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K1385

Sigma-Aldrich

KN-93

≥98% (HPLC)

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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
PubChem Substance ID:
329817125

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

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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  5. Is Product No. K1385, KN-93, a salt?

    Yes.  It is the phosphate salt.  

  6. What is Product No. K1385, KN-93, soluble in?

    Product K1385 is a water soluble form of KN-93, soluble in water at least at 5 mg/ml. It is also soluble in dimethyl sulfoxide (DMSO) to at least 1 mg/ml.  Solutions and solid should be protected from light.

  7. How to store solutions of Product No. K1385, KN-93?

    Sigma has not performed solution stability studies. However, stock solutions may be stable for 1-3 months, if aliquotted and stored frozen at -20°C.

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