Bromodeoxyuridine

Bromodeoxyuridine (5-bromo-2'-deoxyuridine, BrdU, BUdR, BrdUrd, broxuridine) is a synthetic nucleoside that is an analog of thymidine. BrdU is commonly used in the detection of proliferating cells in living tissues.[1] 5-Bromodeoxycytidine is deaminated to form BrdU.[2]

Bromodeoxyuridine

Identifiers
CAS Number	59-14-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL222280 N
ChemSpider	5294121 Y 5813 N
ECHA InfoCard	100.000.378
MeSH	Bromodeoxyuridine
PubChem CID	6035
UNII	G34N38R2N1 Y
CompTox Dashboard (EPA)	DTXSID7033105
InChI InChI=1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1 N Key: WOVKYSAHUYNSMH-RRKCRQDMSA-N N InChI=1/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1 Key: WOVKYSAHUYNSMH-RRKCRQDMBM
SMILES c1c(c(=O)[nH]c(=O)n1[C@H]2C[C@@H]([C@H](O2)CO)O)Br
Properties
Chemical formula	C9H11BrN2O5
Molar mass	307.100 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

BrdU can be incorporated into the newly synthesized DNA of replicating cells (during the S phase of the cell cycle during which DNA is replicated), substituting for thymidine during DNA replication. Antibodies specific for BrdU can then be used to detect the incorporated chemical (see immunohistochemistry), thus indicating cells that were actively replicating their DNA. Binding of the antibody requires denaturation of the DNA, usually by exposing the cells to acid or heat.[3]

BrdU can be passed to daughter cells upon replication.[4] BrdU has been demonstrated to be detectable over two years post-infusion.[5]

Because BrdU can replace thymidine during DNA replication, it can cause mutations, and its use is therefore potentially a health hazard.[3] However, because it is neither radioactive nor myelotoxic at labeling concentrations, it is widely preferred for in vivo studies of cancer cell proliferation.[6][7] However, at radiosensitizing concentrations, BrdU becomes myelosuppressive, thus limiting its use for radiosensitizing.[2]

BrdU differs from thymidine in that BrdU substitutes a bromine atom for thymidine's CH₃ group. The Br substitution can be used in X-ray diffraction experiments in crystals containing either DNA or RNA. The Br atom acts as an anomalous scatterer and its larger size will affect the crystal's X-ray diffraction enough to detect isomorphous differences as well.[8][9]

Bromodeoxyuridine releases gene silencing caused by DNA methylation.[10]

BrdU can also be used to identify microorganisms that respond to specific carbon substrates in aquatic[11] and soil[12] environments. A carbon substrate added to incubations of environmental samples will cause the growth of microorganisms that can utilize that substrate. These microorganisms will then incorporate BrdU into their DNA as they grow. Community DNA can then be isolated and BrdU-labeled DNA purified using an immunocapture technique.[13] Subsequent sequencing of the labeled DNA can then be used to identify the microbial taxa that participated in the degradation of the added carbon source.

However, it is not certain whether all microbes present in an environmental sample can incorporate BrdU into their biomass during de novo DNA synthesis. Therefore, a group of microorganisms may respond to a carbon source but go undetected using this technique. Additionally, this technique is biased towards identifying microorganisms with A- and T-rich genomes.