5-methyl-2-thiouridine

Names

[ Name ]:
5-methyl-2-thiouridine

[Synonym ]:
2-Sulfamyl-4-methyl-phenyl-thioharnstoff
5-Methyl-2-thio-uridin
5-methyl-2-thioureido-benzenesulfonamide
5-Methyl-1-pentofuranosyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone
4-Methyl-2-sulphamylphenylthiourea
Benzenesulfonamide,2-[(aminothioxomethyl)amino]-5-methyl

Biological Activity

[Description]:

5-Methyl-2-thiouridine (2-Thio-5-methyluridine) is a purine nucleoside analogue. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Research Areas >> Others

[References]

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Chemical & Physical Properties

[ Density]:
1.63g/cm3

[ Melting Point ]:
216-219 °C

[ Molecular Formula ]:
C₁₀H₁₄N₂O₅S

[ Molecular Weight ]:
274.29

[ Exact Mass ]:
274.06200

[ PSA ]:
140.06000

[ Index of Refraction ]:
1.703

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Molecular mechanism of codon recognition by tRNA species with modified uridine in the first position of the anticodon.

Proc. Natl. Acad. Sci. U. S. A. 82 , 4905-4909, (1985)

Proton NMR analyses have been made to elucidate the conformational characteristics of modified nucleotides as found in the first position of the anticodon of tRNA [derivatives of 5-methyl-2-thiouridin...

CD spectra of 5-methyl-2-thiouridine in tRNA-Met-f from an extreme thermophile.

Nucleic Acids Res. 3 , 1703-1713, (1976)

5-Methyl-2-thiouridine (S) in tRNA-Met-f from an extreme thermophile is located in the TpsiC region, replacing T, and has a positive CD band centered at 310 nm. Upon heating, the profiles of the chang...

Stabilizing contributions of sulfur-modified nucleotides: crystal structure of a DNA duplex with 2'-O-[2-(methoxy)ethyl]-2-thiothymidines.

Nucleic Acids Res. 33 , 5297-5307, (2005)

Substitution of oxygen atoms by sulfur at various locations in the nucleic acid framework has led to analogs such as the DNA phosphorothioates and 4'-thio RNA. The phosphorothioates are excellent mimi...