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[CAS NO. 19916-73-5]  O6-Benzylguanine

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PRODUCTS SPECIFICATIONS [19916-73-5]

Distributor
Catalog
HY-W002585
Brand
MCE
CAS
19916-73-5

DESCRIPTION [19916-73-5]

Overview

MDLMFCD00269931
Molecular Weight241.25
Molecular FormulaC12H11N5O
SMILESNC(N=C1OCC2=CC=CC=C2)=NC3=C1NC=N3

For research use only. We do not sell to patients.

1 Publications Citing Use of MCE


Summary

O6-Benzylguanine, a guanine analog, is the DNA repair enzyme O6-alkylguanine-DNA alkyltransferase (MGMT/AGT) inhibitor. O6-Benzylguanine acts as an AGT substrate, which transfers its benzyl group to the AGT cysteine residue, thereby irreversibly inactivating AGT and preventing DNA repair. O6-Benzylguanine induces tumor cell apoptosis . Antineoplastic activity [1] [2] .


In Vitro

The L3.6pl cells are relatively sensitive to O6-Benzylguanine (24-72 hours) in a dose- and time-dependent manner. The IC 50 is 50 μg (at 48 hours) [2] .
O6-Benzylguanine (50 μg; 48 hours) modulates p53 downstream target protein expression, induces apoptosis, and decreases cell proliferation [2] .
O6-Benzylguanine (50 μg; 48 hours) significantly decreases the MGMT transcriptional activity in L3.6pl [2] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis [2]

Cell Line: L3.6pl and PANC1 cells
Concentration: 50 μg
Incubation Time: 48 hours
Result: Expressions of O6 methyl guanine DNA methyl transferase (MGMT), cyclin B1, cyclin B2, cyclin A, p53, and ki-67 were decreased, whereas p21 was increased. The levels of cyto C and caspase 9 were increased, whereas the levels of PARP1 protein were decreased.

RT-PCR [2]

Cell Line: L3.6pl cells
Concentration: 50 μg
Incubation Time: 48 hours
Result: Decreased the MGMT transcriptional activity in L3.6pl.

In Vivo

O6-Benzylguanine (100 μg; i.p.; daily for 35 days) inhibits pancreatic cancer cell growth and increases pancreatic cell sensitivity to Gemcitabine (100 mg/kg) [2] .
O6-Benzylguanine inhibits pancreatic cancer cell proliferation and induces tumor cell apoptosis in vivo [2] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Male athymic nude mice (NCI-nu) (bearing human pancreatic cancer L3.6pl cells) [2]
Dosage: 100 μg
Administration: i.p; daily for 35 days
Result: Significantly decreased median tumor volume and weight.

Clinical Trial

NCT Number Sponsor Condition Start Date Phase
NCT00612989 Duke University|Schering-Plough|Keryx + AOI Pharmaceuticals, Inc.
Glioblastoma|Gliosarcoma
February 2005 Phase 1
NCT00006474 Duke University|National Cancer Institute (NCI)
Brain and Central Nervous System Tumors
March 2001 Phase 1
NCT00005961 National Cancer Institute (NCI)
Melanoma (Skin)
June 2000 Phase 2

Appearance

Solid


Shipping

Room temperature in continental US; may vary elsewhere.


Storage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)


Solvent & Solubility

In Vitro:

DMSO : 110 mg/mL ( 455.96 mM ; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.1451 mL 20.7254 mL 41.4508 mL
5 mM 0.8290 mL 4.1451 mL 8.2902 mL
10 mM 0.4145 mL 2.0725 mL 4.1451 mL
* Please refer to the solubility information to select the appropriate solvent.
In Vivo:
  • 1.

    Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

    Solubility: ≥ 2.75 mg/mL (11.40 mM); Clear solution

  • 2.

    Add each solvent one by one: 10% DMSO >> 90% corn oil

    Solubility: ≥ 2.75 mg/mL (11.40 mM); Clear solution

* All of the co-solvents are available by MCE.


Synonyms

9H-Purin-2-amine, 6-(phenylmethoxy)-
Purine, 2-amino-6-(benzyloxy)-
1H-Purin-2-amine, 6-(phenylmethoxy)-
6-(Phenylmethoxy)-9H-purin-2-amine
2-Amino-6-(benzyloxy)purine
6-(Benzyloxy)guanine
2-Amino-6-(phenylmethoxy)-9H-purine
6-O-Benzylguanine
NSC 637037
O6-Benzylguanine
O6-Benzylguanine
Benzylguanine

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