Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H5N5 |
| Molecular Weight | 135.1267 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=C2NC=NC2=N1
InChI
InChIKey=MWBWWFOAEOYUST-UHFFFAOYSA-N
InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
| Molecular Formula | C5H5N5 |
| Molecular Weight | 135.1267 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
2-aminopurine is a purine analogue. It is known for its mutagenic effect by inducing DNA base-pair transitions. 2-aminopurine is widely used fluorescent probe of DNA structure and the perturbation of that structure by interaction with enzymes and other molecules. 2-aminopurine is a fluorescent nucleobase that provides the means to probe structure and dynamics of RNA molecules. 2-Aminopurine inhibits the double-stranded RNA-dependent protein kinase.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7905506 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Valacyclovir and famciclovir therapy in herpes zoster. | 2002-11 |
|
| Sequence requirements in the catalytic core of the "10-23" DNA enzyme. | 2002-10-25 |
|
| Using 2-aminopurine fluorescence to measure incorporation of incorrect nucleotides by wild type and mutant bacteriophage T4 DNA polymerases. | 2002-10-25 |
|
| Understanding pain in herpes zoster: an essential for optimizing treatment. | 2002-10-15 |
|
| Progress in meeting today's demands in genital herpes: an overview of current management. | 2002-10-15 |
|
| Challenges in genital herpes simplex virus management. | 2002-10-15 |
|
| Cyclobutylpyrimidine dimer base flipping by DNA photolyase. | 2002-10-11 |
|
| Local conformational changes in the catalytic core of the trans-acting hepatitis delta virus ribozyme accompany catalysis. | 2002-10-08 |
|
| Treatment of recurrent hepatitis B infection in liver transplant recipients. | 2002-10 |
|
| Antiviral agents: Non-antiretroviral [correction of Nonantiviral] drugs. | 2002-10 |
|
| Fatal hepatitis B reactivation following discontinuation of nucleoside analogues for chronic hepatitis B. | 2002-10 |
|
| Use of 2-aminopurine and tryptophan fluorescence as probes in kinetic analyses of DNA polymerase beta. | 2002-09-17 |
|
| Fidelity of Escherichia coli DNA polymerase IV. Preferential generation of small deletion mutations by dNTP-stabilized misalignment. | 2002-09-13 |
|
| Role of DNA flexibility in sequence-dependent activity of uracil DNA glycosylase. | 2002-09-10 |
|
| Viral dynamics in chronic hepatitis B patients treated with lamivudine, lamivudine-famciclovir or lamivudine-ganciclovir. | 2002-09 |
|
| The use of antiviral monotherapy and combination therapy for patients with hepatitis B virus infection after liver transplantation. | 2002-09 |
|
| 5-propynyluracil.diaminopurine: an efficient base-pair for non-enzymatic transcription of DNA. | 2002-08-07 |
|
| Anti-angiogenic activity of the purine analog 6-thioguanine. | 2002-08 |
|
| Nucleoside analogues for chronic hepatitis B: antiviral efficacy and viral resistance. | 2002-07 |
|
| Comparison of the efficacy of lamivudine and famciclovir in Asian patients with chronic hepatitis B: results of 24 weeks of therapy. | 2002-07 |
|
| Thymosin-alpha1 and famciclovir combination therapy activates T-cell response in patients with chronic hepatitis B virus infection in immune-tolerant phase. | 2002-07 |
|
| Antiviral agents in women's health: pharmacotherapeutics of treating influenza and herpes. | 2002-06-20 |
|
| Comparison of different treatment combinations for chronic hepatitis B infection. | 2002-06 |
|
| Successful antiviral treatment for fulminant reactivated hepatitis B after autologous stem cell transplantation and prophylaxis during subsequent allogeneic stem cell transplantation. | 2002-06 |
|
| Presteady-state analysis of a single catalytic turnover by Escherichia coli uracil-DNA glycosylase reveals a "pinch-pull-push" mechanism. | 2002-05-31 |
|
| In the fluorescent spotlight: global and local conformational changes of small catalytic RNAs. | 2002-05-03 |
|
| Adenoviral transfer of the melanoma differentiation-associated gene 7 (mda7) induces apoptosis of lung cancer cells via up-regulation of the double-stranded RNA-dependent protein kinase (PKR). | 2002-04-15 |
|
| Using 2-aminopurine fluorescence to detect base unstacking in the template strand during nucleotide incorporation by the bacteriophage T4 DNA polymerase. | 2002-04-02 |
|
| [Perspectives for the treatment and prevention of herpes simplex infections]. | 2002-04 |
|
| [Genital herpes: epidemiology, transmission, clinic, asymptomatic viral excretion, impact on other sexually transmitted diseases, prevention, and treatment]. | 2002-04 |
|
| Distinguishing "looped-out" and "stacked-in" DNA bulge conformation using fluorescent 2-aminopurine replacing a purine base. | 2002-04 |
|
| Temporal pattern of herpes simplex virus type 1 infection and cell death in the mouse brain stem: influence of guanosine nucleoside analogues. | 2002-04 |
|
| Reduction of postherpetic neuralgia in herpes zoster. | 2002-03-22 |
|
| Seroconversion after the addition of famciclovir therapy in a child with hepatitis B virus infection after liver transplantation who developed lamivudine resistance. | 2002-03-15 |
|
| Local disruption of DNA-base stacking by bulky base surrogates. | 2002-03-07 |
|
| Drugs for non-HIV viral infections. | 2002-02-04 |
|
| Lack of association between CYP2A5 induction and apoptosis in mouse primary hepatocytes. | 2002-02-01 |
|
| The epizootic haematopoietic necrosis virus (Iridoviridae) induces apoptosis in vitro. | 2002-02 |
|
| [Prevention and treatment of HBV reinfection following liver transplantation]. | 2002-02 |
|
| How will we use the new antiviral agents for hepatitis B? | 2002-02 |
|
| Human interferon-gamma mRNA autoregulates its translation through a pseudoknot that activates the interferon-inducible protein kinase PKR. | 2002-01-25 |
|
| Herpes simplex virus infection. | 2002-01 |
|
| Lamivudine and famciclovir combination therapy with or without addition of interferon-alpha-2b for HBeAg-positive chronic hepatitis B: a pilot study. | 2002 |
|
| Genital herpes simplex virus infection in the adolescent: special considerations for management. | 2002 |
|
| Induction of premature mitosis in root meristem cells of Vicia faba and Pisum sativum by various agents is correlated with an increased level of protein phosphorylation. | 2002 |
|
| Conformation and dynamics of normal and damaged DNA. | 2001-12 |
|
| Antiepiligrin (laminin 5) cicatricial pemphigoid complicated and exacerbated by herpes simplex virus type 2 infection. | 2001-11 |
|
| Therapeutic advances in the management of hepatitis B and hepatitis C. | 2001-10 |
|
| Recent developments in herpesvirus therapy. | 2001-03 |
|
| [Treatment of genital herpes]. | 2001 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12802279
5 mM 2-aminopurine enables wild-type p53-containing HCT116 cells to bypass adriamycin-induced G2/M arrest
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
O14B3U97FW
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2-AMINOPURINE
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