10.1021/jo800805w
The research focuses on the efficient synthesis of peptides, specifically targeting the extension at the N- and C-termini of arginine. The study employs L-N?-Nitroarginine and L-arginine, coupling them with N-(Cbz-R-aminoacyl)benzotriazoles and N-Cbzdipeptidoylbenzotriazoles to synthesize various peptides, including LL-dipeptides, LLL-tripeptides, and diastereomeric mixtures. The synthesis is conducted with an emphasis on retaining the original chirality, which is confirmed through NMR and HPLC analysis, yielding results in isolated yields of 66-95%. The methodology also extends to the synthesis of the protected RGD peptide. The research provides a convenient and efficient approach to peptide synthesis, utilizing simple preparative procedures, inexpensive reagents, and free amino acids as coupling components. The article also discusses the biological significance of L-arginine and its involvement in various physiological processes, highlighting the importance of selective inhibitors in treating pathological NO production.
10.1002/cbic.201000759
The research presents an in-depth study on the transport of free and peptide-bound glycated amino acids, focusing on their synthesis, transepithelial flux across Caco-2 cell monolayers, and interactions with apical membrane transport proteins. The experiments involved the synthesis of various glycated amino acids and dipeptides through non-enzymatic chemical processes known as the Maillard reaction, using reactants like lysine, arginine, glucose, and other sugars. The synthesized products were analyzed using techniques such as high-pressure liquid chromatography (HPLC), amino acid analysis (AAA), nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and elemental analysis. The study also measured the inhibition of lysine and glycylsarcosine uptakes in Caco-2 cells, which express transporters like PEPT1 and lysine transport systems, to understand the affinities and transport characteristics of these glycated compounds. The results provided insights into the intestinal absorption mechanisms of dietary Maillard reaction products and their potential impact on human health.
10.3184/030823409X12615671424822
The study investigates the use of L-arginine as a cost-effective and recyclable catalyst for the synthesis of α,β-unsaturated nitriles and ketones through the Knoevenagel condensation reaction in an ionic liquid medium. The chemicals used include aromatic, heteroaromatic, and α,β-unsaturated aldehydes, which react with malononitrile and acetylacetone to produce the desired nitriles and ketones. The ionic liquid, 1-ethyl-3-methylimidazolium ethylsulfate, serves as a green and recyclable reaction medium, while L-arginine acts as the catalyst, providing moderate to excellent yields (45–100%) and being successfully recycled for five runs without significant loss of activity. This approach offers a green and facile method for the synthesis of these important fine chemical industry products, which have applications as pre-polymers, antihypertensive agents, and calcium antagonists.
10.1002/adfm.201103147
The research focuses on the development of a new family of cationic charged biocompatible hybrid hydrogels, based on arginine unsaturated poly(ester amide) (Arg-UPEA) and Pluronic diacrylate (Pluronic-DA), which were fabricated through UV photocrosslinking in an aqueous medium. The purpose of this study was to improve the cellular interactions of synthetic hydrogels for potential biomedical applications by introducing cationic Arg-UPEA, which possesses biocompatibility and cationic properties. The conclusions drawn from the research indicate that the incorporation of Arg-UPEA into Pluronic-DA hydrogels significantly enhanced cell attachment, proliferation, and viability of both Detroit 539 human fibroblasts and bovine aortic endothelial cells. The chemicals used in the process include Pluronic F127, acryloyl chloride, triethylamine, Irgacure 2959 (as a photoinitiator), L-arginine, p-toluenesulfonic acid monohydrate, fumaryl chloride, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and p-nitrophenol, among others. These chemicals were utilized in the synthesis of the hydrogel precursors and for the characterization of their physicochemical properties.
10.1111/cbdd.12881
The research focuses on the discovery and biological evaluation of selective Protein Arginine Methyltransferase 5 (PRMT5) inhibitors, which are potential therapeutic targets for diseases, particularly cancer. The study aimed to identify novel PRMT5 inhibitors using virtual screening and structure-activity relationship (SAR) studies. The most active compound identified was P5i-6, which exhibited a significant inhibitory potency against PRMT5 with an IC50 value of 0.57μM and high selectivity for PRMT5 against other tested PRMTs. P5i-6 demonstrated good anti-viability activity against certain cancer cell lines, including colorectal and hepatic cancer cells. The research concluded that P5i-6 could serve as a chemical probe for investigating PRMT5's biological functions and as a lead compound for developing new PRMT5-targeting therapeutic agents. Chemicals used in the process included various synthesized and purchased compounds, such as 2-((5-(4-chlorophenyl)furan-2-yl)methylene)hydrazinecarboxamide (4a), 2-((5-(4-nitrophenyl)furan-2-yl)methylene)hydrazinecarboxamide (4f), and 2-((5-(4-chlorophenyl)pyridin-2-yl)methylene)hydrazinecarboxamide (9g), among others, which were tested for their inhibitory effects on PRMT5.
10.1021/jm980728e
The study "Synthesis and Antiviral Activity of Ethidium-Arginine Conjugates Directed Against the TAR RNA of HIV-1" investigates the design and biological evaluation of ethidium-arginine conjugates targeting the TAR RNA of HIV-1 to inhibit viral replication. The researchers synthesized six ethidium derivatives with arginine side chains, aiming to disrupt the interaction between the Tat protein and TAR RNA. These conjugates were evaluated for their anti-HIV-1 activity in infected CEM-SS, MT4, and PBMC cells. Compounds 17 and 20 exhibited significant antiviral activity at micromolar concentrations without toxicity. The most active compound, 20, showed strong binding to TAR RNA, as evidenced by melting temperature studies and RNase footprinting experiments. Molecular modeling suggested that the ethidium moiety of compound 20 intercalates near the A17 residue, while the arginine side chain occupies the pyrimidine bulge, providing insights into the mechanism of action and potential for further development of HIV-1 inhibitors.
10.1021/jm900622d
The study focuses on the discovery of new structural classes of short antimicrobial peptides, specifically Trp-His and His-Arg analogues, as potential alternatives to combat antibiotic-resistant microbial infections. The researchers synthesized a series of peptide analogues based on these frameworks and evaluated their antimicrobial activity against several Gram-negative and Gram-positive bacterial strains, as well as a fungal strain. The peptides were found to be active with minimum inhibitory concentration (MIC) values ranging from 5-20 μg/mL and showed no cytotoxic effects up to 200 μg/mL, indicating their potential as novel antimicrobial therapeutics. The chemicals used in the study included various amino acids (Trp, His, Arg), synthetic peptide analogues, and reagents for peptide synthesis (such as DCC, DIC, HONB, and CDI). These chemicals served the purpose of constructing and evaluating the antimicrobial potential of the synthesized peptides, with the aim of developing smaller, more stable, and less immunogenic alternatives to naturally occurring antimicrobial peptides.
10.1016/j.ejmech.2007.09.009
The study focuses on the design, synthesis, and evaluation of seventeen tetrahydroisoquinoline derivatives for their ability to inhibit nitric oxide (NO) production in lipopolysaccharide-stimulated BV-2 microglial cells. These derivatives were synthesized to potentially control inflammation-related damages by targeting the overproduction of NO, which is implicated in various diseases such as stroke, Alzheimer’s, and Parkinson’s. The chemicals used in the study include L-arginine, nitric oxide synthase (NOS) subtypes, tetrahydrobiopterin (BH4), and a series of tetrahydroisoquinoline derivatives with variable alkyl and acyl groups at different positions. The purpose of these chemicals was to investigate their inhibitory effects on NO production and to understand the structure-activity relationships, with the aim of identifying potent compounds that can reduce NO and BH4 production effectively. The study found that certain derivatives, particularly N-ethylcarbonyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline (11a), showed a significant reduction in NO and BH4 production, suggesting their potential as therapeutic candidates for diseases associated with NO overproduction.
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