Merck

A9501

Sigma-Aldrich

腺苷-3′,5′-环单磷酸

≥98.5% (HPLC), powder

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别名:
cAMP, 环化腺苷酸, 腺苷环磷酸酯
Empirical Formula (Hill Notation):
C10H12N5O6P
CAS号:
分子量:
329.21
Beilstein:
52645
EC 号:
MDL编号:
eCl@ss:
32160414
PubChem化学物质编号:
NACRES:
NA.77

质量水平

检测方案

≥98.5% (HPLC)

形式

powder

颜色

white

mp

260 °C (dec.) (lit.)

溶解性

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

储存温度

−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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此商品
A6885G6129C9630
form

powder

form

powder

form

powder

form

powder

color

white

color

white

color

white

color

-

solubility

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

solubility

H2O: 10 mg/mL

solubility

H2O: 50 mg/mL

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

mp

260 °C (dec.) (lit.)

mp

-

mp

-

mp

-

应用

腺苷3′,5′-环一磷酸已用于:
  • 在胚胎脊髓神经细胞培养中作为细胞培养基补充剂
  • 作为灌注研究中林格溶液的一个组成部分
  • 在人肺癌细胞系中诱导神经内分泌分化

生化/生理作用

环化腺苷酸依赖性蛋白激酶 (PKA) 的自然活化剂。cAMP 是一种重要的第二信使,并且在很多系统中与神经递质或激素诱导的受体激活相关。已有显示,cAMP/PKA 信号通路可抑制细胞增殖,诱导分化并导致细胞凋亡。

特点和优势

该化合物是用于ADME Tox和环核苷酸研究的特色产品。发现更多精选用于 ADME Tox环核苷酸 研究的产品。了解更多有关用于其他研究领域的生物活性小分子的信息,请访问 sigma.com/discover-bsm

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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Generation of human brain region-specific organoids using a miniaturized spinning bioreactor
Qian X, et al.
Nature Protocols, 13(3), 565-565 (2018)
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)
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
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)
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

商品

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.

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