38017-65-1

Usage

Uses

Used in Pharmaceutical Industry:
H-PHE-PHE-OME HCL is used as a key component in the preparation of polymer nanoparticles for the inhibition of amyloid-β fibrillation. This application is particularly relevant in the development of treatments for neurodegenerative diseases, such as Alzheimer's, where the aggregation of amyloid-β peptides plays a significant role in the pathology of the condition.
The use of H-PHE-PHE-OME HCL in the creation of polymer nanoparticles allows for the targeted delivery of the dipeptide to the affected areas, potentially reducing the overall concentration required for therapeutic effects and minimizing side effects. Additionally, the hydrophobic nature of the dipeptide may enhance its interaction with the hydrophobic regions of amyloid-β peptides, further contributing to its inhibitory effects on fibrillation.

Upstream product

• 13122-89-9 (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropanoate 
• 133992-84-4 (S)-3-Phenyl-2-[(S)-3-phenyl-2-((Z)-4,4,4-trifluoro-3-oxo-but-1-enylamino)-propionylamino]-propionic acid methyl ester 
• 67-56-1 methanol 
• 2577-40-4 Phe-Phe 
• 133992-79-7 3-phenyl-2-[(Z)-4,4,4-trifluoro-3-oxo-1-butenylamino]propanoic acid 
• 63-91-2 L-phenylalanine 
• 4192-12-5 dicyclohexylammonium N-(tert-butoxycarbonyl)-L-phenylalaninate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 143674-02-6 IBH-Phe-Phe-OMe 
• 89344-16-1 Z-Tau-Phe-Phe-OCH₃ 
• 161083-57-4 <(2R)-3--2--2-methylpropanoyl>-phenylalanyl-phenylalanine methyl ester 
• 103025-51-0 Boc-Gly-Pro-Pro-Phe-Phe-NH-NH₂ 
• 103025-53-2 H-Gly-Pro-Pro-Phe-Phe-NH-NH₂*2HCl 
• 1394312-63-0 C₂₂H₂₄N₂O₄ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of Doxorubicin-containing conjugate targeting PSMA

Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), has recently emerged as a prominent biomarker of prostate cancer (PC) and as an attractive protein trap for drug targeting. At the present time, several drugs and molecular diagnostic tools conjugated with selective PSMA ligands are actively evaluated in different preclinical and clinical trials. In the current work, we discuss design, synthesis and a preliminary biological evaluation of PSMA-specific small-molecule carrier equipped by Doxorubicin (Dox). We have introduced an unstable azo-linker between Dox and the carrier hence the designed compound does release the active substance inside cancer cells thereby providing a relatively high Dox concentration in nuclei and a relevant cytotoxic effect. In contrast, we have also synthesized a similar conjugate with a stable amide linker and it did not release the drug at all. This compound was predominantly accumulated in cytoplasm and did not cause cell death. Preliminary in vivo evaluation has showed good efficiency for the degradable conjugate against PC3-PIP(PSMA+)-containing xenograft mine. Thus, we have demonstrated that the conjugate can be used as a template to design novel analogues with improved targeting, anticancer activity and lower rate of potential side effects. 3D molecular docking study has also been performed to elucidate the underlying mechanism of binding and to further optimization of the linker area for improving the target affinity.

A novel aggregation-induced emission enhancement triggered by the assembly of a chiral gelator: from non-emissive nanofibers to emissive micro-loops

In this study, a novel aggregation-induced emission (AIE) enhancement triggered by the self-assembly of chiral gelator is described. Tuning of molecular chirality in situ triggers different assemblies of superstructures exhibiting fluorescence. This novel AIE material can constitute an emerging library of chiral supramolecules for turn-on fluorescent sensors. It will also help in better understanding the effects of chiral factors on the photophysical process.

Design, synthesis, and characterisation of glyoxylamide-based short peptides as self-assembled gels

The synthesis and supramolecular properties of novel glyoxylamide-based short peptides formed via the ring-opening reaction of N-acetylisatins in solution phase are described. The short peptides self-assembled into gels, which were examined for their mechanical and morphological characteristics using multiple spectroscopic and microscopy techniques. The critical gel concentration and mechanical strength of the self-assembled gels were influenced by the presence of electronegative substituents (such as fluoro, in 5b) or hydrophobic substituents (such as bromo, 5d) respectively in the short peptides. Moreover, in vitro cytotoxicity assays demonstrated that these compounds were non-toxic to mammalian cells.

Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination

We describe herein a crystallographic and NMR study of the secondary structural attributes of a β-turn-containing tetra-peptide, Boc-Dmaa-d-Pro-Acpc-Leu-NMe2, which was recently reported as a highly effective catalyst in the atroposelective bromination of 3-arylquinazolin-4(3H)-ones. Inquiries pertaining to the functional consequences of residue substitutions led to the discovery of a more selective catalyst, Boc-Dmaa-d-Pro-Acpc-Leu-OMe, the structure of which was also explored. This new lead catalyst was found to exhibit a type I′ β-turn secondary structure both in the solid state and in solution, a structure that was shown to be an accessible conformation of the previously reported catalyst, as well.

Building Nanowires from Micelles: Hierarchical Self-Assembly of Alternating Amphiphilic Glycopolypeptide Brushes with Pendants of High-Mannose Glycodendron and Oligophenylalanine

Mimicking the diverse glyco-conjugate structures in nature is always the dream of scientists. Right now, hierarchical self-assembled structures of natural conjugates of peptides and sugars could not easily be achieved via linear glycopolypeptide with mono

Design, synthesis and preliminary bioactivity studies of imidazolidine-2,4-dione derivatives as Bcl-2 inhibitors

Anti-apoptotic B-cell lymphoma-2 (Bcl-2) proteins are promising targets for cancer therapy. In the present study, a series of imidazolidine-2,4-dione derivatives were designed and synthesized to test their inhibitory activities against anti-apoptotic Bcl-

Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors

Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50=2.51±0.2 M) showed similar inhibitory effect compared with control compound Bestatin (IC50=6.25±0.4 M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.

Environmentally benign peptide synthesis using liquid-assisted ball-milling: Application to the synthesis of Leu-enkephalin

This paper describes an original methodology for peptide bond synthesis avoiding toxic solvents and reactants. Ball-milling stoichiometric amounts of Boc-protected α-amino acid N-carboxyanhydrides (Boc-AA-NCA) or Boc-protected α-amino acid N-hydroxysuccin

Engineered polymer nanoparticles containing hydrophobic dipeptide for inhibition of amyloid-β fibrillation

Protein aggregation into amyloid fibrils is implicated in the pathogenesis of many neurodegenerative diseases. Engineered nanoparticles have emerged as a potential approach to alter the kinetics of protein fibrillation process. Yet, there are only a few reports describing the use of nanoparticles for inhibition of amyloid-β 40 (Aβ40) peptide aggregation, involved in Alzheimer's disease (AD). In the present study, we designed new uniform biocompatible amino-acid-based polymer nanoparticles containing hydrophobic dipeptides in the polymer side chains. The dipeptide residues were designed similarly to the hydrophobic core sequence of Aβ. Poly(N-acryloyl-l- phenylalanyl-l-phenylalanine methyl ester) (polyA-FF-ME) nanoparticles of 57 ± 6 nm were synthesized by dispersion polymerization of the monomer A-FF-ME in 2-methoxy ethanol, followed by precipitation of the obtained polymer in aqueous solution. Cell viability assay confirmed that no significant cytotoxic effect of the polyA-FF-ME nanoparticles on different human cell lines, e.g., PC-12 and SH-SY5Y, was observed. A significantly slow secondary structure transition from random coil to β-sheets during Aβ40 fibril formation was observed in the presence of these nanoparticles, resulting in significant inhibition of Aβ40 fibrillation kinetics. However, the polyA-FF-ME analogous nanoparticles containing the l-alanyl-l-alanine (AA) dipeptide in the polymer side groups, polyA-AA-ME nanoparticles, accelerate the Aβ40 fibrillation kinetics. The polyA-FF-ME nanoparticles and the polyA-AA-ME nanoparticles may therefore contribute to a mechanistic understanding of the fibrillation process, leading to the development of therapeutic strategies against amyloid-related diseases.

Synthesis of hydantoins from enantiomerically pure α-amino amides without epimerization

A method for the preparation of enantiomerically pure hydantoins from optically pure α-amino amides utilizing triphosgene is described. We also propose that the racemization observed with 1,1′-carbonyldiimidazole (CDI) for this type of reaction is due to