T0642
Tubercidin
from Streptomyces tubercidicus, ~95%
Sinônimo(s):
7-Deazaadenosine
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About This Item
Fórmula empírica (Notação de Hill):
C11H14N4O4
Número CAS:
Peso molecular:
266.25
Beilstein:
38498
Número CE:
Número MDL:
Código UNSPSC:
51102829
ID de substância PubChem:
NACRES:
NA.85
Produtos recomendados
fonte biológica
Streptomyces tubercidicus
Nível de qualidade
Ensaio
~95%
Formulário
powder
cor
off-white
espectro de atividade do antibiótico
fungi
parasites
viruses
Modo de ação
DNA synthesis | interferes
cadeia de caracteres 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
chave InChI
HDZZVAMISRMYHH-KCGFPETGSA-N
Informações sobre genes
rat ... Adora1(29290)
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Categorias relacionadas
Descrição geral
Chemical structure: nucleoside
Aplicação
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.
Ações bioquímicas/fisiológicas
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.
Outras notas
Keep container tightly closed in a dry and well-ventilated place.
Palavra indicadora
Danger
Frases de perigo
Declarações de precaução
Classificações de perigo
Acute Tox. 2 Oral
Código de classe de armazenamento
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
Equipamento de proteção individual
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
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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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