A4882
6-硫代鸟嘌呤
≥98%, Guanine antimetabolite, powder
别名:
2-氨基-6-巯嘌呤, 2-氨基-6巯基嘌呤
产品名称
6-硫代鸟嘌呤, ≥98%
生物来源
synthetic (organic)
质量水平
方案
≥98%
表单
powder
mp
≥300 °C (lit.)
溶解性
1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow
储存温度
room temp
SMILES字符串
NC1=Nc2nc[nH]c2C(=S)N1
InChI
1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
基因信息
human ... IMPDH1(3614), IMPDH2(3615)
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一般描述
6-硫鸟嘌呤是鸟嘌呤的变体,在嘌呤环的 N-7 位有氢键。它与胞嘧啶的结合改变了碱基堆积的维度。6-硫鸟嘌呤是治疗炎症性肠病 (IBD) 的有效药物,可导致肝脏结节性再生性增生 (NRH)。
应用
6-硫鸟嘌呤已用于:
- 诱导结直肠癌细胞系 HCT116 的自噬和凋亡
- 在中国仓鼠肺成纤维细胞培养 V79 的突变和存活试验中作为选择标记
- 在 4T1-luc 细胞的克隆源性肺转移试验中作为选择标记
生化/生理作用
核糖基化并通过与天然嘌呤碱相同的途径磷酸化;作为核苷酸,抑制参与核酸合成的多种细胞过程。作为白血病的有效治疗方法已有悠久的历史。
用于治疗白血病的抗代谢药。与次黄嘌呤和鸟嘌呤竞争次黄嘌呤-鸟嘌呤磷酸核糖转移酶,后者是生成嘌呤核苷酸的关键步骤。
警示用语:
Danger
危险声明
预防措施声明
危险分类
Acute Tox. 3 Oral
储存分类代码
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
6-thioguanine can cause serious liver injury in inflammatory bowel disease patients
Dubinsky MC, et al.
Gastroenterology, 125(2), 298-303 (2003)
Jen-Hwey Chiu et al.
Scientific reports, 10(1), 8060-8060 (2020-05-18)
Our previous study demonstrated that upregulation of multiple epidermal growth factor-like domains 11 (MEGF11) gene expression is involved in the mechanism by which recurrence of Triple Negative Breast Cancer (TNBC) occurs. Our aim was to elucidate the role of MEGF11
Interconnections between apoptotic and autophagic pathways during thiopurine-induced toxicity in cancer cells: the role of reactive oxygen species
Chaabane W and Appell ML
Testing, 7(46), 75616-75616 (2016)
Tumor-suppressor inactivation of GDF11 occurs by precursor sequestration in triple-negative breast cancer
Bajikar SS, et al.
Developmental Cell, 43(4), 418-435 (2017)
Crystal and molecular structure of 6-thioguanine
Bugg CE and Thewalt U
Journal of the American Chemical Society, 92(25), 7441-7445 (1970)
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