S6069

Sigma-Aldrich

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
Empirical Formula (Hill Notation):
C12H10Cl2N2O5PSNa
CAS Number:
Molecular Weight:
419.15
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

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

SMILES string

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

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Stepan Gambaryan et al.
American journal of physiology. Endocrinology and metabolism, 290(3), E423-E433 (2005-10-13)
Aldosterone production in zona glomerulosa (ZG) cells of adrenal glands is regulated by various extracellular stimuli (K(+), ANG II, ACTH) that all converge on two major intracellular signaling pathways: an increase in cAMP production and calcium (Ca(2+)) mobilization. However, molecular...
Hiroshi Harayama et al.
Journal of andrology, 26(6), 732-740 (2005-11-18)
The aim of this study was to reveal a downstream part of the intracellular signaling that is mediated by cyclic adenosine monophosphate (cAMP)-dependent tyrosine kinases, including spleen tyrosine (Y) kinase (SYK), in boar spermatozoa. Ejaculated spermatozoa were incubated with cBiMPS...
Hiroshi Harayama et al.
Molecular reproduction and development, 75(9), 1396-1407 (2008-01-24)
A cAMP-induced protein tyrosine phosphorylation and flagellar hyperactivation are controlled via complicated signaling cascades in mammalian spermatozoa. For instance, these events seem to be regulated positively by the PKA-mediated signaling and negatively by the PI3K/PDK1-mediated signaling. In this article, we...
Soledad Negrotto et al.
Experimental hematology, 34(10), 1420-1428 (2006-09-20)
Although cAMP is involved in a number of physiologic functions, its role in hematopoietic cell fate decision remains poorly understood. We have recently demonstrated that in CD34(+)-derived megakaryocytes, cAMP-related agents prevent apoptosis. In this study we addressed the question of...
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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