435930
LIM Kinase Inhibitor I, LIMKi 3
The LIM Kinase Inhibitor I, LIMKi 3 controls the biological activity of LIM Kinase. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.
Synonym(s):
LIM Kinase Inhibitor I, LIMKi 3, N-(5-(1-(2,6-Dichlorophenyl)-3-(difluoromethyl)-1H-pyrazol-5-yl)thiazol-2-yl)isobutyramide
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C17H14Cl2F2N4OS
CAS Number:
Molecular Weight:
431.29
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
Quality Level
assay
≥95% (HPLC)
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
beige
solubility
DMSO: 100 mg/mL
shipped in
ambient
storage temp.
2-8°C
SMILES string
ClC1=CC=CC(Cl)=C1N2N=C(C=C2C3=CN=C(NC(C(C)C)=O)S3)C(F)F
InChI
1S/C17H14Cl2F2N4OS/c1-8(2)16(26)23-17-22-7-13(27-17)12-6-11(15(20)21)24-25(12)14-9(18)4-3-5-10(14)19/h3-8,15H,1-2H3,(H,22,23,26)
InChI key
IVUGBSGLHRJSSP-UHFFFAOYSA-N
General description
A cell-permeable pyrazolylthiazolo-isobutyramide compound that acts as a potent LIM kinase inhibitor (IC50 = 7 and 8 nM against LIMK1 and LIMK2, respectively) and effectively suppresses cellular cofilin phosphorylation (IC50 ~ 1 µM in A549 and MDA-MB-231 cultures) without affecting tubulin polymerization or inducing cytotoxicity (EC50 >10 µM in A549 proliferation & colony formation assays). Shown to effectively destabilize F-actin structure in MDA-MB-231 breast cancer cells (3 to 10 µM) with concomitant blockage of invasion (by 93% at 10 µM).
A cell-permeable pyrazolylthiazolo-isobutyramide compound that acts as a potent LIM kinase inhibitor (IC50 = 7 and 8 nM against LIMK1 and LIMK2, respectively) and effectively suppresses cellular cofilin phosphorylation (IC50 ~ 1 µM in A549 and MDA-MB-231 cultures) without affecting tubulin polymerization or inducing cytotoxicity (EC50 >10 µM in A549 proliferation and colony formation assays). Shown to effectively destabilize F-actin structure in MDA-MB-231 breast cancer cells (3 to 10 µM) with concomitant blockage of invadopedia-mediated ECM degradation (13% and 10% of control, respectively, by 3 and 10 µM inhibitor) and invasion (45% and 7% of control invasion rate, respectively, by 3 and 10 µM inhibitor). Although reported to exhibit affinity toward AMPKα1 and AMPKα2 in T7 phage-based competition binding studies, inhibitory activity of LIMKi 3 against AMPKα1/2 is not yet directly demonstrated.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
LIMK1 and LIMK2
LIMK1 and LIMK2
Reversible: yes
Secondary Target
AMPKA1, AMPKA2, DDR1, PAK3, DCAMKL2
AMPKA1, AMPKA2, DDR1, PAK3, DCAMKL2
Target IC50: 7 and 8 nM against LIMK1 and LIMK2, respectively
Packaging
Packaged under inert gas
Warning
Toxicity: Standard Handling (A)
Reconstitution
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Other Notes
Scott, R.W., et al. 2010. J. Cell. Biol.191, 169.
Ross-Macdonald, P., et al. 2008. Mol. Cancer Ther.7, 3490.
Ross-Macdonald, P., et al. 2008. Mol. Cancer Ther.7, 3490.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class
11 - Combustible Solids
wgk_germany
WGK 2
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’.
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Mariana Morales-Quinones et al.
Hypertension (Dallas, Tex. : 1979), 76(2), 393-403 (2020-07-01)
Increased arterial stiffness and vascular remodeling precede and are consequences of hypertension. They also contribute to the development and progression of life-threatening cardiovascular diseases. Yet, there are currently no agents specifically aimed at preventing or treating arterial stiffening and remodeling.
Thomas J Jurrissen et al.
American journal of physiology. Heart and circulatory physiology, 323(5), H879-H891 (2022-09-10)
Adropin is a peptide largely secreted by the liver and known to regulate energy homeostasis; however, it also exerts cardiovascular effects. Herein, we tested the hypothesis that low circulating levels of adropin in obesity and type 2 diabetes (T2D) contribute
Catarina Domingues et al.
Frontiers in cell and developmental biology, 8, 678-678 (2020-09-10)
The mechanical properties of the extracellular environment are interrogated by cells and integrated through mechanotransduction. Many cellular processes depend on actomyosin-dependent contractility, which is influenced by the microenvironment's stiffness. Here, we explored the influence of substrate stiffness on the proteome
Xing Duan et al.
Journal of cellular physiology, 233(8), 6088-6097 (2018-01-11)
LIM kinases (LIMK1/2) are LIM domain-containing serine/threonine/tyrosine kinases that mediate multiple cellular processes in mitosis. In the present study, we explored the functional roles and potential signaling pathway of LIMK1/2 during mouse oocyte meiosis. Disruption of LIMK1/2 activity and expression
Anjali Bisaria et al.
Science (New York, N.Y.), 368(6496), 1205-1210 (2020-06-13)
Cell migration is driven by local membrane protrusion through directed polymerization of F-actin at the front. However, F-actin next to the plasma membrane also tethers the membrane and thus resists outgoing protrusions. Here, we developed a fluorescent reporter to monitor
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