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C8988

Sigma-Aldrich

8-(4-Chlorophenylthio)-2′-O-methyladenosine 3′,5′-cyclic monophosphate monosodium hydrate

≥98% (HPLC)

Synonym(s):

8-pCPT-2′-O-Me-cAMP

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About This Item

Empirical Formula (Hill Notation):
C17H16N5O6ClPSNa · xH2O
CAS Number:
634207-53-7
Molecular Weight:
507.82 (anhydrous basis)
MDL number:
MFCD11045952
UNSPSC Code:
41106305
PubChem Substance ID:
24893122
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white

mp

235.5-237.5 °C (lit.)

solubility

H2O: >10 mg/mL

storage temp.

−20°C

SMILES string

O.[Na+].CO[C@@H]1[C@@H]2OP([O-])(=O)OC[C@H]2O[C@H]1n3c(Sc4ccc(Cl)cc4)nc5c(N)ncnc35

InChI

1S/C17H17ClN5O6PS.Na.H2O/c1-26-13-12-10(6-27-30(24,25)29-12)28-16(13)23-15-11(14(19)20-7-21-15)22-17(23)31-9-4-2-8(18)3-5-9;;/h2-5,7,10,12-13,16H,6H2,1H3,(H,24,25)(H2,19,20,21);;1H2/q;+1;/p-1/t10-,12-,13-,16-;;/m1../s1

InChI key

NVPSOXGMFVFZIS-IPBMGFFTSA-M

Biochem/physiol Actions

Analog of natural cAMP, potent and specific membrane-permeant activator of exchange factors directly activated by cAMP (Epac or cAMP-GEF), a new receptor for cyclic AMP

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

Light sensitive

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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Andrzej J Chruscinski et al.
PloS one, 8(12), e82164-e82164 (2013-12-18)
β-adrenergic receptors (β-ARs) are model G-protein coupled receptors that mediate signal transduction in the sympathetic nervous system. Despite the widespread clinical use of agents that target β-ARs, the signaling pathways that operate downstream of β-AR stimulation have not yet been
Mengye Li et al.
Clinical and experimental pharmacology & physiology, 44(6), 686-692 (2017-03-21)
Recent papers have attributed arrhythmic substrate in murine RyR2-P2328S hearts to reduced action potential (AP) conduction velocities (CV), reflecting acute functional inhibition and/or reduced expression of sodium channels. We explored for acute effects of direct exchange protein directly activated by
Shuang Tao et al.
Journal of oncology, 2022, 5483523-5483523 (2022-07-12)
Chemoresistance poses a great hindrance in the treatment of breast cancer (BC). Interestingly, exosome (Exo)-mediated transfer of long noncoding RNAs (lncRNAs) has been reported to regulate chemoresistance in diverse diseases. We herein investigate the potential role of lncRNA metastasis-associated lung
Ana-Caroline Raulin et al.
STAR protocols, 4(1), 101976-101976 (2023-01-05)
Cholesterol is a structural component of cell membranes. Most cells are incapable of its catabolism, and intracellular cholesterol accumulation is linked to several disorders including cardiovascular and neurodegenerative diseases. Cholesterol efflux, essential to its metabolism, is dependent on acceptors such
Ángeles Domínguez-Soto et al.
Scientific reports, 7(1), 14761-14761 (2017-11-09)
Peripheral serotonin (5-hydroxytryptamine, 5-HT) regulates cell growth and differentiation in numerous cell types through engagement of seven types of cell surface receptors (HTR1-7). Deregulated 5-HT/HTR levels contribute to pathology in chronic inflammatory diseases, with macrophages being relevant targets for the
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