Page last updated: 2024-12-07

8-azidoadenosine-3',5'-monophosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

8-Azidoadenosine-3',5'-monophosphate (8-N3-AMP) is a photoaffinity analog of adenosine 3',5'-monophosphate (cAMP). It is a useful tool for studying cAMP-dependent protein kinases (PKA) and other cAMP-binding proteins. 8-N3-AMP is synthesized by reacting adenosine 3',5'-monophosphate with azidotrimethylsilane. Upon UV irradiation, the azido group of 8-N3-AMP undergoes a photochemical reaction that generates a highly reactive nitrene species. This nitrene can then react with nearby molecules, including proteins, forming covalent adducts. This covalent labeling allows for the identification of proteins that bind cAMP and the determination of their binding sites. 8-N3-AMP has been used to study the structure and function of PKA, as well as other cAMP-binding proteins, such as guanine nucleotide regulatory proteins (G proteins) and cyclic nucleotide phosphodiesterases (PDEs). It has also been used to investigate the role of cAMP in cell signaling pathways. 8-N3-AMP is a valuable tool for studying the role of cAMP in cellular processes.'

Cross-References

ID SourceID
PubMed CID115296
CHEMBL ID3272800
SCHEMBL ID14167816
MeSH IDM0067487

Synonyms (14)

Synonym
8-n3-camp
8-azidoadenosine cyclic 3',5'-(hydrogen phosphate)
8-azidoadenosine-3',5'-cyclic-monophosphate
31966-52-6
(4ar,6r,7r,7as)-6-(6-amino-8-azidopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
8-azidoadenosine-3',5'-monophosphate
adenosine, 8-azido-, cyclic 3',5'-(hydrogen phosphate)
8-azidoadenosine 3',5'-monophosphate
CHEMBL3272800
SCHEMBL14167816
8-azido-camp
DTXSID70953852
6-(6-amino-8-azido-9h-purin-9-yl)-2,7-dihydroxytetrahydro-2h,4h-2lambda~5~-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
HY-134321

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The latter mutations exhibited dominant traits when gene dosage was increased."( Yeast cAMP-dependent protein kinase regulatory subunit mutations display a variety of phenotypes.
Cannon, JF; Gitan, R; Tatchell, K, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1145763Inhibition of rabbit lung PDE assessed as inhibition 8-[3H]-cAMP substrate hydrolysis1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
AID1145762Activity of rabbit kidney PDE assessed as enzyme-mediated compound hydrolysis after 10 to 60 mins by colorimetric assay relative to cAMP1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
AID1145764Inhibition of bovine heart PDE assessed as inhibition 8-[3H]-cAMP substrate hydrolysis1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
AID1145761Ratio of Ka for cAMP to Ka for compound for bovine brain protein kinase in presence of 0.5 nmol [32P]ATP-gamma by liquid scintillation spectrometer1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Synthesis of some 1, 8- and 2, 8-disubstituted derivatives of adenosine cyclic 3', 5'-phosphate and their interaction with some enzymes of cAMP metabolism.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (118)

TimeframeStudies, This Drug (%)All Drugs %
pre-199089 (75.42)18.7374
1990's25 (21.19)18.2507
2000's3 (2.54)29.6817
2010's1 (0.85)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.84%)5.53%
Reviews2 (1.68%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other116 (97.48%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]