Nucleoside Analogs

8-Hydroxy-2'-deoxyguanosine is a critical biomarker of oxidative stress and carcinogenesis.

N1-methyl-pseudouridine (1-Methylpseudouridine), a methylpseudouridine, outperforms 5 mC and 5 mC/N1-methyl-pseudouridine in translation. N1-methyl-pseudouridine in mRNA enhances translation through eIF2α-dependent and independent mechanisms by increasing ribosome density.

5-Hydroxymethyl-2’-deoxycytidine (5hmdC) is an oxidation derivative of 5-methyl-2'-deoxycytidine (5-mdC) in DNA. 5-Hydroxymethyl-2’-deoxycytidine may serve as a marker of irreversibly damaged cells.

N-6-Methyl-2-deoxyadenosine (m6dA) is an adenine nucleoside analogue. N-6-Methyl-2-deoxyadenosine targets nuclear processes and DNA replication machineries including WER, SATB1, TFAM, Jumu, SSBP1, DNA polymerase η and phage polymerase Gp90 exo⁻. N-6-Methyl-2-deoxyadenosine acts as a multifunctional epigenetic regulator that modulates transcription, DNA damage response, cell cycle, transposon silencing, stress adaptation, epigenetic crosstalk, and nucleosome organization in both prokaryotes and eukaryotes. N-6-Methyl-2-deoxyadenosine regulates mitochondrial epigenetic inheritance and is required for fear extinction memory in mice. N-6-Methyl-2-deoxyadenosine exhibits dysregulated levels in cancers. N-6-Methyl-2-deoxyadenosine can be used for the research of glioblastoma, triple negative breast cancer, and conditioned fear (fear extinction impairment).

2'-O-Methylcytidine is an orally active 2'-substituted nucleoside as a inhibitor of HCV replication with antiviral activity. 2'-O-Methylcytidine inhibits RNA-dependent RNA polymerase (NS5B)-catalyzed RNA synthesis in vitro, in a manner that is competitive with substrate nucleoside triphosphate.

2'-O-Methylguanosine is a modified nucleoside produced in tRNAs by the action of tRNA guanosine-2’-O-methyltransferase. 2'-O-Methylguanosine results in apoptotic changes of cells.

2’-O-Methyluridine is a modified nucleoside that can be found in T. thermophile tRNA. 2’-O-Methyluridine level in serum is decreased in patients with breast cancer.

Azvudine (RO-0622) is a potent nucleoside reverse transcriptase inhibitor (NRTI), with antiviral activity on HIV, HBV and HCV. Azvudine exerts highly potent inhibition on HIV-1 (EC₅₀s ranging from 0.03 to 6.92 nM) and HIV-2 (EC₅₀s ranging from 0.018 to 0.025 nM). Azvudine inhibits NRTI-resistant viral strains. Azvudine is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

2'-Deoxyinosine is the major product of 2'-deoxyadenosine in the absence of deoxycoformycin. 2'-Deoxyinosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency.

4-Thiothymidine is a thymidine analog with UVA photosensitizing properties. 4-Thiothymidine incorporates into the DNA of dividing cells via the thymidine kinase-mediated salvage pathway, replacing thymine and sensitizing cells to UVA irradiation, thereby inducing apoptosis. 4-Thiothymidine induces DNA damage upon UVA activation and inhibits DNA replication. 4-Thiothymidine is used in research related to non-melanoma skin malignancies such as squamous cell carcinoma.

Succinyladenosine, the metabolic product of dephosphorylation of intracellular adenylosuccinic acid (S-AMP) by cytosolic 5-nucleotidase, is a biochemical marker of adenylosuccinase (ASL) deficiency.

3-Methylcytidine, a urinary nucleoside, can be used as a biomarker of four different types of cancer: lung cancer, gastric cancer, colon cancer, and breast cancer.

Didanosine (2',3'-Dideoxyinosine; ddI) is a a potent and orally active dideoxynucleoside analogue, and also is a potent nucleoside reverse transcriptase inhibitor. Didanosine shows antiretroviral activity for HIV.

5-Bromouridine is a brominated uridine nucleoside. The triphosphate form of 5-Bromouridine, 5BrdUTP, can substitute for TTP as a substrate for DNA polymerase and be incorporated into nascent DNA strands, rendering the resulting 5-bromouridine-labeled DNA photosensitive to 300 nm UV irradiation; upon UV irradiation, the 5BrdU signal decreases and dU is generated, accompanied by DNA strand breaks and cross-link formation. 5-Bromouridine is useful for studies on nucleoside structure and halogenated nucleoside-labeled nucleic acids.

Tetrahydrouridine dihydrate (THU dihydrate) is potent inhibitor of cytidine deaminase (CDA), which competitively blocks the enzyme's active site more effectively than intrinsic cytidine.

5-Azidomethyl-uridine is a click chemistry reagent containing an azide group. The azide function is widely used for coupling to alkyne-containing fragments via the renowned Click reaction.

2'-Deoxy-2'-fluoro-5-iodouridine (FIRU) is a nucleoside analog. When labeled with ¹²³I, 2'-Deoxy-2'-fluoro-5-iodouridine accumulates highly selectively in tumors expressing the HSV1-tk gene. Radiolabeled 2'-Deoxy-2'-fluoro-5-iodouridine enables imaging of adenovirus-mediated HSV1-tk suicide gene transfer.

Bz-OMe-rA (N-Benzoyl-2′-O-methyladenosine) is a nucleoside analog with an N-benzoyl protecting group and a 2'-O-methyladenosine phosphoramidite unit. Bz-OMe-rA serves as a starting material for the chemical synthesis of the 5'-terminal cap structure of cytoplasmic polyhedrosis virus mRNA and also acts as a building block for solid-phase RNA oligonucleotide synthesis.

2'-Deoxycytidine-5'-monophosphate (5'-dCMP) is a compound that binds to the adenovirus terminal protein with a molecular weight of 80000 daltons. 2'-Deoxycytidine-5'-monophosphate forms a covalent complex with this protein and is associated with adenovirus DNA replication.

2'-Deoxyguanosine monohydrate is a nucleoside composed of guanine and 2'-deoxyribose, and it is one of the basic structural units of DNA. The oxidation products of 2'-Deoxyguanosine monohydrate may participate in DNA damage, which in turn may affect gene expression or induce cancer.