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SML2464

Sigma-Aldrich

KRN2

≥98% (HPLC)

Synonym(s):

KRN2, 13-[(2-Fluorophenyl)methyl]-5,6-dihydro-9,10-dimethoxy-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium chloride

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About This Item

Empirical Formula (Hill Notation):
C27H23FClNO4
CAS Number:
248260-75-5
Molecular Weight:
479.93
MDL number:
MFCD31728343
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

faint yellow to dark orange

solubility

H2O: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

FC(C=CC=C1)=C1CC2=C([N+](CC3)=CC4=C2C=CC(OC)=C4OC)C5=C3C=C(OCO6)C6=C5.[Cl-]

InChI key

RPHFGOXVJGNJJH-UHFFFAOYSA-M

Biochem/physiol Actions

KRN2 is a specific and potent inhibitor of nuclear factor of activated T cells 5 (NFAT5) that inhibits formation of NF-κB p65-DNA complexes. KRN2 suppresses migration of Fibroblast-like synoviocytes stimulated with TGF-β. KRN2 ameliorates experimental arthritis in mice.
KRN2 or 13-(2-fluorobenzyl)-berberine is a berberine derivative that effectively blocks the invasiveness of fibroblast-like synoviocytes (FLS). It is stable and orally bioavailable. It suppresses the production of proinflammatory cytokines to ameliorate arthritis severity.
specific and potent inhibitor of nuclear factor of activated T cells 5 (NFAT5) that inhibits formation of NF-κB p65-DNA complexes

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000064624
0000064625
0000058945

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Eun-Jin Han et al.
EBioMedicine, 18, 261-273 (2017-04-12)
Nuclear factor of activated T cells 5 (NFAT5) has been implicated in the pathogenesis of various human diseases, including cancer and arthritis. However, therapeutic agents inhibiting NFAT5 activity are currently unavailable. To discover NFAT5 inhibitors, a library of >40,000 chemicals
Naeun Lee et al.
Frontiers in immunology, 10, 270-270 (2019-03-16)
The nuclear factor of activated T cells (NFAT5), also known as a tonicity-responsive enhancer-binding protein, was originally identified as a key transcription factor involved in maintaining cellular homeostasis against hypertonic and hyperosmotic environments. Although NFAT5 has been expressed and studied
Inessa Yanovsky et al.
Journal of medicinal chemistry, 55(23), 10700-10715 (2012-11-16)
The cascade of events that occurs in Alzheimer's disease involving oxidative stress and the reduction in cholinergic transmission can be better addressed by multifunctional drugs than cholinesterase inhibitors alone. For this purpose, we prepared a large number of derivatives of

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