| Identification | Back Directory | [Name]
Cyclosporin H | [CAS]
83602-39-5 | [Synonyms]
CYCLOSPORIN H
Sandoz 37-839
Cyclosporin H, >=95%
Cyclosporine IMpurity-H
Cyclosporin H, froM MicroMonospora
5-(N-Methyl-D-valine)cyclosporin A
5-(N-Methyl-D-valine)cyclosporine A
Cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-D-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl]
Cyclo[L-alanyl-D-alanyl-N-Methyl-L-
leucyl-N-Methyl-L-leucyl-N-Methyl-D-valyl-(3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-diMethyl-L-2-aMinooctanoyl-L-2-aMinobutanoyl-N-Methylglycyl-N-Methyl-L-leucyl-L-valyl-N-Methyl-L-leucyl] | [Molecular Formula]
C62H111N11O12 | [MDL Number]
MFCD04039488 | [MOL File]
83602-39-5.mol | [Molecular Weight]
1202.61 |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [Melting point ]
148-151°C | [Boiling point ]
1293.8±65.0 °C(Predicted) | [density ]
1.016±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated) | [form ]
powder | [pka]
13.32±0.70(Predicted) | [color ]
white to beige | [biological source]
Tolypocladium inflatum | [Optical Rotation]
[α]/D -100 to -115°, c = 0.5 in methanol | [Sequence]
Cyclo[{Abu}-{Sar}-{N(Me)Leu}-Val-{N(Me)Leu}-Ala-{d-Ala}-{N(Me)Leu}-{N(Me)Leu}-{d-N(Me)Val}-{N(Me)Bmt(E)}] | [InChIKey]
BQQHPBPTWWXRMU-SXHXJWHLSA-N |
| Hazard Information | Back Directory | [Chemical Properties]
White Powder | [Uses]
An immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection.
A group of nonpolar cyclic oligopeptides with immunosupppressant activity. | [Uses]
Cyclosporin H is a minor analogue of the cyclosporin family which is immunologically inactive as it does not bind to immunophilin. Cyclopsorin H is the most extensively investigated of the minor cyclosporin analogues and displays a range of activities. It is a potent inhibitor of tumour-promoting phorbol esters on mouse skin in vivo, and of calcium/calmodulin-dependent EF-2 phosphorylation in vitro, a potent and selective antagonist of formyl peptide receptor and inhibitor of formyl peptide-induced superoxide formation.
| [Uses]
Cyclosporin H is a minor analogue of the cyclosporin family which is immunologically inactive as it does not bind to immunophilin. Cyclosporin H is the most extensively investigated of the minor cyclosporin analogues . It is a potent inhibitor of tumor-promoting phorbol esters on mouse skin in vivo, and of calcium/calmodulin-dependent EF-2 phosphorylation in vitro, a potent and selective antagonist of formyl peptide receptor and inhibitor of formyl peptide-induced superoxide formation. | [Description]
Cyclosporin H is a natural cyclic undecapeptide that selectively antagonizes the formyl peptide receptor at concentrations ranging from 0.1 to 10 μM.1,2,3 Unlike cyclosporin A (Item No. 12088), cyclosporin H does not bind cyclophilin to evoke an immunosuppressant response.4 Cyclosporin H has been reported to inhibit phorbol ester-mediated effects in mouse skin and block calcium/calmodulin-dependent EF-2 phosphorylation in vitro.5 | [Biochem/physiol Actions]
Cyclosporin H is a selective inhibitor of formyl peptide receptor-1 (FPR-1) and formyl peptide-induced superoxide formation in neutrophils. Cyclosporin H does not bind cyclophilin or evoke an immunosuppressant response. Cyclosporin H has been reported to inhibit tumor promoting phorbol ester TPA/PMA in mouse skin cells and to inhibit calcium/calmodulin-dependent EF-2 phosphorylation. | [storage]
+4°C | [References]
[1]. wenzel-seifert k, seifert r. cyclosporin h is a potent and selective formyl peptide receptor antagonist. comparison with n-t-butoxycarbonyl-l-phenylalanyl-l-leucyl-l-phenylalanyl-l- leucyl-l-phenylalanine and cyclosporins a, b, c, d, and e. j immunol, 1993, 150(10): 4591-4599.
[2]. wenzel-seifert k, grünbaum l, seifert r. differential inhibition of human neutrophil activation by cyclosporins a, d, and h. cyclosporin h is a potent and effective inhibitor of formyl peptide-induced superoxide formation. j immunol, 1991, 147(6): 1940-1946.
[3]. de paulis a, ciccarelli a, de crescenzo g, et al. cyclosporin h is a potent and selective competitive antagonist of human basophil activation by n-formyl-methionyl-leucyl-phenylalanine. j allergy clin immunol, 1996, 98(1): 152-164.
[4]. kitagaki k, nagai h, hayashi s, et al. facilitation of apoptosis by cyclosporins a and h, but not fk506 in mouse bronchial eosinophils. eur j pharmacol, 1997, 337(2-3): 283-289. |
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J & K SCIENTIFIC LTD.
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