P0872

Sigma-Aldrich

8-PIP-cAMP

≥98% (HPLC), solid

Synonym(s):
8-Piperidinoadenosine 3′,5′-monophosphate sodium salt
Empirical Formula (Hill Notation):
C15H20N6O6PNa
CAS Number:
Molecular Weight:
434.32
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

Packaging

1 vial in glass bottle

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

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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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