Malformin C
(Synonyms: 畸形素C) 目录号 : GC41186
A natural bicyclic pentapeptide
Cas No.:59926-78-2
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Malformin C is a natural fungus-derived bicyclic pentapeptide that has antibacterial properties, particularly against species of Bacillus. Malformin C potently blocks the ability of bleomycin to induce G2 arrest in human T-cell leukemia-derived Jurkat cells (IC50 = 0.9 nM). It less potently abrogates colchicine-induced M phase arrest in Jurkat cells (IC50 = 24 nM). Malformin C inhibits cell growth dose-dependently in Colon 38 and HCT 115 cancer cells (IC50s = 0.27 and 0.18 µM, respectively) but has a low therapeutic index against cancer xenografts when tested in mice.
| Cas No. | 59926-78-2 | SDF | |
| 别名 | 畸形素C | ||
| Canonical SMILES | O=C1[C@H](CC(C)C)NC([C@@H](CC(C)C)NC([C@H](C(C)C)NC([C@@H]2NC([C@@H](CSSC2)N1)=O)=O)=O)=O | ||
| 分子式 | C23H39N5O5S2 | 分子量 | 529.7 |
| 溶解度 | Chloroform: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 1.8879 mL | 9.4393 mL | 18.8786 mL |
| 5 mM | 0.3776 mL | 1.8879 mL | 3.7757 mL |
| 10 mM | 0.1888 mL | 0.9439 mL | 1.8879 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。
Malformin C, an algicidal peptide from marine fungus Aspergillus species
Ecotoxicology 2021 Jul;30(5):996-1003.PMID:33755843DOI:10.1007/s10646-021-02389-3.
A natural compound with the algicidal effect was isolated from the culture medium of Aspergillus sp. SCSIOW2 and was identified as Malformin C, which was based on the data of 1H-NMR, 13C-NMR, and ESI-MS. Malformin C exhibited dose-dependent algicidal activities against two strains of noxious red tide algae, Akashiwo sanguinea and Chattonella marina. The activity against A. sanguinea was stronger than that against C. marina (the algicidal activity of 58 and 36% at 50 μM treatment for 2 h, respectively). Morphology changes including perforation, plasmolysis, and fragmentation of algal cells were observed. Malformin C induced a significant increase in ROS level, caused the damage of SOD activity, and led to the massive generation of MDA contents in algae cells. To our knowledge, this is the first report of the cyclic peptide described as an algicidal compound against HABs.
Study of Malformin C, a Fungal Source Cyclic Pentapeptide, as an Anti-Cancer Drug
PLoS One 2015 Nov 5;10(11):e0140069.PMID:26540166DOI:10.1371/journal.pone.0140069.
Malformin C, a fungal cyclic pentapeptide, has been claimed to have anti-cancer potential, but no in vivo study was available to substantiate this property. Therefore, we conducted in vitro and in vivo experiments to investigate its anti-cancer effects and toxicity. Our studies showed Malformin C inhibited Colon 38 and HCT 116 cell growth dose-dependently with an IC50 of 0.27±0.07μM and 0.18±0.023μM respectively. This inhibition was explicated by Malformin C's effect on G2/M arrest. Moreover, we observed up-regulated expression of phospho-histone H2A.X, p53, cleaved CASPASE 3 and LC3 after Malformin C treatment, while the apoptosis assay indicated an increased population of necrotic and late apoptotic cells. In vivo, the pathological study exhibited the acute toxicity of Malformin C at lethal dosage in BDF1 mice might be caused by an acute yet subtle inflammatory response, consistent with elevated IL-6 in the plasma cytokine assay. Further anti-tumor and toxicity experiments proved that 0.3mg/kg injected weekly was the best therapeutic dosage of Malformin C in Colon 38 xenografted BDF1 mice, whereas 0.1mg/kg every other day showed no effect with higher resistance, and 0.9mg/kg per week either led to fatal toxicity in seven-week old mice or displayed no advantage over 0.3mg/kg group in nine-week old mice. Overall, we conclude that Malformin C arrests Colon 38 cells in G2/M phase and induces multiple forms of cell death through necrosis, apoptosis and autophagy. Malformin C has potent cell growth inhibition activity, but the therapeutic index is too low to be an anti-cancer drug.
Solid-phase synthesis and biological activity of Malformin C and its derivatives
J Antibiot (Tokyo) 2009 Dec;62(12):681-6.PMID:19876076DOI:10.1038/ja.2009.100.
We accomplished the solid-phase total synthesis of Malformin C, which is adaptable for the easy preparation of various derivatives. A solid-phase total synthesis of Malformin C was achieved by on-resin macrolactamization and disulfide bond formation, with concurrent cleavage from the resin. Antimalarial and antitrypanosomal activities were examined, which helped elucidate partial structure-activity relationships. Results indicate that the disulfide bond is essential and branched amino acids are also crucial components if the compound is to exhibit potent antimalarial and antitrypanosomal properties.
Total synthesis of Malformin C, an inhibitor of bleomycin-induced G2 arrest
J Antibiot (Tokyo) 2008 May;61(5):297-302.PMID:18653995DOI:10.1038/ja.2008.42.
Total synthesis of a fungal cyclic peptide, Malformin C, recently rediscovered as a G2 checkpoint inhibitor was completed. Our synthesis involved a convergent approach with respect to a linear pentapeptide, cyclization, and oxidative disulfide formation.
Fungal malformins inhibit bleomycin-induced G2 checkpoint in Jurkat cells
Biol Pharm Bull 2007 Aug;30(8):1379-83.PMID:17666789DOI:10.1248/bpb.30.1379.
A DNA-damaging agent, bleomycin, arrests the cell cycle at the G2 phase of Jurkat cells, which are defective in the G1 checkpoint, while microtubule-disrupting colchicine arrests it at M phase. Fungal cyclopeptides, malformin A1 and Malformin C, were found to abrogate bleomycin-induced G2 arrest (IC(50); 0.48 microM and 0.9 nM, respectively), resulting in a drastic decrease in cells in G2 phase and increase in cells in subG1 phase. On the other hand, malformins showed little effect on the colchicine-induced M phase arrest in Jurkat cells (IC(50); 2.7 microM and 24 nM, respectively). Malformin C (0.026 microM) also abrogated bleomycin-induced G2 arrest in colon cancer-derived HCT-116 cells. These data strongly suggest that Malformin C disrupted the cell cycle at the G2 checkpoint of cancer cells, leading to sensitization of the cancer cells to the anti-cancer reagent.