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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

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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 Code

13 - Non 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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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
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
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
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
Hiroshi Harayama et al.
Journal of andrology, 24(1), 91-99 (2003-01-07)
When boar spermatozoa are incubated in a medium designed for in vitro fertilization, many of them become agglutinated at the acrosomes. We previously reported that bicarbonate and cyclic adenosine 3',5'-monophosphate (cAMP) promote agglutination. The aim of the present study is
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