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Merck
CN

SML3311

NR-160

≥98% (HPLC)

Synonym(s):

4-({N-[(1-Benzyl-1H-1,2,3,4-tetrazol-5-yl)methyl]-1-[2-(trifluoromethyl)phenyl]formamido}methyl-N-hydroxybenzamide, NR 160, NR160

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About This Item

Empirical Formula (Hill Notation):
C25H21F3N6O3
CAS Number:
2484895-50-1
Molecular Weight:
510.47
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI

1S/C25H21F3N6O3/c26-25(27,28)21-9-5-4-8-20(21)24(36)33(14-18-10-12-19(13-11-18)23(35)30-37)16-22-29-31-32-34(22)15-17-6-2-1-3-7-17/h1-13,37H,14-16H2,(H,30,35)

InChI key

MEWDNULKAXEKII-UHFFFAOYSA-N

SMILES string

FC(F)(C1=CC=CC=C1C(N(CC2=CC=C(C=C2)C(NO)=O)CC3=NN=NN3CC4=CC=CC=C4)=O)F

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Active site-targeting, potent and selective histone deacetylase 6 inhibitor that augments the cytotoxicity ofbortezomib, epirubicin, and daunorubicin.
NR-160 is an active site-targeting, potent and selective histone deacetylase 6 inhibitor (HDAC6 IC50 = 30 nM; IC50 >2 μM against HDAC1/2/3/4/8) that upregulates HL60 cellular acetylation of HDAC6 substrate α-tubulin (2.5 μM), but not that of class I HDACs substrate histone H3. NR-160 augments the apoptosis induction by the proteasome inhibitor bortezomib (0.6/1.2 nM BTZ with 2.5/5.0 μM NR-160; HL60) and significantly enhances the cytotoxicity of DNA-intercalating anti-cancer drugs epirubicin and daunorubicin (2.5 or 5.0 μM NR-160 in combination with 10 nM of either compound to T-ALL line HSB-2).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000181233
0000181234
0000176953
0000181234
0000181233

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Nina Reßing et al.
Journal of medicinal chemistry, 63(18), 10339-10351 (2020-08-18)
Histone deacetylase 6 (HDAC6) is an emerging target for the treatment of cancer, neurodegenerative diseases, inflammation, and other diseases. Here, we present the multicomponent synthesis and structure-activity relationship of a series of tetrazole-based HDAC6 inhibitors. We discovered the hit compound

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