O-6-苄基鸟嘌呤
| 中文名称 | O-6-苄基鸟嘌呤 |
|---|---|
| 中文同义词 | 6-苄基鸟嘌呤;更昔洛韦杂质12;O6 - 苄基;2-氨基-6-(苄氧基)嘌呤;O-6-苄基鸟嘌呤;O-6-苄基鸟嘌呤 10G;O-6-苄基鸟嘌呤,MGMT 的抑制剂;苄基鸟嘌呤 |
| 英文名称 | 6-O-Benzylguanine |
| 英文同义词 | O(sup 6)benzylguanidine;O6-Benzylguanine ,98%;2-Amino-6-(benzyloxy)-9H-purine;6-(Benzyloxy)-1H-purin-2-amine;6-(benzyloxy)-7H-purin-2-aMine;6-(PhenylMethoxy)-9H-purin-2-aMine;NSC 637037;6-benzylguanine |
| CAS号 | 19916-73-5 |
| 分子式 | C12H11N5O |
| 分子量 | 241.25 |
| EINECS号 | 1592732-453-0 |
| 相关类别 | 其他化学试剂;抗肿瘤类药物及免疫抑制剂;中间体;生化试剂;嘌呤;医药中间体;恩替卡韦中间体;原料药API;更昔洛韦;医药、农药及染料中间体;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Alkylguanine-DNA alkyltransferase, mammalian DNA repair proteinApoptosis and Cell Cycle;DNA Repair Regulators;A to;DNA metabolism;Enzyme Inhibitors by Enzyme;酶与辅酶;有机化工原料;化工;抗病毒 |
| Mol文件 | 19916-73-5.mol |
| 结构式 |  |
O-6-苄基鸟嘌呤 性质
| 熔点 | 193(dec.) |
|---|---|
| 沸点 | 459.3±55.0 °C(Predicted) |
| 密度 | 1.48±0.1 g/cm3(Predicted) |
| 储存条件 | room temp |
| 溶解度 | 溶于甲醇，溶解度20mg/mL |
| 形态 | 固体 |
| 酸度系数(pKa) | 7.47±0.20(Predicted) |
| 颜色 | 灰白色至浅黄色 |
| InChI | 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) |
| InChIKey | KRWMERLEINMZFT-UHFFFAOYSA-N |
| SMILES | N1C2C(=NC(N)=NC=2OCC2=CC=CC=C2)NC=1 |
| CAS 数据库 | 19916-73-5(CAS DataBase Reference) |
O6-Benzylguanine 是鸟嘌呤类似物，是 DNA 修复酶 O6 烷基鸟嘌呤DNA烷基转移酶 (MGMT/AGT) 抑制剂。
O6-Benzylguanine 作为 AGT 底物，将其苄基转移到 AGT 半胱氨酸残基上，从而不可逆地灭活 AGT 并阻止 DNA 修复。O6-Benzylguanine 诱导肿瘤细胞凋亡，具有抗肿瘤活性。| Target | Value |
|
AGT
() |
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).
O6-Benzylguanine (50 μg; 48 hours) modulates p53 downstream target protein expression, induces apoptosis, and decreases cell proliferation.
O6-Benzylguanine (50 μg; 48 hours) significantly decreases the MGMT transcriptional activity in L3.6pl.
Western Blot Analysis
| 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
| Cell Line: | L3.6pl cells |
| Concentration: | 50 μg |
| Incubation Time: | 48 hours |
| Result: | Decreased the MGMT transcriptional activity in L3.6pl. |
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).
O6-Benzylguanine inhibits pancreatic cancer cell proliferation and induces tumor cell apoptosis in vivo.
| 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 |
| Result: | Significantly decreased median tumor volume and weight. |
10310-21-1
100-51-6
19916-73-5
一般步骤：将苯甲醇（37.5 g，0.347 mol）与氢氧化钠（2.96 g，0.074 mol）混合，加热至氢氧化钠完全溶解。待反应混合物冷却后，加入2-氨基-6-氯嘌呤（6.00 g，0.035 mol），于80-90℃下搅拌反应5小时。反应完成后，向反应混合物中加入甲基叔丁基醚（120 mL），用氢氧化钠溶液（70 mL）进行两次萃取。合并碱水层，用甲苯洗涤，随后蒸发除去甲苯。用35%盐酸将溶液中和至pH 6-8，过滤收集析出的晶体。将所得粗产物2-氨基-6-(苄氧基)嘌呤（7.60 g，0.032 mol，收率92%）在减压下干燥。
参考文献：
[1] Patent: WO2003/84957, 2003, A1. Location in patent: Page/Page column 9-10
[2] Nucleosides and Nucleotides, 1999, vol. 18, # 10, p. 2219 - 2231
[3] Helvetica Chimica Acta, 2012, vol. 95, # 12, p. 2621 - 2634
[4] Tetrahedron, 2007, vol. 63, # 24, p. 5323 - 5327
[5] Synthetic Communications, 2003, vol. 33, # 6, p. 941 - 952
安全信息
| 提供商 | 语言 |
|---|---|
|
英文
|
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2026/03/03 | H60274 | O6-苄基鸟嘌呤, 98% O6-Benzylguanine, 98% | 19916-73-5 | 250mg | 149元 |
| 2026/03/03 | S3658 | O-6-苄基鸟嘌呤 O6-Benzylguanine | 19916-73-5 | 25mg | 795.12元 |