T0642

Tubercidin

from Streptomyces tubercidicus, ~95%

• Synonym(s): 7-Deazaadenosine
• Empirical Formula (Hill Notation): C₁₁H₁₄N₄O₄
• CAS Number: 69-33-0
• Molecular Weight: 266.25
• UNSPSC Code: 51102829
• NACRES: NA.85
• PubChem Substance ID: 24899902
• EC Number: 200-703-4
• Beilstein/REAXYS Number: 38498
• MDL number: MFCD00056012

Properties

• biological source: Streptomyces tubercidicus
• Quality Level: 200
• assay: ~95%
• form: powder
• color: off-white
• antibiotic activity spectrum: fungi, parasites, viruses
• mode of action: DNA synthesis | interferes
• SMILES string: O[C@H]1[C@@H](O)[C@H](N2C=CC3=C2N=CN=C3N)O[C@@H]1CO
• InChI: 1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
• InChI key: HDZZVAMISRMYHH-KCGFPETGSA-N
• Gene Information: rat ... Adora1(29290)

Description

General description

Chemical structure: nucleoside

Application

It is used to study tubercidin′s mechanism of toxicity, tubercidin resistance and is used as a selection agent. Tubercidin is used to study RNAi silencing[1]. It is used to study the role of transmethylation in chemotaxis of eukaryotic cells[2].

Biochem/physiol Actions

Toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. Mode of action: Inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata.

Tubercidin is a toxic adenosine analog with antiviral, antitrypanosomal, and antifungal functions. It inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal, inhibits mammalian SAH hydrolase (SAHH), and blocks purine biosynthesis in Candida famata. Tubercidin inhibits glycolysis in Trypanosoma brucei[1]. Tubercidin inhibits both chemotaxis and chemotaxis-dependent cell streaming of Dictyostelium, and chemotaxis of neutrophils at concentrations that have little effect on cell viability[2].

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H300
• pcodes: P264 - P301 + P310
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges