Thioguanine
(Synonyms: 6-硫鸟嘌呤,Thioguanine; 2-Amino-6-purinethiol) 目录号 : GC14366
Thioguanine是一种抗白血病和免疫抑制剂，对重组USP2和冠状病毒PLpro的IC50值分别为40µM和25µM。
Cas No.:154-42-7
Sample solution is provided at 25 µL, 10mM.
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Thioguanine is an anti-leukemia and immunosuppressant agent, with IC50 values of 40µM and 25μM for recombinant USP2 and coronaviral PLpro, respectively [1]. Thioguanine can be incorporated into CpG sites, affecting methylation of cytosine residues by methyltransferases and reducing the overall methylation level of cytosine[2]. Thioguanine has been widely used to inhibit a wide variety of cancer cells with a high frequency of homozygous deletion of the gene for methylthioadenosine phosphorylase (MTAP) [3].
In vitro, Thioguanine treatment for 48h inhibited the cell viability of MDA-MB-231, HCC1937, and MCF-10A cells with IC50 values of 2.489, 6.3, and 646.5μM, respectively[4]. Thioguanine treatment for 24 hours inhibited Herpes simplex virus 1 (HSV-1) replication in human corneal epithelial cells (HCECs) with an IC50 value of 0.104μM[5]. Treatment with 1µM Thioguanine for 48 hours significantly inhibited DNA polymerase γ replication in HCT116 cells, damaged mitochondrial DNA, and led to mitochondrial dysfunction[6].
In vivo, Thioguanine treatment via oral administration at a dose of 2.5mg/kg/day for 14 days ameliorated dextran sodium sulfate-induced chronic colitis in C57Bl/6 mice [7]. Thioguanine treatment (0.04mg/day; p.o.) for 5 days significantly extended the survival of the mouse model of leptomeningeal carcinomatosis[8].
References:
[1] Chuang S J, Cheng S C, Tang H C, et al. 6-Thioguanine is a noncompetitive and slow binding inhibitor of human deubiquitinating protease USP2[J]. Scientific reports, 2018, 8(1): 3102.
[2] Wang H, Wang Y. 6-Thioguanine perturbs cytosine methylation at the CpG dinucleotide site by DNA methyltransferases in vitro and acts as a DNA demethylating agent in vivo[J]. Biochemistry, 2009, 48(10): 2290-2299.
[3] Munshi P N, Lubin M, Bertino J R. 6-thioguanine: a drug with unrealized potential for cancer therapy[J]. The oncologist, 2014, 19(7): 760-765.
[4] Zhang D, An X, Li Q, et al. Thioguanine induces apoptosis in triple-negative breast cancer by regulating PI3K–AKT pathway[J]. Frontiers in Oncology, 2020, 10: 524922.
[5] Chen D, Liu Y, Zhang F, et al. 6-Thioguanine inhibits herpes simplex virus 1 infection of eyes[J]. Microbiology Spectrum, 2021, 9(3): e00646-21.
[6] Daehn I, Brem R, Barkauskaite E, et al. 6-Thioguanine damages mitochondrial DNA and causes mitochondrial dysfunction in human cells[J]. FEBS letters, 2011, 585(24): 3941-3946.
[7] Oancea I, Movva R, Das I, et al. Colonic microbiota can promote rapid local improvement of murine colitis by thioguanine independently of T lymphocytes and host metabolism[J]. Gut, 2017, 66(1): 59-69.
[8] Nakagawa H, Yui Y, Suzuki T, et al. Investigation of 6-thioguanine as a strategy to overcome methotrexate resistance in a mouse model of leptomeningeal carcinomatosis[J]. Journal of Neuro-Oncology, 2026, 176(1): 64.
Thioguanine是一种抗白血病和免疫抑制剂，对重组USP2和冠状病毒PLpro的IC50值分别为40µM和25µM[1]。Thioguanine可被掺入CpG位点，影响甲基转移酶对胞嘧啶残基的甲基化，并降低胞嘧啶的总体甲基化水平[2]。Thioguanine已被广泛用于抑制多种甲基硫代腺苷磷酸化酶（MTAP）基因纯合缺失高频率的癌细胞[3]。
在体外，Thioguanine处理48小时抑制了MDA-MB-231、HCC1937和MCF-10A细胞的活力，IC50值分别为2.489、6.3和646.5µM[4]。Thioguanine处理24小时抑制了单纯疱疹病毒1型（HSV-1）在人角膜上皮细胞（HCECs）中的复制，IC50值为0.104µM[5]。使用1µM的Thioguanine处理48小时，显著抑制了HCT116细胞中的DNA聚合酶γ复制，损伤了线粒体DNA，并导致线粒体功能障碍[5]。
在体内，以每日2.5mg/kg的剂量口服给予Thioguanine 14天，改善了C57Bl/6小鼠中由葡聚糖硫酸钠诱导的慢性结肠炎[7]。Thioguanine处理（每日0.04mg；p.o.）5天，显著延长了Leptomeningeal carcinomatosis小鼠模型的存活时间[8]。
| Cell experiment [1]: | |
Cell lines | MDA-MB-231 cells |
Preparation Method | MDA-MB-231 cells were cultured in RPMI 1640 medium supplemented with 10% fetal bovine serum, 100IU/ml penicillin, and 100μg/ml streptomycin. The cells were cultured at 37℃ in a humidified environment with 5% CO2. 6.5×103 cells were seeded in each well of a 96-well plate and treated with various concentrations of Thioguanine (0.01, 0.1, 1, 10, 100, and 1000µM) for 48 hours. After that, CCK-8 solution was added and absorbance was measured at 450nm wavelength. |
Reaction Conditions | 0.01, 0.1, 1, 10, 100, and 1000µM; 48h |
Applications | Thioguanine treatment decreased the cell viability of MDA-MB-231 cells in a dose-dependent manner. |
| Animal experiment [2]: | |
Animal models | Female C3H/HeSlc mice |
Preparation Method | 10-week-old female C3H/HeSlc mice acclimated to the environment for one week. A mouse model of Leptomeningeal carcinomatosis was established by injecting 0.05 ml of 2×105 methotrexate -resistant MM46 cells into the cisterna magna through a 26-gauge needle under anesthesia. Mice were maintained under SPF-grade conditions with controlled temperature and humidity, 12h light/12h dark cycles, and had ad libitum access to standard diet and sterilized tap water. The body weight, mobility, and food intake of mice were observed daily. Thioguanine was administered by gavage once a day for five consecutive days at a dose of 0.04mg, and the survival rate was analyzed. |
Dosage form | 0.04mg/day for 5 days; p.o. |
Applications | Thioguanine treatment significantly extended survival of mouse model of leptomeningeal carcinomatosis. |
References: | |
| Cas No. | 154-42-7 | SDF | |
| 别名 | 6-硫鸟嘌呤,Thioguanine; 2-Amino-6-purinethiol | ||
| 化学名 | 2-amino-3,7-dihydropurine-6-thione | ||
| Canonical SMILES | C1=NC2=C(N1)C(=S)N=C(N2)N | ||
| 分子式 | C5H5N5S | 分子量 | 167.19 |
| 溶解度 | ≥ 8.35 mg/mL in DMSO with gentle warming | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.9812 mL | 29.9061 mL | 59.8122 mL |
| 5 mM | 1.1962 mL | 5.9812 mL | 11.9624 mL |
| 10 mM | 598.1 μL | 2.9906 mL | 5.9812 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
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2.
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