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C5493

CyPPA

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H23N5
CAS Number:
73029-73-9
Molecular Weight:
285.39
NACRES:
NA.77
PubChem Substance ID:
329775087
UNSPSC Code:
12352200
MDL number:
MFCD01550586

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Product Name

CyPPA, ≥98% (HPLC), solid

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)

SMILES string

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

InChI key

USEMRPYUFJNFQN-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: <2 mg/mL

storage temp.

2-8°C

Quality Level

100

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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

Autophinib &#8805;98% (HPLC)

Sigma-Aldrich

SML2632

Autophinib

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

form

solid

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

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

color

white

color

off-white

color

white to light brown

color

white to beige

Application

CyPPA has been used:
  • to test its inhibitory functionality on melanogenesis[1]
  • as an activator of small conductance potassium channel-3 (SK3) in mesenteric artery segments[2]
  • in the activation of calcium-activated potassium (SK) channels in murine hippocampal neurons HT-22 cells[3]

Biochem/physiol Actions

CyPPA is a positive modulator of small conductance Ca2+-activated K+ channels; selective for SK3 and SK2.
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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000499644
0000499642
0000499642
0000499644
0000481171

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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
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)
Hyaluronidase 1 deficiency preserves endothelial function and glycocalyx integrity in early streptozotocin-induced diabetes
Dogne S, et al.
Diabetes, 65(9), 2742-2753 (2016)
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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