LIMKi 3 - Moligand™, ≥98%(HPLC) , Inhibitor of LIM domain kinase 1;Inhibitor of LIM domain kinase 2, CAS No.1338247-35-0, Inhibitor of LIM domain kinase 1;Inhibitor of LIM domain kinase 2

CAS: 1338247-35-0 Cat. No.: L288407 分子式: C₁₇H₁₄Cl₂F₂N₄OS 分子量: 431.29

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

J-523083 | LIMKI-3 (BMS-5) | GTPL9839 | HMS3743I19 | BMS 5 | LIM Kinase Inhibitor I | N-[5-[2-(2,6-dichlorophenyl)-5-(difluoromethyl)pyrazol-3-yl]-1,3-thiazol-2-yl]-2-methylpropanamide | BDBM50591090 | FT-0700442 | DTXSID201113664 | LIMKi 3 | BCP17223 | N

Storage

Store at 2-8°C

Shipped In

Wet ice

概要

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 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.

Specifications

同義語

J-523083 | LIMKI-3 (BMS-5) | GTPL9839 | HMS3743I19 | BMS 5 | LIM Kinase Inhibitor I | N-[5-[2-(2,6-dichlorophenyl)-5-(difluoromethyl)pyrazol-3-yl]-1,3-thiazol-2-yl]-2-methylpropanamide | BDBM50591090 | FT-0700442 | DTXSID201113664 | LIMKi 3 | BCP17223 | N

仕様と純度

Moligand™, ≥98%(HPLC)

生化学的・生理学的メカニズム

Potent LIM kinase inhibitor (IC50values are 7 and 8 nM for LIMK1 and LIMK2 respectively). Inhibits cofilin phosphorylation in MDA-MB-231 breast cancer cells. Reduces MDA-MB-231 tumor cell invasion in a 3D matrigel invasion assay.

保管条件

Store at 2-8°C

入荷

Wet ice

この製品は冷冷この冷このこの製品の運送が必要です。地上およびその他の経済サービスは利用できません。

等級

Moligand™

アクションタイプ

INHIBITOR

作用メカニズム

Inhibitor of LIM domain kinase 1;Inhibitor of LIM domain kinase 2

純度

≥98%(HPLC)

名前と識別子

• パブケム・シド: 504771514
• パブケム・シド・ウル: https://pubchem.ncbi.nlm.nih.gov/substance/504771514
• カノニカル・スマイル: CC(C)C(=O)NC1=NC=C(S1)C2=CC(=NN2C3=C(C=CC=C3Cl)Cl)C(F)F
• IUPAC Name: N-[5-[2-(2,6-dichlorophenyl)-5-(difluoromethyl)pyrazol-3-yl]-1,3-thiazol-2-yl]-2-methylpropanamide
• InChIKey: IVUGBSGLHRJSSP-UHFFFAOYSA-N
• 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)
• 異性体SMILES: CC(C)C(=O)NC1=NC=C(S1)C2=CC(=NN2C3=C(C=CC=C3Cl)Cl)C(F)F
• 代替CAS番号: 1338247-35-0
• MeSH用語: LIMKi3;N-(5-(1-(2,6-dichlorophenyl)-3-(difluoromethyl)-1H-pyrazol-5-yl)-2-thiazolyl)-2-methylpropanamide
• 分子量: 431.29
• Reaxy-Rn: 24178549
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24178549&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 分類 Azoles
      • Subclass Pyrazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 分類: Azoles
• Subclass: Pyrazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyrazoles
• Alternative Parents: N-arylamides Dichlorobenzenes 2,5-disubstituted thiazoles Aryl chlorides Heteroaromatic compounds Secondary carboxylic acid amides Azacyclic compounds Organofluorides Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl fluorides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenylpyrazole - N-arylamide - 1,3-dichlorobenzene - 2,5-disubstituted 1,3-thiazole - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Thiazole - Secondary carboxylic acid amide - Carboxamide group - Azacycle - Carboxylic acid derivative - Organic nitrogen compound - Organohalogen compound - Organochloride - Organofluoride - Organonitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alkyl halide - Alkyl fluoride - Aromatic heteromonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

関連ターゲット（人間）

LIMK1 Tchem LIM domain kinase 1 (2 Activities)

Discover Target: LIMK1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

LIMK2 Tchem LIM domain kinase 2 (1 Activities)

Discover Target: LIMK2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

YES1 Tclin Tyrosine-protein kinase YES (2781 Activities)

Discover Target: YES1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LIMK1 Tchem LIM domain kinase 1 (2329 Activities)

Discover Target: LIMK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GBM (188 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HeLa (62764 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LIMK2 Tchem LIM domain kinase 2 (949 Activities)

Discover Target: LIMK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver (3974 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LIMK2 Tchem LIM domain kinase 1/2 (20 Activities)

Discover Target: LIMK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

関連ターゲット（非人間）

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver microsome (341 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

作用メカニズム

化学的性質と物理的性質

• 溶解度: Solvent:DMSO, Max Conc. mg/mL: 43.13, Max Conc. mM: 100
• 分子量: 431.300 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 430.023 Da
• Monoisotopic Mass: 430.023 Da
• Topological Polar Surface Area: 88.100 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 523.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1