CAS 19916-73-5|O6-Benzylguanine
| Common Name | O6-Benzylguanine | ||
|---|---|---|---|
| CAS Number | 19916-73-5 | Molecular Weight | 241.249 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 621.4±63.0 °C at 760 mmHg |
| Molecular Formula | C12H11N5O | Melting Point | 193(dec.) |
| MSDS | ChineseUSA | Flash Point | 329.6±33.7 °C |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | 6-phenylmethoxy-7H-purin-2-amine |
|---|---|
| Synonym | More Synonyms |
O6-Benzylguanine BiologicalActivity
| Description | 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]. |
|---|---|
| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerSignaling Pathways >>Cell Cycle/DNA Damage >>DNA/RNA Synthesis |
| In Vitro | The L3.6pl cells are relatively sensitive to O6-Benzylguanine (24-72 hours) in a dose- and time-dependent manner. The IC50 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]. 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]. 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. |
| References | [1]. Rabik CA, Njoku MC, Dolan ME. Inactivation of O6-alkylguanine DNA alkyltransferase as a means to enhance chemotherapy. Cancer Treat Rev. 2006;32(4):261‐276. [2]. Konduri, Santhi D et al. Blockade of MGMT expression by O6 benzyl guanine leads to inhibition of pancreatic cancer growth and induction of apoptosis. Clinical cancer research : an official journal of the American Association for Cancer Research vol. 15,19 (2009): 6087-95. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 621.4±63.0 °C at 760 mmHg |
| Melting Point | 193(dec.) |
| Molecular Formula | C12H11N5O |
| Molecular Weight | 241.249 |
| Flash Point | 329.6±33.7 °C |
| Exact Mass | 241.096359 |
| PSA | 89.71000 |
| LogP | 1.95 |
| Vapour Pressure | 0.0±1.8 mmHg at 25°C |
| Index of Refraction | 1.743 |
| InChIKey | KRWMERLEINMZFT-UHFFFAOYSA-N |
| SMILES | Nc1nc(OCc2ccccc2)c2[nH]cnc2n1 |
| Storage condition | -20°C Freezer |
| Water Solubility | methanol: 20 mg/mL |
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xi:Irritant; |
| Risk Phrases | R36/37/38 |
| Safety Phrases | S26-S36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles29
More Articles| Differential expression of miR200a-3p and miR21 in grade II-III and grade IV gliomas: evidence that miR200a-3p is regulated by O⁶-methylguanine methyltransferase and promotes temozolomide responsiveness. Cancer Biol. Ther. 15(7) , 938-50, (2014) Glioblastoma multiforme (GBM) is the most common primary brain tumor and is among the deadliest of human cancers. Dysregulation of microRNAs (miRNAs) expression is an important step in tumor progressi... | |
| Formation and repair of pyridyloxobutyl DNA adducts and their relationship to tumor yield in A/J mice. Chem. Res. Toxicol. 25(10) , 2167-78, (2012) The nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a known human carcinogen. It generates methyl and pyridyloxobutyl DNA adducts. The role of the methyl DNA adducts has been well-... | |
| Evaluation of novel imidazotetrazine analogues designed to overcome temozolomide resistance and glioblastoma regrowth. Mol. Cancer Ther. 14(1) , 111-9, (2015) The cellular responses to two new temozolomide (TMZ) analogues, DP68 and DP86, acting against glioblastoma multiforme (GBM) cell lines and primary culture models are reported. Dose-response analysis o... |
Synonyms
| O(6)-Benzylguanine |
| 7H-purin-2-amine, 6-(phenylmethoxy)- |
| O6-Benzylguanine |
| 2-amino-6-(phenylmethoxy)-9H-purine |
| O(6)-bGua |
| 2-Amino-6-benzyloxy-9H-purine |
| O-6-Benzylguanine |
| 6-Benzyloxy guanine |
| 6-(Benzyloxy)-3H-purin-2-amine |
| 2-Amino-6-(benzyloxy)purine |
| 6-O-Benzylguanine |
| 9H-Purin-2-amine, 6-(phenylmethoxy)- |
| 6-(benzyloxy)guanine |
| O-Benzylguanine |
| 6-(phenylmethoxy)-9H-purin-2-amine |
| MFCD00269931 |
| amino-6-(phenylmethoxy)-9H-purine |
| 6-(Benzyloxy)-7H-purin-2-amine |
