Merck
Todas las fotos(2)

A9501

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate

≥98.5% (HPLC), powder

Todas las fotos(2)
Sinónimos:
3′,5′-Cyclic AMP, cAMP, Adenosine 3′,5′-cyclophosphate
Empirical Formula (Hill Notation):
C10H12N5O6P
Número de CAS:
60-92-4
Peso molecular:
329.21
Beilstein:
52645
Número de EC:
200-492-9
Número MDL:
MFCD00005845
eCl@ss:
32160414
ID de la sustancia en PubChem:
24278245
NACRES:
NA.77

Nivel de calidad

200

ensayo

≥98.5% (HPLC)

formulario

powder

color

white

mp

260 °C (dec.) (lit.)

solubilidad

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

temp. de almacenamiento

−20°C

SMILES string

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

InChI key

IVOMOUWHDPKRLL-KQYNXXCUSA-N

Gene Information

human ... OPRK1(4986)

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Aplicación

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

Envase

1, 5, 25 g in poly bottle

Acciones bioquímicas o 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 y beneficios

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 clase de almacenamiento

13 - Non Combustible Solids

WGK

WGK 3

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificado de Análisis

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Certificado de origen

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Quotes and Ordering

Bulk Quote-Order Product
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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Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

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