8-Bromo-2'-deoxyguanosine, 8-Br-dG, C10H12BrN5O4 , CAS 13389-03-2, 2-Amino-8-bromo-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one, 8-bromo-2'-dG, 8-Br-2'-dG. Mw: 346.14 g/mol.
The organobromine compound 8-bromo-2’-deoxyguanosine is a modified 2'-deoxyguanosine having a bromo substituent at position 8 of the guanine ring system and a member of guanosines. A dG to 8Br-dG substitution is useful approach for the study of DNA and RNA structures, for example, the study of DNA and RNA G-quadruplexes.
Purine nucleosides with bulky substituents at the 8-position favor the syn conformation at the N-glycoside bond. The substitution of Guanosine by 8-bromoguanine on an alternating CG decamer stabilizes the Z-form in such a way that the B-form is not observed. Also, measurements of melting temperatures indicated that duplexes in which 8-bromo-2'-deoxyguanosine paired with natural bases are less stable. The incorporation of 8-bromo-2'-deoxyguanosine into oligonucleotides allows probing syn-anti conformational preferences in G-quartet structures. The bromination of poly (d(GC)) stabilizes the Z-DNA form. For example, a modification of 38% 8-bromoguanine and 18% 5-bromocytosine is enough to favor a stable Z-DNA helix in physiological conditions.
A single dG to 8Br-dG substitution at position 21 in oligonucleotide d[(G4C2)3G4] and optimization of folding conditions enabled the formation of mostly a single G-quadruplex species.
Molecular models of 8-Br-dG, dG, and the GGGGCC repeat derived from the solution structure of a DNA quadruplex containing ALS and FTD related GGGGCC repeat stabilized by 8-bromodeoxyguanosine substitution [PDB 2N2D].
Reference
Brčić J, Plavec J. Solution structure of a DNA quadruplex containing ALS and FTD related GGGGCC repeat stabilized by 8-bromodeoxyguanosine substitution. Nucleic Acids Res. 2015 Sep 30;43(17):8590-600. doi: 10.1093/nar/gkv815. Epub 2015 Aug 7. PMID: 26253741; [PMCID: PMC4787828].
Fábrega, C., Macías, M.J., Eritja, R.; Synthesis and properties of oligonucleotides containing 8-bromo-2’-deoxyguanosine. Nucleosides Nucleotides & Nucleic Acids, 20(3), 251- 260 (2001). PMID: 11393401, doi: 10.1081/NCN-100002085. [ACS]
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