Cyclo(-L-Trp-L-Tyr) (BAT-004983)
* For research use only

Category
Others
Catalog number
BAT-004983
CAS number
20829-53-2
Molecular Formula
C20H19N3O3
Molecular Weight
349.39
Cyclo(-L-Trp-L-Tyr)
Synonyms
Cyclo(-Trp-Tyr); (3s,6s)-3-(4-Hydroxybenzyl)-6-(1h-Indol-3-Ylmethyl)Piperazine-2,5-Dione
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Storage
Store at -20°C
InChI
InChI=1S/C20H19N3O3/c24-14-7-5-12(6-8-14)9-17-19(25)23-18(20(26)22-17)10-13-11-21-16-4-2-1-3-15(13)16/h1-8,11,17-18,21,24H,9-10H2,(H,22,26)(H,23,25)/t17-,18-/m0/s1
InChI Key
ZJDMXAAEAVGGSK-ROUUACIJSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)CC3C(=O)NC(C(=O)N3)CC4=CC=C(C=C4)O
1.Anti-Apoptotic Gene Delivery with cyclo-(d-Trp-Tyr) Peptide Nanotube via Eye Drop Following Corneal Epithelial Debridement.
Lee YH1, Chang SF2, Liaw J3. Pharmaceutics. 2015 Jul 17;7(3):122-36. doi: 10.3390/pharmaceutics7030122.
Corneal keratocyte apoptosis triggered by cornel debridement is one mechanism of corneal disorders. In this study, the feasibility of cyclo-(d-Trp-Tyr) peptide nanotubes (PNTs) as carriers of caspase 3 silence shRNA delivery was assessed. A model of epithelial injury by epithelial debridement was applied to investigate the feasibility of PNTs as gene delivery carriers on corneal injury. First, the PNTs were found within 2 μm in length and 300 nm in width by an atomic force microscope and confocal laser microscope system. Plasmid DNAs were observed to be associated with PNTs by atomic force microscope and confocal laser scanning microscope. The plasmids were associated with tyrosine of PNTs with a binding constant of 2.7 × 108 M-1. The stability of plasmid DNA with PNTs against the DNase was found at 60 min. Using thioflavin T pre-stained PNTs on the corneal eye drop delivery, the distribution of PNTs was in the epithelial and stroma regions.
2.Cyclo-(His,Leu): a new microbial diketopiperazine from a terrestrial Bacillus subtilis strain B38.
Elkahoui S1, Abdel rahim H, Tabbene O, Shaaban M, Limam F, Laatsch H. Nat Prod Res. 2013;27(2):108-16. doi: 10.1080/14786419.2012.660635. Epub 2012 Feb 16.
In continuation of our search for bioactive secondary metabolites from terrestrial Bacillus spp., a new microbial diketopiperazine, cis-cyclo-(His,Leu) (1) was isolated from the ethyl acetate extract of a strain B. subtilis B38, together with cis-cyclo-(Phe,Phe) (2), tryptophane (3), cis-cyclo-(Leu,Tyr) (4), cis-cyclo-(Trp,Tyr) (5) and macrolactin A (6). The chemical structures of the isolated compounds were identified by comparison of their 1D, 2D NMR and HRESIMS data with authentic spectra and literatures. To the best of our knowledge, this is the first time that cyclo-(His,Leu) has been isolated from natural products.
3.Oral gene delivery with cyclo-(D-Trp-Tyr) peptide nanotubes.
Hsieh WH1, Chang SF, Chen HM, Chen JH, Liaw J. Mol Pharm. 2012 May 7;9(5):1231-49. doi: 10.1021/mp200523n. Epub 2012 Apr 18.
The feasibility of cyclo-(D-Trp-Tyr) peptide nanotubes (PNTs) as oral gene delivery carriers was investigated in nude mice with eight 40 μg doses of pCMV-lacZ in 2 days at 3 h intervals. The association between DNA and PNTs, the DNase I stability of PNTs-associated DNA, and in vitro permeability of DNA were estimated. The results showed that the cyclo-(D-Trp-Tyr) PNTs self-associated at concentrations above 0.01 mg/mL. Plasmid DNA associated with PNTs with a binding constant of 3.2 × 10(8) M(-1) calculated by a fluorescence quenching assay. PNTs were able to protect DNA from DNase I, acid, and bile digestion for 50 min, 60 min, and 180 min, respectively. The in vitro duodenal apparent permeability coefficient of pCMV-lacZ calculated from a steady state flux was increased from 49.2 ± 21.6 × 10(-10) cm/s of naked DNA to 395.6 ± 142.2 × 10(-10) cm/s of pCMV-lacZ/PNT formulation. The permeation of pCMV-lacZ formulated with PNTs was found in an energy-dependent process.
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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