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B3306

Sigma-Aldrich

Bisindolylmaleimide IV

≥98% (TLC), solid

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Synonym(s):
Ro 31-6233
Empirical Formula (Hill Notation):
C20H13N3O2
CAS Number:
119139-23-0
Molecular Weight:
327.34
MDL number:
MFCD00236432
UNSPSC Code:
12352111
PubChem Substance ID:
24891709
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (TLC)

form

solid

color

dark red

solubility

DMSO: soluble
methanol: soluble

storage temp.

−20°C

SMILES string

O=C1NC(=O)C(c2c[nH]c3ccccc23)=C1c4c[nH]c5ccccc45

InChI

1S/C20H13N3O2/c24-19-17(13-9-21-15-7-3-1-5-11(13)15)18(20(25)23-19)14-10-22-16-8-4-2-6-12(14)16/h1-10,21-22H,(H,23,24,25)

InChI key

DQYBRTASHMYDJG-UHFFFAOYSA-N

Gene Information

human ... CDK2(1017) , EGFR(1956)
rat ... Prkca(24680)

Biochem/physiol Actions

Bisindolylmaleimides (BIM) comprises a group of 11 compounds from BIM-I to BIM-XI. BIMs act as an inhibitor of protein kinase C (PKC). They are derived from staurosporine. BIM IX due to its proapoptotic functionality could be useful in targeting tumor proliferation.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Abdullah Mayati et al.
PloS one, 10(12), e0144667-e0144667 (2015-12-15)
Ro 31-8220 is a potent protein kinase C (PKC) inhibitor belonging to the chemical class of bisindolylmaleimides (BIMs). Various PKC-independent effects of Ro 31-8220 have however been demonstrated, including inhibition of the ATP-binding cassette drug transporter breast cancer resistance protein.
Sibasish Dolai et al.
Proteomics, 11(13), 2683-2692 (2011-06-02)
Basal-like breast cancers are commonly negative for expression of estrogen and progesterone receptors and HER-2 (triple-negative breast cancer), which makes this subtype of breast cancers more aggressive and less responsive to standard treatment. We have applied a small-scale chemical proteomics
Hui He et al.
The Prostate, 70(10), 1119-1126 (2010-03-25)
We have reported that human prostate cancer ARCaP(E) cells undertake epithelial to mesenchymal transition (EMT) when stimulated by certain soluble factors, and that EMT is regulated by surface receptor-elicited signaling pathways through protein phosphorylation. It is known that phorbol ester
Ansar A Khan et al.
Toxicology in vitro : an international journal published in association with BIBRA, 24(3), 822-829 (2009-12-17)
The vitamin D receptor (VDR) regulates the expression of drug metabolizing enzymes and transporters in intestine and liver, but the regulation of VDR expression in intestine and liver is incompletely understood. We studied the regulation of VDR mRNA expression by
Neil Grodsky et al.
Biochemistry, 45(47), 13970-13981 (2006-11-23)
The conventional protein kinase C isoform, PKCII, is a signaling kinase activated during the hyperglycemic state and has been associated with the development of microvascular abnormalities associated with diabetes. PKCII, therefore, has been identified as a therapeutic target where inhibitors
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