aug 25;10:396. doi: 10.1186/1471-2164-10-396. PubMed PMID: 19706155; PubMed Central PMCID: PMC2739229. 10: Hanessian S, Wang X, Ersmark K, Del Valle JR, Klegraf E. Total synthesis and structural revision of the presumed aeruginosins 205A and B. Org Lett. 2009 Sep 17;11(18):4232-5. doi: 10.1021/ol901702k. Erratum in: Org Lett. 2009 Dec 3;11(23):5566. PubMed PMID: 19691354. 11: Ishida K, Welker M, Christiansen G, Cadel-Six S, Bouchier C, Dittmann E, Hertweck C, Tandeau de Marsac N. Plasticity and evolution of aeruginosin biosynthesis in cyanobacteria. Appl Environ Microbiol. 2009 Apr;75(7):2017-26. doi: 10.1128/AEM.02258-08. Epub 2009 Feb 5. PubMed PMID: 19201978; PubMed Central PMCID: PMC2663223. 12: Ella-Menye JR, Nie X, Wang G. Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from D-mannose. Carbohydr Res. 2008 Jul 21;343(10-11):1743-53. doi: 10.1016/j.carres.2008.03.017. Epub 2008 Mar 15. PubMed PMID: 18433739. 13: Nishizawa A, Arshad AB, Nishizawa T, Asayama M, Fujii K, Nakano T, Harada K, Shirai M. Cloning and characterization of a new hetero-gene cluster of nonribosomal peptide synthetase and polyketide synthase from the cyanobacterium Microcystis aeruginosa K-139. J Gen Appl Microbiol. 2007 Feb;53(1):17-27. PubMed PMID: 17429158. 14: Radau G, Gebel J, Rauh D. New cyanopeptide-derived low molecular weight thrombin inhibitors. Arch Pharm (Weinheim). 2003 Aug;336(8):372-80. PubMed PMID: 14502757. 15: Radau G, Schermuly S, Fritsche A. New cyanopeptide-derived low molecular weight inhibitors of trypsin-like serine proteases. Arch Pharm (Weinheim). 2003 Aug;336(6-7):300-9. PubMed PMID: 12953218. 16: Radau G, Stürzebecher J. Cyanopeptide analogues: new lead structures for the design and synthesis of new thrombin inhibitors. Pharmazie. 2002 Nov;57(11):729-32. PubMed PMID: 12611274. 17: Valls N, Vallribera M, López-Canet M, Bonjoch J. Synthesis of microcin SF608. J Org Chem. 2002 Jul 12;67(14):4945-50. PubMed PMID: 12098309. 18: Valls N, López-Canet M, Vallribera M, Bonjoch J. First total syntheses of aeruginosin 298-A and aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2-carboxylic acid. Chemistry. 2001 Aug 17;7(16):3446-60. PubMed PMID: 11560314. 19: Bentley RK, Holliman FG. Pigments of pseudomonas species. 3. The synthesis of demethylaeruginosin B and aeruginosin B. J Chem Soc Perkin 1. 1970;18:2447-57. PubMed PMID: 5532402. 20: Herbert RB, Holliman FG. Pigments of pseudomonas species. II. Structure of aeruginosin B. J Chem Soc Perkin 1. 1969;18:2517-20. PubMed PMID: 4982927.