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SML0192

Cyclosporin C

Name: Cyclosporin C
Brand: SIGMA

≥95% (HPLC), from Acremonium luzulae

Synonym(s):

7-Threonine-cyclosporin A, Cyclosporine C

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About This Item

Empirical Formula (Hill Notation):

C₆₂H₁₁₁N₁₁O₁₃

CAS Number:

59787-61-0

Molecular Weight:

1218.61

UNSPSC Code:

12352200

NACRES:

NA.77

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biological source

Acremonium luzulae

assay

≥95% (HPLC)

solubility

DMSO: ≥10 mg/mL, H₂O: insoluble, hexane: insoluble

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

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

Application

Cyclosporin C may be used to study the cell signaling involved in autoimmune disorders.

Biochem/physiol Actions

Cyclosporins are a family of neutral, highly lipophilic, cyclic undecapeptides containing some unusual amino acids.

Cyclosporins are a family of neutral, highly lipophilic, cyclic undecapeptides containing some unusual amino acids. Cyclosporin A (CsA) is the main representative of cyclosporins. It has antifungal activity and is the strongest immunosuppressive compound discovered so far. Cyclosporin C has the same activity with reduced potency. CsA has potent anti-Hepatitis C Virus (HCV) activity towards both HCV replicons. Cyclophilins are intracellular proteins, highly conserved, involved in cis-trans isomerization of peptidyl-prolyl bonds and protein folding which bind cyclosporins and as a complex inhibit the activity of calcineurin, a phosphatase necessary for T-cell activation. Cyclosporin is therefore used for treating autoimmune disorders such as rheumatoid arthritis, systemic lupus erythematosus (SLE), and psoriasis.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

064M4124V

14111012

101M4097V

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Pseudoprolines (psiPro) in drug design: direct insertion of psiPro systems into cyclosporin C.

M Keller et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 6(23), 4358-4363 (2001-01-05)

The insertion of acetals that exhibit variable structural features into complex peptides such as cyclosporin C (CsC) results in oxazolidine derivatives (pseudoprolines, psiPro) of tailored physico-chemical and biological properties. N,O-Acetalation of the 2-threonine hydroxyl group and the preceding amide nitrogen

Experimental murine hyalohyphomycosis with soil-derived isolates of Fusarium solani.

Y Sugiura et al.

Medical mycology, 41(3), 241-247 (2003-09-11)

Two strains of soil-borne Fusarium solani, both characterized for their ability to produce cyclosporin A and C, were examined for their pathogenicity in severe combined immunodeficiency (SCID) and BALB/c male mice. Intravenous (i.v.) infections with F. solani conidia were performed.

Comparison of the properties of the CsA analogs monoacetyl CyC (o-acetyl-threonine2 cyclosporin) and methyl-alanyl CsA (N-methyl-L-alanyl6 cyclosporin); monoacetyl cyclosporin is immunosuppressive without binding to cyclophilin.

S el Rouby et al.

Clinical and experimental immunology, 89(1), 136-142 (1992-07-01)

Cyclosporin (CsA) is an immunosuppressant which binds to cyclophilin (Cyp). The relationship between Cyp binding and immunosuppression has been questioned since one of the analogs of CsA, N-methyl-L-alanyl6 cyclosporin (methyl-alanyl CsA) binds to Cyp but is not immunosuppressive. We compared

[Effect of P-glycoprotein on the absorption of buagafuran in rat intestinal lumen].

En Li et al.

Yao xue xue bao = Acta pharmaceutica Sinica, 43(4), 361-365 (2008-07-31)

To study the effect of P-glycoprotein (P-gp) on the absorption of buagafuran in ileum, the concentration of buagafuran in Caco-2 cells, rat averted intestinal sacs and recirculating perfusion were determined by UV-HPLC method. Verapamil and cyclospirin A (CsA) were used

[Effect of the quality of fat substrate on the dynamics of fatty acid utilization during biosynthesis of cephalosporin C].

V V Revin et al.

Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic], 36(1), 5-8 (1991-01-01)

Influence of the quality of the fats used on their utilization in the process of cephalosporin C fermentation and accumulation was studied. A decrease in the level of all the fractions of the fatty acids was observed during the fermentation

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