Merck
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C240

Sigma-Aldrich

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

≥98% (HPLC), solid

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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
Empirical Formula (Hill Notation):
C16H15ClN5O6PS2 · C6H15N
CAS Number:
Molecular Weight:
605.07
MDL number:
PubChem Substance ID:
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

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This Item
C0735B2557B6684
form

solid

form

solid

form

solid

form

powder

color

white

color

-

color

-

color

white to beige

solubility

H2O: 5 mg/mL

solubility

-

solubility

water: soluble

solubility

H2O: 15 mg/mL at ≤60 °C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

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

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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
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
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
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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