D5782
2′,3′-Dideoxycytidine
≥98% (HPLC)
Synonym(s):
ddC
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All Photos(4)
About This Item
Empirical Formula (Hill Notation):
C9H13N3O3
CAS Number:
Molecular Weight:
211.22
Beilstein:
654956
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.52
Recommended Products
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
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
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Alexander N Patananan et al.
Cell reports, 33(13), 108562-108562 (2020-12-31)
Generating mammalian cells with desired mitochondrial DNA (mtDNA) sequences is enabling for studies of mitochondria, disease modeling, and potential regenerative therapies. MitoPunch, a high-throughput mitochondrial transfer device, produces cells with specific mtDNA-nuclear DNA (nDNA) combinations by transferring isolated mitochondria from
Anindya Roy Chowdhury et al.
iScience, 23(8), 101370-101370 (2020-08-02)
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
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
Jun Xiang et al.
International journal of pharmaceutics, 231(1), 57-66 (2001-11-24)
Permeation of 2',3'-dideoxycytidine (ddC), an ionic compound, through buccal mucosa was investigated in this in vitro study to identify the major permeation barrier within the epithelium of buccal mucosa and explore the feasibility of transbuccal delivery of ddC. In vitro
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