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D5782

2′,3′-Dideoxycytidine

Name: 2&#8242;,3&#8242;-Dideoxycytidine
Brand: SIGMA

≥98% (HPLC), synthetic (organic), powder

Synonym(s):

ddC

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₃N₃O₃

CAS Number:

7481-89-2

Molecular Weight:

211.22

NACRES:

NA.52

PubChem Substance ID:

24278377

UNSPSC Code:

41106305

MDL number:

MFCD00012188

Beilstein/REAXYS Number:

654956

Assay:

≥98% (HPLC)

Biological source:

synthetic (organic)

Form:

powder

Solubility:

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

Storage temp.:

−20°C

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Properties

Product Name

2′,3′-Dideoxycytidine, ≥98% (HPLC)

biological source

synthetic (organic)

Quality Segment

200

assay

≥98% (HPLC)

form

powder

feature

PCR Additives

technique(s)

PCR: suitable

color

colorless

input

crude DNA

mp

217-218 °C (lit.)

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

WREGKURFCTUGRC-POYBYMJQSA-N

Description

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.

pictograms

GHS08

signalword

Warning

hcodes

H351

pcodes

P281

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c