A brominated derivative of guanosine
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8-Bromoguanosine

Item No. 18152

Technical Information
Formal Name
8-bromo-guanosine
CAS Number
4016-63-1
Synonyms
  • 2-Amino-8-bromo-6-hydroxypurine riboside
  • NSC 79211
  • NSC 174257
Molecular Formula
C10H12BrN5O5
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 20 mg/ml
λmax
261 nm
SMILES
O=C1C2=C(N([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C(Br)=N2)N=C(N)N1
InChi Code
InChI=1S/C10H12BrN5O5/c11-9-13-3-6(14-10(12)15-7(3)20)16(9)8-5(19)4(18)2(1-17)21-8/h2,4-5,8,17-19H,1H2,(H3,12,14,15,20)/t2-,4-,5-,8-/m1/s1
InChi Key
ASUCSHXLTWZYBA-UMMCILCDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    8-Bromoguanosine is a brominated derivative of guanosine. Purine nucleobases with bromine at position eight are known to preferentially adopt the syn conformation as nucleosides and, thus, can be used to reduce the conformational heterogeneity of RNA to potentially enhance its function.1 It is reported to activate lymphocytes through an intracellular mechanism to exert immunostimulatory effects.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yajima, R., Proctor, D.J., Kierzek, R., et alA conformationally restricted guanosine analog reveals the catalytic relevance of three structures of an RNA enzyme. Chem. Biol. 14, 23-30 (2007).

    2. Goodman, M.G., and Weigle, W.O. Intracellular lymphocyte activation and carrier-mediated transport of C8-substituted guanine ribonucleosides. Proc. Natl. Acad. Sci. USA 81, 862-866 (1984).

    3. Giorgio, S., and Barao, S.C. Intracellular Leishmania amazonensis killing induced by the guanine nucleoside 8-bromoguanosine. Rev. Inst. Med. Trop. Sao Paulo 40(4), 237-240 (1998).