K1385

KN-93

≥98% (HPLC)

• Synonym(s): N-[2-[N-(4-Chlorocinnamyl)-N-methylaminomethyl]phenyl]-N-(2-hydroxyethyl)-4-methoxybenzenesulfonamide phosphate salt, N-[2-[[[3-(4′-Chlorophenyl)-2-propenyl]methylamino]methyl]phenyl]-N-(2-hydroxyethyl)-4′-methoxybenzenesulfonamide phosphate salt
• Empirical Formula (Hill Notation): C₂₆H₂₉ClN₂O₄S · H₃PO₄
• CAS Number: 139298-40-1
• Molecular Weight: 599.03
• MDL number: MFCD03788201
• UNSPSC Code: 51111800
• PubChem Substance ID: 329817125
• NACRES: NA.77

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• assay: ≥98% (HPLC)
• form: powder
• color: white
• solubility: DMSO: 1 mg/mL; H₂O: soluble
• storage temp.: 2-8°C
• SMILES string: OP(O)(O)=O.COc1ccc(cc1)S(=O)(=O)N(CCO)c2ccccc2CN(C)C\C=C\c3ccc(Cl)cc3
• InChI: 1S/C26H29ClN2O4S.H3O4P/c1-28(17-5-6-21-9-11-23(27)12-10-21)20-22-7-3-4-8-26(22)29(18-19-30)34(31,32)25-15-13-24(33-2)14-16-25;1-5(2,3)4/h3-16,30H,17-20H2,1-2H3;(H3,1,2,3,4)/b6-5+;
• InChI key: NNKJTPOXLIILMB-IPZCTEOASA-N

Description

Application

KN-93 has been used:

• as an inhibitor to block αCaMKII (Ca²⁺/calmodulin-dependent protein kinase IIα)
• as CaMKII inhibitor to pre-treat hippocampal slices
• to treat the cells, to alter the cytoskeleton (CSK) structure and function during the experiment

Biochem/physiol Actions

KN-93 is a selective Ca²⁺/calmodulin-dependent protein kinase II inhibitor, which has been implicated in the regulation of smooth muscle contractility. CaM kinase II activation was inhibited by KN-93 pretreatment (IC₅₀ ~1 μM). KN-93 inhibited histamine-induced tonic force maintenance, whereas early force development and MLC20 phosphorylation responses during the entire time course were unaffected. Both force development and maintenance in response to KCl were inhibited by KN-93. Rapid increases in KCl-induced MLC20 phosphorylation were also inhibited by KN-93, whereas steady-state MLC20 phosphorylation responses were unaffected. In contrast, phorbol 12,13-dibutyrate (PDBu) did not activate CaM kinase II and PDBu-stimulated force development was unaffected by KN-93. Thus KN-93 appears to target a step(s) essential for force maintenance in response to physiological stimuli, suggesting a role for CaM kinase II in regulating tonic contractile responses in arterial smooth muscle. Pharmacological activation of protein kinase C bypasses the KN-93 sensitive step.

Features and Benefits

This compound is featured on the Ca/CaMKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Photosensitive

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)