Marinopyrrole A

ChemicalBook > CAS DataBase List > Marinopyrrole A

Product Name: Marinopyrrole A
CAS No.: 1227962-62-0
Chemical Name: Marinopyrrole A
Synonyms: )-MARINOPYRROLE A;Maritoclax, 10 mM in DMSO;Marinopyrrole A(Maritoclax);Maritoclax, (±)-Marinopyrrole A;(+/-)-Marinopyrrole A >=95% (HPLC);Inhibitor,Maritoclax,Bcl-2 Family,inhibit;(4,4',5,5'-Tetrachloro-1'H-[1,3'-bipyrrole]-2,2'-diyl)bis((2-hydroxyphenyl)methanone);1,1'-(4,4',5,5'-Tetrachloro[1,3'-bi-1H-pyrrole]-2,2'-diyl)bis[1-(2-hydroxyphenyl)methanone];Methanone, 1,1'-(4,4',5,5'-tetrachloro[1,3'-bi-1H-pyrrole]-2,2'-diyl)bis[1-(2-hydroxyphenyl)-
CBNumber: CB92677047
Molecular Formula: C22H12Cl4N2O4
Formula Weight: 510.15
MOL File: 1227962-62-0.mol

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Marinopyrrole A Property

Melting point:: 205-207℃
Boiling point:: 732.4±60.0 °C(Predicted)
Density: 1.62±0.1 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: Soluble in DMSO
form: A solid
pka: 6.87±0.30(Predicted)
color: Light yellow to yellow

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: T291055
Product name: 1,1''-(4,4'',5,5''-Tetrachloro[1,3''-bi-1H-pyrrole]-2,2''-diyl)bis[1-(2-hydroxyphenyl)methanone]
Packaging: 50mg
Price: $760
Updated: 2021/12/16

ApexBio Technology

Product number: B1080
Product name: MarinopyrroleA
Packaging: 50mg
Price: $929
Updated: 2021/12/16

ApexBio Technology

Product number: B1080
Product name: MarinopyrroleA
Packaging: 2mg
Price: $95
Updated: 2021/12/16

ApexBio Technology

Product number: B1080
Product name: MarinopyrroleA
Packaging: 5mg
Price: $150
Updated: 2021/12/16

ApexBio Technology

Product number: B1080
Product name: MarinopyrroleA
Packaging: 10mg
Price: $268
Updated: 2021/12/16

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Marinopyrrole A Chemical Properties,Usage,Production

Uses

1,1''-(4,4'',5,5''-Tetrachloro[1,3''-bi-1H-pyrrole]-2,2''-diyl)bis[1-(2-hydroxyphenyl)methanone] is a marine anticancer compound. Also, it possesses anti-bacterial properties against methicillin-resistant Staphylococcus aureus.

Definition

ChEBI: (-)-marinopyrrole A is a member of the class of pyrroles that is 1'H-1,3'-bipyrrole substituted by four chloro groups at positions 4, 4', 5 and 5' and two 2-hydroxybenzoyl moieties at positions 2 and 2'. It is isolated from Streptomyces sp.CNQ-418 and exhibits cytotoxic and antibacterial activities. It has a role as an antimicrobial agent, an antibacterial agent, an antineoplastic agent, a marine metabolite and a bacterial metabolite. It is a member of pyrroles, an organochlorine compound, a member of phenols and an aromatic ketone.

Biological Activity

marinopyrrole a is a selective inhibitor of mcl-1 with ic50 value of 10.1μm [1].marinopyrrole a is a natural product froma species of marine-derived streptomycetes and is reported to be an antagonist of mcl-1. mcl-1 is a member of the anti-apoptotic bcl-2 family, which is a well-validated drug target for cancer treatment. nmr titration experiments show that marinopyrrole a can directly interact with mcl-1. it can prevent bim-bh3 peptides from binding to mcl-1 but not bcl-xl. the cell based assay shows a high selectivity of marinopyrrole a. treatment with marinopyrrole a inhibit the viability of k562 cells transfected with mcl-1 gene with ec50 value of 1.6μm. the selectivity is more than 40-fold greater over the cells transfected with bcl-xl gene. moreover, marinopyrrole a can decreases mcl-1 expression by increasing the cleavage of caspase-3 and parp. marinopyrrole a is also reported to completely restore the sensitivity of multidrug resistant leukemia cells to abt-737 [1].

References

[1] doi k, li r, sung ss, et al. discovery of marinopyrrole a (maritoclax) as a selective mcl-1 antagonist that overcomes abt-737 resistance by binding to and targeting mcl-1 for proteasomal degradation. j biol chem. 2012 mar, 287(13): 10224-35.

Marinopyrrole A Preparation Products And Raw materials

Raw materials

Preparation Products

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1227962-62-0, Marinopyrrole ARelated Search:

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

Marinopyrrole A(Maritoclax)

Maritoclax, (±)-Marinopyrrole A

Methanone, 1,1'-(4,4',5,5'-tetrachloro[1,3'-bi-1H-pyrrole]-2,2'-diyl)bis[1-(2-hydroxyphenyl)-

(+/-)-Marinopyrrole A >=95% (HPLC)

)-MARINOPYRROLE A

(4,4',5,5'-Tetrachloro-1'H-[1,3'-bipyrrole]-2,2'-diyl)bis((2-hydroxyphenyl)methanone)

Inhibitor,Maritoclax,Bcl-2 Family,inhibit

Maritoclax, 10 mM in DMSO

1227962-62-0

C22H12Cl4N2O4