ACHP
- Product Name
- ACHP
- CAS No.
- 406208-42-2
- Chemical Name
- ACHP
- Synonyms
- ACHP;2-Amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-(4-piperidinyl)nicotinonitrile;2-Amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-(4-piperidinyl)-3-pyridinecarbonitrile;3-Pyridinecarbonitrile, 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-(4-piperidinyl)-
- CBNumber
- CB22669276
- Molecular Formula
- C21H24N4O2
- Formula Weight
- 364.44
- MOL File
- 406208-42-2.mol
ACHP Property
- storage temp.
- Store at -20°C
- solubility
- <7.29mg/ml in DMSO
- form
- solid
- color
- Yellow
- InChI
- 1S/C21H24N4O2/c22-11-16-15(14-6-8-24-9-7-14)10-17(25-21(16)23)20-18(26)2-1-3-19(20)27-12-13-4-5-13/h1-3,10,13-14,24,26H,4-9,12H2,(H2,23,25)
- InChIKey
- DYVFBWXIOCLHPP-UHFFFAOYSA-N
- SMILES
- N1CCC(CC1)c2c(c(nc(c2)c3c(cccc3O)OCC4CC4)N)C#N
Safety
- WGK Germany
- WGK 2
- Storage Class
- 11 - Combustible Solids
N-Bromosuccinimide Price
- Product number
- 401487
- Product name
- IKK-2 Inhibitor VIII - CAS 406208-42-2 - Calbiochem
- Packaging
- 1MG
- Price
- $201
- Updated
- 2025/07/31
- Product number
- 4547
- Product name
- ACHP
- Purity
- ≥97%(HPLC)
- Packaging
- 10
- Price
- $303
- Updated
- 2021/12/16
- Product number
- 254533
- Product name
- ACHP
- Packaging
- 10mg
- Price
- $573
- Updated
- 2021/12/16
- Product number
- A189823
- Product name
- ACHP
- Packaging
- 10mg
- Price
- $285
- Updated
- 2021/12/16
- Product number
- 1434EM
- Product name
- 2-Amino-6-(2-(cyclopropylmethoxy)-6-hydroxyphenyl)-4-(4-piperidinyl)-3-pyridinecarbonitrile
- Packaging
- 1mg
- Price
- $174
- Updated
- 2021/12/16
ACHP Chemical Properties,Usage,Production
Uses
ACHP is an IkB kinase inhibitor, which has dose-dependently inhibited cell growth with inhibition of phosphorylation of IκBα/p65 and NF-κB DNA-binding, down-regulation of NF-κB target genes and induced apoptosis in human myeloma cell lines.
Definition
ChEBI: 2-amino-6-[2-(cyclopropylmethoxy)-6-oxo-1-cyclohexa-2,4-dienylidene]-4-(4-piperidinyl)-1H-pyridine-3-carbonitrile is a member of quinomethanes.
Biological Activity
achp is an iκb kinase inhibitor. nuclear factor-kb (nf-kb) involved in cell survival and proliferation of multiple myeloma has been well established.
in vitro
achp is selective for ikkα and ikkβ over ikk3, syk and mapkkk4 (ic50 > 20 μm), dna binding activity of nf-κb is inhibited. achp is an effective blockade nf-κb pathway in multiple myeloma cell lines, and induces cell growth arrest and apoptosis. it was observed that nf-kb is constitutively activated in all human myeloma cell lines, thus confirming the previous studies. in addition, it was found the phosphorylation of p65 subunit of nf-kb besides the phosphorylation of ikba and the activation of nf-kb dna binding and that various target genes of nf-kb including bcl-xl, xiap, c-iap1, cyclin d1, and il-6 are up-regulated. 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-piperidin-4-yl nicotinenitrile (achp) is a novel ikb kinase inhibitor. treatment of myeloma cells with achp showed the cell growth was efficiently inhibited (ic50 values ranging from 18 to 35 mmol/l) concomitantly with inhibition of the phosphorylation of ikba/p65 and nf-kb dna-binding, down-regulation of the nf-kb target genes, and then induction of apoptosis. in addition, the treatment of achp potentiated the cytotoxic effects of vincristine and melphalan (l-phenylalanine mustard), conventional antimyeloma drugs. these findings suggest that by blocking the antiapoptotic nature of myeloma cells endowed by the constitutive activation of nf-kb, ikb kinase inhibitors such as achp can sensitize myeloma cells to the cytotoxic effects of chemotherapeutic agents.
Enzyme inhibitor
This novel IKK inhibitor (FW = 364.44 g/mol; CAS 406208-42-2; Soluble to 20 mM in DMSO), also named 2-amino-6-[2-(cyclopropylmethoxy)-6hydroxyphenyl]-4-(4-piperidinyl)-3-pyridinecarbonitrile, targets IκB kinases, with respective IC50 values of 8.5 and 250 nM for IKKβ and IKKα. ACHP’s selectivity is indicated by its > 20-μM IC50 values toward IKK3, Syk, and MAPKKK4. Inhibition of the TNFα-mediated gene expression could occur at low ACHP concentration (<1 μmol/L), with higher concentrations (>10 μmol/L) required to inhibit the constitutive phosphorylation of p65, expression of NF-κB-mediated genes (e.g., CYCLIN D1, BCL-xL, XIAP, c-IAP1, and IL-6), ultimately achieving myeloma cytostasis. Such findings indicate that ACHP’s growth inhibitory effects may be mediated through inhibition of both IKKα and IKKβ. By inhibiting NF-κB’s DNA binding activity, ACHP blocks the NF-κB pathway in multiple myeloma cell lines, inducing growth arrest and apoptosis.
IC 50
8.5 and 250 nm for ikkβ and ikkα, respectively
storage
Store at -20°C
References
[1] sanda t, iida s, ogura h, asamitsu k, murata t, bacon kb, ueda r, okamoto t. growth inhibition of multiple myeloma cells by a novel ikappab kinase inhibitor. clin cancer res. 2005 mar 1;11(5):1974-82.
ACHP Preparation Products And Raw materials
Raw materials
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