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T0642

Sigma-Aldrich

Tubercidin

from Streptomyces tubercidicus, ~95%

Sinónimos:

7-Deazaadenosine

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About This Item

Fórmula empírica (notación de Hill):
C11H14N4O4
Número de CAS:
69-33-0
Peso molecular:
266.25
Beilstein:
38498
Número CE:
200-703-4
Número MDL:
MFCD00056012
Código UNSPSC:
51102829
ID de la sustancia en PubChem:
24899902
NACRES:
NA.85

origen biológico

Streptomyces tubercidicus

Nivel de calidad

200

Ensayo

~95%

Formulario

powder

color

off-white

espectro de actividad antibiótica

fungi
parasites
viruses

Modo de acción

DNA synthesis | interferes

cadena 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

Clave InChI

HDZZVAMISRMYHH-KCGFPETGSA-N

Información sobre el gen

rat ... Adora1(29290)

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Descripción general

Chemical structure: nucleoside

Aplicación

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.

Acciones bioquímicas o fisiológicas

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

Otras notas

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

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H300

Consejos de prudencia

P264 - P301 + P310

Clasificaciones de peligro

Acute Tox. 2 Oral

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
0000276507
0000276507
067K2626
030H7255
010H72041

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Sigma-Aldrich

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Sigma-Aldrich

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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
Laura Piel et al.
Frontiers in cellular and infection microbiology, 8, 325-325 (2018-10-05)
Leishmania biomarker discovery remains an important challenge that needs to be revisited in light of our increasing knowledge on parasite-specific biology, notably its genome instability. In the absence of classical transcriptional regulation in these early-branching eukaryotes, fluctuations in transcript abundance
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
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