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T0642

Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

Synonyme(s) :

7-Deazaadenosine

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About This Item

Formule empirique (notation de Hill):
C11H14N4O4
Numéro CAS:
69-33-0
Poids moléculaire :
266.25
Beilstein:
38498
Numéro CE :
200-703-4
Numéro MDL:
MFCD00056012
Code UNSPSC :
51102829
ID de substance PubChem :
24899902
Nomenclature NACRES :
NA.85

Source biologique

Streptomyces tubercidicus

Niveau de qualité

200

Essai

~95%

Forme

powder

Couleur

off-white

Spectre d'activité de l'antibiotique

fungi
parasites
viruses

Mode d’action

DNA synthesis | interferes

Chaîne SMILES 

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

Clé InChI

HDZZVAMISRMYHH-KCGFPETGSA-N

Informations sur le gène

rat ... Adora1(29290)

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Description générale

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300

Conseils de prudence

P264 - P301 + P310

Classification des risques

Acute Tox. 2 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
067K2626
072K8632
042K8624
081K8616
056H7070

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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
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
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
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
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