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B2292

Sigma-Aldrich

O6-Benzylguanine

≥98% (TLC), solid, O⁶-alkylguanine DNA alkyltransferase inhiitor

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About This Item

Fórmula empírica (notación de Hill):
C12H11N5O
Número de CAS:
19916-73-5
Peso molecular:
241.25
MDL number:
MFCD00269931
UNSPSC Code:
12352200
PubChem Substance ID:
24278259
NACRES:
NA.77
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Nombre del producto

O6-Benzylguanine, ≥98% (TLC), solid

Quality Level

200

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[1]
  • as a O6-alkylguanine-alkyltransferase (AGT) enzyme inhibitor in embryonic stem cells prior to N-ethyl-N-nitrosourea(ENU) treatment[2]
  • as an inhibitor of AGT in growth inhibition assays of HL-60 human promyelocytic leukemia cells[3]

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)[4] by blocking the active site through benzyl group transfer.[5] The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.[6]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000354417
0000351536
0000354417
0000351536
0000227497

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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
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
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)
Brian C Beard et al.
The Journal of clinical investigation, 120(7), 2345-2354 (2010-06-17)
HSC transplantation using genetically modified autologous cells is a promising therapeutic strategy for various genetic diseases, cancer, and HIV. However, for many of these conditions, the current efficiency of gene transfer to HSCs is not sufficient for clinical use. The
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
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