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A166

Sigma-Aldrich

Sp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate

≥98% (HPLC), solid

别名:

Sp-Cyclic 3′,5′-hydrogen phosphorothioate adenosine hydrate, Sp-cAMPS triethylammonium salt

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About This Item

经验公式（希尔记法）:
C10H11N5O5PS · C6H16N · xH2O
CAS号:
93602-66-5
分子量:
446.46 (anhydrous basis)
MDL编号:
MFCD01459901
UNSPSC代码:
41106305
PubChem化学物质编号:
24890576
NACRES:
NA.77

质量水平

100

方案

≥98% (HPLC)

表单

solid

旋光性

[α]22/D −25.43°, c = 0.99 in H2O(lit.)

颜色

white

溶解性

H2O: soluble

储存温度

−20°C

SMILES字符串

CCN(CC)CC.Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4CO[P@@](S)(=O)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6H2,1-3H3/t4-,6-,7-,10-,21+;/m1./s1

InChI key

OXIPZMKSNMRTIV-BIQAKYJPSA-N

生化/生理作用

Sp-Diastereomer of adenosine 3′,5′-cyclic monophosphorothioate is a potent, membrane-permeable activator of cAMP dependent protein kinase I and II that mimics the effects of cAMP as a second messenger in numerous systems while being resistant to cyclic nucleotide phosphodiesterases; exhibits greater specificity and affinity than forskolin and cAMP analogs such as dibutyryl-cAMP.

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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分析证书(COA)

Lot/Batch Number
0000057410
104M4752V
0000057410
0000227622
0000227622

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H G Scholübbers et al.
European journal of biochemistry, 138(1), 101-109 (1984-01-02)
The ability of 24 systematically modified analogues of adenosine 3',5'-monophosphate (cAMP) to enhance the synthesis of beta-galactosidase in glucose-repressed Escherichia coli strains KNBL 1001 and cpd- Crookes has been investigated. The properties of the analogues in comparison with cAMP are
B Yusta et al.
Journal of neurochemistry, 51(6), 1808-1818 (1988-12-01)
We have compared the effects of forskolin, N6,2'-O-dibutyryladenosine 3':5'-cyclic monophosphate (dibutyryl cyclic AMP, Bt2-cAMP), and butyrate on several aspects of neuroblastoma cell physiology. The morphology of Neuro 2A cells was similar after incubation with forskolin and Bt2-cAMP, which caused extensive
John M E Nichols et al.
Developmental cell, 48(4), 491-505 (2019-01-08)
Signaling from chemoattractant receptors activates the cytoskeleton of crawling cells for chemotaxis. We show using phosphoproteomics that different chemoattractants cause phosphorylation of the same core set of around 80 proteins in Dictyostelium cells. Strikingly, the majority of these are phosphorylated

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