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B2292

Sigma-Aldrich

O6-Benzylguanine

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

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About This Item

Empirical Formula (Hill Notation):
C12H11N5O
CAS Number:
19916-73-5
Molecular Weight:
241.25
MDL number:
MFCD00269931
UNSPSC Code:
12352200
PubChem Substance ID:
24278259
NACRES:
NA.77

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)

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Application

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

Biochem/physiol Actions

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Quantitative relationship between guanine O6-alkyl lesions produced by Onrigin? and tumor resistance by O6-alkylguanine-DNA alkyltransferase
Ishiguro K, et al.
Biochemical Pharmacology, 80(9), 1317-1325 (2010)
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
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