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Documentos Principais

D5782

Sigma-Aldrich

2′,3′-Dideoxycytidine

≥98% (HPLC)

Sinônimo(s):

ddC

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About This Item

Fórmula empírica (Notação de Hill):
C9H13N3O3
Número CAS:
Peso molecular:
211.22
Beilstein:
654956
Número MDL:
Código UNSPSC:
41106305
ID de substância PubChem:
NACRES:
NA.52

fonte biológica

synthetic (organic)

Ensaio

≥98% (HPLC)

Formulário

powder

cor

colorless

pf

217-218 °C (lit.)

solubilidade

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

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

WREGKURFCTUGRC-POYBYMJQSA-N

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Aplicação

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

Ações bioquímicas/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

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

Classificações de perigo

Carc. 2

Código de classe de armazenamento

11 - Combustible Solids

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, Gloves, type P3 (EN 143) respirator cartridges


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Maja M Janas et al.
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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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Cellular & molecular immunology, 18(9), 2211-2223 (2020-05-14)
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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This study shows that multiple modes of mitochondrial stress generated by partial mtDNA depletion or cytochrome c oxidase disruption cause ryanodine receptor channel (RyR) dysregulation, which instigates the release of Ca2+ in the cytoplasm of C2C12 myoblasts and HCT116 carcinoma
Didier Desmaële et al.
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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