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1.
Skin Res Technol ; 29(11): e13465, 2023 Nov.
Article in English | MEDLINE | ID: mdl-38009021

ABSTRACT

OBJECTIVE: We aimed to develop an electroactive antibacterial material for the treatment of skin wound diseases. METHOD: To this aim, we modified chitosan (CS), a biocompatible polymer, by coupling it with graphene (rGO) and an antimicrobial polypeptide DOPA-PonG1. The material's effect on skin injury healing was studied in combination with external electrical stimulation (EEM). The structure, surface composition, and hydrophilicity of the modified CS materials were evaluated using scanning electron microscopy (SEM), Fourier-transform infrared spectroscopy (FTIR), and contact angle measurements. We studied NIH3T3 cells cultured with modified materials and subjected to EEM to assess viability, adhesion, and tissue repair-related gene expression. RESULTS: SEM data demonstrated that rGO was distributed uniformly on the surface of the CS material, increasing surface roughness, and antimicrobial peptides had minimal impact on surface morphology. FTIR confirmed the uniform distribution of rGO and antibacterial peptides on the material surface. Both rGO and DOPA-PonG1 enhanced the hydrophilicity of CS materials, with rGO also improving tensile strength. The dual modification of CS with rGO and DOPA-PonG1 synergistically increased antibacterial efficacy. Cellular events and gene expression relevant to tissue repair process were enhanced by these modifications. Furthermore, EEM accelerated epidermal regeneration more than the material alone. In a rat skin wound model, DOPA-PonG1@CS/rGO dressing combined with electrical stimulation exhibited accelerated healing of skin defect. CONCLUSION: Overall, our results demonstrate that CS materials modified with rGO and DOPA-PonG1 have increased hydrophilicity, antibacterial characteristics, and tissue regeneration capacities. This modified material in conjunction with EEM hold promise for the clinical management for dermal wounds.


Subject(s)
Anti-Bacterial Agents , Chitosan , Mice , Rats , Animals , NIH 3T3 Cells , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/therapeutic use , Chitosan/pharmacology , Chitosan/chemistry , Electric Stimulation , Bandages , Dihydroxyphenylalanine
2.
Angew Chem Int Ed Engl ; 62(50): e202315748, 2023 12 11.
Article in English | MEDLINE | ID: mdl-37906608

ABSTRACT

Here we report a simple electrochemical route towards the synthesis of S-arylated peptides by a site selective coupling of peptides with aryl halides under base free conditions. This approach demonstrates the power of electrochemistry to access both highly complex peptide conjugates and cyclic peptides.


Subject(s)
Cysteine , Nickel , Nickel/chemistry , Catalysis , Peptides , Peptides, Cyclic
3.
Org Lett ; 23(20): 8001-8006, 2021 10 15.
Article in English | MEDLINE | ID: mdl-34582221

ABSTRACT

A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions.


Subject(s)
Cross-Linking Reagents/chemistry , Cysteine/chemistry , Palladium/chemistry , Peptides/chemistry , Catalysis , Cyclization , Cysteine/metabolism , Molecular Structure
4.
Org Biomol Chem ; 18(9): 1738-1742, 2020 03 04.
Article in English | MEDLINE | ID: mdl-32077880

ABSTRACT

A novel and efficient method for the generation of alkyl radicals and the alkylation of quinoline and pyridine derivatives under mild conditions has been developed. This strategy allows the direct alkylation of heteroaromatics in the absence of an external oxidant. A preliminary mechanistic study suggests that the present reaction probably proceeds via an intermolecular HAT process.

5.
J Org Chem ; 84(19): 12358-12365, 2019 10 04.
Article in English | MEDLINE | ID: mdl-31532668

ABSTRACT

The first palladium-catalyzed Hiyama cross-coupling reactions of arylsilanes with 3-iodoazetidine were described. The protocol provides a convenient access to a variety of useful 3-arylazetidines which are of great interest in pharmaceutical laboratories in moderate to good yields (30%-88%). In addition, this strategy has the advantage of easy operation and mild reaction conditions.

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