6-(benzyloxy)-7H-purin-2-amine
6-benzylguanine
CAS: 19916-73-5
Molecular Formula: C12H11N5O
6-(benzyloxy)-7H-purin-2-amine - Names and Identifiers
| Name | 6-benzylguanine |
| Synonyms | NSC 637037 6-benzylguanine 6-O-Benzylguanine 6-Benzyloxy Guanine O(sup 6)benzylguanidine 2-amino-6-benzyloxypurine 6-(benzyloxy)-7H-purin-2-aMine 6-(Benzyloxy)-1H-purin-2-amine 6-(benzyloxy)-7H-purin-2-amine 2-Amino-6-(benzyloxy)-9H-purine 6-(PhenylMethoxy)-9H-purin-2-aMine |
| CAS | 19916-73-5 |
| EINECS | 1592732-453-0 |
| InChI | InChI=1/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) |
6-(benzyloxy)-7H-purin-2-amine - Physico-chemical Properties
| Molecular Formula | C12H11N5O |
| Molar Mass | 241.25 |
| Density | 1.48±0.1 g/cm3(Predicted) |
| Melting Point | 193(dec.) |
| Boling Point | 459.3±55.0 °C(Predicted) |
| Flash Point | 329.6°C |
| Solubility | methanol: 20mg/mL |
| Vapor Presure | 2.3E-15mmHg at 25°C |
| Appearance | Crystalline powder |
| Color | Off-White to Light Yellow |
| pKa | 7.47±0.20(Predicted) |
| Storage Condition | room temp |
| Refractive Index | 1.743 |
| MDL | MFCD00269931 |
| Use | Used for various DNA repair mechanism research. |
6-(benzyloxy)-7H-purin-2-amine - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| HS Code | 29339900 |
| Hazard Note | Irritant |
6-(benzyloxy)-7H-purin-2-amine - Reference Information
| Introduction | O6-Benzylguanine is a guanine analog and an inhibitor of the DNA repair enzyme O6 alkyl guanine DNA alkyltransferase (MGMT/AGT). |
| Pharmacological activity | The O6-Benzylguanine acts as an AGT substrate and transfers its benzyl group to the AGT cysteine residue, thereby irreversibly inactivating AGT and preventing DNA repair. O6-Benzylguanine induces apoptosis of tumor cells and has anti-tumor activity. |
| Target | Value |
| Cell Line: | L3.6pl and PANC1 cells L3.6pl cells |
| Concentration: | 50 μg 50 μg |
| Incubation Time: | 48 hours 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. Decreased the MGMT transcriptional activity in L3.6pl. Significantly decreased median tumor volume and weight. |
| Animal Model: | Male athymic nude mice (NCI-nu) (bearing human pancreatic cancer L3.6pl cells) |
| Dosage: | 100 μg |
| Administration: | i.p; daily for 35 days |
| use | is used to study various DNA repair mechanisms. |
Last Update：2024-04-09 02:00:07
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