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B2292

Sigma-Aldrich

O6-Benzylguanine

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

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50 MG
€ 88,80

About This Item

Empirische Formel (Hill-System):
C12H11N5O
CAS-Nummer:
19916-73-5
Molekulargewicht:
241.25
MDL-Nummer:
MFCD00269931
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278259
NACRES:
NA.77

€ 88,80

Voraussichtliches Versanddatum30. Mai 2025

Bulk-Bestellung anfordern

Produktbezeichnung

O6-Benzylguanine, ≥98% (TLC), solid

Qualitätsniveau

200

Assay

≥98% (TLC)

Form

solid

Löslichkeit

methanol: 20 mg/mL

Lagertemp.

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)

InChIKey

KRWMERLEINMZFT-UHFFFAOYSA-N

Angaben zum Gen

human ... MGMT(4255)

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Anwendung

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. Wirkung

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]

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000354417
0000354417
0000351536
0000252699
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
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)
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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