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SML1533

Sigma-Aldrich

(±)-Marinopyrrole A

≥95% (HPLC)

Synonym(s):

(±)-Maritoclax, 1,1′-(4,4′,5,5′-Tetrachloro[1,3′-bi-1H-pyrrole]-2,2′-diyl)bis[1-(2-hydroxyphenyl)-methanone

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About This Item

Empirical Formula (Hill Notation):
C22H12Cl4N2O4
CAS Number:
1227962-62-0
Molecular Weight:
510.15
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

light yellow to dark yellow

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

InChI

1S/C22H12Cl4N2O4/c23-12-9-13(19(31)10-5-1-3-7-14(10)29)28(22(12)26)18-16(24)21(25)27-17(18)20(32)11-6-2-4-8-15(11)30/h1-9,27,29-30H

InChI key

QYPJBTMRYKRTFG-UHFFFAOYSA-N

General description

Marinopyrrole A (Maritoclax) is a member of phenolic 1,3′-bipyrroles family targeting actin group.

Biochem/physiol Actions

Marinopyrrole A (Maritoclax) is a potent and selective inhibitor of Bcl-2 family member Mcl-1, originally isolated from marine streptomycetes for its antimicrobial activity against methicillin-resistant Staphylococcus aureus. Marinopyrrole A directly binds to Mcl-1 and targets it for proteasomal degradation. Marinopyrrole A induced apoptosis in Mcl-1-dependent cancer cells and sensitized cancer cells to ABT-737.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Chambers C Hughes et al.
Journal of the American Chemical Society, 131(34), 12094-12096 (2009-08-14)
The targeting of marinopyrrole A to actin was identified using a fluorescent dye transfer strategy. The process began by appending a carboxylic acid terminal tag to a phenol in the natural product. The resulting probe was then studied in live

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