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Cyclosporin A (CAS 59865-13-3)

Cyclosporin A | CAS 59865-13-3 is rated 5.0 out of 5 by 4.

| 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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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 :

n²⁰_D 1.47

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

WGK Germany :

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

Download SDS (MSDS)

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

Rated 5 out of 5 by Wan from works as expected works as expected

Date published: 2015-11-19

Rated 5 out of 5 by JT 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 Wanichaya 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 Thompson from No comment No comment

Date published: 2015-03-25

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