A fungal metabolite with diverse biological activities
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Cyclosporin C

Item No. 29152

Technical Information
Formal Name
7-L-threonine-cyclosporin A
CAS Number
59787-61-0
Molecular Formula
C62H111N11O13
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:3): 0.25 mg/mlDMSO: 3 mg/mlEthanol: 14 mg/ml
SMILES
CC(C)C[C@@H](C(N[C@@H](C)C(N[C@H](C)C(N([C@@H](CC(C)C)C(N(C)[C@@H](CC(C)C)C1=O)=O)C)=O)=O)=O)N(C([C@H](C(C)C)NC([C@@H](N(C(CN(C([C@@]([C@H](O)C)([H])NC([C@](N(C([C@H](C(C)C)N1C)=O)C)([H])[C@H](O)[C@H](C)C/C=C/C)=O)=O)C)=O)C)CC(C)C)=O)=O)C
InChi Code
InChI=1S/C62H111N11O13/c1-25-26-27-39(14)52(76)51-56(80)66-49(42(17)74)60(84)67(18)32-47(75)68(19)43(28-33(2)3)55(79)65-48(37(10)11)61(85)69(20)44(29-34(4)5)54(78)63-40(15)53(77)64-41(16)57(81)70(21)45(30-35(6)7)58(82)71(22)46(31-36(8)9)59(83)72(23)50(38(12)13)62(86)73(51)24/h25-26,33-46,48-52,74,76H,27-32H2,1-24H3,(H,63,78)(H,64,77)(H,65,79)(H,66,80)/b26-25+/t39-,40+,41-,42-,43+,44+,45+,46+,48+,49+,50+,51+,52-/m1/s1
InChi Key
JTOKYIBTLUQVQV-QRVTZXGZSA-N
Origin
Fungi
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cyclosporin C is a fungal metabolite that has been found in T. inflatum and has diverse biological activities, including antifungal, antiviral, and immunosuppressant properties.1,2,3,4 It is active against isolates of B. cinerea, A. niger, and Alternaria, Mucor, and Penicillium species (MICs = 0.1-5 μg/ml).2 Cyclosporin C (15 μg/ml) inhibits vaccinia virus replication in infected BSC40 cells by 98.82%.3 It inhibits lymphocyte proliferation induced by the mitogens concanavalin A (ConA; Item No. 14951), phytohemagglutinin L (PHA), and pokeweed mitogen (PWM), as well as proliferation induced by alloantigen in mixed lymphocyte culture when used at a concentration of 100 ng/ml.4 Cyclosporin C (100 ng/ml) inhibits the local graft versus host (GVH) reaction in mice receiving splenocyte grafts.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. von Wartburg, A., and Traber, R. Cyclosporins, fungal metabolites with immunosuppressive activities. Prog. Med. Chem. 25, 1-33 (1988).

    2. Moussaïf, M., Jacques, P., Schaarwächter, P., et alCyclosporin C is the main antifungal compound produced by Acremonium luzulae. Appl. Environ. Microbiol. 63(5), 1739-1743 (1997).

    3. Damaso, C.R., and Moussatché, N. Inhibition of vaccinia virus replication by cyclosporin A analogues correlates with their affinity for cellular cyclophilins. J. Gen. Virol. 79(Pt 2), 339-346 (1998).

    4. Sadeg, N., Pham-Huy, C., Rucay, P., et alIn vitro and in vivo comparative studies on immunosuppressive properties of cyclosporines A, C, D and metabolites M1, M17 and M21. Immunopharmacol. Immunotoxicol. 15(2-3), 163-177 (1993).