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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
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
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
Yi-Fei Chen et al.
Respiratory research, 20(1), 285-285 (2019-12-20)
β2 receptor agonists induce airway smooth muscle relaxation by increasing intracellular cAMP production. PKA is the traditional downstream signaling pathway of cAMP. Exchange protein directly activated by cAMP (Epac) was identified as another important signaling molecule of cAMP recently. The
Hechang Huang et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 25(4), 819-829 (2009-10-14)
Murine MC3T3-E1 and MC-4 cells were stably transfected with -371/+70 bp of the murine cyclooxygenase-2 (COX-2) promoter fused to a luciferase reporter (Pluc371) or with Pluc371 carrying site-directed mutations. Mutations were made in (1) the cAMP response element (CRE) at
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Articles

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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