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T0642

Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

Synonyma:

7-Deazaadenosine

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C11H14N4O4
Číslo CAS:
69-33-0
Molekulová hmotnost:
266.25
Beilstein/REAXYS Number:
38498
EC Number:
200-703-4
MDL number:
MFCD00056012
UNSPSC Code:
51102829
PubChem Substance ID:
24899902
NACRES:
NA.85

biological source

Streptomyces tubercidicus

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)

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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.

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
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Sigma-Aldrich

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Ping Ding et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(48), 14385-14396 (2010-12-01)
Nucleobase-directed spin-labeling by the azide-alkyne 'click' (CuAAC) reaction has been performed for the first time with oligonucleotides. 7-Deaza-7-ethynyl-2'-deoxyadenosine (1) and 5-ethynyl-2'-deoxyuridine (2) were chosen to incorporate terminal triple bonds into DNA. Oligonucleotides containing 1 or 2 were synthesized on a
Marco Singer et al.
Journal of the American Chemical Society, 132(24), 8372-8377 (2010-05-21)
Photochromic nucleosides were designed that combine the structural features and molecular recognition properties of nucleic acids with the light-sensitivity of diarylethenes. Target compounds 1a-c consist of a 7-deazaadenosine unit that is linked to a thiophene as the second aryl functionality
Feng Sun et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 879(3-4), 285-290 (2011-01-05)
A sensitive and selective LC-MS/MS based bioanalytical method was developed and validated for the quantification of 3-deazaneplanocin A (DZNep), a novel epigenetic anti-tumor drug candidate, in Sprague-Dawley (SD) rat biosamples (plasma, urine, feces and tissue samples). The method comprises a
David B Olsen et al.
Antimicrobial agents and chemotherapy, 55(2), 937-939 (2010-12-01)
Efforts to develop novel, interferon-sparing therapies for treatment of chronic hepatitis C (HCV) infection are contingent on the ability of combination therapies consisting of direct antiviral inhibitors to achieve a sustained virologic response. This work demonstrates a proof of concept
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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