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 Formula: C₁₇H₁₄Cl₂F₂N₄OS Peso molecolare: 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

Conservare a 2-8°C

Shipped In

Ghiaccio umido

Panoramica

Descrizione generale：Composto pirazolitiazolo-isobutiramide permeabile alle cellule che agisce come potente inibitore delle chinasi LIM (IC50 = 8 nM contro LIMK1 e LIMK2)

Un composto pirazolitiazolo-isobutiramide permeabile alle cellule che agisce come potente inibitore della chinasi LIM (IC50 = 7 e 8 nM contro LIMK1 e LIMK2, rispettivamente) e sopprime efficacemente la fosforilazione della cofilina cellulare (IC50 ~ 1 µM in colture A549 e MDA-MB-231) senza influenzare la polimerizzazione della tubulina o indurre citotossicità (EC50 >10 µM in saggi di proliferazione A549 e formazione di colonie). Ha dimostrato di destabilizzare efficacemente la struttura della F-actina nelle cellule di carcinoma mammario MDA-MB-231 (da 3 a 10 µM) con un blocco concomitante della degradazione della ECM mediata dall'invadopedia (13% e 10% del controllo, rispettivamente, con l'inibitore a 3 e 10 µM) e dell'invasione (45% e 7% del tasso di invasione del controllo, rispettivamente, con l'inibitore a 3 e 10 µM). Sebbene sia stata segnalata un'affinità verso AMPKα1 e AMPKα2 in studi di legame di competizione basati su fagi T7, l'attività inibitoria di LIMKi 3 nei confronti di AMPKα1/2 non è ancora stata dimostrata direttamente.

Specifications

Sinonimi

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

Specifiche e purezza

Moligand™, ≥98% (HPLC)

Meccanismi biochimici e fisiologici

Potente inibitore della chinasi LIM (i valori IC50 sono 7 e 8 nM per LIMK1 e LIMK2 rispettivamente). Inibisce la fosforilazione della cofilina nelle cellule di cancro al seno MDA-MB-231. Riduce l'invasione delle cellule tumorali MDA-MB-231 in un saggio di

Condizioni di conservazione di stoccaggio

Conservare a 2-8°C

Spedito in

Ghiaccio umido

Grado

Moligand™

Tipo di azione

INHIBITOR

Meccanismo d'azione

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

Purezza

≥98%(HPLC)

Nomi e identificatori

• Pubchem Sid: 504771514
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771514
• Sorrisi canonici: 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)
• Isomeri SMILES: CC(C)C(=O)NC1=NC=C(S1)C2=CC(=NN2C3=C(C=CC=C3Cl)Cl)C(F)F
• CAS alternativo: 1338247-35-0
• Termini MeSH: LIMKi3;N-(5-(1-(2,6-dichlorophenyl)-3-(difluoromethyl)-1H-pyrazol-5-yl)-2-thiazolyl)-2-methylpropanamide
• Peso molecolare: 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
    • Classe Azoles
      • Subclass Pyrazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: 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
• Descrizione: 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

Obiettivi associati (umani)

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

Obiettivi associati (non umani)

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

Meccanismi d'azione

Proprietà chimiche e fisiche

• Solubilità: Solvent:DMSO, Max Conc. mg/mL: 43.13, Max Conc. mM: 100
• Peso molecolare: 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