| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C10H12BrN5O4 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
8-Bromo-2'-deoxyguanosine is an inflammation-related DNA halogenated adduct and an early biomarker of inflammation-induced oxidative tissue damage; its formation precedes that of oxidative and nitrative products and can occur via the MPO-H2O2-Cl⁻-Br⁻ system. It serves as the immunogen for preparing the monoclonal antibody mAb8B3, used to detect early DNA modifications in preclinical models, and its urinary level rises significantly in inflammatory disease models. It can also form in the dermis of UV-B-irradiated mice, an effect significantly reduced by extract of Coprinus comatus, and it can be used in studies of inflammatory diseases, diabetes, hepatocellular carcinoma, and UV-B-induced skin inflammation[1][2][3]. It is supplied as an off-white to light yellow solid (C10H12BrN5O4, MW 346.14) at 98.0% purity.
Physical & Chemical Properties
| CAS Number | 13389-03-2 |
|---|---|
| Molecular Formula | C10H12BrN5O4 |
| Molecular Weight | 346.14 g/mol |
| Purity | 98.0% |
| Appearance | Solid |
| Color | Off-white to light yellow |
| SMILES | OC[C@@H]1[C@@H](O)C[C@H](N2C(Br)=NC3=C2N=C(N)NC3=O)O1 |
| Signaling Pathway | Cell Cycle/DNA Damage |
| Solubility | In Vitro: DMSO: ≥ 100 mg/mL (288.90 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) * "≥" means soluble, but saturation unknown. |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 6 months; -20°C, 1 month. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | ≥ 100 mg/mL (288.90 mM) | use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
Competitive indirect ELISA shows high, specific cross-reactivity of the monoclonal antibody mAb8B3 toward 8-Bromo-2'-deoxyguanosine (10-3-100 mM; overnight at 4 °C); reactivity toward 8-BrdG is 10-fold greater than toward 8-CldG[1]. In a myeloperoxidase-mediated inflammatory system, 1,000 μM ergothioneine derived from Coprinus comatus, or 1 mg/mL of Coprinus comatusextract, inhibits the activity of 8-Bromo-2'-deoxyguanosine almost completely[2]. A competitive ELISA assay without cells shows that 8-Bromo-2'-deoxyguanosine arises when 2'-deoxyguanosine reacts with hypobromous acid, and that this formation is inhibited by ergothioneine and Coprinus comatus extract[3].
In Vivo
8-Bromo-2'-deoxyguanosine is an early, transient biomarker for inflammation induced by LPS in rat liver and urine. Hepatic levels stay comparable at 6 and 12 h after LPS treatment, and increased urinary excretion can be detected as early as 1 day after LPS treatment[1]. A conjugate of 8-Bromo-2'-deoxyguanosine with keyhole limpet hemocyanin (0.2 mg/mL-0.6 mg/mL; given by intraperitoneal or intravenous injection) elicits a specific monoclonal antibody (mAb8B3). The antibody reacts with 8-Bromo-2'-deoxyguanosine (8-BrdG) approximately 10-fold more strongly than with 8-CldG and shows no significant cross-reactivity with 8-bromoguanosine[1].
| Animal Model | BALB/c mice (6-week-old female; immunization model)[1] |
|---|---|
| Dosage | The conjugate of 8-Bromo-2'-deoxyguanosine and keyhole limpet hemocyanin: 0.6 mg/mL (initial immunization); 0.2 mg/mL (boost); 0.5 mg/mL (final boost) |
| Administration | i.p. (initial immunization; boost); i.v. (final boost); 2 weeks interval between initial immunization and boost; 3 days after final boost |
| Result | Generated a monoclonal antibody (mAb8B3) that recognizes both 8-BrdG and 8-CldG, with ~10-fold higher reactivity to 8-BrdG relative to 8-CldG, and shows no significant cross-reactivity to 8-OxodG, 8-bromoguanosine, guanosine, or unmodified deoxyguanosine. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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