A166

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

Name: Sp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₁N₅O₅PS · C₆H₁₆N · xH₂O

CAS Number:

93602-66-5

Molecular Weight:

446.46 (anhydrous basis)

MDL number:

MFCD01459901

NACRES:

NA.77

PubChem Substance ID:

24890576

UNSPSC Code:

41106305

Key Documents

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Product Name

Sp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate, ≥98% (HPLC), solid

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

SMILES string

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

InChI key

OXIPZMKSNMRTIV-BIQAKYJPSA-N

assay

≥98% (HPLC)

form

solid

optical activity

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

color

white

solubility

H₂O: soluble

storage temp.

−20°C

Quality Level

100

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Show Differences

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This Item	A165	C240	A6885
Sigma-Aldrich A166 Sp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate	Sigma-Aldrich A165 Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt	Sigma-Aldrich C240 8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt	Sigma-Aldrich A6885 Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98.0% (HPLC)
form solid	form powder	form solid	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 200
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
solubility H₂O: soluble	solubility H₂O: 10 mg/mL	solubility H₂O: 5 mg/mL	solubility H₂O: 10 mg/mL
color white	color white to beige	color white	color white

Biochem/physiol Actions

A potent, membrane-permeable activator of cAMP-dependent protein kinase I and II.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Comparison of the effects of forskolin and dibutyryl cyclic AMP in neuroblastoma cells: evidence that some of the actions of dibutyryl cyclic AMP are mediated by butyrate.

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

Investigations on stimulation of lac transcription in vivo in Escherichia coli by cAMP analogues. Biological activities and structure-activity correlations.

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

The Atypical MAP Kinase ErkB Transmits Distinct Chemotactic Signals through a Core Signaling Module.

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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