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Merck

K1385

KN-93

synthetic (organic), ≥98% (HPLC),  Ca2+/calmodulin-dependent protein kinase II inhibitor, powder

Sinónimos:

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

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C26H29ClN2O4S · H3PO4
Número CAS:
139298-40-1
Peso molecular:
599.03
UNSPSC Code:
51111800
PubChem Substance ID:
329817125
NACRES:
NA.77
MDL number:
MFCD03788201

Documentos clave

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Nombre del producto

KN-93, ≥98% (HPLC)

SMILES string

OP(O)(O)=O.COc1ccc(cc1)S(=O)(=O)N(CCO)c2ccccc2CN(C)C\C=C\c3ccc(Cl)cc3

InChI key

NNKJTPOXLIILMB-IPZCTEOASA-N

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+;

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 1 mg/mL
H2O: soluble

storage temp.

2-8°C

Quality Level

200

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Categorías relacionadas

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.
KN-93 is a selective Ca2+/calmodulin-dependent protein kinase II inhibitor.

Disclaimer

Photosensitive

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000497870
0000497869
0000497870
0000497869
0000427943

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  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.

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Kristen H Jardine et al.
Scientific reports, 10(1), 9209-9209 (2020-06-10)
Reactivated long-term memories can become labile and sensitive to modification. Memories in this destabilized state can be weakened or strengthened, but there is limited research characterizing the mechanisms underlying retrieval-induced qualitative updates (i.e., information integration). We have previously implicated cholinergic
Wingless-type mammary tumor virus integration site family, member 5A (Wnt5a) regulates human immunodeficiency virus type 1 (HIV-1) envelope glycoprotein 120 (gp120)-induced expression of pro-inflammatory cytokines via the Ca2+/calmodulin-dependent protein kinase II (CaMKII) and c-Jun N-terminal kinase (JNK) signaling pathways
Li B, et al.
Test, 288(19), 13610-13619 (2013)
Differential Responses of Cultured MC3T3-E1 Cells to Dynamic and Static Stimulated Effect of Microgravity in Cell Morphology, Cytoskeleton Structure and Ca2+ Signaling
Luo M, et al.
mBio, 13(2), 137-157 (2016)
Thomas Hennig et al.
PLoS pathogens, 14(3), e1006954-e1006954 (2018-03-27)
Lytic herpes simplex virus 1 (HSV-1) infection triggers disruption of transcription termination (DoTT) of most cellular genes, resulting in extensive intergenic transcription. Similarly, cellular stress responses lead to gene-specific transcription downstream of genes (DoG). In this study, we performed a
Potentiation of Schaffer-Collateral CA1 Synaptic Transmission by eEF2K and p38 MAPK Mediated Mechanisms
Weng W, et al.
Frontiers in Cellular Neuroscience, 247-247 (2016)
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