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C5493

Sigma-Aldrich

CyPPA

≥98% (HPLC), solid

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Synonym(s):
Cyclohexyl-[2-(3,5-dimethyl-pyrazol-1-yl)-6-methyl-pyrimidin-4-yl]-amine
Empirical Formula (Hill Notation):
C16H23N5
CAS Number:
Molecular Weight:
285.39
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: <2 mg/mL

storage temp.

2-8°C

SMILES string

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)

InChI key

USEMRPYUFJNFQN-UHFFFAOYSA-N

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This Item
P0036SML0217PZ0355
CyPPA &#8805;98% (HPLC), solid

Sigma-Aldrich

C5493

CyPPA

PP121 &#8805;98% (HPLC)

Sigma-Aldrich

P0036

PP121

GSK2334470 &#8805;98% (HPLC)

Sigma-Aldrich

SML0217

GSK2334470

PF-05085727 &#8805;98% (HPLC)

Sigma-Aldrich

PZ0355

PF-05085727

form

solid

form

powder

form

powder

form

powder

color

white

color

off-white

color

white to light brown

color

white to beige

solubility

DMSO: >10 mg/mL, H2O: <2 mg/mL

solubility

DMSO: >10 mg/mL

solubility

DMSO: ≥10 mg/mL

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

room temp

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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

Biochem/physiol Actions

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.

Features and Benefits

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

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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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)
The ion channel activator CyPPA inhibits melanogenesis via the GSK3betabeta-catenin pathway
Noh TK, et al.
Chemico-Biological Interactions, 300, 1-7 (2019)
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
N-N Song et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society (2018-03-10)
A major complication related to gastrointestinal (GI) symptoms in diabetic patients is chronic constipation. Constipation has serious negative impacts on quality of life; however, without a comprehensive understanding of the disease, currently available treatments cannot provide a cure. Platelet-derived growth
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.

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