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
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Product Name
O6-Benzylguanine, ≥98% (TLC), solid
Quality Level
Assay
≥98% (TLC)
form
solid
solubility
methanol: 20 mg/mL
storage temp.
room temp
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
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Antonio S J Lee et al.
Stem cells (Dayton, Ohio), 27(5), 1098-1108 (2009-05-06)
Cell replacement therapy using stem cell transplantation holds much promise in the field of regenerative medicine. In the area of hematopoietic stem cell transplantation, O(6)-methylguanine-DNA methyltransferase MGMT (P140K) gene-mediated drug resistance-based in vivo enrichment strategy of donor stem cells has
Andre Larochelle et al.
The Journal of clinical investigation, 119(7), 1952-1963 (2009-06-11)
Major limitations to gene therapy using HSCs are low gene transfer efficiency and the inability of most therapeutic genes to confer a selective advantage on the gene-corrected cells. One approach to enrich for gene-modified cells in vivo is to include
Quantitative relationship between guanine O6-alkyl lesions produced by Onrigin? and tumor resistance by O6-alkylguanine-DNA alkyltransferase
Ishiguro K, et al.
Biochemical Pharmacology, 80(9), 1317-1325 (2010)
Lynn Martin et al.
Radiation research, 172(4), 405-413 (2009-09-24)
Low-dose hyper-radiosensitivity (HRS) is the phenomenon whereby cells exposed to radiation doses of less than approximately 0.5 Gy exhibit increased cell killing relative to that predicted from back-extrapolating high-dose survival data using a linear-quadratic model. While the exact mechanism remains
Mako Kamiya et al.
Analytical chemistry, 82(15), 6472-6479 (2010-07-02)
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
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