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344092

SMIFH2

Name: SMIFH2
Brand: MM

The Formin FH2 Domain Inhibitor, SMIFH2, also referenced under CAS 340316-62-3, controls the biological activity of Formin FH2 Domain. This small molecule/inhibitor is primarily used for Membrane applications.

Synonym(s):

Formin FH2 Domain Inhibitor, SMIFH2, Small Molecule Inhibitor of Formin Homology 2 domain, 1-(3-Bromophenyl)-5-(2-furylmethylene)-2-thioxo-hexahydropyrimidine-4,6-dione, Actin Assembly Inhibitor XV

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₉BrN₂O₃S

CAS Number:

340316-62-3

Molecular Weight:

377.21

MDL number:

MFCD02195147

UNSPSC Code:

12352200

NACRES:

NA.28

Assay:

≥98% (sum of two geometrical isomers, HPLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, protect from light

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Properties

Product Name

Formin FH2 Domain Inhibitor, SMIFH2, The Formin FH2 Domain Inhibitor, SMIFH2, also referenced under CAS 340316-62-3, controls the biological activity of Formin FH2 Domain. This small molecule/inhibitor is primarily used for Membrane applications.

Quality Level

100

assay

≥98% (sum of two geometrical isomers, HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

darkdeep green

solubility

DMSO: 50 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

S=C1N(C(=O)\C(=C\c3[o]ccc3)\C(=O)N1)c2cc(ccc2)Br

InChI

1S/C15H9BrN2O3S/c16-9-3-1-4-10(7-9)18-14(20)12(13(19)17-15(18)22)8-11-5-2-6-21-11/h1-8H,(H,17,19,22)/b12-8+

InChI key

MVFJHEQDISFYIS-XYOKQWHBSA-N

Description

General description

A cell-permeable thiooxodihydropyrimidinedione compound that inhibits both formin-mediated, profilin-independent actin nucleation (IC₅₀ ~15 µM using mDia1 or mDia2) and formin-mediated elongation of actin filaments in the presence of profilin (IC₅₀ ~4 µM using Cdc12 or mDia2), but not the Arp2/3-mediated or formin-independent actin assembly. SMIFH2 targets the FH2 (formin homology 2) domain of formins from a large variety of species, including murine mDia1/2, C. elegans CYK-1, S. pombe Cdc12, S. pombe Fus1, and S. cerevisiae Bni1, and decreases formin affinity for the actin filament barbed end. SMIFH2, at 25 µM, is shown to selectively disrupt formin-dependent actin cables and contractile rings, but not Arp2/3-dependent, CK-666- (Cat. No. 182515) sensitive actin patches, in fission yeast. SMIFH2 is also demonstrated to affect F-actin cytoskeleton structures and cell migration (by a 2-fold decrease at 10 µM) in NIH 3T3 fibroblast cultures.

Packaging

Packaged under inert gas

Preparation Note

Use only fresh DMSO. Following reconstiution, aliquot an freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Rizvi, S.A., et al. 2009. Chem. Biol.16, 1158.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c