Skip to Content
Merck

344092

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.

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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.

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

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

Quality Level

100

Related Categories

Disclaimer

Toxicity: Standard Handling (A)

Other Notes

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

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.

Legal Information

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Shintaro Miyazaki et al.
iScience, 26(5), 106594-106594 (2023-05-30)
It has been reported that the MDCK cell tight junction shows stochastic fluctuation and forms the interdigitation structure, but the mechanism of the pattern formation remains to be elucidated. In the present study, we first quantified the shape of the
Tushna Kapoor et al.
Cell reports, 34(13), 108918-108918 (2021-04-01)
Membrane curvature recruits Bin-Amphiphysin-Rvs (BAR)-domain proteins and induces local F-actin assembly, which further modifies the membrane curvature and dynamics. The downstream molecular pathway in vivo is still unclear. Here, we show that a tubular endomembrane scaffold supported by contractile actomyosin stabilizes
Jia C Wang et al.
eLife, 11 (2022-04-12)
B-cell activation and immune synapse (IS) formation with membrane-bound antigens are actin-dependent processes that scale positively with the strength of antigen-induced signals. Importantly, ligating the B-cell integrin, LFA-1, with ICAM-1 promotes IS formation when antigen is limiting. Whether the actin
Daniel Blumenthal et al.
eLife, 9 (2020-07-29)
T cell activation by dendritic cells (DCs) involves forces exerted by the T cell actin cytoskeleton, which are opposed by the cortical cytoskeleton of the interacting antigen-presenting cell. During an immune response, DCs undergo a maturation process that optimizes their
Syncytin-mediated open-ended membrane tubular connections facilitate the intercellular transfer of cargos including Cas9 protein.
Zhang, et al.
eLife, 12 (2023)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service