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A166

Sigma-Aldrich

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

≥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
UNSPSC Code:
41106305
PubChem Substance ID:
24890576
NACRES:
NA.77

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

SMILES string

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

Biochem/physiol Actions

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

A166-1MG:
A166-BULK:
A166-5MG:
A166-10MG:
A166-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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