5-Bromo-2'-Deoxycytidine
Basic information
- CAS
1022-79-3- Standard SMILES
Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1Br- InChIKey
KISUPFXQEHWGAR-RRKCRQDMSA-N- Molecular formula
- C9H12BrN3O4
- Average molar mass
- 306.11 g/mol
- Monoisotopic mass
- 305.00112
Overview
5-Bromo-2'-deoxycytidine. Can be incorporated into DNA in the presence of DNA polymerase, replacing dCTP.
Names & identifiers
- Preferred name
- 5-Bromo-2'-Deoxycytidine
- IUPAC
- 4-amino-5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- English name
- 5-Bromo-2'-deoxycytidine
- Molecular formula
- C9H12BrN3O4
- Molecular weight
- 306.11
Names & synonyms
5-Bromo-2'-deoxycytidine1022-79-3Bromodeoxycytidine5-BromodeoxycytidineCYTIDINE, 5-BROMO-2'-DEOXY-6M3TP1AIBHNSC-61765DTXSID30907194RefChem:1215745 Bromo 2' DeoxycytidineDTXCID001775571213-824-2
Show more names
5-BR-DCAids0723785-Br-2'-dCAids-0723785-Br-2'-deoxycytidine2'-DEOXY-5-BROMOCYTIDINE5-bromo-2’-deoxy-cytidin
4-Amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-oneC9H12BrN3O4MFCD000474965-bromo-2'-deoxy-d-cytidineNSC 617654-amino-5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one4-amino-5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one5-Bromo-dCrd
Database identifiers
- CAS
1022-79-3- PubChem CID
- 472175
- ChEMBL
CHEMBL386413- UNII
- 6M3TP1AIBH
- EC Number
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 108 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 398
Physicochemical properties
- Boiling point
- 510.8 · 510.8±60.0 °C(Predicted)
- Density
- 2.12 · 2.12±0.1 g/cm3(Predicted)
- RTECS
- 3705000 · HA3705000
- storage temp.
- 0 °C · Store at 0°C
- solubility
- DMSO: SolubleWater: Soluble
- pka
- 14.03 · 14.03±0.60(Predicted)
- form
- Powder
- color
- White to Pale Yellow
- CAS DataBase Reference
- 1022 · 1022-79-3(CAS DataBase Reference)
- FDA UNII
- 6 M3TP1AIBH · 6M3TP1AIBH
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Hazard Codes
- Xn
- Risk Statements
- 40 · 40
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesCarc. 2 (100%)
Safety data
- hs_code
- 29389090
- risk_code
- 40
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-36
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Uses5-Bromo-2'-deoxycytidine (BrdC) is a brominated derivative of the deoxyribonucleoside 2’-deoxycytidine. It induces DNA cross-linking and the formation of DNA strand breaks when incorporated into a DNA fragment in place of cytosine and exposed to UVB damage. BrdC inhibits cytopathogenicity induced by herpes simplex virus 1 (HSV-1) and HSV-2 in infected primary rabbit kidney (PRK) cells (MICs = 0.2-0.3 μg/ml). It decreases the survival of U-1 melanoma cells and AG1522 non-cancerous cells and induces sensitization of both to radiation. BrdC also sensitizes tumors to radiation and reduces tumor volume in a mouse model of glioma using RT-2 cells infused with an adenovirus expressing HSV thymidine kinase (ADV-TK) after implantation. In vivo, BrdC is converted to 5-bromo-2'-deoxyuridine (BrdU) and has been used to label cardiac progenitor cells (CPCs) in a rat model of myocardial infarction.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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