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B6684

Sigma-Aldrich

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

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 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 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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Ulrike Beckert et al.
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