BioViotica

Pentabromopseudilin

Name: Pentabromopseudilin
Brand: BioViotica
SKU: BVT-0441
Price: 190.00 CHF
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BVT-0441-C500500 µgCHF 190.00

Specifications / Handling

More Information
Product Details
Synonyms	PBP; 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
Product Type	Chemical
Properties
Formula	C₁₀H₄Br₅NO
MW	553.7
CAS	10245-81-5
RTECS	SK8150000
Source/Host Chemicals	Isolated from sea water proteobacteria Alteromonas Iuteo-violaceus.
Purity Chemicals	≥98% (HPLC)
Appearance	Off-white powder.
Solubility	Soluble in DMSO (5mg/ml), acetone, butanol, ethylacetate or diethylether.
Identity	Determined by ¹H-NMR.
Declaration	Manufactured by BioViotica.
InChi Key	LXMNWKJHYOZUQL-UHFFFAOYSA-N
Smiles	OC1=C(Br)C=C(Br)C=C1C1=C(Br)C(Br)=C(Br)N1
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.
Documents
Safety Data Sheet	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Scientific Background Information

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-specific References

Production of a pyrrole antibiotic by a marine bacterium: P.R. Burkholder, et al.; Appl. Microbiol. 14, 649 (1966)
The structure of a bromine-rich marine antibiotic: F.M. Lovell; JACS 88, 4510 (1966)
Marine bacteria. I. Synthesis of pentabromopseudilin, a cytotoxic phenylpyrrole from Alteromonas luteoviolaceus: H. Laatsch & H. Pudleiner; Liebigs Ann. Chem. 9, 863 (1989)
Biosynthesis of the marine antibiotic pentabromopseudilin. Part 1. The benzene ring: U. Hanefeld, et al.; J. Org. Chem. 8, 847 (1993)
Structure-activity relationships of phenyl- and benzoylpyrroles: H. Laatsch, et al.; Chem. Pharm. Bull. 43, 537 (1995)
Biosynthesis of the marine antibiotic pentabromopseudilin. Part 2. The pyrrole ring: J. Peschke, et al.; Biosci. Biotechnol. Biochem. 69, 628 (2005)
A rev(V)-catalysed C-N bond-forming route to human lipoxygenase inhibitors: O. Rachana, et al.; Org. Lett. 7, 2501 (2005)
The mechanism of pentabromopseudilin inhibition of myosin motor activity: R. Fedorov, et al.; Nat. Struct. Mol. Biol. 16, 80 (2009)
Highly brominated antimicrobial metabolites from a marine Pseudoalteromonas sp.: D. Feher, et al.; J. Nat. Prod. 73, 1963 (2010)
Inhibition of myosin ATPase activity by halogenated pseudilins: a structure-activity study: M. Preller, et al.; J. Med. Chem. 54, 3675 (2011)
Agrochemicals against malaria, sleeping sickness, leishmaniasis and chagas Disease: M. Witschel, et al.; PLoS Negl. Trop. Dis. 6, 1805 (2012)
Small-molecule inhibitors of myosin proteins: L.M. Bond, et al.; Future Med. Chem. 5, 41 (2013)
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)
Pseudilins: halogenated, allosteric inhibitors of the non-mevalonate pathway enzyme IspD: A. Kunfermann, et al.; Angew. Chem. Int. Ed. Engl. 53, 2235 (2014)
Myosin-II-mediated cell shape changes and cell intercalation contribute to primitive streak formation: E. Rozbicki, et al.; Nat. Cell Biol. 17, 397 (2015)
Actomyosin and CSI1/POM2 cooperate to deliver cellulose synthase from Golgi to cortical microtubules in Arabidopsis: L. Liu, et al.; Nature Commun. 14, 7442 (2023)

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