Page last updated: 2024-11-06

2',3'-dideoxythymidine triphosphate

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

Description

2',3'-dideoxythymidine triphosphate (ddTTP) is a nucleotide analog that inhibits DNA polymerase. It is a chain terminator because it lacks the 3'-hydroxyl group necessary for the formation of a phosphodiester bond with the next nucleotide. This property makes it a powerful tool for research and medicine. ddTTP has been used extensively in the study of DNA replication, DNA repair, and gene expression. It is also used in the synthesis of oligonucleotides, which are short sequences of DNA that can be used for a variety of purposes, including gene therapy and molecular diagnostics. The synthesis of ddTTP involves modifying the thymidine nucleoside, which is a building block of DNA. The 2' and 3' positions of the sugar moiety are deoxygenated, resulting in a molecule that is structurally similar to thymidine triphosphate but lacks the 3' hydroxyl group. This modified nucleoside is then reacted with a triphosphate group, yielding ddTTP. ddTTP is a potent inhibitor of HIV replication, as it effectively blocks the synthesis of viral DNA, leading to viral suppression and a decline in viral load. It is a key component of highly active antiretroviral therapy (HAART) and has revolutionized the treatment of HIV infection. ddTTP also plays a vital role in the development of antiviral drugs, including those for treating hepatitis B and herpes simplex virus infections. Due to its ability to interfere with DNA polymerase, ddTTP is used in research to study various aspects of DNA replication and repair. For example, it can be used to identify the role of different proteins involved in these processes. Its impact on the scientific community is significant as it aids in advancing our understanding of fundamental biological processes.'

ddTTP : A pyrimidine 2',3'-dideoxyribonucleoside 5'-triphosphate having thymine as the nucleobase. [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 CID65051
CHEMBL ID566812
CHEBI ID41846
SCHEMBL ID77582
MeSH IDM0067812

Synonyms (28)

Synonym
thymidine 5'-(tetrahydrogen triphosphate), 3'-deoxy-
ddttp
611-60-9
ddt-tp
[hydroxy-[[(2s,5r)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate
2',3'-dideoxy-thymidine-5'-triphosphate
[hydroxy-[[(2s,5r)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] phosphono hydrogen phosphate
2',3'-dideoxythymidine triphosphate
3'-deoxythymidine 5'-triphosphate
chebi:41846 ,
CHEMBL566812 ,
2',3'-dideoxythymidine 5'-triphosphate
ia883wyu21 ,
unii-ia883wyu21
dideoxy-ttp
3'-deoxythymidine 5'-(tetrahydrogen triphosphate)
SCHEMBL77582
AKOS022179912
3'-deoxythymidine triphosphate
2',3'-ddttp
2',3'-dideoxy ttp
2',3'-dideoxyribosylthymine 5'-triphosphate
bdbm50020676
DTXSID90209989
Q27104485
CS-0141229
HY-137694
PD192649
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
thymidine phosphate
pyrimidine 2',3'-dideoxyribonucleoside 5'-triphosphate
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA polymerase betaHomo sapiens (human)IC50 (µMol)19.00001.40006.56679.0000AID1449539
DNA polymerase betaRattus norvegicus (Norway rat)IC50 (µMol)30.80003.70006.20008.5000AID1155639
DNA polymerase lambdaHomo sapiens (human)IC50 (µMol)28.70005.20005.30005.4000AID1323393
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
nucleotide-excision repair, DNA gap fillingDNA polymerase betaHomo sapiens (human)
in utero embryonic developmentDNA polymerase betaHomo sapiens (human)
DNA-templated DNA replicationDNA polymerase betaHomo sapiens (human)
DNA repairDNA polymerase betaHomo sapiens (human)
base-excision repairDNA polymerase betaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase betaHomo sapiens (human)
pyrimidine dimer repairDNA polymerase betaHomo sapiens (human)
inflammatory responseDNA polymerase betaHomo sapiens (human)
DNA damage responseDNA polymerase betaHomo sapiens (human)
salivary gland morphogenesisDNA polymerase betaHomo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damageDNA polymerase betaHomo sapiens (human)
response to gamma radiationDNA polymerase betaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase betaHomo sapiens (human)
response to ethanolDNA polymerase betaHomo sapiens (human)
lymph node developmentDNA polymerase betaHomo sapiens (human)
spleen developmentDNA polymerase betaHomo sapiens (human)
homeostasis of number of cellsDNA polymerase betaHomo sapiens (human)
neuron apoptotic processDNA polymerase betaHomo sapiens (human)
response to hyperoxiaDNA polymerase betaHomo sapiens (human)
immunoglobulin heavy chain V-D-J recombinationDNA polymerase betaHomo sapiens (human)
DNA biosynthetic processDNA polymerase betaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase betaHomo sapiens (human)
double-strand break repair via homologous recombinationDNA polymerase lambdaHomo sapiens (human)
DNA replicationDNA polymerase lambdaHomo sapiens (human)
base-excision repair, gap-fillingDNA polymerase lambdaHomo sapiens (human)
nucleotide-excision repairDNA polymerase lambdaHomo sapiens (human)
double-strand break repair via nonhomologous end joiningDNA polymerase lambdaHomo sapiens (human)
somatic hypermutation of immunoglobulin genesDNA polymerase lambdaHomo sapiens (human)
DNA biosynthetic processDNA polymerase lambdaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
damaged DNA bindingDNA polymerase betaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase betaHomo sapiens (human)
DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
protein bindingDNA polymerase betaHomo sapiens (human)
microtubule bindingDNA polymerase betaHomo sapiens (human)
lyase activityDNA polymerase betaHomo sapiens (human)
enzyme bindingDNA polymerase betaHomo sapiens (human)
metal ion bindingDNA polymerase betaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase betaHomo sapiens (human)
class I DNA-(apurinic or apyrimidinic site) endonuclease activityDNA polymerase betaHomo sapiens (human)
DNA bindingDNA polymerase lambdaHomo sapiens (human)
DNA-directed DNA polymerase activityDNA polymerase lambdaHomo sapiens (human)
protein bindingDNA polymerase lambdaHomo sapiens (human)
metal ion bindingDNA polymerase lambdaHomo sapiens (human)
5'-deoxyribose-5-phosphate lyase activityDNA polymerase lambdaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleusDNA polymerase betaHomo sapiens (human)
nucleoplasmDNA polymerase betaHomo sapiens (human)
cytoplasmDNA polymerase betaHomo sapiens (human)
microtubuleDNA polymerase betaHomo sapiens (human)
spindle microtubuleDNA polymerase betaHomo sapiens (human)
protein-containing complexDNA polymerase betaHomo sapiens (human)
nucleusDNA polymerase betaHomo sapiens (human)
site of double-strand breakDNA polymerase lambdaHomo sapiens (human)
nucleusDNA polymerase lambdaHomo sapiens (human)
nucleoplasmDNA polymerase lambdaHomo sapiens (human)
nucleusDNA polymerase lambdaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID449346Inhibition of HIV1 reverse transcriptase-mediated viral DNA synthesis at 10 uM by PAGE2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
The nucleoside analogue D-carba T blocks HIV-1 reverse transcription.
AID1155640Cytotoxicity against human HCT116 cells assessed as inhibition of cell proliferation after 24 hrs by WST-1 assay2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Polyketides from the cultured lichen mycobiont of a Vietnamese Pyrenula sp.
AID1155638Inhibition of calf thymus DNA polymerase alpha assessed as incorporation of [3H]dTTP into poly(dA)/oligo(dT)18 DNA-template primer after 60 mins2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Polyketides from the cultured lichen mycobiont of a Vietnamese Pyrenula sp.
AID1449540Inhibition of human DNA polymerase gamma using 5' end radiolabeled 24nt DNA/36nt DNA as primer/template after 120 mins by PAGE analysis2017Journal of medicinal chemistry, 07-13, Volume: 60, Issue:13
2'-Chloro,2'-fluoro Ribonucleotide Prodrugs with Potent Pan-genotypic Activity against Hepatitis C Virus Replication in Culture.
AID83421The inhibition of compound was determined by reverse transcriptase assay using DNA as template1989Journal of medicinal chemistry, Feb, Volume: 32, Issue:2
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent.
AID1323393Inhibition of recombinant human His-tagged DNA polymerase lambda assessed as reduction in [3H]dTTP incorporation using poly(dA)/oligo(dT)18 as template/primer preincubated for 10 mins followed by template/primer addition measured after 60 mins2016Journal of natural products, 07-22, Volume: 79, Issue:7
Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits of Garcinia schomburgkiana.
AID1323392Inhibition of calf thymus DNA polymerase alpha assessed as reduction in [3H]dTTP incorporation using poly(dA)/oligo(dT)18 as template/primer preincubated for 10 mins followed by template/primer addition measured after 60 mins2016Journal of natural products, 07-22, Volume: 79, Issue:7
Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits of Garcinia schomburgkiana.
AID1323394Cytotoxicity against human HeLa cells assessed as reduction in cell viability after 24 hrs by MTT assay2016Journal of natural products, 07-22, Volume: 79, Issue:7
Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits of Garcinia schomburgkiana.
AID1155639Inhibition of rat recombinant DNA polymerase beta expressed in Escherichia coli JMpbeta5 cells assessed as incorporation of [3H]dTTP into poly(dA)/oligo(dT)18 DNA-template primer after 60 mins2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Polyketides from the cultured lichen mycobiont of a Vietnamese Pyrenula sp.
AID1449539Inhibition of human DNA polymerase beta using 5' end radiolabeled 24nt DNA/48nt DNA as primer/template after 5 mins by PAGE analysis2017Journal of medicinal chemistry, 07-13, Volume: 60, Issue:13
2'-Chloro,2'-fluoro Ribonucleotide Prodrugs with Potent Pan-genotypic Activity against Hepatitis C Virus Replication in Culture.
AID83422The inhibition of compound was determined by reverse transcriptase assay using RNA as template1989Journal of medicinal chemistry, Feb, Volume: 32, Issue:2
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (101)

TimeframeStudies, This Drug (%)All Drugs %
pre-199035 (34.65)18.7374
1990's50 (49.50)18.2507
2000's9 (8.91)29.6817
2010's6 (5.94)24.3611
2020's1 (0.99)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.73

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 Index9.73 (24.57)
Research Supply Index4.64 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.97%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other102 (99.03%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]