All Photos(3)

T0642

Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

Synonym(s):
7-Deazaadenosine
Empirical Formula (Hill Notation):
C11H14N4O4
CAS Number:
Molecular Weight:
266.25
Beilstein:
38498
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces tubercidicus

Quality Level

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

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Related Categories

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1B - Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Aurelie Bourderioux et al.
Journal of medicinal chemistry, 54(15), 5498-5507 (2011-06-30)
A series of 7-aryl- and 7-hetaryl-7-deazaadenosines was prepared by the cross-coupling reactions of unprotected or protected 7-iodo-7-deazaadenosines with (het)arylboronic acids, stannanes, or zinc halides. Nucleosides bearing 5-membered heterocycles at the position 7 exerted potent in vitro antiproliferative effects against a...
Misaki Matsui et al.
Oncogenesis, 9(6), 60-60 (2020-06-17)
The nucleus of mammalian cells is compartmentalized by nuclear bodies such as nuclear speckles, however, involvement of nuclear bodies, especially nuclear speckles, in DNA repair has not been actively investigated. Here, our focused screen for nuclear speckle factors involved in...
Hodaya Hochberg-Laufer et al.
Nucleic acids research, 47(9), 4778-4797 (2019-03-14)
Eukaryotic cells contain sub-cellular compartments that are not membrane bound. Some structures are always present, such as nuclear speckles that contain RNA-binding proteins (RBPs) and poly(A)+ RNAs. Others, like cytoplasmic stress granules (SGs) that harbor mRNAs and RBPs, are induced...
Li-Xing Zhao et al.
Journal of natural products, 74(9), 1990-1995 (2011-08-30)
Our current natural product program utilizes new actinomycetes originating from unexplored and underexplored ecological niches, employing cytotoxicity against a selected panel of cancer cell lines as the preliminary screen to identify hit strains for natural product dereplication, followed by mechanism-based...
Mark E Drew et al.
The Journal of biological chemistry, 278(47), 46596-46600 (2003-09-16)
We used an RNA interference (RNAi) library in a forward genetic selection to study the mechanism of toxicity of tubercidin (7-deazaadenosine) to procyclic Trypanosoma brucei. Following transfection of cells with an RNAi-based genomic library, we used 5 microm tubercidin to...

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