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Merck
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Documentos

D5782

Sigma-Aldrich

2′,3′-Dideoxycytidine

≥98% (HPLC)

Sinónimos:

ddC

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About This Item

Fórmula empírica (notación de Hill):
C9H13N3O3
Número de CAS:
7481-89-2
Peso molecular:
211.22
Beilstein:
654956
Número MDL:
MFCD00012188
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
24278377
NACRES:
NA.52

origen biológico

synthetic (organic)

Análisis

≥98% (HPLC)

formulario

powder

color

colorless

mp

217-218 °C (lit.)

solubilidad

water: 50 mg/mL, clear, colorless to faintly yellow

temp. de almacenamiento

−20°C

cadena SMILES

NC1=NC(=O)N(C=C1)[C@H]2CC[C@@H](CO)O2

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

Clave InChI

WREGKURFCTUGRC-POYBYMJQSA-N

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Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Health hazard
GHS08

Palabra de señalización

Warning

Frases de peligro

H351

Consejos de prudencia

P281

Clasificaciones de peligro

Carc. 2

Código de clase de almacenamiento

11 - Combustible Solids

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, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Maja M Janas et al.
Nucleic acids research, 47(7), 3306-3320 (2019-03-02)
For oligonucleotide therapeutics, chemical modifications of the sugar-phosphate backbone are frequently used to confer drug-like properties. Because 2'-deoxy-2'-fluoro (2'-F) nucleotides are not known to occur naturally, their safety profile was assessed when used in revusiran and ALN-TTRSC02, two short interfering
Shuang-Xi Gu et al.
Bioorganic & medicinal chemistry, 19(17), 5117-5124 (2011-08-10)
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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Exposure to ionizing radiation, a physical treatment that inactivates live tumor cells, has been extensively applied to enhance the antitumor responses induced by cancer cell vaccines in both animal research and human clinical trials. However, the mechanisms by which irradiated
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Journal of controlled release : official journal of the Controlled Release Society, 161(2), 609-618 (2011-08-16)
Squalene is a triterpene widely distributed in nature that is an intermediate in the cholesterol biosynthesis pathway. The remarkable dynamic folded conformation of squalene has been used to chemically conjugate this lipid with various therapeutic molecules to construct nanoassemblies of
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