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5.04712

β-Catenin/Tcf Inhibitor VI, ICG-001

Name: β-Catenin/Tcf Inhibitor VI, ICG-001
Brand: MM

Synonym(s):

β-Catenin/Tcf Inhibitor VI, ICG-001, (6 S,9a S)-Hexahydro-6-((4-hydroxyphenyl)methyl)-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide, (6 S)-N-Benzyl-6-(p-hydroxyphenylmethyl)-8-(1-naphthylmethyl)-4,7-dioxohexahydro-2H-, (6S,9aS)-Hexahydro-6-((4-hydroxyphenyl)methyl)-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide, (6S)-N-Benzyl-6-(p-hydroxyphenylmethyl)-8-(1-naphthylmethyl)-4,7-dioxohexahydro-2H-pyra

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About This Item

Empirical Formula (Hill Notation):

C₃₃H₃₂N₄O₄

CAS Number:

847591-62-2

Molecular Weight:

548.63

MDL number:

MFCD21362415

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥99% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

OK to freeze, protect from light

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Properties

assay

≥99% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

off-white

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

SMILES string

N21[C@@H](N(CCC2=O)C(=O)NCc6ccccc6)CN(C(=O)[C@@H]1Cc5ccc(cc5)O)Cc3c4c(ccc3)cccc4

InChI

1S/C33H32N4O4/c38-27-15-13-23(14-16-27)19-29-32(40)35(21-26-11-6-10-25-9-4-5-12-28(25)26)22-30-36(18-17-31(39)37(29)30)33(41)34-20-24-7-2-1-3-8-24/h1-16,29-30,38H,17-22H2,(H,34,41)/t29-,30+/m0/s1

InChI key

HQWTUOLCGKIECB-XZWHSSHBSA-N

Description

General description

A cell-permeable pyrazinopyrimidinecarboxamide that competes against β-catenin for CBP (CREB-binding protein) binding (5 to 10 µM for 24 h in SW480 and C2C12 cultures) and selectively prevents CBP- but not p300-, dependent TCF/β-catenin transcriptional regulations both in cultures in vitro (5 to 25 µM in SW480, HCT116, rat RLT-6TN, and primary human IPF lung fibroblasts; 4 to 24 h) and in mice in vivo (5 mg/kg/day via osmotic pump infusion), while not affecting CBP-dependent transcriptional activities mediated by the AP-1 or CRE complex. Selective blockage of CBP/TCF/β-catenin complex formation by ICG-001 is shown to reactivate p300//TCF/β-catenin-mediated neuronal differentiation upon NGF stimulation in PS-1 L286V mutant-expressing PC-12 cultures (cell population with neurite outgrowth = 90% and 17% of wt PS-1 control level, respectively, with or without 10 µM ICG-001) and be efficacious in alleviating bleomycin- (0,08 units/50 µL/mouse; administered intranasally; induced pulmonary fibrosis in mice (5 mg/kg/day via osmotic pump infusion; 10 d treatment starting 1 d before bleomycin induction or 21 d treatment starting d 21 post bleomycin induction).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
CREB-binding protein

Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Use only fresh DMSO for reconstitution.

Other Notes

Yan, D., et al. 2012. J. Biol. Chem.287, 8598.
Henderson, W.R. Jr, et al. 2010. Proc. Natl. Acad. Sci. USA.107, 14309.
Eguchi, M., et al. 2005. Med Chem.1, 467.
Ma, H., et al. 2005. Oncogene.24, 3619.
Teo, J.L., et al. 2005. Proc. Natl. Acad. Sci. USA.102, 12171.
Emami, K.H., et al. 2004. Proc. Natl. Acad. Sci. USA.101, 12682.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c