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;酶与辅酶;中间体;生化试剂;嘌呤;医药中间体;Alkylguanine-DNA alkyltransferase, mammalian DNA repair proteinApoptosis and Cell Cycle;DNA Repair Regulators;A to;DNA metabolism;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;有机化工原料;化工;抗病毒;Nucleotides and Nucleosides;Bases Related Reagents;Nucleotides;Enzyme Inhibitors by Enzyme

Mol文件:

19916-73-5.mol

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 

methanol: 20 mg/mL

酸度系数(pKa)

7.47±0.20(Predicted)

形态

solid

CAS 数据库

19916-73-5(CAS DataBase Reference)

生物活性

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。

靶点

Target Value AGT ()

Target

Value

AGT ()

体外研究

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.

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.

Cell Line:

L3.6pl cells

Concentration:

50 μg

Incubation Time:

48 hours

Result:

Decreased the MGMT transcriptional activity in L3.6pl.

体内研究

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.

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.

用途 

用于各种DNA修复机制研究。

危险品标志 

Xi

危险类别码 

36/37/38

安全说明 

26-36

WGK Germany 

3

Hazard Note 

Irritant

海关编码 

29339900