A natural bicyclic pentapeptide
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Malformin C

Item No. 21613

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo(D-cysteinyl-D-cysteinyl-L-valyl-D-leucyl-L-leucyl), cyclic (1→2)-disulfide
CAS Number
59926-78-2
Synonyms
  • Malformin B1b
Molecular Formula
C23H39N5O5S2
Formula Weight
529.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
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
InChi Code
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
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $250

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    1 mg

    $423

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    Cayman Chemical
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    Product Description

    Malformin C is a natural fungus-derived bicyclic pentapeptide that has antibacterial properties, particularly against species of Bacillus.1 Malformin C potently blocks the ability of bleomycin (Item No. 13877) to induce G2 arrest in human T-cell leukemia-derived Jurkat cells (IC50 = 0.9 nM).2 It less potently abrogates colchicine-induced M phase arrest in Jurkat cells (IC50 = 24 nM).2 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.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kobbe, B., Cushman, M., Wogan, G.N., et al. Production and antibacterial activity of malforming C, a toxic metabolite of Aspergillus niger. Appl. Environ. Microbiol. 33(4), 996-997 (1977).

    2. Hagimori, K., Fukuda, T., Hasegawa, Y., et al. Fungal malformins inhibit bleomycin-induced G2 checkpoint in Jurkat cells. Biol. Pharm. Bull. 30(8), 1379-1383 (2007).

    3. Wang, J., Jiang, Z., Lam, W., et al. Study of malformin C, a fungal source cyclic pentapeptide, as an anti-cancer drug. PLoS One 10(11), e0140069 (2015).