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B2311

Sigma-Aldrich

5-(2-Benzothiazolyl)-3-ethyl-2-[2-(methylphenylamino)ethenyl]-1-phenyl-1H-benzimidazolium iodide

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C31H27IN4S
CAS Number:
681281-88-9
Molecular Weight:
614.54
MDL number:
MFCD00570739
UNSPSC Code:
12352200
PubChem Substance ID:
24724416
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

[I-].CC[n+]1c(\C=C\N(C)c2ccccc2)n(-c3ccccc3)c4ccc(cc14)-c5nc6ccccc6s5

InChI

1S/C31H27N4S.HI/c1-3-34-28-22-23(31-32-26-16-10-11-17-29(26)36-31)18-19-27(28)35(25-14-8-5-9-15-25)30(34)20-21-33(2)24-12-6-4-7-13-24;/h4-22H,3H2,1-2H3;1H/q+1;/p-1

InChI key

NAYRELMNTQSBIN-UHFFFAOYSA-M

Biochem/physiol Actions

5-(2-Benzothiazolyl)-3-ethyl-2-[2-(methylphenylamino)-ethenyl]-1-phenyl-1H-benzimidazolium, or Akt Inhibitor IV, is a cell-permeable benzimidazole compound that inhibits Akt phosphorylation/activation by targeting the ATP binding site of a kinase upstream of Akt, but downstream of PI3K. Shown to block Akt-mediated FOXO1a nuclear export (IC50 = 0.625μM) and cell proliferation (IC50 < 1.25μM) in 786-O cells. Unlike phosphatidylinositol analog-based Akt inhibitors, this inhibitor does not affect PI3K.

Features and Benefits

This compound is featured on the PKB/Akt page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

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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Emmanuel Chautard et al.
Neuro-oncology, 12(5), 434-443 (2010-04-22)
Radiation therapy plays a central role in the treatment of glioblastoma, but it is not curative due to the high tumor radioresistance. Phosphatidyl-inositol 3-kinase/protein kinase B (Akt) and Janus kinase (JAK)/signal transducer and activator of transcription 3 (STAT3) pathways serve
Jinxia Liu et al.
Oncogenesis, 9(9), 84-84 (2020-09-26)
β-Adrenergic receptor (β-AR) signalling is strongly associated with tumour progression by the coupling of β-ARs with either a G protein or β-arrestin; however, the related mechanism underlying hepatocellular carcinoma (HCC) metastasis is not clear. Here, we reveal that the transcription
Wenda Di et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(2), 2075-2086 (2020-01-08)
In the free-living nematode Caenorhabditis elegans, the serine/threonine-specific protein kinase, AKT, is known to play a key role in dauer formation, life-span, and stress-resistance through the insulin-like signaling pathway. Although the structure and function of AKT-coding genes of C. elegans
Pavithra Lakshminarasimhan Chavali et al.
The Journal of biological chemistry, 286(11), 9393-9404 (2010-12-08)
Hypoxia promotes neural stem cell proliferation, the mechanism of which is poorly understood. Here, we have identified the nuclear orphan receptor TLX as a mediator for proliferation and pluripotency of neural progenitors upon hypoxia. We found an enhanced early protein
Kenji Hayata et al.
Journal of pharmacological sciences, 108(3), 348-354 (2008-11-15)
To obtain compounds that promote glucose uptake in muscle cells, the novel cell lines A31-IS derived from Balb/c 3T3 A31 and C2C12-IS from mouse myoblast C2C12 were established. In both cell lines, glucose consumption was induced by insulin and suppressed
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