From Wikipedia, the free encyclopedia
O6-Benzylguanine
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Names
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IUPAC name
6-(Benzyloxy)-7H-purin-2-amine
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Other names
6-(Benzyloxy)guanine; 6-O-Benzylguanine; O(6)-bGua; O6-BG
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Identifiers
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ChemSpider
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ECHA InfoCard
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100.161.788
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UNII
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InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17) Key: KRWMERLEINMZFT-UHFFFAOYSA-N InChI=1/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17) Key: KRWMERLEINMZFT-UHFFFAOYAI
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Nc3nc(OCc1ccccc1)c2nc[nH]c2n3
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Properties
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C12H11N5O
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Molar mass
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241.254 g·mol−1
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Density
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1.432 g/mL
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
O6-Benzylguanine (O6-BG) is a synthetic
derivative of
guanine. It is an
antineoplastic agent. It exerts its effect by acting as a
suicide inhibitor of the enzyme
O6-alkylguanine-DNA alkyltransferase which leads to interruption of DNA repair. O6-BG was used clinically in combination with the
alkylating agent
temozolomide for
glioblastoma, however the combination was found to be overly toxic without adding significant benefit.
[1]
[2]
[3]
O6-BG is also used as a biochemical tool in the study of DNA repair mechanisms.[
citation needed]
References
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^ Quinn, JA; Desjardins, A; Weingart, J; Brem, H; Dolan, ME; Delaney, SM; Vredenburgh, J; Rich, J; et al. (2005).
"Phase I trial of temozolomide plus O6-benzylguanine for patients with recurrent or progressive malignant glioma". Journal of Clinical Oncology. 23 (28): 7178–87.
doi:
10.1200/JCO.2005.06.502.
PMID
16192602.
{{
cite journal}}
: CS1 maint: numeric names: authors list (
link)
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^ Quinn, J. A.; Jiang, S. X.; Reardon, D. A.; Desjardins, A.; Vredenburgh, J. J.; Rich, J. N.; Gururangan, S.; Friedman, A. H.; et al. (2009).
"Phase II Trial of Temozolomide Plus O6-Benzylguanine in Adults with Recurrent, Temozolomide-Resistant Malignant Glioma". Journal of Clinical Oncology. 27 (8): 1262–7.
doi:
10.1200/JCO.2008.18.8417.
PMC
2667825.
PMID
19204199.
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^ Blumenthal, Deborah T. (2015).
"A phase III study of radiation therapy (RT) and O6-benzylguanine, (O6-BG) plus BCNU versus RT and BCNU alone and methylation status in newly-diagnosed glioblastoma (GBM) and gliosarcoma: Southwest Oncology Group (SWOG) Study S0001". International Journal of Clinical Oncology. 20 (4): 650–8.
doi:
10.1007/s10147-014-0769-0.
PMC
4465052.
PMID
25407559.
External links