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Merck
CN

S6069

Sp 5,6-DCl-cBIMPS

≥98% (HPLC), solid

Synonym(s):

5,6-Dichloro-1-b-D-ribofuranosylbenzimidazole-3′,5′-cyclic monophosphorothioate, Sp- isomer sodium salt

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About This Item

Empirical Formula (Hill Notation):
C12H10Cl2N2O5PSNa
CAS Number:
Molecular Weight:
419.15
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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SMILES string

[Na+].O[C@@H]1[C@@H]2O[P@]([S-])(=O)OC[C@H]2O[C@H]1n3cnc4cc(Cl)c(Cl)cc34

assay

≥98% (HPLC)

form

solid

color

white

solubility

H2O: 1 mM, DMSO: freely soluble, ethanol: freely soluble

shipped in

dry ice

storage temp.

−70°C

Application

Sp 5,6-DCl-cBIMPS may be used in cAMP-dependent protein kinase-mediated cell signaling studies.

Biochem/physiol Actions

Selective cAMP-dependent protein kinase (PKA) activator. Especially suitable for intact cells showing preference for site B of type II isozyme. Completely stable against mammalian cPDE types I & III and only extremely slowly hydrolized by cPDE type II. Surpasses the widely used but problematic dibutyryl cAMP or 8-CPT-cAMP in terms of metabolic stability, membrane permeability and potency.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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William V Holt et al.
Journal of andrology, 23(4), 557-565 (2002-06-18)
Because poorly motile sperm samples can often be stimulated by treatments that increase intracellular levels of cyclic adenosine monophosphate (cAMP), it has been supposed that such samples are unable to maintain an adequate supply of the cyclic nucleotide with which
Dirk Motzkus et al.
Journal of molecular neuroscience : MN, 18(1-2), 105-109 (2002-04-05)
The mammalian period (Per) genes which are components of the circadian clock are mainly regulated via an autoregulatory feedback loop. Here we show that a human PER1 (hPER1) reporter gene activity is stimulated by interleukin-6 (IL-6), a member of the
A V Makarevich et al.
Animal reproduction science, 81(1-2), 125-136 (2004-01-30)
To understand the role of protein kinase A (PKA) in the control of ovarian secretory activity, we examined effects of stimulators (db-cAMP, 6-Phe-cAMP, Sp-cDBIMPS) or inhibitors (Rp-cAMPS, KT5720) of PKA on the release of insulin-like growth factor I (IGF-I), progesterone
L Lubomirov et al.
British journal of pharmacology, 134(7), 1564-1570 (2001-11-29)
1. Urocortin is an endogenous vasodilator although the mechanism of vasorelaxation is not completely understood. The hypothesis that an alteration of smooth muscle calcium concentration is involved was tested using isometric tension recording and calcium fluorimetry. The relationship between contraction
Namiko Goto et al.
The Journal of reproduction and development, 55(3), 327-334 (2009-03-19)
Protein serine/threonine phosphorylation in mammalian sperm flagella has been considered to play important roles in regulation of motility. Protein phosphorylation state reflects balance of enzymatic activities between protein phosphatases and protein kinases [predominantly protein kinase A (PKA)]. The aims of

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