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SML2428

Sigma-Aldrich

Pentabromopseudilin

≥97% (HPLC)

Synonym(e):

Pentabromopseudilin, 2,4-dibromo-6-(3,4,5-tribromo-1H-pyrrol-2-yl)phenol, PBP

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About This Item

Empirische Formel (Hill-System):
C10H4Br5NO
CAS-Nummer:
10245-81-5
Molekulargewicht:
553.66
UNSPSC-Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

Form

solid

Lagertemp.

−20°C

SMILES String

OC1=C(Br)C=C(Br)C=C1C2=C(Br)C(Br)=C(Br)N2

InChI

1S/C10H4Br5NO/c11-3-1-4(9(17)5(12)2-3)8-6(13)7(14)10(15)16-8/h1-2,16-17H

InChIKey

LXMNWKJHYOZUQL-UHFFFAOYSA-N

Allgemeine Beschreibung

Pentabromopseudilin (PBP) is a potent antibiotic originally isolated from the marine bacterium Pseudomonas bromoutilis. 2 PBP exhibits cytotoxic, antibacterial and phytotoxic activities, including the inhibition of human 12- and 15-lipoxygenases3 and potent inhibition of myosin-dependent processes. 4-5 PBP was identified as a potent inhibitor of the motor activity of vertebrate myosin V with an IC50 value of 1.2μM. 5 PBP inhibits the ATPase activity of myosin by increasing its affinity for ADP, reducing ATP-binding and hydrolysis rates, and through coupling between actin and nucleotide-binding sites in the motor domain. 4 Recently, it was also demonstrated that PBP suppresses TGF-β activity.

Sonstige Hinweise

Solubility: Chloroform/dichloromethane (at least 10 mg/ml), methanol/ethanol (at least 1 mg/ml), DMSO (10mM)
Working Stock: PBP can be dissolved in DMSO at concentration of 10mM, solution should be stored in the dark at -80°C.

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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P R Burkholder et al.
Applied microbiology, 14(4), 649-653 (1966-07-01)
Evidence is presented for the isolation and identification of bacteria able to synthesize an unusual antibiotic containing five bromine atoms per molecule. The identification and taxonomic position of these bacteria was made by use of a computer in conjunction with
Total synthesis of pentabromo- and pentachloropseudilin, and synthetic analogues--allosteric inhibitors of myosin ATPase.
René Martin et al.
Angewandte Chemie (International ed. in English), 48(43), 8042-8046 (2009-09-10)
Rachana V Ohri et al.
Organic letters, 7(12), 2501-2504 (2005-06-04)
[reaction: see text] A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air- and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing
Matthias Preller et al.
Journal of medicinal chemistry, 54(11), 3675-3685 (2011-05-04)
Myosin activity is crucial for many biological functions. Strong links have been established between changes in the activity of specific myosin isoforms and diseases such as cancer, cardiovascular failure, and disorders of sensory organs and the central nervous system. The
Roman Fedorov et al.
Nature structural & molecular biology, 16(1), 80-88 (2009-01-06)
We have identified pentabromopseudilin (PBP) as a potent inhibitor of myosin-dependent processes such as isometric tension development and unloaded shortening velocity. PBP-induced reductions in the rate constants for ATP binding, ATP hydrolysis and ADP dissociation extend the time required per
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