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SML0192

Sigma-Aldrich

Cyclosporin C

≥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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
064M4124V
14111012
101M4097V

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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
P Y Wong et al.
Clinical chemistry, 32(3), 492-495 (1986-03-01)
We synthesized an 125I-labeled-histamine-cyclosporin C tracer, to obviate the use of tritiated tracer in radioimmunoassay of cyclosporine. With this tracer, the assay results varied linearly with concentration up to at least 800 micrograms/L. The within-assay CV was 6.6% at 39
Monitoring cyclosporine by HPLC with cyclosporin C as internal standard.
P M Jones et al.
Clinical chemistry, 39(1), 168-168 (1993-01-01)
M Nogami et al.
The American review of respiratory disease, 141(5 Pt 1), 1289-1295 (1990-05-01)
The transnasal administration of an extract of the parasite Ascaris suum (Asc) to C57BL/6 mice for 3 wk produced marked eosinophilia in the bronchoalveolar lavage (BAL) fluid. This pulmonary eosinophilia was not accompanied by blood eosinophilia. The oral administration of
Tachykinin antagonists screening from microbial origin.
K Hayashi et al.
The Journal of antibiotics, 49(1), 110-112 (1996-01-01)
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