Synthesis and Biological Properties of Polyphenol-Containing Linear and Dendrimeric Cationic Peptides

Natural polyphenols are promising compounds for the pharmacological control of oxidative stress in various diseases. However, low bioavailability and rapid metabolism of polyphenols in a form of glycosides or aglycones have stimulated the search for the vehicles that would provide their efficient de...

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Published in:	Biochemistry (Moscow) Vol. 89; no. 1; pp. 173 - 183
Main Authors:	Shatilov, Artem A., Andreev, Sergey M., Shatilova, Anastasiya V., Turetskiy, Evgeny A., Kurmasheva, Renata A., Babikhina, Marina O., Saprygina, Larisa V., Shershakova, Nadezhda N., Bolyakina, Dar’ya K., Smirnov, Valeriy V., Shilovsky, Igor P., Khaitov, Musa R.
Format:	Journal Article
Language:	English
Published:	Moscow Pleiades Publishing 2024 Springer Nature B.V
Subjects:	Aglycones Anti-Bacterial Agents - chemistry Antibacterial activity Antioxidants Antioxidants - chemistry Antioxidants - pharmacology Ascorbic acid Bioavailability Biochemistry Biological properties Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Biosynthesis Cationic peptides Cations Conjugates Conjugation E coli Flavonoids Gallic acid Gallic Acid - chemistry Gallic Acid - pharmacology Glycosides Life Sciences Metabolism Microbiology N-Terminus Neurodegeneration Neurodegenerative diseases Oxidative stress Peptides Peptides - chemistry Peptides - pharmacology Pharmacology Phenolic acids Phenols Polyphenols Polyphenols - chemistry Polyphenols - pharmacology Reporter gene Synthesis Toxicity Transfection HyPer dendrimers ROS transfection cationic peptides gallic acid anti-radical activity hemolysis cytotoxicity
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Summary:	Natural polyphenols are promising compounds for the pharmacological control of oxidative stress in various diseases. However, low bioavailability and rapid metabolism of polyphenols in a form of glycosides or aglycones have stimulated the search for the vehicles that would provide their efficient delivery to the systemic circulation. Conjugation of polyphenols with cationic amphiphilic peptides yields compounds with a strong antioxidant activity and ability to pass through biological barriers. Due to a broad range of biological activities characteristic of polyphenols and peptides, their conjugates can be used in the antioxidant therapy, including the treatment of viral, oncological, and neurodegenerative diseases. In this work, we synthesized linear and dendrimeric cationic amphiphilic peptides that were then conjugated with gallic acid (GA). GA is a non-toxic natural phenolic acid and an important functional element of many flavonoids with a high antioxidant activity. The obtained GA-peptide conjugates showed the antioxidant (antiradical) activity that exceeded 2-3 times the antioxidant activity of ascorbic acid. GA attachment had no effect on the toxicity and hemolytic activity of the peptides. GA-modified peptides stimulated the transmembrane transfer of the pGL3 plasmid encoding luciferase reporter gene, although GA attachment at the N-terminus of peptides reduced their transfection activity. Several synthesized conjugates demonstrated the antibacterial activity in the model of Escherichia coli Dh5α growth inhibition.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0006-2979 1608-3040
DOI:	10.1134/S0006297924010115