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B2292

Sigma-Aldrich

O6-Benzylguanine

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

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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

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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Die Dokumentenbibliothek aufrufen

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
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
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)
Kotaro Makita et al.
International journal of oncology, 54(5), 1864-1874 (2019-03-14)
Malignant melanoma is a highly aggressive skin cancer that is highly resistant to chemotherapy. Adjuvant therapy is administered to patients with melanoma that possess no microscopic metastases or have a high risk of developing microscopic metastases. Methylating agents, including dacarbazine (DTIC)
M E Dolan et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 3(6), 837-847 (1997-06-01)
The presence of the DNA repair protein, O6-alkylguanine-DNA alkyltransferase (AGT) in tumor cells is a significant source of resistance to chemotherapeutic alkylnitrosoureas and alkyltriazenes. O6-Benzylguanine provides a means to effectively inactivate the AGT protein and increase the chemotherapeutic effectiveness of
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