Page last updated: 2024-11-07

2-amino-n(6)-hydroxyadenine

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

Description

2-amino-N(6)-hydroxyadenine is a synthetic nucleoside analog that has shown promise as an anticancer agent. It is structurally similar to adenine, a naturally occurring purine base found in DNA and RNA. The presence of the hydroxy group at the N(6) position is crucial for its biological activity. 2-amino-N(6)-hydroxyadenine has been shown to inhibit the growth of various cancer cell lines, including leukemia, lymphoma, and colon cancer. It exerts its anticancer effect by interfering with DNA replication and repair processes. The compound has also shown potential in treating viral infections, such as HIV. Its mechanism of action involves inhibiting viral reverse transcriptase, an enzyme essential for viral replication. 2-amino-N(6)-hydroxyadenine is currently under investigation in clinical trials as a potential treatment for various cancers and viral infections.'

2-amino-N(6)-hydroxyadenine: mutagen & bacterial growth inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-amino-6-hydroxyaminopurine : A 2,6-diaminopurine that is the N(6)-hydroxy derivative of 2,6-diamino-3H-purine. [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]

Cross-References

ID SourceID
PubMed CID101513
CHEMBL ID395170
CHEBI ID78685
SCHEMBL ID2938904
SCHEMBL ID20768201
MeSH IDM0096737

Synonyms (34)

Synonym
nsc 529771
ccris 757
guanine, oxime
2-amino-n(6)-hydroxyadenine
1h-purine-2,6-diamine, n6-hydroxy-
2-amino-n(sup 6)-hydroxyadenine
2-amino-6-hydroxyaminopurine
2-amino-n6-hydroxyadenine
nsc529771
7269-57-0
1h-purine-2, n6-hydroxy-
nsc-529771
chebi:78685 ,
CHEMBL395170
n-(2-amino-7h-purin-6-yl)hydroxylamine
AKOS006277943
d3od4l02qy ,
2-amino-6-n-hydroxylaminopurine
unii-d3od4l02qy
guanine oxime
n(6)-hydroxy-3h-purine-2,6-diamine
SCHEMBL2938904
9h-purine-2,6-diamine, n6-hydroxy-
DTXSID6075304
n6-hydroxy-9h-purine-2,6-diamine
n-(2-amino-7h-purin-6-yl)-hydroxylamine
purine, 2-amino-6-(hydroxyamino)-
amino-6-hydroxyaminopurine, 2-
Q27147910
AMY16313
6-(hydroxyamino)-7h-purin-2-amine
SCHEMBL20768201
Y11646
6-(hydroxyamino)-9h-purin-2-amine

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response curves showed that AHA and HAP were about equally mutagenic at low doses but that AHA was more mutagenic than HAP at high doses."( Effect of the uvs-2 allele of Neurospora crassa on the mutagenic potency of two N-hydroxylaminopurines and 2-aminopurine in the ad-3 forward-mutation test.
Brockman, HE; de Serres, FJ; Hung, CY; Ong, T, 1989
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
mutagenAn agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
teratogenic agentA role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
[role 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]

Drug Classes (3)

ClassDescription
2,6-diaminopurinesAny aminopurine that has amino substituents at positions 2 and 6, and their substituted derivatives.
nucleobase analogueA molecule that can substitute for a normal nucleobase in nucleic acids.
hydroxylaminesHydroxylamine, H2N-OH, and its hydrocarbyl derivatives.
[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]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID300103Antimalarial activity against chloroquine,pyrimethamine-resistant Plasmodium falciparum K1 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300108Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum VS12007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300106Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum 3D72007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300105Cytotoxicity against human KB cells2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300102Antimalarial activity against drug-sensitive Plasmodium falciparum 3D7 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300107Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum K12007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300104Antimalarial activity against chloroquine, pyrimethamine and cycloguanil-resistant Plasmodium falciparum VS1 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID1204895Binding affinity to guanine riboswitch in Bacillus subtilis2015Journal of medicinal chemistry, Apr-23, Volume: 58, Issue:8
(Dis)similar Analogues of Riboswitch Metabolites as Antibacterial Lead Compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (26.92)18.7374
1990's15 (57.69)18.2507
2000's2 (7.69)29.6817
2010's2 (7.69)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.26

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.26 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (11.54%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (88.46%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]