Cyclosporin A A fungal metabolite calcineurin inhibitor

Cyclosporin A (CAS 59865-13-3)

Cyclosporin A | CAS 59865-13-3 is rated 5.0 out of 5 by 4.
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| See product citations (22)
Application: A fungal metabolite calcineurin inhibitor
CAS Number: 59865-13-3
Purity: ≥99%
Molecular Weight: 1202.6
Molecular Formula: C62H111N11O12
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ordering Information

PRODUCT NAME CATALOG # UNIT PRICE QTY FAVORITES
Cyclosporin A sc-3503 100 mg $55.00
Cyclosporin A sc-3503A 500 mg $217.00

Cyclosporin A is a metabolite of the fungi Trichoderma polysporum, Cyclosporin A (CsA) is a cyclic polypeptide consisting of 9 amino-acids to inhibit nitric oxide synthesis induced by interleukin 1alpha, lipopolysaccharides and TNFα. CsA is an immunosuppressant. Studies in animals indicate that cyclosporin inhibits the development of cell-mediated reactions, including allograft immunity, delayed cutaneous hypersensitivity, experimental allergic encephalomyelitis, Freund's adjuvant arthritis, graft-versus-host disease and also T-cell dependent antibody production. Also inhibits lymphokine production and release and appears to block resting lymphocytes in the G0 or G1 phase of the cell cycle. CsA binds to cyclophilin and inhibits the T-cell receptor signal transduction pathway via the formation of cyclpsporin A-cyclophilin complex. The CsA-cyclophilin complex inhibits PP2 (calcineurin, a type 2B phosphatase). Calcineurin inhibition interferes with other physiological processes as well. It inhibits mitochondrial permeability transition pore opening. However, pore inhibition becomes less efficient at increasing Ca2+ loads and inhibition is transient. Inhibits staurosporin-induced apoptosis in cultured neural cells and rotenone-induced apoptosis in PC-12 cells.


References

1. Gonatas, J.O., et al. 1989. J. Biol. Chem. 264: 646-653. PMID: 2909545
2. Bernardi, P., et al. 1993. J. Biol. Chem. 268: 1005-1010. PMID: 8419309
3. Kunz, J. and Hall, M.N. 1993. Trends Biochem. Sci. 18: 334-338. PMID: 7694398
4. Liu, J. 1993. Trends Pharmacol. Sci. 14: 182-188. PMID: 7692652
5. Broekemeier, K.M., et al. 1995. Biochemistry. 34: 16440-16449. PMID: 8845372
6. Seaton, T.A., et al. 1998. Brain Res. 809: 12-17. PMID: 9795106
7. Kruman, I.I. and Mattson, M.P. 1999. J. Neurochem. 72: 529-540. PMID: 9930724

Physical State :
Solid
Solubility :
Soluble in acetone, chloroform (6 mg/ml), DMSO (25 mg/ml), 100%ethanol (25 mg/ml), methanol, ether, petroleum ether, and dichloromethane (10 mg/ml). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
148-151° C
Boiling Point :
~1293.8° C at 760 mmHg (Predicted)
Density :
~1.0 g/cm3 (Predicted)
Refractive Index :
n20D 1.47
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GZ4120000
PubChem CID :
5284373
Merck Index :
14: 2752
MDL Number :
MFCD00274558
Beilstein Registry :
3647785
SMILES :
CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C

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Certificate of Analysis

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Cyclosporin AProduct Citations

See how others have used Cyclosporin A. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 22 total

PMID: # 27529070
Chen, D. et al. 2016. HMBA Enhances Prostratin-Induced Activation of Latent HIV-1 via Suppressing the Expression of Negative Feedback Regulator A20/TNFAIP3 in NF-κB Signaling. Biomed Res Int. 2016: 5173205.

PMID: # 27725441
Asai, M. et al. 2016. Perturbed Calcineurin-NFAT Signaling Is Associated with the Development of Alzheimer's Disease. Biol. Pharm. Bull.. 39: 1646-1652.

PMID: # 27552406
Kam, WR. et al. 2016. Do Cyclosporine A, an IL-1 Receptor Antagonist, Uridine Triphosphate, Rebamipide, and/or Bimatoprost Regulate Human Meibomian Gland Epithelial Cells? Invest. Ophthalmol. Vis. Sci.. 57: 4287-94.

PMID: # 25444914
Li, X. et al. 2015. Synergistic antitumor activity of withaferin A combined with oxaliplatin triggers reactive oxygen species-mediated inactivation of the PI3K/AKT pathway in human pancreatic cancer cells. Cancer letters. 357: 219-30.

PMID: # 26173181
Li, X. et al. 2015. Nur77 prevents excessive osteoclastogenesis by inducing ubiquitin ligase Cbl-b to mediate NFATc1 self-limitation. eLife. 4: e07217.

PMID: # 22767227
Cai, Q. et al. 2012. Elevated and secreted phospholipase A₂ activities as new potential therapeutic targets in human epithelial ovarian cancer. FASEB J.. 26: 3306-20.

PMID: # 21078663
Farrow, MA. et al. 2011. NFAT and IRF proteins regulate transcription of the anti-HIV gene, APOBEC3G. J. Biol. Chem.. 286: 2567-2577.

PMID: # 19555495
Krücken, J. et al. 2009. In silico analysis of the cyclophilin repertoire of apicomplexan parasites. Parasit Vectors. 2: -.

PMID: # 19680534
Kaul, A. et al. 2009. Essential role of cyclophilin A for hepatitis C virus replication and virus production and possible link to polyprotein cleavage kinetics. PLoS Pathog.. 5: -.

PMID: # 18216318
Edemir, B. et al. 2008. Acute rejection modulates gene expression in the collecting duct. J. Am. Soc. Nephrol.. 19: 538-546.

Citations 1 to 10 of 22 total

How long cyclosporin is active in cell medium?

Asked by: lara91
Thank you for your question. The time sc-3503 (Cyclosporin A) stays active in cell medium has not been tested, however, there are a lot of published journal articles that reference this chemical. Cyclosporin A has been proven to be active for 18h in cultured rat hepatocytes in the following article. https://www.ncbi.nlm.nih.gov/pubmed/3183963
Answered by: Technical Support
Date published: 2017-08-03

What is the appearance of the compound?

Asked by: two2igm05
This chemical, Cyclosporin A (CAS 59865-13-3), is a powder.
Answered by: Chemical Support 1
Date published: 2017-03-24

Is this product natural or synthetic? If natural, what does it come from?

Asked by: two2igm05
Thank you for your question. The compound, sc-3503, is a synthetic compound. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-20

What is the solubility of this chemical?

Asked by: two2igm05
Thank you for your question. This chemical is soluble in acetone and chloroform at 6 mg/ml, DMSO and ethanol at 35 mg/ml, and methanol, ether, and petroleum ether at 10 mg/ml. It is insoluble in water. Please contact Technical Service if you have further questions concerning this product.
Answered by: Tech Service 9
Date published: 2016-12-15
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Rated 5 out of 5 by from works as expected works as expected
Date published: 2015-11-19
Rated 5 out of 5 by from Farrow et Farrow et. al. used cyclosporin A, product sc-3503, to confirm the significance of A3G regulation by the binding of NFAT and IRF-4 to the A3G promoter. Cyclosporin A directly inhibits calcineurin, thus inhibiting NFAT nuclear translocation (PubMed ID 21078663). -SCBT Publication Review
Date published: 2015-04-11
Rated 5 out of 5 by from The cyclosporin seems to be working The cyclosporin seems to be working, we haven't done any quantification so can't say for sure.
Date published: 2015-03-30
Rated 5 out of 5 by from No comment No comment
Date published: 2015-03-25
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