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S6069

Sp 5,6-DCl-cBIMPS

Name: Sp 5,6-DCl-cBIMPS
Brand: SIGMA

≥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:

120912-54-1

Molecular Weight:

419.15

MDL number:

MFCD06795834

UNSPSC Code:

12352200

PubChem Substance ID:

24724615

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.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Activation of cyclic AMP pathway prevents CD34(+) cell apoptosis.

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

Regulation of aldosterone production from zona glomerulosa cells by ANG II and cAMP: evidence for PKA-independent activation of CaMK by cAMP.

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

A cyclic adenosine 3',5'-monophosphate stimulates phospholipase Cgamma1-calcium signaling via the activation of tyrosine kinase in boar spermatozoa.

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

Changes of PKA and PDK1 in the principal piece of boar spermatozoa treated with a cell-permeable cAMP analog to induce flagellar hyperactivation.

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

Calyculin A-sensitive protein phosphatases are involved in maintenance of progressive movement in mouse spermatozoa in vitro by suppression of autophosphorylation of protein kinase A.

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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