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T0642 Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

Synonym: 7-Deazaadenosine

  • CAS Number 69-33-0

  • Empirical Formula (Hill Notation) C11H14N4O4

  • Molecular Weight 266.25

  •  Beilstein/REAXYS Number 38498

  •  EC Number 200-703-4

  •  MDL number MFCD00056012

  •  PubChem Substance ID 24899902

  •  NACRES NA.85

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Mechanism of Action, Antifungal,
Quality Level   200
biological source   Streptomyces tubercidicus
assay   ~95%
form   powder
color   off-white
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   fungi
  parasites
  viruses
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. It is used to study the role of transmethylation in chemotaxis of eukaryotic cells.

Packaging

10 mg in poly bottle

50, 250 mg in glass bottle

Biochem/physiol Actions

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. Tubercidin inhibits both chemotaxis and chemotaxis-dependent cell streaming of Dictyostelium, and chemotaxis of neutrophils at concentrations that have little effect on cell viability.

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.

Other Notes

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

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
UY8870000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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