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B6684

Rp-8-Bromo-β-phenyl-1,N2-ethenoguanosine 3′,5′-cyclic monophosphorothioate sodium salt

≥98% (HPLC), powder

Synonym(s):

Rp-β-Phenyl-1,N2-etheno-8-bromoguanosine 3′,5′-cyclic monophosphorothioate sodium salt, Rp-8-Br-PET-cGMPS

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About This Item

Empirical Formula (Hill Notation):
C18H14BrN5NaO6PS
CAS Number:
185246-32-6
Molecular Weight:
562.27
UNSPSC Code:
41106305
PubChem Substance ID:
24724424
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Quality Level

100

assay

≥98% (HPLC)

form

powder

potency

30 nM Ki

color

white to beige

mp

240-300 °C (lit.)

solubility

H2O: 15 mg/mL at ≤60 °C

storage temp.

−20°C

SMILES string

O.[Na+].O[C@@H]1[C@@H]2O[P@]([O-])(=S)OC[C@H]2O[C@H]1n3c(Br)nc4C(=O)n5cc(nc5Nc34)-c6ccccc6

InChI

1S/C18H15BrN5O6PS.Na/c19-17-21-11-14(24(17)16-12(25)13-10(29-16)7-28-31(27,32)30-13)22-18-20-9(6-23(18)15(11)26)8-4-2-1-3-5-8;/h1-6,10,12-13,16,25H,7H2,(H,20,22)(H,27,32);/q;+1/p-1/t10-,12-,13-,16-,31-;/m1./s1

InChI key

SVMPQLHYWRTQCX-DBHVCDLJSA-M

Biochem/physiol Actions

Rp-8-Br-PET-cGMPS is a metabolically stable, competitive inhibitor of both PKG I (Ki = 30 nM) and PKG II. Blocks cGMP-gated retinal type ion channels (IC50 = 25 micromoles).
Rp-8-Br-PET-cGMPS is metabolically stable, competitive inhibitor of cGMP-dependent protein kinase G. Inhibits both PKG I (Ki = 30 nM) and PKG II and blocks cGMP-gated retinal type ion channels (IC50 = 25 micromoles).

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.

Legal Information

U.S. Patent 5,625,056, DE Patent 4,217,679.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000089194
0000082250
0000016938
0000016216
125M4724V

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Ulrike Beckert et al.
Biochemical and biophysical research communications, 451(4), 497-502 (2014-08-12)
In addition to the well-known second messengers cAMP and cGMP, mammalian cells contain the cyclic pyrimidine nucleotides cCMP and cUMP. The Pseudomonas aeruginosa toxin ExoY massively increases cGMP and cUMP in cells, whereas the Bordetella pertussis toxin CyaA increases cAMP
Chrisen H Maharaj et al.
Reproductive biology and endocrinology : RB&E, 7, 34-34 (2009-04-25)
Sildenafil citrate, a specific phosphodiesterase-5 inhibitor, is increasingly used for pulmonary hypertension in pregnancy. Sildenafil is also emerging as a potential candidate for the treatment of intra-uterine growth retardation and for premature labor. Its effects in the feto-placental circulation are
Junli Ping et al.
Neural plasticity, 2010, 540940-540940 (2010-01-01)
Long-term potentiation (LTP) at thalamic input synapses to the lateral nucleus of the amygdala (LA) has been proposed as a cellular mechanism of the formation of auditory fear memories. We have previously shown that signaling via ERK/MAPK in both the
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Global Trade Item Number

SKUGTIN
B6684-5MG04061832895796
B6684-1MG04061826671214