CAS Number19916-73-5
SynonymsO(6)-Benzylguanine; 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; 6-(benzyloxy)guanine; O-Benzylguanine; 6-(phenylmethoxy)-9H-purin-2-amine; MFCD00269931; amino-6-(phenylmethoxy)-9H-purine; 6-(Benzyloxy)-7H-purin-2-amine
Molecular FormulaC12H11N5O
Molecular Weight241.25
Purity≥98 (TLC)%
Density1.4±0.1 g/cm3
Boiling Point621.4±63.0 °C at 760 mmHg
Melting Point193(dec.)
Appearancesolid
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 19916-73-5 |
| Catalog No. | 2A-9038262 |
| Chinese Name | O-6-苄基鸟嘌呤 |
| Synonyms | O(6)-Benzylguanine; 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; 6-(benzyloxy)guanine; O-Benzylguanine; 6-(phenylmethoxy)-9H-purin-2-amine; MFCD00269931; amino-6-(phenylmethoxy)-9H-purine; 6-(Benzyloxy)-7H-purin-2-amine |
| Molecular Formula | C12H11N5O |
| Molecular Weight | 241.25 |
| Purity | ≥98 (TLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 621.4±63.0 °C at 760 mmHg |
| Melting Point | 193(dec.) |
| Appearance | solid |
| Water Solubility | methanol: 20 mg/mL |
| Storage Condition | Sealed in a cool, dry environment |
| Application | O6-Benzylguanine is a guanine analogue and inhibitor of the DNA repair enzyme O6 alkylguanine DNA alkyltransferase (MGMT/AGT). O6-Benzylguanine acts as an AGT substrate and transfers its benzyl group |
| HTC | 2933990090 |
| PubChem ID | 24278259 |
| MDL Number | MFCD00269931 |
| SMILES | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/38262_1_19916_73_5.pdf |
| Bioactivity | 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 >> Apoptosis Research Areas >> Cancer Signaling 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 |
| Use of | 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]. Properties Articles29 Name 6-phenylmethoxy-7H-purin-2-amine Synonym More Synonyms O6-Benzylguanine Biological Activity 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 >> Apoptosis Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis 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 Molecular Formula C12H11N5O Exact Mass 241.096359 PSA 89.71000 Index of Refraction 1.743 InChIKey KRWMERLEINMZFT-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: 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% |
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