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SML1412

Sigma-Aldrich

KRIBB11 trifluoroacetate salt

≥98% (HPLC)

Synonym(s):

2,6-Pyridinediamine trifluoroacetate salt, N2-(1H-Indazol-5-yl)-N6-methyl-3-nitropyridine-2,6-diamine trifluoroacetate salt, N2-1H-Indazol-5-yl-N6-methyl-3-nitro-2,6-pyridinediamine trifluoroacetate salt

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About This Item

Empirical Formula (Hill Notation):
C13H12N6O2 · C2HF3O2
CAS Number:
342639-96-7
Molecular Weight:
398.30
UNSPSC Code:
12352200
PubChem Substance ID:
329825859
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

CNC1=NC(NC2=CC=C(NN=C3)C3=C2)=C([N+]([O-])=O)C=C1.FC(F)(C(O)=O)F

InChI

1S/C13H12N6O2.C2HF3O2/c1-14-12-5-4-11(19(20)21)13(17-12)16-9-2-3-10-8(6-9)7-15-18-10;3-2(4,5)1(6)7/h2-7H,1H3,(H,15,18)(H2,14,16,17);(H,6,7)

InChI key

DNBQMABUWGNHGB-UHFFFAOYSA-N

Biochem/physiol Actions

KRIBB11 is an inhibitor of the transcription factor Heat Shock Factor 1 (HSF1) with an IC50 value of 1.2 μM. KRIBB11 blocks induction of HSF1 downstream target proteins such as HSP27 and HSP70 by impairing the recruitment of Positive Transcription Elongation Factor b (P-TEFb) to the HSF1 transcriptional complex, preventing HSF1-mediated gene expression KRIBB11 inhibits tumor growth in vivo and acts synergistically to increase apoptosis in cancer cells treated with the HSP90 inhibitors Geldanamycin and 17-AAG.
KRIBB11 is capable of preventing the proliferation of cancer cells. It has the ability to stimulate apoptosis and can arrest the cell cycle at G2/M phase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Young Ju Yoon et al.
The Journal of biological chemistry, 286(3), 1737-1747 (2010-11-17)
Heat shock factor 1 (HSF1) is the master switch for heat shock protein (HSP) expression in eukaryotes. A synthetic chemical library was screened to identify inhibitors of HSF1 using a luciferase reporter under the control of a heat shock element.

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