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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號碼:
MFCD01459901
分類程式碼代碼:
41106305
PubChem物質ID:
24890576
NACRES:
NA.77

品質等級

100

化驗

≥98% (HPLC)

形狀

solid

光學活性

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

顏色

white

溶解度

H2O: soluble

儲存溫度

−20°C

SMILES 字串

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 密鑰

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)

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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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