B2292

O⁶-Benzylguanine

Name: O<SUP>6</SUP>-Benzylguanine
Brand: SIGMA
Price: 440 PLN

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

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50 MG

PLN 440.00

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₁N₅O

CAS Number:

19916-73-5

Molecular Weight:

241.25

UNSPSC Code:

12352200

PubChem Substance ID:

24278259

NACRES:

NA.77

MDL number:

MFCD00269931

Assay:

≥98% (TLC)

Form:

solid

Quality level:

200

Key Documents

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Product Name

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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Show Differences

1 of 4

This Item	B8279	A9657	J3770
Sigma-Aldrich B2292 O⁶-Benzylguanine	Sigma-Aldrich B8279 4-(3-Butoxy-4-methoxybenzyl)imidazolidin-2-one	Sigma-Aldrich A9657 DL-Aminoglutethimide	Sigma-Aldrich J3770 JNJ7777120
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: >20 mg/mL, H₂O: insoluble
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

Storage Class

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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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)

Interferon-β sensitizes human malignant melanoma cells to temozolomide-induced apoptosis and autophagy.

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)

O6-benzylguanine and its role in chemotherapy.

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

Methylguanine DNA methyltransferase-mediated drug resistance-based selective enrichment and engraftment of transplanted stem cells in skeletal muscle.

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

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