Cyclosporine metabolite M17
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| Category | Cyclosporin Analogue Set |
| Catalog number | BBF-05748 |
| CAS | 89270-28-0 |
| Molecular Weight | 1218.61 |
| Molecular Formula | C62H111N11O13 |
| Purity | ≥90% by HPLC |
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Description
Cyclosporine metabolite M17 is a metabolite of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.
Specification
| Synonyms | Cyclosporin AM 1; 6-[(2S,3R,4R,6E)-3,8-Dihydroxy-4-methyl-2-(methylamino)-6-octenoic acid]cyclosporin A; Cyclosporin A Metabolite M17; Cyclosporin metabolite AM1; OL-17; 1,4,7,10,13,16,19,22,25,28,31-Undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone, 33-[(1R,2R,4E)-1,6-dihydroxy-2-methyl-4-hexen-1-yl]-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-3,21-bis(1-methylethyl)-6,9,18,24-tetrakis(2-methylpropyl)-, (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)- |
| Storage | Store at -20°C |
| IUPAC Name | (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(E,1R,2R)-1,6-dihydroxy-2-methylhex-4-enyl]-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone |
| Canonical SMILES | CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CCO)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C |
| InChI | InChI=1S/C62H111N11O13/c1-24-43-58(82)67(17)33-48(75)68(18)44(29-34(2)3)55(79)66-49(38(10)11)61(85)69(19)45(30-35(4)5)54(78)63-41(15)53(77)64-42(16)57(81)70(20)46(31-36(6)7)59(83)71(21)47(32-37(8)9)60(84)72(22)50(39(12)13)62(86)73(23)51(56(80)65-43)52(76)40(14)27-25-26-28-74/h25-26,34-47,49-52,74,76H,24,27-33H2,1-23H3,(H,63,78)(H,64,77)(H,65,80)(H,66,79)/b26-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1 |
| InChI Key | ZPZHKIOMBYYVRD-WRDPQARASA-N |
Properties
| Appearance | White Solid |
| Application | A cyclosporine metabolite specifically inhibits growth of renal cells in culture. |
| Boiling Point | 1325.2±65.0 °C at 760 mmHg |
| Melting Point | >145°C (dec.) |
| Density | 1.0±0.1 g/cm3 |
| Solubility | Soluble in Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
Reference Reading
1. Adenovirus endocytosis via alpha(v) integrins requires phosphoinositide-3-OH kinase
E Li, D Stupack, R Klemke, D A Cheresh, G R Nemerow J Virol. 1998 Mar;72(3):2055-61. doi: 10.1128/JVI.72.3.2055-2061.1998.
Integrins mediate cell adhesion and motility on the extracellular matrix, yet they also promote viral attachment and/or entry. Evidence is presented that adenovirus internalization by alpha(v) integrins requires activation of phosphoinositide-3-OH kinase (PI3K), whereas alpha(v) integrin-mediated cell motility depends on the ERK1/ERK2 mitogen-activated protein kinase pathway. Interaction of adenovirus with alpha(v), integrins induced activation of PI3K. Pharmacologic or genetic disruption of endogenous PI3K activity blocked adenovirus internalization and virus-mediated gene delivery yet had no effect on integrin-mediated cell adhesion or motility. Therefore, integrin ligation engages distinct signaling pathways that promote viral endocytosis or cell movement.
2. Cyclosporin A and hydroxycyclosporine (M-17) affect the secretory phenotype of human gingival fibroblasts
A Mariotti, T Hassell, D Jacobs, C J Manning, A F Hefti J Oral Pathol Med. 1998 Jul;27(6):260-6. doi: 10.1111/j.1600-0714.1998.tb01953.x.
The responsiveness of human gingival fibroblast populations to cyclosporin A (CsA) and its principal metabolite, hydroxycyclosporine (M17), was evaluated in cell culture. Gingival fibroblasts exhibited a dose-dependent accumulation and bell-shaped distribution of dansylated CsA. A 100-fold excess of non-labeled CsA prevented the accumulation of the fluorescent probe in the fibroblasts. Both CsA (400 ng/ml) and M17 (100 ng/ml) stimulated mean gingival fibroblast cell number to 23.2% and 36.7% above controls, and reduced mean collagen production by 37.7% and 37.4% below controls, respectively; however, neither CsA nor M17 affected mean protein production in comparison to control cultures. Analyses of responses to CsA and M17 by ligand-accumulating and non-accumulating fibroblasts sorted out from the parent cultures did not provide consistent interstrain responses either by cells representing the upper quartile of fluorescence or cells representing the bottom quartiles of fluorescence. These data demonstrate that CsA is accumulated by gingival fibroblasts and that CsA and M17 are potent modulators of gingival fibroblast phenotype.
3. The determination of metabolite M17 and its meaning for immunosuppressive cyclosporin therapy
G Khoschsorur, T Auer, G Lanzer, P Petritsch, H Holzer, K H Tscheliessnigg Angiology. 1998 Apr;49(4):307-14. doi: 10.1177/000331979804900409.
Cyclosporin A (CyA) is intensively metabolized by the hepatic cytochrome p450 III monooxygenase A system in the human liver, the most important metabolites being M1, M17, and M21. Because CyA and its metabolites have nephrotoxic, hepatotoxic, and neurotoxic side effects, CyA dosage must be calculated to avoid the risk of organ rejection through underdosage and toxic organ damage through overdosage or accumulation of metabolites. In this study, we determined the whole-blood concentrations of cyclosporin and metabolite M17 by high-pressure liquid chromatography (HPLC) and by monoclonal specific and polyclonal nonspecific fluorescence polarization immunoassay (Abbott) in patients after immunosuppressive treatment. Patients with different resorption and metabolization rates showed high individual variations. CyA concentrations in patients with good liver function and low concentrations of CyA metabolites showed a good correlation between the HPLC and the FPIA (TDx-monoclonal assay) methods in ranges between 25 and 180 ng/mL. TDx-monoclonal was not always as precise as HPLC. In cases of metabolic disorders, we found false high CyA concentrations assayed with the immunologic method, caused by a crossreaction of the elevated metabolite concentration. We found that HPLC rendered more information about the extent of immunosuppressive activity and the metabolization rate and showed a good correlation with the concentration of metabolite M17 and total metabolites measured with the Abbott CyA polyclonal kit.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
