Sinefungin
(Synonyms: 西奈芬净,Adenosyl-Ornithine; A-9145; Antibiotic 32232RP) 目录号 : GC34784
Sinefungin是一种S-腺苷甲硫氨酸类似物的天然核苷类抗生素，可抑制多种甲基转移酶（包括蛋白、DNA和RNA甲基转移酶）的活性。
Cas No.:58944-73-3
Sample solution is provided at 25 µL, 10mM.
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Sinefungin is a natural nucleoside antibiotic analog of S-adenosylmethionine that inhibits the activity of various methyltransferases (including protein, DNA, and RNA methyltransferases)[1-2]. Sinefungin can be used to explore epigenetic mechanisms and to support research in the development of antiviral, antiparasitic, and antifungal drugs[3-4].
In vitro, Sinefungin (10μM) applied to mouse L cells pre-infected with Newcastle disease virus and vaccinia virus for 72 hours significantly inhibited the formation of viral plaques[5]. Pretreatment of Candida albicans (C. albicans) strains with Sinefungin (0.25–4μM) for 5 days markedly inhibited hyphal elongation and long-term biofilm formation. Co-incubation of HEK293T and H1299 cells with C. albicans in the presence of Sinefungin for 2 hours reduced the ability of C. albicans to infect cells[6].
In vivo, pretreatment of mice with Sinefungin (10mg/kg/day) via intraperitoneal injection for 5 days, followed by induction of cardiac ischemia/reperfusion (I/R) model (left anterior descending coronary artery ligation for 45 minutes, reperfusion for 24 hours), significantly improved cardiac function (increased ejection fraction and fractional shortening), reduced myocardial infarct size, and lowered serum lactate dehydrogenase (LDH) levels[7]. Pretreatment of peritoneal fibrosis model C57/BL6 mice with Sinefungin (10mg/kg) via subcutaneous injection (once daily, 5 days/week for 3 weeks), significantly suppressed the increase in peritoneal cell density and thickening of the subperitoneal compact zone[8].
References:
[1] Neal RA, Iwobi MV, Robert-Gero M. Antileishmanial effect of free and encapsulated sinefungin against Leishmania donovani infections in BALB/c mice. C R Acad Sci III. 1989;308(18):485-8.
[2] Dube DK, Mpimbaza G, Allison AC, et al. Antitrypanosomal activity of sinefungin. Am J Trop Med Hyg. 1983 Jan;32(1):31-3.
[3] Bachrach U, Schnur LF, El-On J, et al. Inhibitory activity of sinefungin and SIBA (5'-deoxy-5'-S-isobutylthio-adenosine) on the growth of promastigotes and amastigotes of different species of Leishmania. FEBS Lett. 1980 Dec 1;121(2):287-91.
[4] Sala L, Franco-Valls H, Stanisavljevic J, et al. Abrogation of myofibroblast activities in metastasis and fibrosis by methyltransferase inhibition. Int J Cancer. 2019 Dec 1;145(11):3064-3077.
[5] Pugh CS, Borchardt RT, Stone HO. Sinefungin, a potent inhibitor of virion mRNA(guanine-7-)-methyltransferase, mRNA(nucleoside-2'-)-methyltransferase, and viral multiplication. J Biol Chem. 1978 Jun 25;253(12):4075-7.
[6] Nayak A, Khedri A, Chavarria A, et al. Sinefungin, a natural nucleoside analog of S-adenosyl methionine, impairs the pathogenicity of Candida albicans. NPJ Antimicrob Resist. 2024;2(1):23.
[7] Yu ST, Sun ZY, Li N, et al. Mettl1 knockdown alleviates cardiac I/R injury in mice by inactivating the Mettl1-CYLD-P53 positive feedback loop. Acta Pharmacol Sin. 2025 Mar;46(3):592-605.
[8] Tamura R, Doi S, Nakashima A, et al. Inhibition of the H3K4 methyltransferase SET7/9 ameliorates peritoneal fibrosis. PLoS One. 2018 May 3;13(5):e0196844.
Sinefungin是一种S-腺苷甲硫氨酸类似物的天然核苷类抗生素，可抑制多种甲基转移酶（包括蛋白、DNA和RNA甲基转移酶）的活性[1-2]。Sinefungin可用于探索表观遗传学机制，以及开发抗病毒、抗寄生虫和抗真菌药物方面的研究[3-4]。
在体外，Sinefungin (10μM)作用于预感染纽卡斯尔病病毒和痘苗病毒的小鼠L细胞72小时，能显著抑制病毒斑块的形成[5]。Sinefungin（0.25–4μM）预处理白色念珠菌（C. albicans）菌株5天。Sinefungin显著抑制C. albicans的菌丝伸长和长期生物膜形成。Sinefungin与C. albicans共孵育HEK293T和H1299 2h，可降低C. albicans对细胞的感染能力[6]。
在体内，Sinefungin（10mg/kg/day）通过腹腔注射预处理小鼠5天，随后建立心脏缺血/再灌注（I/R）模型（左前降支冠状动脉结扎45分钟，再灌注24小时）。Sinefungin显著改善心脏功能（提高射血分数和缩短分数），减小心肌梗死面积，并降低血清乳酸脱氢酶（LDH）水平[7]。Sinefungin（10mg/kg）通过皮下注射预处理腹膜纤维化C57/BL6小鼠（每日一次，连续5天/周，持续3周）。Sinefungin显著抑制腹膜细胞密度增加和腹膜下致密区增厚[8]。
| Cell experiment [1]: | |
Cell lines | HEK293T cells (human embryonic kidney epithelial cell line) and H1299 cells (human lung epithelial cell line) |
Preparation Method | HEK293T cells were cultured in DMEM, and H1299 cells were cultured in RPMI-1640. Both media were supplemented with penicillin-streptomycin and 10% fetal bovine serum (FBS) at 37°C, 5% CO₂. For adhesion assays, the SC5314 strain or clinical isolates of Candida albicanswere grown to exponential phase at 30°C in YPD medium. The yeast cells were then collected, washed with PBS, and added to the human epithelial cell cultures at a density of approximately 10⁶cells/mL. Co-cultures were incubated at 37°C with 5% CO₂ and gentle shaking for 2 hours. Human epithelial cells were treated with varying concentrations of Sinefungin (0.25–4μM; for 2h), which was added to the medium concurrently with the C. albicanscells. |
Reaction Conditions | 0.25-4μM; 2h |
Applications | Treatment of Candida albicans with low concentrations of Sinefungin (0.5µM) significantly reduced the adhesion of the fungal cells to both HEK293T and H1299 epithelial cell lines. |
| Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | Mice were intraperitoneally administered Sinefungin (10mg/kg) once daily for five consecutive days. Cardiac ischemia/reperfusion (I/R) injury was induced by ligating the left anterior descending coronary artery (LAD) for 45 minutes, followed by 24 hours of reperfusion. |
Dosage form | 10mg/kg/day; i.p.; 5 days. |
Applications | Sinefungin significantly ameliorated cardiac I/R injury by reducing myocardial infarct size, improving cardiac function, and decreasing serum lactate dehydrogenase (LDH) levels. Sinefungin suppressed cardiomyocyte apoptosis. Mechanistically, Sinefungin inhibited METTL1-mediated m7G RNA methylation, leading to decreased CYLD mRNA stability and subsequent suppression of P53 protein accumulation via ubiquitination pathways. |
References: | |
| Cas No. | 58944-73-3 | SDF | |
| 别名 | 西奈芬净,Adenosyl-Ornithine; A-9145; Antibiotic 32232RP | ||
| Canonical SMILES | O[C@H]([C@@H]1O)[C@@H](O[C@@H]1C[C@@H](N)CC[C@H](N)C(O)=O)N2C(N=CN=C3N)=C3N=C2 | ||
| 分子式 | C15H23N7O5 | 分子量 | 381.39 |
| 溶解度 | Water : 100 mg/mL (262.20 mM) | 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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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.622 mL | 13.1099 mL | 26.2199 mL |
| 5 mM | 524.4 μL | 2.622 mL | 5.244 mL |
| 10 mM | 262.2 μL | 1.311 mL | 2.622 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。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
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- Purity: >95.00%
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