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5.09105

STAT3/STAT5 Dual Inhibitor, SH-4-54

Name: STAT3/STAT5 Dual Inhibitor, SH-4-54
Brand: MM

Synonym(s):

STAT3/STAT5 Dual Inhibitor, SH-4-54, SH-04-54, SH0454, SH454, 4-(N-(4-Cyclohexylbenzyl)-2-(2,3,4,5,6-pentafluoro-N-methylphenylsulfonamido)acetamido)benzoic acid, STAT3 Inhibitor XIX, STAT5 Inhibitor IV

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₂₇F₅N₂O₅S

CAS Number:

1456632-40-8

Molecular Weight:

610.59

MDL number:

MFCD28143917

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥94% (HPLC)

Form:

powder

Storage condition:

OK to freeze, protect from light

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Properties

assay

≥94% (HPLC)

Quality Segment

100

form

powder

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

SMILES string

Fc1c(c(c(c(c1F)F)[S](=O)(=O)N(CC(=O)N(Cc3ccc(cc3)C4CCCCC4)c2ccc(cc2)C(=O)O)C)F)F

InChI

1S/C29H27F5N2O5S/c1-35(42(40,41)28-26(33)24(31)23(30)25(32)27(28)34)16-22(37)36(21-13-11-20(12-14-21)29(38)39)15-17-7-9-19(10-8-17)18-5-3-2-4-6-18/h7-14,18H,2-6,15-16H2,1H3,(H,38,39)

InChI key

VFPYGNNOSJWBHF-UHFFFAOYSA-N

Description

General description

A cell-permeable, salicyclic-to-benzoic acid-substituted BP-1-102 (Cat. no. 573132-M) analog that targets STAT3 and STAT5 with comparable affinity (k_off/k_on = K_D = 300 and 464 nM, respectively) and is 4-fold more potent in competing against phosphopeptide for binding to SH2 domain of STAT3 over STAT1 (K_i = 23.5 and 92.3 µM, respectively; [phosphopeptide] = 10 nM), exhibiting little potency against the kinase activity of upstream kinases (Akt1, Erk1, JAK1/2, c-Src) or the activation of 21 GPCRs, and displaying much reduced or no affinity toward other kinases in a 101-panel screen. Selectively inhibits cellular STAT3 Y705, but not S727, phosphorylation (0.5 to 5 µM) and is a more potent anticancer agent than BP-1-102 against gliobalstoma (GMB) patients-derived brain tumor stem cell (BTSC) cultures (IC₅₀ from 42 to 530 nM). Reported to penetrate blood-brain-barrier in mice (Conc in brain = 313 nM 30 min post 10 mg/kg i.p. dosing) and effectively inhibit BT73 glioma proliferation in xenografted murine brain via apoptosis induction (10 doses: 10 mg/kg i.p., 4 d on/ 3 d off) in vivo.

Biochem/physiol Actions

Cell permeable: yes

Reversible: yes

Secondary Target
STAT5

Packaging

Packaged under inert gas

Other Notes

Haftchenary, S., et al. 2013. ACS Med. Chem. Lett.4, In press.

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