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C240

Sigma-Aldrich

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt

≥98% (HPLC), solid

Synonym(s):

Rp-8-CPT-cGMPS, Rp-8-[(4-Chlorophenyl)thio]-cGMPS triethylammonium salt, Rp-8-[(4-Chlorophenyl)thio]-guanosine-cyclic 3′,5′-hydrogen phosphorothioate triethylammonium salt

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About This Item

Empirical Formula (Hill Notation):
C16H15ClN5O6PS2 · C6H15N
CAS Number:
276696-61-8
Molecular Weight:
605.07
MDL number:
MFCD04037247
UNSPSC Code:
41106305
PubChem Substance ID:
329775000
NACRES:
NA.77

biological source

synthetic

Assay

≥98% (HPLC)

form

solid

color

white

solubility

H2O: 5 mg/mL

storage temp.

−20°C

SMILES string

CCN(CC)CC.NC1=Nc2c(nc(Sc3ccc(Cl)cc3)n2[C@@H]4O[C@@H]5CO[P@@](O)(=S)O[C@H]5[C@H]4O)C(=O)N1

InChI

1S/C16H15ClN5O6PS2.C6H15N/c17-6-1-3-7(4-2-6)31-16-19-9-12(20-15(18)21-13(9)24)22(16)14-10(23)11-8(27-14)5-26-29(25,30)28-11;1-4-7(5-2)6-3/h1-4,8,10-11,14,23H,5H2,(H,25,30)(H3,18,20,21,24);4-6H2,1-3H3/t8-,10-,11-,14-,29-;/m1./s1

InChI key

KVOYZBYGWGWWTD-TXBWCVORSA-N

Biochem/physiol Actions

Rp-8-CPT-cGMP is a potent inhibitor of protein kinase G Ia, Ib, and type II.

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.

Linkage

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt is more cell permeable than Rp-cGMPS triethylamine.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

C240-5MG:
C240-VAR:
C240-BULK:
C240-1MG:

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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S AbdAlla et al.
European journal of biochemistry, 241(2), 498-506 (1996-10-15)
The hormone-induced depletion of cellular Ca stores provides a signal for the Ca2+ influx into electrically non-excitable cells; however, the underlying molecular mechanisms remain elusive. Therefore, we analyzed bradykinin-activated Ca2+ influx into human foreskin fibroblast cells, HF-15, by fura-2 and
J Pineda et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 16(4), 1389-1399 (1996-02-15)
Nitric oxide (NO) and carbon monoxide (CO) have been identified as two diffusible signaling messengers in the brain, capable of stimulating soluble guanylate cyclase. Locus coeruleus (LC) is rich in the alpha 1 and beta 1 subunits of soluble guanylate
E Butt et al.
European journal of pharmacology, 269(2), 265-268 (1994-10-14)
In the present study, the inhibitory effect of the cGMP analog (Rp)-8-(para-chlorophenylthio)guanosine-3',5'-cyclic monophosphorothioate ((Rp)-8-pCPT-cGMPS) on the cGMP-dependent protein kinase-mediated protein phosphorylation in intact human platelets was investigated. In vitro phosphorylation experiments with the substrate kemptide demonstrated an inhibition of the
Jia-Shuan Wu et al.
Oncotarget, 8(25), 40906-40921 (2017-04-14)
Chemotherapy of brain glioma faces a major obstacle owing to the inability of drug transport across the blood-brain barrier (BBB). Besides, neovasculatures in brain glioma site result in a rapid infiltration, making complete surgical removal virtually impossible. Herein, we reported
C Mathes et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 16(5), 1702-1709 (1996-03-01)
Inward currents activated by 8-bromc-cGMP and by muscarinic agonist were compared in N1E-115 mouse neuroblastoma cells using perforated-patch voltage clamp and Fura-2 imaging. The cGMP analog activates a voltage-independent inward current that is carried at least in part by Ca2+

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