D5782
2′,3′-Dideoxycytidine
≥98% (HPLC), synthetic (organic), powder
Sinónimos:
ddC
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Fórmula empírica (notación de Hill):
C9H13N3O3
Número CAS:
Peso molecular:
211.22
NACRES:
NA.52
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
Beilstein/REAXYS Number:
654956
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Permítanos ayudarleNombre del producto
2′,3′-Dideoxycytidine, ≥98% (HPLC)
InChI
1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1
SMILES string
NC1=NC(=O)N(C=C1)[C@H]2CC[C@@H](CO)O2
InChI key
WREGKURFCTUGRC-POYBYMJQSA-N
biological source
synthetic (organic)
assay
≥98% (HPLC)
form
powder
color
colorless
mp
217-218 °C (lit.)
solubility
water: 50 mg/mL, clear, colorless to faintly yellow
storage temp.
−20°C
Quality Level
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Categorías relacionadas
Application
2′,3′-Dideoxycytidine is used:
- as a DNA chain-terminating nucleotide for DNA sequencing methods based on the Sanger chain-termination method
- as a nucleoside reverse transcriptase inhibitor (NRTI) to study its effects on the development of mechanical allodynia in aging mice
- as a mitochondrial DNA (mtDNA) replication inhibitor to inhibit the activation of cGAS-STING pathway and study its effects on signaling protein-stimulator of interferon genes (STING), cyclic GMP-AMP synthase (cGAS), and phospho-interferon regulator factor 3 (p-IRF3) expression in mouse hippocampal and microglial cells
- as an NRTI inhibitor to study its effects on the drug induced-mitochondrial toxicity in Caenorhabditis elegans
Biochem/physiol Actions
2′,3′-Dideoxycytidine (ddC), is an ionic compound and a nucleoside analog. It acts as a nucleoside reverse transcriptase inhibitor and exhibits therapeutic effects against human immunodeficiency virus (HIV) infection. 2′,3′-Dideoxycytidine possesses anti-adenovirus activity and inhibits the adenovirus polymerase.
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R Mentel et al.
Antiviral research, 47(2), 79-87 (2000-09-21)
The antiviral activity of 2',3'-dideoxycytidine (ddC) has been investigated in a mouse pneumonia model. Consolidation of lung, histopathological changes, DNA synthesis as well as levels of TNFalpha were assayed. In this in vivo model, the oral administration of ddC twice
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A series of 26 diarylpyrimidines, characterized by the hydroxymethyl linker between the left wing benzene ring and the central pyrimidine, were synthesized and evaluated for in vitro anti-HIV activity. Most of the compounds exhibited moderate to excellent activities against wild-type
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