| Identification | Back Directory | [Name]
CYCLOSPORIN D | [CAS]
63775-96-2 | [Synonyms]
CYCLOSPORIN D
Val2-cyclosporine
Cyclosporin D, >=95%
Cyclosporin D solution
7-L-Valinecyclosporin A
Cyclosporine IMpurity-D
7-L-valinecyclosporine A
Cyclosporin D, froM MicroMonospora
1-(3-Chlorophenyl)piperazine-D8 hydrochloride solution
(3R,4R)-3-Hydroxy-N-methyl-5-[(E)-1-propenyl]cyclo(L-Leu-L-Val-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-D-Ala-N-methyl-L-Leu-N-methyl-L-Leu-N-methyl-L-Val-)
(3R,4R)-3-Hydroxy-N-methyl-5-[(E)-1-propenyl]-cyclo(L-Leu-L-Val-Sar-N-methyl-L-Leu-L-Val-N-methyl-L-Leu-L-Ala-D-Ala-N-methyl-L-Leu-N-methyl-L-Leu-N-methyl-L-Val-)
Cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-valyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl] | [EINECS(EC#)]
200-835-2 | [Molecular Formula]
C63H111N11O12 | [MDL Number]
MFCD00907207 | [MOL File]
63775-96-2.mol | [Molecular Weight]
1214.62 |
| Chemical Properties | Back Directory | [Appearance]
Colorless Crystalline Solid | [Melting point ]
148-1510C | [alpha ]
D20 -245° (c = 0.52 in CHCl3); D20 -211° (c = 0.51 in methanol) | [Boiling point ]
1294.7±65.0 °C(Predicted) | [density ]
1.015±0.06 g/cm3(Predicted) | [Fp ]
9 °C | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Sparingly), Ethyl Aceatate (Slightly), Methanol (Slightly) | [form ]
Colorless to off-white crystalline solid. | [pka]
13.22±0.70(Predicted) | [color ]
White to Off-White | [Sequence]
cyclo ({Aaa}-Val-{Sar}-Leu-Val-Leu-Ala-Ala-Leu-Leu-{d-Val}) | [InChIKey]
YJDYDFNKCBANTM-QCWCSKBGSA-N |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless Crystalline Solid | [Uses]
A group of nonpolar cyclic oligopeptides with immunosupppressant activity. | [Uses]
Cyclosporin D is a minor analogue of the cyclosporin family which is only weakly immunologically active. Cyclosporin D is a potent inhibitor of tumor-promoting phorbol esters on mouse skin in vivo, and a potent inhibitor of calcium/calmodulin-dependent EF-2 phosphorylation in vitro. | [Uses]
Cyclosporin D is a minor analogue of the cyclosporin family which is only weakly immunologically active. Cyclosporin D is a potent inhibitor of tumour-promoting phorbol esters on mouse skin in vivo, and a potent inhibitor of calcium/calmodulin-dependent EF-2 phosphorylation in vitro. | [Biological Activity]
cyclosporin d is an immunosuppressive agent [1].cyclosporin d (csd) is an analogue of cyclosporine a with weak immunosuppressive activity. cyclosporin d has been used as an internal standard for the quantification of cyclosporin a. in human multidrug-resistant ovarian cancer cells, cyclosporin d significantly overcame adriamycin resistance [2]. in lymphocyte, csd weakly inhibited pha-, pwm-, and pma + ca2+-induced cell proliferation [3].in mice, csd inhibited edema in mouse ear and alkaline phosphatase activity in mouse skin induced by tpa by 98% and 88%, respectively. in cytosol of mouse pancreas, csd inhibited the ca2+/calmodulin-dependent phosphorylation of the elongation factor 2 (ef-2) and the tpa-induced increase of ef-2 [1]. cyclosporin d was effective in inhibiting p. falciparum parasite in vitro and p. berghei malaria parasite development in vivo when administered orally [4]. | [in vivo]
Cyclosporine D is a potent inhibitor in vivo of phorbol ester TPA-induced biological effects in mouse skin[1]. | [storage]
+4°C | [References]
[1]. gschwendt m, kittstein w, marks f. the weak immunosuppressant cyclosporine d as well as the immunologically inactive cyclosporine h are potent inhibitors in vivo of phorbol ester tpa-induced biological effects in mouse skin and of ca2+/calmodulin dependent ef-2 phosphorylation in vitro. biochem biophys res commun, 1988, 150(2): 545-551.
[2]. mizuno k, furuhashi y, misawa t, et al. modulation of multidrug resistance by immunosuppressive agents: cyclosporin analogues, fk506 and mizoribine. anticancer res, 1992, 12(1): 21-25.
[3]. sadeg n, pham-huy c, rucay p, et al. in vitro and in vivo comparative studies on immunosuppressive properties of cyclosporines a, c, d and metabolites m1, m17 and m21. immunopharmacol immunotoxicol, 1993, 15(2-3): 163-177.
[4]. uadia po1, ezeamuzie ic, ladan mj, et al. antimalarial activity of cyclosporins a, c and d. afr j med med sci, 1994, 23(1): 47-51. |
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