Cyclosporin C
(Synonyms: 环孢菌素C) 目录号 : GC45904
A fungal metabolite with diverse biological activities
Cas No.:59787-61-0
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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 , 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.
|1. von Wartburg, A., and Traber, R. Cyclosporins, fungal metabolites with immunosuppressive activities. Prog. Med. Chem. 25, 1-33 (1988).|2. Moussa•f, M., Jacques, P., Schaarw•chter, P., et al. Cyclosporin 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 al. In 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).
| Cas No. | 59787-61-0 | SDF | |
| 别名 | 环孢菌素C | ||
| Canonical 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 | ||
| 分子式 | C62H111N11O13 | 分子量 | 1218.6 |
| 溶解度 | DMF: 20 mg/ml,DMF:PBS (pH 7.2) (1:3): 0.25 mg/ml,DMSO: 3 mg/ml,Ethanol: 14 mg/ml | 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 | 0.8206 mL | 4.1031 mL | 8.2061 mL |
| 5 mM | 0.1641 mL | 0.8206 mL | 1.6412 mL |
| 10 mM | 0.0821 mL | 0.4103 mL | 0.8206 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。
Lethal and Sublethal Toxicity Assessment of Cyclosporin C (a Fungal Toxin) against Plutella xylostella (L.)
Toxins (Basel) 2022 Jul 28;14(8):514.PMID:36006176DOI:10.3390/toxins14080514.
Secondary metabolites/toxins produced by Purpeocillium lilacinum (Hypocreales; Phiocordycipitaceae), a well-known insect pathogen, can be used for the management of different insect pests. We report the lethal and sublethal effects of Cyclosporin C (a toxin produced by P. lilacinum) against a major vegetable pest, Plutella xylostella, at specific organismal (feeding rate, larval growth, adult emergence, fecundity, and adult longevity) and sub-organismal levels (changes in antioxidant and neurophysiological enzyme activities). The toxicity of Cyclosporin C against different larval instars of P. xylostella increased with increasing concentrations of the toxin and the maximum percent mortality rates for different P. xylostella larval instars at different times were observed for the 300 µg/mL Cyclosporin C treatment, with an average mortality rate of 100% for all larval instars. The median lethal concentrations (LC50) of Cyclosporin C against the first, second, third, and fourth larval instars of P. xylostella 72 h post-treatment were 78.05, 60.42, 50.83, and 83.05 μg/mL, respectively. Different concentrations of Cyclosporin C caused a reduction in the average leaf consumption and average larval weight. Different life history parameters, such as the pupation rate (%), adult emergence (%), female fecundity, and female longevity were also inhibited when different concentrations of Cyclosporin C were applied topically. The Cyclosporin C concentrations inhibited the activities of different detoxifying (glutathione S-transferase, carboxylesterase, and acetylcholinesterase) and antioxidant enzyme (superoxide dismutase, catalase, and peroxidase) activities of P. xylostella when compared to the control. These findings can serve as baseline information for the development of Cyclosporin C as an insect control agent, although further work on mass production, formulation, and field application is still required.
Identification of Cyclosporin C from Amphichorda felina using a Cryptococcus neoformans differential temperature sensitivity assay
Appl Microbiol Biotechnol 2018 Mar;102(5):2337-2350.PMID:29396588DOI:10.1007/s00253-018-8792-0.
We used a temperature differential assay with the opportunistic fungal pathogen Cryptococcus neoformans as a simple screening platform to detect small molecules with antifungal activity in natural product extracts. By screening of a collection extracts from two different strains of the coprophilous fungus, Amphichorda felina, we detected strong, temperature-dependent antifungal activity using a two-plate agar zone of inhibition assay at 25 and 37 °C. Bioassay-guided fractionation of the crude extract followed by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance spectroscopy (NMR) identified Cyclosporin C (CsC) as the main component of the crude extract responsible for growth inhibition of C. neoformans at 37 °C. The presence of CsC was confirmed by comparison with a commercial standard. We sequenced the genome of A. felina to identify and annotate the CsC biosynthetic gene cluster. The only previously characterized gene cluster for the biosynthesis of similar compounds is that of the related immunosuppressant drug cyclosporine A (CsA). The CsA and CsC gene clusters share a high degree of synteny and sequence similarity. Amino acid changes in the adenylation domain of the CsC nonribosomal peptide synthase's sixth module may be responsible for the substitution of L-threonine compared to L-α-aminobutyric acid in the CsA peptide core. This screening strategy promises to yield additional antifungal natural products with a focused spectrum of antimicrobial activity.
Cyclosporin C is the main antifungal compound produced by Acremonium luzulae
Appl Environ Microbiol 1997 May;63(5):1739-43.PMID:9143111DOI:10.1128/aem.63.5.1739-1743.1997.
A strain of Acremonium luzulae (Fuckel) W. Gams was selected in screening new microorganisms for biological control of fruit postharvest diseases, especially gray and blue mold diseases on apples and strawberries. This strain manifests a very strong activity against a large number of phytopathogenic fungi. In this work, the product responsible for this antifungal activity was isolated from modified Sabouraud dextrose broth cultures of A. luzulae. It was purified to homogeneity by reverse-phase column chromatography. On the basis of UV, infrared, and 1H and 13C nuclear magnetic resonance spectra, mass spectral analysis, and the amino acid composition of the acid hydrolysates, the antibiotic was determined to be Cyclosporin C. Cyclosporin C showed a broad-spectrum activity against filamentous phytopathogenic fungi but no activity against bacteria or yeasts. Its antifungal activity is only fungistatic. In contrast to Tolypocladium inflatum, another cyclosporin-producing strain, A. luzulae, did not produce additional cyclosporins. This was confirmed by in vivo-directed biosynthesis.
Cyclosporin C(2) and C(0) concentration monitoring in stable, long-term heart transplant recipients receiving metabolic inhibitors
J Heart Lung Transplant 2003 Jul;22(7):715-22.PMID:12873538DOI:10.1016/s1053-2498(02)00649-6.
Background: Cyclosporin (CsA) dose selection is complicated by significant pharmacokinetic variability between patients. Although therapeutic drug monitoring (TDM) has proven to be a useful tool for dose individualization, the search for an effective and practical measure of clinical effect has uncovered a number of options. Monitoring the CsA concentration in a blood sample taken 2 hours after the dose (C(2)) has been utilized but has not been rigorously evaluated in all clinical situations. The aim of this study was to evaluate C(2) and trough (C(0)) CsA concentrations as surrogate markers of area under the concentration-time curve (AUC) in stable, long-term heart transplant recipients receiving CsA alone or with diltiazem and/or ketoconazole. Methods: CsA blood concentration-time data were collected at steady state for 47 stable heart transplant recipients after the morning dose of Neoral. CsA concentration in whole blood was quantitated using the EMIT immunoassay. Patients were stratified into 4 groups, depending on the long-term concomitant administration of drugs known to inhibit CsA metabolism, as part of their routine therapy: Group A (n = 11), CsA alone; Group B (n = 10), CsA with slow-release diltiazem; Group C (n = 13), CsA with ketoconazole; and Group D (n = 12), CsA with a combination of diltiazem and ketoconazole. Results: In Group A, C(2) correlated poorly with AUC(0-5) (r(2) = 0.197; p = 0.17), whereas C(0) (trough blood sample) showed a stronger correlation (r(2) = 0.710; p = 0.001). Correlations of C(0) and C(2) with AUC(0-5) were the same, but weaker in patients receiving CsA and diltiazem (r(2) = 0.650; p = 0.005); however, C(2) correlated strongly with AUC(0-5) in patients receiving ketoconazole (r(2) = 0.870; p < 0.0001) or ketoconazole with diltiazem (r(2) = 0.898; p < 0.0001). C(0) was a poor predictor of AUC(0-5) in the latter 2 groups. Conclusions: C(2) showed a strong correlation with AUC(0-5) in cardiothoracic transplant recipients receiving CsA with ketoconazole, but not with CsA alone or diltiazem. TDM using C(2) as an estimate of AUC requires further evaluation before being applied in long-term, stable cardiac transplant patients, as it may lead to inappropriate dose adjustment of CsA in patients receiving concomitant metabolic inhibitors.
Dosage, timing, and route of administration of cyclosporin A and nonimmunosuppressive derivatives of dihydrocyclosporin A and Cyclosporin C against Schistosoma mansoni in vivo and in vitro
Antimicrob Agents Chemother 1987 Oct;31(10):1567-71.PMID:3435104DOI:10.1128/AAC.31.10.1567.
The prophylactic and therapeutic effects of cyclosporin A (CsA) against percutaneous Schistosoma mansoni infection in MF1 mice were dose related and dependent on the temporal relationship between drug administration and infection. Antischistosomal activity, assessed by worm recovery from the host 6 weeks after infection, was most effective (complete worm elimination) when CsA was administered at the time of infection. Oral administration of CsA was less effective than subcutaneous injection, and no prophylactic activity was demonstrated by the former route. Derivatives of dihydrocyclosporin A and Cyclosporin C, which have been reported to exert only poor immunosuppressive activity, exhibited efficacy against S. mansoni similar to that of CsA and were also less effective when given orally. Subcutaneous, but not oral CsA reduced cercarial skin penetration and transformation success; the derivative of dihydrocyclosporin A, however, was without effect. Moreover, CsA, but not the derivative of dihydrocyclosporin A, reduced the number of worms established after intraperitoneal injection of cercariae. These data provide further insight into the antischistosomal activity of cyclosporins, which appears to be distinct from their immunomodulatory properties, since parasite killing was retained both in immunologically disparate mice and with poorly immunosuppressive cyclosporin derivatives.