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B2292

O6-Benzylguanine

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

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Pack SizeSKUAvailabilityPrice
50 mg
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CLP 88,900

About This Item

Empirical Formula (Hill Notation):
C12H11N5O
CAS Number:
19916-73-5
Molecular Weight:
241.25
UNSPSC Code:
12352200
PubChem Substance ID:
24278259
NACRES:
NA.77
MDL number:
MFCD00269931
Assay:
≥98% (TLC)
Form:
solid
Quality level:
200

CLP 88,900

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Product Name

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)

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
  • 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.[2] The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.[3]

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This Item
B8279J3770I7160
O6-Benzylguanine ≥98% (TLC), solid

Sigma-Aldrich

B2292

O6-Benzylguanine

4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one solid

Sigma-Aldrich

B8279

4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one

JNJ7777120 ≥98% (HPLC)

Sigma-Aldrich

J3770

JNJ7777120

IMS2186 ≥98% (HPLC), solid

Sigma-Aldrich

I7160

IMS2186

form

solid

form

solid

form

solid

form

solid

assay

≥98% (TLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

solubility

methanol: 20 mg/mL

solubility

ethanol: 7 mg/mL, H2O: insoluble

solubility

DMSO: >20 mg/mL, H2O: insoluble

solubility

DMSO: >20 mg/mL

Gene Information

human ... MGMT(4255)

Gene Information

human ... LITAF(9516), PDE4B(5142), PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)
rat ... Pde4a(25638)

Gene Information

-

Gene Information

-

pictograms

Exclamation mark
GHS07

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

H302

Hazard Classifications

Acute Tox. 4 Oral

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Certificates of Analysis (COA)

Lot/Batch Number
0000354417
0000351536
0000354417
0000351536
0000252699

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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
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)
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
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Global Trade Item Number

SKUGTIN
B2292-50MG04061833020623

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