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Chemical Structure| 14985-44-5 Chemical Structure| 14985-44-5

Structure of 8-Bromo-2'-deoxyadenosine
CAS No.: 14985-44-5

Chemical Structure| 14985-44-5

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Synonyms: 8-Bromo-9-(2-deoxypentofuranosyl)-9H-purin-6-amine

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Product Citations

Product Citations

Datta, Magdalena ; Szczyrba, Adrian ; Czaja, Anna ; Zdrowowicz, Magdalena ; Demkowicz, Sebastian ; Rak, Janusz

Abstract: To verify whether the recently synthesized nucleoside, 8-(4-Trifluoromethoxy)benzylamino-2′-deoxyadenosine, can sensitize tumorous cells to X-rays, radiolytic and in vitro studies have been conducted. Molecular modeling demonstrated that excess electrons should lead to efficient dissociative electron attachment (DEA) to dA-NHbenzylOCF3 resulting in a radical product that can potentially damage DNA. The computationally predicted DEA process was confirmed via stationary radiolysis of a dA-NHbenzylOCF3 water solution followed by LC-MS analysis of the obtained radiolytes. Moreover, dA-NHbenzylOCF3 was tested against its cytotoxicity and clonogenicity. We showed that the modified nucleoside is not cytotoxic to PC3, MCF-7, and HaCaT cell lines. Additionally, the clonogenic test exhibited a statistically significant radiosensitization of PC3 and MCF-7 cells to X-rays. On the other hand, flow cytometry assays demonstrated that the action of dA-NHbenzylOCF3 is related to its influence on the cell cycle rather than the level of DNA double-strand breaks induced by ionizing radiation. Our findings indicate that the compound enters the cell and predominantly localizes in the cytoplasm, with a notable amount also detected in the nucleus. Moreover, we established that the compound is not phosphorylated by cellular kinases nor integrated into genomic DNA by the replication machinery.

Keywords: Radiosensitizing nucleosides ; Dissociative electron attachment ; Clonogenic assay ; MTT test ; Cell cycle

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Product Details of 8-Bromo-2'-deoxyadenosine

CAS No. :14985-44-5
Formula : C10H12BrN5O3
M.W : 330.14
SMILES Code : O[C@@H]1[C@@H](CO)O[C@@H](N2C(Br)=NC3=C(N)N=CN=C23)C1
Synonyms :
8-Bromo-9-(2-deoxypentofuranosyl)-9H-purin-6-amine
MDL No. :MFCD01630970

Safety of 8-Bromo-2'-deoxyadenosine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Related Pathways of 8-Bromo-2'-deoxyadenosine

DNA

Isoform Comparison

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Preparing Stock Solutions 1mg 5mg 10mg

1 mM

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3.03mL

0.61mL

0.30mL

15.15mL

3.03mL

1.51mL

30.29mL

6.06mL

3.03mL

 

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