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P0872

Sigma-Aldrich

8-PIP-cAMP

≥98% (HPLC), solid

Synonym(s):

8-Piperidinoadenosine 3′,5′-monophosphate sodium salt

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About This Item

Empirical Formula (Hill Notation):
C15H20N6O6PNa
CAS Number:
31357-06-9
Molecular Weight:
434.32
MDL number:
MFCD06798348
UNSPSC Code:
12352200
PubChem Substance ID:
24724572
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

packaging

pkg of 10 μmol

color

white

solubility

H2O: freely soluble

shipped in

dry ice

storage temp.

−70°C

SMILES string

[Na+].Nc1ncnc2n([C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)c(nc12)N5CCCCC5

InChI

1S/C15H21N6O6P.Na/c16-12-9-13(18-7-17-12)21(15(19-9)20-4-2-1-3-5-20)14-10(22)11-8(26-14)6-25-28(23,24)27-11;/h7-8,10-11,14,22H,1-6H2,(H,23,24)(H2,16,17,18);/q;+1/p-1/t8-,10-,11-,14-;/m1./s1

InChI key

FNCWZMQKRRKCEF-ZBMQJGODSA-M

Biochem/physiol Actions

Selective cAMP-dependent protein kinase (PKA) activator. Site selective cyclic AMP analog with high selectivity for site A of protein kinase A type I and for site B of type II. Acts synergistically together with analogs having opposite site-selectivity.

Features and Benefits

This compound is featured on the PKA & PKG page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

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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Simona Lucchi et al.
PloS one, 6(6), e20785-e20785 (2011-06-23)
Cyclic AMP (cAMP) inhibits the proliferation of several tumor cells. We previously reported an antiproliferative effect of PKA I-selective cAMP analogs (8-PIP-cAMP and 8-HA-cAMP) on two human cancer cell lines of different origin. 8-Cl-cAMP, another cAMP analog with known antiproliferative
Elisa Stellaria Grassi et al.
Endocrine, 56(2), 388-398 (2016-07-28)
The main purpose of our work was to evaluate the effects of different cyclic adenosine monophosphate analogs on thyroid cancer-derived cell lines. In particular we studied 8-chloroadenosine-3',5'-cyclic monophosphate, the most powerful cyclic adenosine monophosphate analog, and the protein kinase A
G Gausdal et al.
Cell death & disease, 4, e516-e516 (2013-03-02)
We show that cyclic AMP (cAMP) elevating agents protect blasts from patients with acute promyelocytic leukemia (APL) against death induced by first-line anti-leukemic anthracyclines like daunorubicin (DNR). The cAMP effect was reproduced in NB4 APL cells, and shown to depend

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