T0642
杀结核菌素
from Streptomyces tubercidicus, ~95%
别名:
7-Deazaadenosine
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关于此项目
经验公式（希尔记法）:
C11H14N4O4
化学文摘社编号:
分子量:
266.25
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
EC Number:
200-703-4
Beilstein/REAXYS Number:
38498
MDL number:
InChI key
HDZZVAMISRMYHH-KCGFPETGSA-N
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
SMILES string
O[C@H]1[C@@H](O)[C@H](N2C=CC3=C2N=CN=C3N)O[C@@H]1CO
biological source
Streptomyces tubercidicus
assay
~95%
form
powder
color
off-white
antibiotic activity spectrum
fungi, parasites, viruses
mode of action
DNA synthesis | interferes
Quality Level
Gene Information
rat ... Adora1(29290)
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
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.
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 2 Oral
存储类别
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
法规信息
涉药品监管产品
此项目有
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
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
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