Enfumafungin
目录号 : GC61518
Enfumafungin是一种来源于真菌的天然产物，属于三萜类糖苷抗生素，具有显著的抗真菌活性。
Cas No.:260979-95-1
Sample solution is provided at 25 µL, 10mM.
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Enfumafungin is a natural product derived from fungi, belonging to the triterpene glycoside antibiotic class, and possesses significant antifungal activity[1]. Enfumafungin specifically inhibits 1,3-β-D-glucan synthase, an enzyme essential for fungal cell wall synthesis, thereby disrupting cell wall integrity and leading to fungal death [2]. Enfumafungin can be used to treat systemic infections caused by pathogenic fungi such as Candida and Aspergillus species[3]. Enfumafungin derivatives also demonstrate good activity against azole-resistant fungi, providing lead compounds for the development of new antifungal agents[4].
In vitro, treatment of Candida albicans MY1055 cells with Enfumafungin (0.2–0.5μg/ml) for 4 hours significantly inhibited β-(1,3)-glucan synthase activity, leading to the disruption of cell wall integrity and morphological changes, resulting in cell swelling, aggregate formation, and abnormal branching structures[5].
In vivo, intraperitoneal administration of Enfumafungin (90–162mg/kg) twice daily for two days to immunosuppressed mice with systemic Candida albicans infection significantly reduced the fungal load in the kidneys (ED90=90mg/kg, ED99=162mg/kg). This effect was mediated by the specific inhibition of fungal cell wall β-(1,3)-glucan synthase activity, leading to abnormal fungal cell morphology and death[6].
References:
[1] Kuhnert E, Li Y, Lan N, et al. Enfumafungin synthase represents a novel lineage of fungal triterpene cyclases. Environ Microbiol. 2018 Sep;20(9):3325-3342.
[2] Cao ZQ, Wang GQ, Luo R, et al. Biosynthesis of Enfumafungin-type Antibiotic Reveals an Unusual Enzymatic Fusion Pattern and Unprecedented C-C Bond Cleavage. J Am Chem Soc. 2024 May 8;146(18):12723-12733.
[3] Jiménez-Ortigosa C, Paderu P, Motyl MR, et al. Enfumafungin derivative MK-3118 shows increased in vitro potency against clinical echinocandin-resistant Candida Species and Aspergillus species isolates. Antimicrob Agents Chemother. 2014;58(2):1248-51.
[4] Cheng Z, Wu W, Liu Y, et al. Natural Enfumafungin Analogues from Hormonema carpetanum and Their Antifungal Activities. J Nat Prod. 2023 Oct 27;86(10):2407-2413.
[5] Onishi J, Meinz M, Thompson J, et al. Discovery of novel antifungal (1,3)-beta-D-glucan synthase inhibitors. Antimicrob Agents Chemother. 2000 Feb;44(2):368-77.
[6] Peláez F, Cabello A, Platas G, et al. The discovery of enfumafungin, a novel antifungal compound produced by an endophytic Hormonema species biological activity and taxonomy of the producing organisms. Syst Appl Microbiol. 2000 Oct;23(3):333-43.
Enfumafungin是一种来源于真菌的天然产物，属于三萜类糖苷抗生素，具有显著的抗真菌活性[1]。Enfumafungin可特异性抑制真菌细胞壁合成所必需的1,3-β-D-葡聚糖合成酶，从而破坏细胞壁完整性导致真菌死亡[2]。Enfumafungin可用于治疗由念珠菌和曲霉菌等病原真菌引起的系统性感染[3]。Enfumafungin的衍生物对唑类耐药真菌也表现出良好活性，为研发新型抗真菌药物提供了先导化合物[4]。
在体外，Enfumafungin（0.2–0.5μg/ml）处理白色念珠菌MY1055细胞4小时，显著抑制β-(1,3)-葡聚糖合成酶活性，导致细胞壁完整性破坏和形态学改变，促使细胞膨大、聚集体形成及异常分枝结构[5]。
在体内，Enfumafungin（90–162mg/kg）腹腔注射处理免疫抑制小鼠每日两次持续两天，显著降低系统性白色念珠菌感染小鼠肾脏真菌载量（ED90=90mg/kg，ED99=162mg/kg），同时通过特异性抑制真菌细胞壁β-(1,3)-葡聚糖合成酶活性导致真菌细胞形态异常和死亡[6]。
| Cell experiment [1]: | |
Cell lines | Candida albicans MY1055 (human pathogenic yeast) and Aspergillus fumigatus MF5668 (human pathogenic mold). |
Preparation Method | Yeast cells were grown in an enriched synthetic medium (CM: Difco yeast nitrogen base supplemented with 1% Bacto Peptone, 0.5% yeast extract, 10μM adenine, and 0.1% glucose). 0.2–0.5μg/mL Enfumafungin was added for 24-48h. |
Reaction Conditions | 0.2–0.5μg/mL; 24-48h |
Applications | Enfumafungin specifically inhibits fungal (1,3)-β-D-glucan synthase, disrupting cell wall biosynthesis. Enfumafungin induces severe morphological alterations, including cell swelling, aggregation, and formation of irregularly shaped cells in yeasts |
| Animal experiment [2]: | |
Animal models | Immunosuppressed mice with disseminated candidiasis |
Preparation Method | Mice were challenged intravenously with Candida albicans and treated with titrated dilutions of Enfumafungin (90–162mg/kg) administered intraperitoneally twice daily for two days. Five mice per group were used. After 7 days, mice were sacrificed and their kidneys were removed, homogenized, and serial dilutions were plated for colony enumeration. |
Dosage form | 90–162mg/kg; i.p. |
Applications | Enfumafungin produced a significant dose-dependent decrease in fungal burden (colony forming units) in kidneys of mice challenged with C. albicans, demonstrating efficacy in a systemic fungal infection model. Enfumafungin antifungal activity was modest compared to control compounds pneumocandin A₀ (ED90=0.51mg/kg) and amphotericin B (ED90=0.02mg/kg) in the same model. |
References: | |
| Cas No. | 260979-95-1 | SDF | |
| Canonical SMILES | OC(OC1)[C@@]([C@](CC2)([H])[C@@]1([C@H]3O[C@]([C@@H]([C@H]4O)O)([H])O[C@@H]([C@H]4O)CO)C)(C[C@H]3OC(C)=O)C([C@@]2([H])[C@]5(CC[C@]6(C)[C@H](C)C(C)C)C)=CC[C@]5([C@@H]6C(O)=O)C | ||
| 分子式 | C38H60O12 | 分子量 | 708.88 |
| 溶解度 | DMSO : 100 mg/mL (141.07 mM; Need ultrasonic) | 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 | 1.4107 mL | 7.0534 mL | 14.1068 mL |
| 5 mM | 282.1 μL | 1.4107 mL | 2.8214 mL |
| 10 mM | 141.1 μL | 705.3 μL | 1.4107 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。
Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
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