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Pentabromopseudilin

BVT-0441-C500 500 µg $150.00
BVT-0441-M001 1 mg $240.00
BVT-0441-M005 5 mg $720.00
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Product Data
Synonyms Pentabrompseudilin; NSC641543; NSC288032; PBQ; 2-(3,5-Dibromo-2-hydroxyphenyl)-3,4,5-tribromopyrrol; 2,4-Dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol
Properties
Formula C10H4Br5NO
MW 553.7
CAS 10245-81-5
RTECS SK8150000
Source/Host Chemicals Isolated from sea water proteobacteria Alteromonas Iuteo-violaceus.
Purity ≥98% (HPLC)
Appearance Off-white powder.
Solubility Soluble in DMSO (5mg/ml), acetone, butanol, ethylacetate or diethylether.
Identity Determined by 1H-NMR.
Origin Manufactured by BioViotica.
InChi Key LXMNWKJHYOZUQL-UHFFFAOYSA-N
Product Type Chemical
Shipping and Handling
Shipping BLUE ICE
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry. Protect from light.
Use/Stability Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
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Product Description

  • Antibiotic [1, 2, 4, 6].
  • Antibacterial, cytotoxic, herbicidal and antimalarial compound [3, 9, 11, 13].
  • Human lipoxygenase inhibitor [7].
  • Potent myosin ATPase inhibitor [8, 10, 14].
  • Inhibitor of the non-mevalonate pathway enzyme IspD [13].

Product References

  1. Production of a pyrrole antibiotic by a marine bacterium: P.R. Burkholder, et al.; Appl. Microbiol. 14, 649 (1966)
  2. The structure of a bromine-rich marine antibiotic: F.M. Lovell; JACS 88, 4510 (1966)
  3. Marine bacteria. I. Synthesis of pentabromopseudilin, a cytotoxic phenylpyrrole from Alteromonas luteoviolaceus: H. Laatsch & H. Pudleiner; Liebigs Ann. Chem. 9, 863 (1989)
  4. Biosynthesis of the marine antibiotic pentabromopseudilin. Part 1. The benzene ring: U. Hanefeld, et al.; J. Org. Chem. 8, 847 (1993)
  5. Structure-activity relationships of phenyl- and benzoylpyrroles: H. Laatsch, et al.; Chem. Pharm. Bull. 43, 537 (1995)
  6. Biosynthesis of the marine antibiotic pentabromopseudilin. Part 2. The pyrrole ring: J. Peschke, et al.; Biosci. Biotechnol. Biochem. 69, 628 (2005)
  7. A rev(V)-catalysed C-N bond-forming route to human lipoxygenase inhibitors: O. Rachana, et al.; Org. Lett. 7, 2501 (2005)
  8. The mechanism of pentabromopseudilin inhibition of myosin motor activity: R. Fedorov, et al.; Nat. Struct. Mol. Biol. 16, 80 (2009)
  9. Highly brominated antimicrobial metabolites from a marine Pseudoalteromonas sp.: D. Feher, et al.; J. Nat. Prod. 73, 1963 (2010)
  10. Inhibition of myosin ATPase activity by halogenated pseudilins: a structure-activity study: M. Preller, et al.; J. Med. Chem. 54, 3675 (2011)
  11. Agrochemicals against malaria, sleeping sickness, leishmaniasis and chagas Disease: M. Witschel, et al.; PLoS Negl. Trop. Dis. 6, 1805 (2012)
  12. Toxicity of bioactive and probiotic marine bacteria and their secondary metabolites in Artemia sp. and Caenorhabditis elegans as eukaryotic model organisms: A.K. Neu, et al.; Appl. Environ. Microbiol. 80, 146 (2014)
  13. Pseudilins: halogenated, allosteric inhibitors of the non-mevalonate pathway enzyme IspD: A. Kunfermann, et al.; Angew. Chem. Int. Ed. Engl. 53, 2235 (2014)
  14. Myosin-II-mediated cell shape changes and cell intercalation contribute to primitive streak formation: E. Rozbicki, et al.; Nat. Cell Biol. 17, 397 (2015)
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