Phebestin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-02384 |
| CAS | 187402-73-9 |
| Molecular Weight | 441.52 |
| Molecular Formula | C24H31N3O5 |
| Purity | ≥99% |
Online Inquiry
Description
It is produced by the strain of Str. sp. MJ 716-m3. It has inhibitory effect on aminopeptidase N (AP-N), AP-A, AP-B with IC50 (μg/mL) of 0.18, 9.0 and 9.1, respectively, but it has no antimicrobial activity (100 μg/mL).
Specification
| Synonyms | N-((2S,3R)-3-Amino-2-hydroxy-1-oxo-4-phenylbuty)-L-valyl-L-phenylalanine; ((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-valyl-L-phenylalanine; L-Phenylalanine, N-((2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbuty)-L-valyl- |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[[(2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-3-methylbutanoyl]amino]-3-phenylpropanoic acid |
| Canonical SMILES | CC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)O)NC(=O)C(C(CC2=CC=CC=C2)N)O |
| InChI | InChI=1S/C24H31N3O5/c1-15(2)20(22(29)26-19(24(31)32)14-17-11-7-4-8-12-17)27-23(30)21(28)18(25)13-16-9-5-3-6-10-16/h3-12,15,18-21,28H,13-14,25H2,1-2H3,(H,26,29)(H,27,30)(H,31,32)/t18-,19+,20+,21+/m1/s1 |
| InChI Key | GGMURINELPSPEF-ANULTFPQSA-N |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 784.3°C at 760 mmHg |
| Melting Point | 190-192°C |
| Density | 1.234 g/cm3 |
| Solubility | Soluble in Acetic acid, Methanol |
Reference Reading
1. Transcriptional regulation of cytosol and membrane alanyl-aminopeptidase in human T cell subsets
Alicja Bukowska, Janine Tadje, Marco Arndt, Carmen Wolke, Thilo Kähne, Jaqueline Bartsch, Jürgen Faust, Klaus Neubert, Yuichi Hashimoto, Uwe Lendeckel Biol Chem. 2003 Apr;384(4):657-65. doi: 10.1515/BC.2003.073.
Aminopeptidase inhibitors strongly affect the proliferation and function of immune cells in man and animals and are promising agents for the pharmacological treatment of inflammatory or autoimmune diseases. Membrane alanyl-aminopeptidase (mAAP) has been considered as the major target of these anti-inflammatory aminopeptidase inhibitors. Recent evidence also points to a role of the cytosol alanyl-aminopeptidase (cAAP) in the immune response. In this study we used quantitative RT-PCR to determine the mRNA expression of both cAAP and mAAP in resting and activated peripheral T cells and also in CD4+, CD8+, Th1, Th2 and Treg (CD4+ CD25+) subpopulations. Both mAAP and cAAP mRNAs were expressed in all cell types investigated, and in response to activation their expression appeared to be upregulated in CD8+ cells, but downregulated in Treg cells. In CD4+ cells, mAAP and cAAP mRNAs were affected in opposite ways in response to activation. The cAAP-specific inhibitor, PAQ-22, did not affect either cAAP or mAAP expression in activated CD4+ or CD8+ cells, whereas in activated Treg cells it markedly upregulated the mRNA levels of both aminopeptidases. The non-discriminatory inhibitor, phebestin, significantly increased the amount of mAAP and cAAP mRNA in CD4+ and that of cAAP in Treg cells.
2. Inhibition of alanyl-aminopeptidase on CD4+CD25+ regulatory T-cells enhances expression of FoxP3 and TGF-beta1 and ameliorates acute colitis in mice
Ute Bank, Janine Tadje, Michael Täger, Carmen Wolke, Alicja Bukowska, Annelore Ittenson, Dirk Reinhold, Martin Helmuth, Siegfried Ansorge, Ann Shakespeare, Michael Vieth, Peter Malfertheiner, Michael Naumann, Uwe Lendeckel Int J Mol Med. 2007 Oct;20(4):483-92.
Inhibitors of alanyl-aminopeptidase e.g. phebestin increase the expression of transforming growth factor (TGF)-beta1 in mononuclear cells. We investigated whether phebestin also produced this effect in CD4+CD25+ T-cells and whether phebestin-treated CD4+CD25+ T-cells were capable of ameliorating acute colitis in mice. The suppressive activity of mouse CD4+CD25+ T-cells was assessed in vitro by co-culture with splenocytes. mRNA expression associated with the suppressive phenotype was determined in vitro and in vivo. The in vivo role of phebestin-exposed CD4+CD25+ T-cells was studied in sodium dextran sulfate-induced acute colitis in mice. The proliferation of activated effector T-cells or splenocytes in vitro was inversely correlated with the number of CD4+CD25+ T-cells. Phebestin pre-treatment substantially enhanced the suppressive activity of these cells and increased expression levels of TGF-beta1 and FoxP3. Furthermore, transfer of CD4+CD25+ T-cells exposed to phebestin for a short time ex vivo significantly reduced the mouse colitis disease activity index. We conclude that aminopeptidase inhibitors support the suppressive activity as well as TGF-beta1 and FoxP3 expression of natural regulatory T-cells.
3. Isolation and characterization of aminopeptidase (Jc-peptidase) from Japanese cedar pollen (Cryptomeria japonica)
Yukinori Noguchi, Hiroyuki Nagata, Hajime Koganei, Yoh Kodera, Misao Hiroto, Hiroyuki Nishimura, Yuji Inada, Ayako Matsushima J Agric Food Chem. 2002 Jun 5;50(12):3540-3. doi: 10.1021/jf0200063.
An aminopeptidase, Jc-peptidase, was purified from Japanese cedar pollen by seven steps, including precipitation with ammonium sulfate, ion-exchange chromatography, gel filtration, hydrophobic interaction chromatography on phenyl-agarose, and high-performance liquid chromatography. Purified Jc-peptidease has a molecular weight of 42 kDa and hydrolyzes the synthetic substrates of L-phenylalanyl-4-methylcoumaryl-7-amide (Phe-MCA) with Km = 5 x 10(-5) M, Tyr-MCA with Km = 7 x 10(-4) M, Leu-MCA with Km = 1 x 10(-3) M, and Met-MCA with Km = 1 x 10(-3) M. Other MCA analogues such as Arg-MCA or Glu-MCA failed to serve as its substrates. The activity was inhibited in the presence of phebestin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-L-valyl]-L-phenylalanine, with Ki = 4.7 x 10(-5) M, or bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, with Ki = 1.1 x 10(-4) M. According to amino acid sequence analysis, the N-terminal amino group seems to be blocked. The physiological function of the aminopeptidase (Jc-peptidase) has not been clarified in vivo.
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
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 ╳
