| Identification | Back Directory | [Name]
Marinopyrrole A | [CAS]
1227962-62-0 | [Synonyms]
)-MARINOPYRROLE A
Marinopyrrole A(Maritoclax)
Maritoclax, (±)-Marinopyrrole A
(+/-)-Marinopyrrole A >=95% (HPLC)
(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)- | [Molecular Formula]
C22H12Cl4N2O4 | [MDL Number]
MFCD28167731 | [MOL File]
1227962-62-0.mol | [Molecular Weight]
510.15 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. |
|
| Company Name: |
SPIRO PHARMA
|
| Tel: |
|
| Website: |
www.spiropharma.com.cn |
|