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P5865

Rp-8-PIP-cAMPS

Name: Rp-8-PIP-cAMPS
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

8-Piperidinoadenosine-3′,5′-cyclic monophosphorothioate, Rp-isomer sodium salt

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₂₀N₆O₅PSNa

Molecular Weight:

450.39

UNSPSC Code:

41106305

PubChem Substance ID:

329820237

MDL number:

MFCD04037244

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Properties

assay

≥98% (HPLC)

form

solid

mol wt

apparent mol wt 457.40

storage temp.

−20°C

SMILES string

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

InChI

1S/C15H21N6O5PS.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(25-14)6-24-27(23,28)26-11;/h7-8,10-11,14,22H,1-6H2,(H,23,28)(H2,16,17,18);/q;+1/p-1/t8-,10-,11-,14-,27-;/m1./s1

InChI key

ILHHHOJPVCBSBI-RYTXRTGRSA-M

Description

Biochem/physiol Actions

Site-selective, lipophilic analogue of the phosphodiesterase-stable protein kinase A inhibitor Rp-cAMPS (Prod. No. A-165).

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

096K1415

116K1158

091K1156

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(Rp)- and (Sp)-8-piperidino-adenosine 3',5'-(cyclic)thiophosphates discriminate completely between site A and B of the regulatory subunits of cAMP-dependent protein kinase type I and II.

D Ogreid et al.

European journal of biochemistry, 221(3), 1089-1094 (1994-05-01)

8-Piperidino-cAMP has been shown to bind with high affinity to site A of the regulatory subunit of cAMP-dependent protein kinase type I (AI) whereas it is partially excluded from the homologous site (AII) of isozyme II [Ogreid, D., Ekanger, R.

N6-substituted cAMP analogs inhibit bTREK-1 K+ channels and stimulate cortisol secretion by a protein kinase A-independent mechanism.

Haiyan Liu et al.

Molecular pharmacology, 76(6), 1290-1301 (2009-09-08)

Bovine adrenal zona fasciculata (AZF) cells express bTREK-1 K+ channels whose inhibition by cAMP is coupled to membrane depolarization and cortisol secretion through complex signaling mechanisms. cAMP analogs with substitutions in the 6 position of the adenine ring selectively activate

Internalized TSH receptors en route to the TGN induce local G

Amod Godbole et al.

Nature communications, 8(1), 443-443 (2017-09-07)

A new paradigm of G-protein-coupled receptor (GPCR) signaling at intracellular sites has recently emerged, but the underlying mechanisms and functional consequences are insufficiently understood. Here, we show that upon internalization in thyroid cells, endogenous TSH receptors traffic retrogradely to the