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C3912

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt

≥97.0% (HPLC), cAMP analog, powder

Synonym(s):

pCPT-cAMP

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About This Item

Empirical Formula (Hill Notation):
C16H14ClN5NaO6PS
CAS Number:
93882-12-3
Molecular Weight:
493.79
NACRES:
NA.77
PubChem Substance ID:
24278024
UNSPSC Code:
41106305
EC Number:
299-413-9
MDL number:
MFCD00057683
Assay:
≥97.0% (HPLC)
Form:
powder
Quality level:
200

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Product Name

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt, ≥97.0% (HPLC), powder

InChI key

YIJFVHMIFGLKQL-DNBRLMRSSA-M

InChI

1S/C16H15ClN5O6PS.Na/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-;/m1./s1

SMILES string

[Na+].Nc1ncnc2n([C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)c(Sc5ccc(Cl)cc5)nc12

assay

≥97.0% (HPLC)

form

powder

color

white

solubility

H2O: 25 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)

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1 of 4

This Item
C8988C0735C5438
8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt ≥97.0% (HPLC), powder

Sigma-Aldrich

C3912

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic monophosphate monosodium hydrate ≥98% (HPLC)

Sigma-Aldrich

C8988

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic monophosphate monosodium hydrate

8-(4-Chlorophenylthio)adenosine-3′,5′-cyclic Monophosphorothioate, Rp-isomer sodium salt ≥99% (HPLC), solid

Sigma-Aldrich

C0735

8-(4-Chlorophenylthio)adenosine-3′,5′-cyclic Monophosphorothioate, Rp-isomer sodium salt

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt ≥95% (HPLC), powder

Sigma-Aldrich

C5438

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt

assay

≥97.0% (HPLC)

assay

≥98% (HPLC)

assay

≥99% (HPLC)

assay

≥95% (HPLC)

form

powder

form

powder

form

solid

form

powder

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 25 mg/mL

solubility

H2O: >10 mg/mL

solubility

-

solubility

H2O: 25 mg/mL

color

white

color

white

color

-

color

white

Application

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt has been used:
  • to upregulate cellular cholesterol pump (adenosine triphosphate- (ATP-) binding cassette (ABC) transporter-1, ABCA-1)[1]
  • in glucose production assay[2]
  • to stimulate cystic fibrosis transmembrane conductance regulator (CFTR) channel in airway epithelia[3]

Biochem/physiol Actions

Membrane permeable cAMP analog. Used as a selective activator of cAMP dependent protein kinase (PKA). Inhibits cGMP-dependent phosphodiesterase and, at higher concentrations, inhibits cAMP-dependent phosphodiesterase. Inhibits phosphoinositide hydrolysis and secretion stimulated by n-formyl-Met-Leu-Phe but not platelet-activating factor in leukocytes. Renders HL-60 cells more resistant to NO-induced DNA damage.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000523425
0000523423
0000523425
0000523423
0000493637

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Aurora Maria Fontainhas et al.
Investigative ophthalmology & visual science, 52(1), 579-587 (2010-09-24)
An early injury response to retinal detachment is disruption of synaptic connectivity between photoreceptors and second-order neurons. Most dramatic is the retraction of rod cell axons and their terminals away from the outer synaptic layer and toward their cell bodies.
B J Connolly et al.
Biochemical pharmacology, 44(12), 2303-2306 (1992-12-15)
8-(4-Chlorophenyl)thio-cyclic AMP (8-CPT-cAMP), extensively used as selective activator of cyclic AMP-dependent protein kinase, has been found to be a potent inhibitor of the cyclic GMP-specific phosphodiesterase (PDE VA). Indeed, 8-CPT-cAMP (IC50 = 0.9 microM) inhibited PDE VA with a potency
P Chavis et al.
Neuron, 20(4), 773-781 (1998-05-15)
Adenylyl cyclase (AC) modulation of vesicular cycling was visualized at cultured cerebellar granule cell synapses using the sequential uptake of antibodies directed against the intraluminal domain of synaptotagmin I. Vesicle recycling due to spontaneous transmitter release in the absence of
Madhu Nath et al.
Frontiers in neuroscience, 16, 912757-912757 (2022-06-08)
Phosphatidylinositol 3-kinase (PI3K)/Akt signal pathway mediates pro-survival function in neurons. In the retina, PI3K/AKT/mTOR signaling pathway is related to the early pathogenesis of diabetic retinopathy. Signaling molecules in the membrane-initiated signaling pathway exhibiting neuroprotective function interacts with the PI3K/Akt pathway
Olivia J S Macleod et al.
Nature communications, 11(1), 1326-1326 (2020-03-14)
Persistent pathogens have evolved to avoid elimination by the mammalian immune system including mechanisms to evade complement. Infections with African trypanosomes can persist for years and cause human and animal disease throughout sub-Saharan Africa. It is not known how trypanosomes
View All Related Papers

Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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Product Information Sheet - C3912

Product Information Sheet

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