Malformin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04474 |
| CAS | 59926-78-2 |
| Molecular Weight | 529.72 |
| Molecular Formula | C23H39N5O5S2 |
| Purity | ≥95% |
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Description
Malformin C is a fungal cyclic pentapeptide with antibacterial and anticancer activities. Study shows that Malformin C inhibits cell growth in Colon 38 and HCT 116 cells in a dose-dependent manner with IC50 of 0.27±0.07μM and 0.18±0.023μM, respectively.
Specification
| Synonyms | Malformin B1b; Cyclo(D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-leucyl) Cyclic (1→2)-Disulfide; (-)-cyclo[D-Cys(1)-D-Cys(1)-L-Val-D-Leu-L-Leu-] |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4S,7R,10S,13S)-4,7-bis(2-methylpropyl)-10-propan-2-yl-15,16-dithia-2,5,8,11,19-pentazabicyclo[11.4.2]nonadecane-3,6,9,12,18-pentone |
| Canonical SMILES | CC(C)CC1C(=O)NC2CSSCC(C(=O)NC(C(=O)NC(C(=O)N1)CC(C)C)C(C)C)NC2=O |
| InChI | InChI=1S/C23H39N5O5S2/c1-11(2)7-14-20(30)26-16-9-34-35-10-17(27-21(16)31)22(32)28-18(13(5)6)23(33)25-15(8-12(3)4)19(29)24-14/h11-18H,7-10H2,1-6H3,(H,24,29)(H,25,33)(H,26,30)(H,27,31)(H,28,32)/t14-,15+,16+,17+,18-/m0/s1 |
| InChI Key | TZODYIWCRGWHQB-TZNCUMHOSA-N |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Bacteria |
| Boiling Point | 921.3±65.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, DMSO, Ethanol, Methanol |
Reference Reading
1. Mycobacterium smegmatis alters the production of secondary metabolites by marine-derived Aspergillus niger
Kazuo Harada, Kazumasa Hirata, Masayoshi Arai, Miho Sasaoka, Yasumasa Hara, Takahiro Jomori, Atsushi Kimishima, Andi Setiawan J Nat Med . 2020 Jan;74(1):76-82. doi: 10.1007/s11418-019-01345-0.
It is generally accepted that fungi have a number of dormant gene clusters for the synthesis of secondary metabolites, and the activation of these gene clusters can expand the diversity of secondary metabolites in culture. Recent studies have revealed that the mycolic acid-containing bacterium Tsukamurella pulmonis activates dormant gene clusters in the bacterial genus Streptomyces. However, it is not clear whether the mycolic acid-containing bacteria activate dormant gene clusters of fungi. We performed co-culture experiments using marine-derived Aspergillus niger with Mycobacterium smegmatis, a mycolic acid-containing bacteria. The co-cultivation resulted in the production of a pigment by A. niger and increased cytotoxic activity of the extract against human prostate cancer DU145 cells. An analysis of secondary metabolites in the extract of the co-culture broth revealed that the increase in cytotoxic activity was caused by the production of malformin C (1), and that TMC-256A1 (2), desmethylkotanin (3), and aurasperone C (4) were selectively produced under co-culture conditions. In addition, further study suggested that direct interaction between the two microorganisms was necessary for the production of the pigment and the cytotoxic compound malformin C (1) from A. niger. Given the biological activities of malformin C, including cytotoxic activity, our approach for increasing the production of bioactive secondary metabolites has important practical applications and may facilitate structural analyses of novel bioactive compounds.
2. Study of Malformin C, a Fungal Source Cyclic Pentapeptide, as an Anti-Cancer Drug
Jing Wang, Lihui Wang, Zhe Yu, Chunfu Wu, Wing Lam, Ying Wei, Yung-Chi Cheng, Elizabeth A Gullen, Amanda Beck, Zaoli Jiang, Ee-Chun Cheng, Yixuan Zhang, Caroline Zeiss PLoS One . 2015 Nov 5;10(11):e0140069. doi: 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.
3. Production and antibacterial activity of malforming C, a toxic metabolite of Aspergillus niger
G N Wogan, M Cushman, B Kobbe, A L Demain Appl Environ Microbiol . 1977 Apr;33(4):996-7. doi: 10.1128/aem.33.4.996-997.1977.
The production of the new mycotoxin malformin C by a solid substrate fermentation is described. Malformin C is highly toxic (mean lethal dose = 0.9 mg/kg) and exerts antibacterial activity against a variety of gram-positive and gram-negative organisms.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
