Cyclo(-L-Leu-L-Phe)
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Cyclo(-L-Leu-L-Phe)

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Category
Others
Catalog number
BAT-004977
CAS number
7280-77-5
Molecular Formula
C15H20N2O2
Molecular Weight
260.34
Cyclo(-L-Leu-L-Phe)
IUPAC Name
(3S,6S)-3-benzyl-6-(2-methylpropyl)piperazine-2,5-dione
Synonyms
Cyclo(-Leu-Phe)
Appearance
White powder
Purity
≥ 98% (NMR)
Density
1.081 g/cm3
Melting Point
282°C (dec.)
Storage
Store at -20 °C
InChI
InChI=1S/C15H20N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3,(H,16,19)(H,17,18)/t12-,13-/m0/s1
InChI Key
QPDMOMIYLJMOQJ-STQMWFEESA-N
Canonical SMILES
CC(C)CC1C(=O)NC(C(=O)N1)CC2=CC=CC=C2
1.Examination of the signal transduction pathways leading to activation of extracellular signal-regulated kinase by formyl-methionyl-leucyl-phenylalanine in rat neutrophils.
Chang LC1, Wang JP. FEBS Lett. 1999 Jul 2;454(1-2):165-8.
The signaling pathways leading to extracellular signal-regulated kinase (ERK) activation in formyl-methionyl-leucyl-phenylalanine (fMLP)-stimulated rat neutrophils were examined. fMLP-stimulated ERK activation based on immunoblot analysis with antibodies against the phosphorylation form of ERK was attenuated by the pretreatment of cells with pertussis toxin but not with a dual cyclo-oxygenase/lipoxygenase inhibitor BW755C. Exposure of cells to the tyrosine kinase inhibitor genistein, phosphatidylinositol 3-kinase (PI3K) inhibitors wortmannin and LY294002, or protein kinase C (PKC) inhibitors Gö6976, Gö6983, and GF109203X inhibited fMLP-stimulated ERK phosphorylation in a concentration-dependent manner. In addition, both the phospholipase C (PLC) inhibitor U73122 and the Ca2+ chelator BAPTA attenuated ERK activation. These results indicate that G(i/o) protein, tyrosine kinase, P13K, PKC, and PLC/Ca2+, but not arachidonate metabolites, act upstream of fMLP-stimulated ERK activation.
2.[The effect of endothelin on granulocyte-endothelium interaction].
Schmeck J1, Janzen R, Koch T. Anasthesiol Intensivmed Notfallmed Schmerzther. 1998 Mar;33(3):165-70.
PURPOSE: The interaction of activated granulocytes and endothelial cells influences not only capillary permeability but also increases pulmonary vascular resistance. The aim of this study was to evaluate the role of endothelin-1 (ET-1) during the granulocyte-mediated increase in pulmonary pressure.
3.Enzymatic conversion-based method for screening cyclic dipeptide-producing microbes.
Arunrattiyakorn P1, Nitoda T, Kanzaki H. Peptides. 2006 Apr;27(4):633-9. Epub 2005 Oct 13.
We developed a method for screening cyclic dipeptide-producing microbes by enzymatic conversion. In this method, cyclic dipeptides are detected by the combination of: (i) conversion of cyclic dipeptides to dehydro cyclic dipeptides by cyclo(Leu-Phe) oxidase and (ii) detection of the dehydro derivative by UV spectrophotometry using TLC or HPLC analysis based on the absorbance change caused by the conversion. Using this method, the actinomycete strain A8 was isolated as a cyclic dipeptide-producing strain. The cyclic dipeptides were purified from the microbial extract by enzymatic detection-guided fractionation, and their structures were determined to be cyclo(L-Phe-L-Pro) and cyclo(L-Pro-L-Tyr) by spectroscopic methods.
4.Anti-inflammatory and immunomodulatory potential of the novel PDE4 inhibitor roflumilast in vitro.
Hatzelmann A1, Schudt C. J Pharmacol Exp Ther. 2001 Apr;297(1):267-79.
From a series of benzamide derivatives, roflumilast (3-cyclo-propylmethoxy-4-difluoromethoxy-N-[3,5-di-chloropyrid-4-yl]-benzamide) was identified as a potent and selective PDE4 inhibitor. It inhibits PDE4 activity from human neutrophils with an IC(50) of 0.8 nM without affecting PDE1 (bovine brain), PDE2 (rat heart), and PDE3 and PDE5 (human platelets) even at 10,000-fold higher concentrations. Roflumilast is almost equipotent to its major metabolite formed in vivo (roflumilast N-oxide) and piclamilast (RP 73401), however, more than 100-fold more potent than rolipram and Ariflo (cilomilast; SB 207499). The anti-inflammatory and immunomodulatory potential of roflumilast and the reference compounds was investigated in various human leukocytes using cell-specific responses: neutrophils [N-formyl-methyl-leucyl-phenylalanine (fMLP)-induced formation of LTB(4) and reactive oxygen species (ROS)], eosinophils (fMLP- and C5a-induced ROS formation), monocytes, monocyte-derived macrophages, and dendritic cells (lipopolysaccharide-induced tumor necrosis factor-alpha synthesis), and CD4+ T cells (anti-CD3/anti-CD28 monoclonal antibody-stimulated proliferation, IL-2, IL-4, IL-5, and interferon-gamma release).
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