B2292
O6-Benzylguanine
≥98% (TLC), solid, O⁶-alkylguanine DNA alkyltransferase inhiitor
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About This Item
Empirical Formula (Hill Notation):
C12H11N5O
CAS Number:
Molecular Weight:
241.25
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
O6-Benzylguanine, ≥98% (TLC), solid
SMILES string
Nc1nc(OCc2ccccc2)c3nc[nH]c3n1
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)
InChI key
KRWMERLEINMZFT-UHFFFAOYSA-N
assay
≥98% (TLC)
form
solid
solubility
methanol: 20 mg/mL
storage temp.
room temp
Quality Level
Gene Information
human ... MGMT(4255)
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Application
O6-Benzylguanine has been used:
- as an inhibitor of methylguanine methyltransferase (MGMT) in glioblastoma stem cell
- as a O6-alkylguanine-alkyltransferase (AGT) enzyme inhibitor in embryonic stem cells prior to N-ethyl-N-nitrosourea(ENU) treatment
- as an inhibitor of AGT in growth inhibition assays of HL-60 human promyelocytic leukemia cells
Biochem/physiol Actions
O(6)-benzylguanine is an antineoplastic agent that binds the DNA repair enzyme O(6)-alkylguanine DNA alkyltransferase (AGT), resulting in inhibition of AGT-mediated DNA repair. It is widely used in various DNA repair mechanism studies and potentiates the effects of other chemotherapeutic agents that damage DNA.
O6-Benzylguanine (O6BG) inhibits methylguanine methyltransferase (MGMT) by blocking the active site through benzyl group transfer. The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.
signalword
Warning
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
hcodes
Hazard Classifications
Acute Tox. 4 Oral
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Brian C Beard et al.
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We introduce here a new class of BODIPY-based Ca2+ indicators which can be derivatized with biological ligands that permit the localization of the indicators in living cells. The underivatized BODIPY-based Ca2+ indicator (BOCA-1) shows a 250-fold increase in fluorescence intensity
Katharina Stöhr et al.
Analytical chemistry, 82(19), 8186-8193 (2010-09-08)
Recent developments in fluorescence microscopy raise the demands for bright and photostable fluorescent tags for specific and background free labeling in living cells. Aside from fluorescent proteins and other tagging methods, labeling of SNAP-tagged proteins has become available thereby increasing
A Phase III study of radiation therapy (RT) and O 6-benzylguanine+ BCNU versus RT and BCNU alone and methylation status in newly diagnosed glioblastoma and gliosarcoma: Southwest Oncology Group (SWOG) study S0001
Blumenthal DT, et al.
International Journal of Clinical Oncology, 20(4), 650-658 (2015)
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