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A9501

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate

≥98.5% (HPLC), powder, PKA activator

Sinônimo(s):

3′,5′-Cyclic AMP, Adenosine 3′,5′-cyclophosphate, cAMP

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About This Item

Fórmula empírica (Notação de Hill):
C10H12N5O6P
Número CAS:
60-92-4
Peso molecular:
329.21
Beilstein:
52645
Número CE:
200-492-9
Número MDL:
MFCD00005845
Código UNSPSC:
41106305
eCl@ss:
32160414
ID de substância PubChem:
24278245
NACRES:
NA.77

product name

Adenosine 3′,5′-cyclic monophosphate, ≥98.5% (HPLC), powder

Nível de qualidade

200

Ensaio

≥98.5% (HPLC)

forma

powder

cor

white

pf

260 °C (dec.) (lit.)

solubilidade

H2O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

chave InChI

IVOMOUWHDPKRLL-KQYNXXCUSA-N

Informações sobre genes

human ... OPRK1(4986)

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Aplicação

Adenosine 3′,5′-cyclic monophosphate has been used:
  • as cell culture medium supplement in embryonic spinal neurons
  • as a component of ringer solution for perfusion studies
  • to induce neuroendocrine differentiation in human lung cancer cell lines

Ações bioquímicas/fisiológicas

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Características e benefícios

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Neuroendocrine differentiation contributes to radioresistance development and metastatic potential increase in non-small cell lung cancer
Zhu R, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1865(12), 1878-1890 (2018)
Generation of human brain region-specific organoids using a miniaturized spinning bioreactor
Qian X, et al.
Nature Protocols, 13(3), 565-565 (2018)
Tissue engineering the monosynaptic circuit of the stretch reflex arc with co-culture of embryonic motoneurons and proprioceptive sensory neurons
Guo X, et al.
Biomaterials, 33(23), 5723-5731 (2012)
Linghai Yang et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 34(14), 4896-4904 (2014-04-04)
Striatal medium spiny neurons (MSNs) mediate many of the physiological effects of dopamine, including the regulation of feeding and motor behaviors. Dopaminergic inputs from the midbrain modulate MSN excitability through pathways that involve cAMP and protein kinase A (PKA), but
Hengxiang Cui et al.
The Journal of biological chemistry, 289(50), 34871-34885 (2014-09-14)
Angiogenesis, the formation of new blood vessels from pre-existing ones, is essential for development, wound healing, and tumor progression. The VEGF pathway plays irreplaceable roles during angiogenesis, but how other signals cross-talk with and modulate VEGF cascades is not clearly
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