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
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关于此项目
经验公式（希尔记法）:
C5H5N5S
化学文摘社编号:
分子量:
167.19
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
205-827-2
MDL number:
Beilstein/REAXYS Number:
157765
Assay:
≥98%
Biological source:
synthetic (organic)
Form:
powder
Solubility:
1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow
Storage temp.:
room temp
产品名称
6-硫代鸟嘌呤, ≥98%
InChI key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
InChI
1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
SMILES string
NC1=Nc2nc[nH]c2C(=S)N1
biological source
synthetic (organic)
assay
≥98%
form
powder
mp
≥300 °C (lit.)
solubility
1 M NaOH: 50 mg/mL, clear to hazy, colorless to light greenish-yellow
storage temp.
room temp
Quality Level
Gene Information
human ... IMPDH1(3614), IMPDH2(3615)
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Application
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
Biochem/physiol Actions
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。
General description
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)。
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 3 Oral
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Crystal and molecular structure of 6-thioguanine
Bugg CE and Thewalt U
Journal of the American Chemical Society, 92(25), 7441-7445 (1970)
Delayed effects of accelerated heavy ions on the induction of HPRT mutations in V79 hamster cells
Blaha P, et al.
Mutation Research. Fundamental and Molecular Mechanisms of Mutagenesis, 803(46), 35-41 (2017)
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
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)
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