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C0610

Sigma-Aldrich

8-Chloroadenosine-3′,5′-cyclic monophosphorothioate, Rp-isomer

≥99% (HPLC)

Synonym(s):

Rp-8-Cl-cAMPS

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About This Item

Empirical Formula (Hill Notation):
C10H10ClN5O5PSNa
CAS Number:
142754-27-6
Molecular Weight:
401.70
UNSPSC Code:
41106305
PubChem Substance ID:
329774805
NACRES:
NA.77

Quality Level

200

Assay

≥99% (HPLC)

form

solid

packaging

vial of 5 μmol

storage temp.

−20°C

SMILES string

Nc1ncnc2n([C@@H]3O[C@@H]4CO[P@@](S)(=O)O[C@H]4[C@H]3O)c(Cl)nc12

InChI

1S/C10H11ClN5O5PS/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(20-9)1-19-22(18,23)21-6/h2-3,5-6,9,17H,1H2,(H,18,23)(H2,12,13,14)/t3-,5-,6-,9-,22-/m1/s1

InChI key

PJAHPRNGOHUYQD-KVBUDSETSA-N

Biochem/physiol Actions

Competitive inhibitor of cyclic AMP-dependent protein kinase A (PKA) type I. Membrane-permeable analog of the cAMP inhibitor Rp-cAMPS (Prod. No. A-165).

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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H Yokozaki et al.
Cancer research, 52(9), 2504-2508 (1992-05-01)
A set of adenosine 3':5'-monophosphate (cAMP) analogues that combine exocyclic sulfur substitutions in the equatorial (Rp) or the axial (Sp) position of the cyclophosphate ring with modifications in the adenine base of cAMP were tested for their effect on the
Ibtesam Almami et al.
British journal of pharmacology, 171(16), 3946-3960 (2014-05-14)
Tissue transglutaminase (TG2) has been shown to mediate cell survival in many cell types. In this study, we investigated whether the role of TG2 in cytoprotection was mediated by the activation of PKA and PKC in cardiomyocyte-like H9c2 cells. H9c2

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