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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 (Notação de Hill):
C12H11N5O
Número CAS:
19916-73-5
Peso molecular:
241.25
Número MDL:
MFCD00269931
Código UNSPSC:
12352200
ID de substância PubChem:
24278259
NACRES:
NA.77

product name

O6-Benzylguanine, ≥98% (TLC), solid

Nível de qualidade

200

Ensaio

≥98% (TLC)

forma

solid

solubilidade

methanol: 20 mg/mL

temperatura de armazenamento

room temp

cadeia de caracteres SMILES

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)

chave InChI

KRWMERLEINMZFT-UHFFFAOYSA-N

Informações sobre genes

human ... MGMT(4255)

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Aplicação

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

Ações bioquímicas/fisiológicas

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.
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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Radiation research, 172(4), 405-413 (2009-09-24)
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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
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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)
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
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