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C5493

Sigma-Aldrich

CyPPA

≥98% (HPLC), solid

Synonyme(s) :

Cyclohexyl-[2-(3,5-dimethyl-pyrazol-1-yl)-6-methyl-pyrimidin-4-yl]-amine

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About This Item

Formule empirique (notation de Hill):
C16H23N5
Numéro CAS:
73029-73-9
Poids moléculaire :
285.39
Numéro MDL:
MFCD01550586
Code UNSPSC :
12352200
ID de substance PubChem :
329775087
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Couleur

white

Solubilité

DMSO: >10 mg/mL
H2O: <2 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

Cc1cc(NC2CCCCC2)nc(n1)-n3nc(C)cc3C

InChI

1S/C16H23N5/c1-11-10-15(18-14-7-5-4-6-8-14)19-16(17-11)21-13(3)9-12(2)20-21/h9-10,14H,4-8H2,1-3H3,(H,17,18,19)

Clé InChI

USEMRPYUFJNFQN-UHFFFAOYSA-N

Application

CyPPA has been used:
  • to test its inhibitory functionality on melanogenesis
  • as an activator of small conductance potassium channel-3 (SK3) in mesenteric artery segments
  • in the activation of calcium-activated potassium (SK) channels in murine hippocampal neurons HT-22 cells

Actions biochimiques/physiologiques

CyPPA is a positive modulator of small conductance Ca2+-activated K+ channels; selective for SK3 and SK2. CyPPA is a first subtype selective SK channel positive modulator with an EC50 of 5.6 μM and 14 μM, efficacy 90% and 71% for hSK3 and hSK2, respectively. CyPPA is a tool for distinguishing SK2 and SK3 from SK1 and IK; no other agents distinguish these channels.

Caractéristiques et avantages

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335,H413

Classification des risques

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

SK channel activation modulates mitochondrial respiration and attenuates neuronal HT-22 cell damage induced by H2O2
Richter M, et al.
Neurochemistry International, 81, 63-75 (2015)
Sara Traserra et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 32(4), e13778-e13778 (2019-12-18)
Neuromuscular transmission has been extensively studied in the circular layer of the mouse colon where a co-transmission of purines acting on P2Y1 receptors and NO has been previously described. However, the corresponding mechanisms in the longitudinal layer are less known.
The ion channel activator CyPPA inhibits melanogenesis via the GSK3betabeta-catenin pathway
Noh TK, et al.
Chemico-Biological Interactions, 300, 1-7 (2019)
Hyaluronidase 1 deficiency preserves endothelial function and glycocalyx integrity in early streptozotocin-induced diabetes
Dogne S, et al.
Diabetes, 65(9), 2742-2753 (2016)
Amita Shrestha et al.
Developmental neuroscience, 42(1), 59-71 (2020-06-25)
N-methyl-D-aspartate receptor (NMDAR) modulates the structural plasticity of dendritic spines by impacting cytoskeletal organization and kinase signaling. In the developing nervous system, activation of NMDAR is pertinent for neuronal migration, neurite differentiation, and cellular organization. Given that small conductance potassium
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