Page last updated: 2024-12-05

2-fluoroadenosine

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

2-Fluoroadenosine (2-F-Ado) is a nucleoside analog that has shown significant potential in various therapeutic applications. It is a synthetic analog of adenosine, a naturally occurring nucleoside, where the hydroxyl group at the 2' position of the ribose sugar is replaced with a fluorine atom. This substitution introduces a number of interesting biological effects.

**Synthesis:** 2-F-Ado can be synthesized via a variety of chemical pathways, including the direct fluorination of adenosine using a fluorinating agent like diethylaminosulfur trifluoride (DAST).

**Effects:** 2-F-Ado exhibits several pharmacological effects, including:

* **Inhibition of adenosine deaminase (ADA):** 2-F-Ado is a potent inhibitor of ADA, an enzyme responsible for the breakdown of adenosine. This inhibition leads to increased levels of adenosine in the body, which has various physiological effects.
* **Antiviral activity:** 2-F-Ado has demonstrated antiviral activity against certain viruses, including the human immunodeficiency virus (HIV) and hepatitis C virus (HCV).
* **Anticancer activity:** 2-F-Ado has shown potential as an anticancer agent, particularly in treating leukemia and lymphoma. Its mechanism of action involves inhibiting the synthesis of DNA and RNA.

**Importance:** The unique properties of 2-F-Ado, including its ADA inhibitory activity and its potential therapeutic benefits, make it an important compound for research and development.

**Why it is studied:** 2-F-Ado is studied extensively due to its potential applications in various fields, including:

* **Treatment of ADA deficiency:** 2-F-Ado is used as a treatment for severe combined immunodeficiency (SCID) due to ADA deficiency, a genetic disorder affecting the immune system.
* **Development of antiviral therapies:** 2-F-Ado's antiviral activity makes it a promising candidate for the development of new antiviral treatments.
* **Cancer therapy:** 2-F-Ado's anticancer activity is being explored in clinical trials as a potential treatment for various cancers.

**Overall, 2-F-Ado is a versatile nucleoside analog with significant therapeutic potential. Its unique properties and ongoing research make it a promising compound for future medical advancements.'

Cross-References

ID SourceID
PubMed CID8975
CHEMBL ID290077
CHEBI ID39740
SCHEMBL ID977919
MeSH IDM0105223

Synonyms (56)

Synonym
smr000471849
MLS001066367
purine, 6-amino-2-fluoro-9-beta-d-ribofuranosyl-
ai3-52599
brn 0043956
nsc 30605
PDSP1_001071
2-(6-amino-2-fluoro-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
nsc-30605
purine, 6-amino-2-fluoro-9-.beta.-d-ribofuranosyl-
146-78-1
adenosine, 2-fluoro-
2-fluoroadenosine ,
2-fas
sri 727
NCGC00181336-01
PDSP2_001055
2-fluoroadenosine, 97%
DB04441
6-amino-2-fluoro-9-beta-d-ribofuranosylpurine
2FA ,
CHEBI:39740 ,
CHEMBL290077 ,
BRD-K72238567-001-12-4
(2r,3r,4s,5r)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
bdbm50118807
2-fluoroado
cid_8975
(2r,3r,4s,5r)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(2r,3r,4s,5r)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;(2r,3r,4s,5r)-2-(6-amino-2-fluoro-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
A808551
NCGC00181336-02
BCP9000107
AKOS015920272
HMS2231E03
unii-0s67290crj
0s67290crj ,
4-26-00-03723 (beilstein handbook reference)
(2r,3r,4s,5r)-2-(6-amino-2-fluoro-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
BCP0726000182
AM84420
AKOS015853307
2-fluoro-9-.beta.-d-ribofuranosyladenine
HBUBKKRHXORPQB-UUOKFMHZSA-N
SCHEMBL977919
AC-22363
mfcd00866394
DTXSID70163252
2-fluoroade-nosine
DS-15294
Q27095228
EN300-7361945
(2r,3r,4s,5r)-2-(6-amino-2-fluoro-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
PD016313
Z2065671281
BP-58636
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
adenosinesAny purine ribonucleoside that is a derivative of adenosine.
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (19)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glp-1 receptor, partialHomo sapiens (human)Potency1.99530.01846.806014.1254AID624417
TDP1 proteinHomo sapiens (human)Potency0.11080.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency0.66220.00527.809829.0929AID588855; AID720534; AID720536; AID720537
67.9K proteinVaccinia virusPotency1.06100.00018.4406100.0000AID720579; AID720580
hepatitis C virus polyproteinPotency1.98570.444510.437124.9988AID720575
IDH1Homo sapiens (human)Potency0.65130.005210.865235.4813AID686970
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency0.92000.00419.984825.9290AID504444
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency0.01410.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency0.01410.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency0.01410.15855.287912.5893AID540303
gemininHomo sapiens (human)Potency12.35290.004611.374133.4983AID624296; AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A3Homo sapiens (human)Ki0.09900.00000.930610.0000AID34574
Adenylate cyclase type 5Rattus norvegicus (Norway rat)Ki0.09900.00140.04950.1180AID34574
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, BCL-2-RELATED PROTEIN A1Homo sapiens (human)EC50 (µMol)350.00008.0570121.1218338.0000AID2765
Hsf1 proteinMus musculus (house mouse)EC50 (µMol)5.46400.160024.4900236.5000AID2382
glycogen synthase kinase-3 beta isoform 1Homo sapiens (human)EC50 (µMol)300.00000.212522.156283.9400AID434954
bcl-2-like protein 11 isoform 1Homo sapiens (human)EC50 (µMol)350.00008.0570121.1218338.0000AID2765
Adenosine receptor A3Homo sapiens (human)EC50 (µMol)2.66000.00010.42587.9800AID34265
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, BCL-2-RELATED PROTEIN A1Homo sapiens (human)AC50234.93800.920095.9176498.8000AID449754; AID449755; AID449757
Hsf1 proteinMus musculus (house mouse)AC501.29400.171030.8718167.9780AID493083; AID493085
Bcl-2-like protein 11Homo sapiens (human)AC50350.00009.841085.8882287.1000AID449757
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (53)

Processvia Protein(s)Taxonomy
intrinsic apoptotic signaling pathway in response to DNA damageBcl-2-like protein 11Homo sapiens (human)
in utero embryonic developmentBcl-2-like protein 11Homo sapiens (human)
B cell homeostasisBcl-2-like protein 11Homo sapiens (human)
kidney developmentBcl-2-like protein 11Homo sapiens (human)
myeloid cell homeostasisBcl-2-like protein 11Homo sapiens (human)
apoptotic processBcl-2-like protein 11Homo sapiens (human)
cell-matrix adhesionBcl-2-like protein 11Homo sapiens (human)
spermatogenesisBcl-2-like protein 11Homo sapiens (human)
male gonad developmentBcl-2-like protein 11Homo sapiens (human)
post-embryonic developmentBcl-2-like protein 11Homo sapiens (human)
mammary gland developmentBcl-2-like protein 11Homo sapiens (human)
positive regulation of protein-containing complex assemblyBcl-2-like protein 11Homo sapiens (human)
response to endoplasmic reticulum stressBcl-2-like protein 11Homo sapiens (human)
tube formationBcl-2-like protein 11Homo sapiens (human)
odontogenesis of dentin-containing toothBcl-2-like protein 11Homo sapiens (human)
regulation of apoptotic processBcl-2-like protein 11Homo sapiens (human)
T cell homeostasisBcl-2-like protein 11Homo sapiens (human)
positive regulation of apoptotic processBcl-2-like protein 11Homo sapiens (human)
positive regulation of neuron apoptotic processBcl-2-like protein 11Homo sapiens (human)
ear developmentBcl-2-like protein 11Homo sapiens (human)
positive regulation of cell cycleBcl-2-like protein 11Homo sapiens (human)
regulation of organ growthBcl-2-like protein 11Homo sapiens (human)
developmental pigmentationBcl-2-like protein 11Homo sapiens (human)
regulation of developmental pigmentationBcl-2-like protein 11Homo sapiens (human)
spleen developmentBcl-2-like protein 11Homo sapiens (human)
thymus developmentBcl-2-like protein 11Homo sapiens (human)
positive regulation of T cell apoptotic processBcl-2-like protein 11Homo sapiens (human)
thymocyte apoptotic processBcl-2-like protein 11Homo sapiens (human)
cellular response to glucocorticoid stimulusBcl-2-like protein 11Homo sapiens (human)
positive regulation of release of cytochrome c from mitochondriaBcl-2-like protein 11Homo sapiens (human)
extrinsic apoptotic signaling pathway in absence of ligandBcl-2-like protein 11Homo sapiens (human)
positive regulation of mitochondrial membrane permeability involved in apoptotic processBcl-2-like protein 11Homo sapiens (human)
positive regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayBcl-2-like protein 11Homo sapiens (human)
apoptotic process involved in embryonic digit morphogenesisBcl-2-like protein 11Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseBcl-2-like protein 11Homo sapiens (human)
positive regulation of fibroblast apoptotic processBcl-2-like protein 11Homo sapiens (human)
meiosis IBcl-2-like protein 11Homo sapiens (human)
inflammatory responseAdenosine receptor A3Homo sapiens (human)
signal transductionAdenosine receptor A3Homo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A3Homo sapiens (human)
regulation of heart contractionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A3Homo sapiens (human)
response to woundingAdenosine receptor A3Homo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell migrationAdenosine receptor A3Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activityAdenosine receptor A3Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A3Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A3Homo sapiens (human)
adenosine catabolic processAdenosine deaminase Bos taurus (cattle)
cell adhesionAdenosine deaminase Bos taurus (cattle)
nucleotide metabolic processAdenosine deaminase Bos taurus (cattle)
purine ribonucleoside monophosphate biosynthetic processAdenosine deaminase Bos taurus (cattle)
inosine biosynthetic processAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein bindingBcl-2-like protein 11Homo sapiens (human)
microtubule bindingBcl-2-like protein 11Homo sapiens (human)
protein kinase bindingBcl-2-like protein 11Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A3Homo sapiens (human)
adenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
protein bindingAdenosine deaminase Bos taurus (cattle)
zinc ion bindingAdenosine deaminase Bos taurus (cattle)
2'-deoxyadenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneBcl-2-like protein 11Homo sapiens (human)
cytosolBcl-2-like protein 11Homo sapiens (human)
endomembrane systemBcl-2-like protein 11Homo sapiens (human)
Bcl-2 family protein complexBcl-2-like protein 11Homo sapiens (human)
mitochondrionBcl-2-like protein 11Homo sapiens (human)
plasma membraneAdenosine receptor A3Homo sapiens (human)
presynaptic membraneAdenosine receptor A3Homo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A3Homo sapiens (human)
dendriteAdenosine receptor A3Homo sapiens (human)
plasma membraneAdenosine receptor A3Homo sapiens (human)
synapseAdenosine receptor A3Homo sapiens (human)
lysosomeAdenosine deaminase Bos taurus (cattle)
cytoplasmic vesicle lumenAdenosine deaminase Bos taurus (cattle)
anchoring junctionAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID22612Kinetic parameter in calf intestine adenosine deaminase.1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds.
AID34265Effect on forskolin-stimulated cyclic AMP production in intact chinese hamster ovary (CHO) cell expressing the human Adenosine A3 receptor2002Journal of medicinal chemistry, Sep-26, Volume: 45, Issue:20
Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.
AID34574Affinity for human Adenosine A3 receptor expressed in CHO cell2002Journal of medicinal chemistry, Sep-26, Volume: 45, Issue:20
Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.
AID33815Kinetic parameter in calf intestine adenosine deaminase.1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds.
AID34272Percent efficacy against human Adenosine A3 receptor expressed in CHO cell2002Journal of medicinal chemistry, Sep-26, Volume: 45, Issue:20
Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.
AID1065714Trypanocidal activity against bloodstream stage of Trypanosoma brucei brucei AnTat1.1E after 72 hrs by WST-1 assay2013Journal of medicinal chemistry, Dec-27, Volume: 56, Issue:24
Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis.
AID1065710Displacement of [2,8-3H]-adenosine from Trypanosoma brucei AT1/P2 expressed in bloodstream stage of Trypanosoma brucei brucei B482013Journal of medicinal chemistry, Dec-27, Volume: 56, Issue:24
Structure-activity relationships of synthetic cordycepin analogues as experimental therapeutics for African trypanosomiasis.
AID1452128Inhibition of ATPgammaS-BODIPY binding to Thermotoga maritima His-tagged HK853 expressed in Escherichia coli BL21(DE3)pLysS Rosetta preincubated for 30 mins prior to ATPgammaS-BODIPY addition measured after 1 hr by coomassie staining-based SDS-PAGE analys2017Journal of medicinal chemistry, 10-12, Volume: 60, Issue:19
Rational Design of Selective Adenine-Based Scaffolds for Inactivation of Bacterial Histidine Kinases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (19.05)18.7374
1990's3 (14.29)18.2507
2000's4 (19.05)29.6817
2010's7 (33.33)24.3611
2020's3 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.51

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.51 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index13.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]