23583-48-4

Usage

Uses

Used in Pharmaceutical Research:
8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE is used as a research tool for studying the effects of cAMP on cellular processes. It is particularly useful in investigating the role of cAMP in signal transduction pathways and its influence on gene expression.
Used in Cell Culture Studies:
In the field of cell culture, 8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE is used as a positive control for CYP19 induction in H295R cells. This application aids researchers in understanding the mechanisms underlying the regulation of gene expression and the role of cAMP in cellular processes.
Used in Electrophysiology:
8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE is used as a membrane-permeable cAMP analog to study its effect on short-circuit current (Isc). This application is valuable in understanding the impact of cAMP on ion transport and membrane potential in various cell types.
Used in Stem Cell Research:
In the field of stem cell research, 8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE is used to investigate its potential as an inducer of differentiation in Wharton's jelly-derived mesenchymal stem cells (WJ-MSCs). This application is crucial in exploring the molecular mechanisms that govern stem cell differentiation and the role of cAMP in this process.
Used in the Pharmaceutical Industry:
8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE is used as an active ingredient in the development of drugs targeting cyclic AMP-dependent protein kinase. Its role in modulating cellular signaling pathways makes it a promising candidate for therapeutic applications in various diseases.
Used in the Biotechnology Industry:
In the biotechnology industry, 8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE is used as a key component in the development of novel drug delivery systems and gene therapy approaches. Its ability to modulate cellular processes and influence gene expression makes it a valuable tool in the design of targeted therapies and personalized medicine.

Biochem/physiol Actions

8-bromo-adenosine?3′,5′-cyclic?monophosphate?(8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.

Upstream product

• 60-92-4 cAMP 

Downstream Products

• 72549-47-4 (4aR,6R,7R,7aS)-6-(6-Amino-8-phenylsulfanyl-purin-9-yl)-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 
• 72549-50-9 (4aR,6R,7R,7aS)-6-[6-Amino-8-(4-bromo-phenylsulfanyl)-purin-9-yl]-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 
• 72549-39-4 (4aR,6R,7R,7aS)-6-(6-Amino-8-cyclohexylsulfanyl-purin-9-yl)-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 
• 72549-49-6 (4aR,6R,7R,7aS)-6-[6-Amino-8-(4-methoxy-phenylsulfanyl)-purin-9-yl]-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 
• 52109-40-7 8-Benzylselenoadenosin-3',5'-phosphorsaeure 
• 72549-48-5 (4aR,6R,7R,7aS)-6-(6-Amino-8-o-tolylsulfanyl-purin-9-yl)-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 
• 61363-29-9 8-(2-amino-ethylamino)-O^3'_,O5'-hydroxyphosphoryl-adenosine 
• 72549-43-0 (4aR,6R,7R,7aS)-6-[6-Amino-8-(4-methoxy-benzylsulfanyl)-purin-9-yl]-2-oxo-tetrahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF AN (RP)-8-SUBSTITUTED CAMPS

This invention relates to a process for the preparation of an (Rp)-8-substituted adenosine-3',5'-cyclic phosphorothioic acid, or a salt or ester thereof, which comprises P-amidating 8-bromoadenosine-3',5'-cyclic phosphoric acid, and reacting the P-amidate with a base and with carbon disulphide to yield (Rp)-8-bromoadenosine-3',5'-cyclic phosphorothioic acid or a salt or ester thereof.

Stereoselective preparation of (RP)-8-hetaryladenosine-3′, 5′-cyclic phosphorothioic acids

Cyclic adenosine monophosphate (cAMP) has been converted into its 8-bromo derivative and 2′O-TBDMS protected before activation of the phosphoric acid moiety with a reagent generated in situ from oxalyl chloride and DMF. Further reactions with primary amines furnished corresponding phosphoramidates with high stereoselectivity at the phosphorus atom. Cross-coupling reactions with the 8-bromopurine yielded 8-hetaryl derivatives. X-Ray analyses showed the amidates to possess the (SP)-configuration. Carbon disulfide effected thiylation under strongly basic conditions stereospecifically provided the (RP)-phosphorothioic acids. The Royal Society of Chemistry.

PURINE NUCLEOTIDE DERIVATIVES

This invention provides novel 8-carbyl substituted cAMPS and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.

Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one- and two-photon photolysis

(Chemical Equation Presented) Shedding light: Efficient activation of cyclic nucleoside monophosphates (cNMPs) can be achieved upon one- and two-photon flash photolysis of novel photolabile coumarinylmethyl esters of cAMP and cGMP (A = adenosine, G = guanosine) as well as their 8-bromosubstituted derivatives. The phototriggers show high solubility in water and permit space- and time-resolved investigations of the molecular mechanisms of cyclic nucleotide dependent processes.