B2292

O⁶-Benzylguanine

Name: O<SUP>6</SUP>-Benzylguanine
Brand: SIGMA
Price: 118 USD
Availability: InStock

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

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50 MG

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Fórmula empírica (notación de Hill):

C₁₂H₁₁N₅O

Número CAS:

19916-73-5

Peso molecular:

241.25

UNSPSC Code:

12352200

PubChem Substance ID:

24278259

NACRES:

NA.77

MDL number:

MFCD00269931

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Nombre del producto

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

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Este artículo	B8279	A9657	J4829
Sigma-Aldrich B2292 O⁶-Benzylguanine	Sigma-Aldrich B8279 4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one	Sigma-Aldrich A9657 DL-Aminoglutethimide	Sigma-Aldrich J4829 JFD00244
form solid	form solid	form powder or crystals	form solid
assay ≥98% (TLC)	assay ≥98% (HPLC)	assay ≥98% (TLC)	assay ≥98% (HPLC)
Quality Level 200	Quality Level 200	Quality Level 200	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 H₂O: slightly soluble 0.2 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.2 mg/mL, 0.1 M HCl: soluble, acetonitrile: soluble, methanol: soluble	solubility DMSO: ≥10 mg/mL, H₂O: <2 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 human ... CYP11A1(1583), CYP17A1(1586), CYP19A1(1588) rat ... Cyp19a1(25147)	Gene Information -

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

GHS07

signalword

Warning

Clase de almacenamiento

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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Recognition of O6MeG lesions by MGMT and mismatch repair proficiency may be a prerequisite for low-dose radiation hypersensitivity.

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

Efficient and stable MGMT-mediated selection of long-term repopulating stem cells in nonhuman primates.

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

Localizable and highly sensitive calcium indicator based on a BODIPY fluorophore.

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

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)

In vivo selection of hematopoietic progenitor cells and temozolomide dose intensification in rhesus macaques through lentiviral transduction with a drug resistance gene.

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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O6-Benzylguanine