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Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity

[Image: see text] During the past years, the synthesis of polymer prodrug structures, based on natural phytochemical compounds with a great range of valuable biological properties, has become a promising solution in cancer prevention, imaging, and detection. Curcumin (Curc) remains one of the most s...

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Autores principales: Yakub, Guldjan, Manolova, Nevena E., Rashkov, Iliya B., Markova, Nadya, Toshkova, Reneta, Georgieva, Ani, Mincheva, Rosica, Toncheva, Antoniya, Raquez, Jean-Marie, Dubois, Philippe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9583079/
https://www.ncbi.nlm.nih.gov/pubmed/36278048
http://dx.doi.org/10.1021/acsomega.2c04173
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author Yakub, Guldjan
Manolova, Nevena E.
Rashkov, Iliya B.
Markova, Nadya
Toshkova, Reneta
Georgieva, Ani
Mincheva, Rosica
Toncheva, Antoniya
Raquez, Jean-Marie
Dubois, Philippe
author_facet Yakub, Guldjan
Manolova, Nevena E.
Rashkov, Iliya B.
Markova, Nadya
Toshkova, Reneta
Georgieva, Ani
Mincheva, Rosica
Toncheva, Antoniya
Raquez, Jean-Marie
Dubois, Philippe
author_sort Yakub, Guldjan
collection PubMed
description [Image: see text] During the past years, the synthesis of polymer prodrug structures, based on natural phytochemical compounds with a great range of valuable biological properties, has become a promising solution in cancer prevention, imaging, and detection. Curcumin (Curc) remains one of the most studied natural products, due to the impressive palette of biological properties and the possibility to be easily loaded in various micro- and nanostructures and chemically modified. In this study, pegylated curcumin derivatives were prepared by a direct esterification reaction between poly(ethylene glycol)diacid (PEG of 600 g/mol molar mass, PEG(600)) and Curc in the presence of N,N′-dicyclohexylcarbodiimide (PEG(600)-Curc). The successful reaction resulted in a water-soluble stable product that was characterized by infrared spectroscopy (Fourier transform infrared (FT-IR)) and proton ((1)H) and carbon ((13)C) NMR. The effect of the pH values of buffer solutions on PEG(600)-Curc spectral properties (absorption and photoluminescence) was investigated by UV–vis and fluorescence spectrophotometry. Based on the biological tests, it was confirmed that PEG(600)-Curc exhibits cytotoxic activity against Graffi cell lines, as a function of the Curc concentration in the conjugate and the incubation time. PEG(600)-Curc antibacterial activity was validated in microbiological tests against pathogenic microorganisms such as Staphylococcus aureus. Most importantly, despite the covalent attachment of Curc to PEG and the slight reduction in the therapeutic index of the conjugate, both the anticancer and antimicrobial activities remain the highest reported, thus opening the gate for further, more clinically oriented studies.
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spelling pubmed-95830792022-10-21 Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity Yakub, Guldjan Manolova, Nevena E. Rashkov, Iliya B. Markova, Nadya Toshkova, Reneta Georgieva, Ani Mincheva, Rosica Toncheva, Antoniya Raquez, Jean-Marie Dubois, Philippe ACS Omega [Image: see text] During the past years, the synthesis of polymer prodrug structures, based on natural phytochemical compounds with a great range of valuable biological properties, has become a promising solution in cancer prevention, imaging, and detection. Curcumin (Curc) remains one of the most studied natural products, due to the impressive palette of biological properties and the possibility to be easily loaded in various micro- and nanostructures and chemically modified. In this study, pegylated curcumin derivatives were prepared by a direct esterification reaction between poly(ethylene glycol)diacid (PEG of 600 g/mol molar mass, PEG(600)) and Curc in the presence of N,N′-dicyclohexylcarbodiimide (PEG(600)-Curc). The successful reaction resulted in a water-soluble stable product that was characterized by infrared spectroscopy (Fourier transform infrared (FT-IR)) and proton ((1)H) and carbon ((13)C) NMR. The effect of the pH values of buffer solutions on PEG(600)-Curc spectral properties (absorption and photoluminescence) was investigated by UV–vis and fluorescence spectrophotometry. Based on the biological tests, it was confirmed that PEG(600)-Curc exhibits cytotoxic activity against Graffi cell lines, as a function of the Curc concentration in the conjugate and the incubation time. PEG(600)-Curc antibacterial activity was validated in microbiological tests against pathogenic microorganisms such as Staphylococcus aureus. Most importantly, despite the covalent attachment of Curc to PEG and the slight reduction in the therapeutic index of the conjugate, both the anticancer and antimicrobial activities remain the highest reported, thus opening the gate for further, more clinically oriented studies. American Chemical Society 2022-10-09 /pmc/articles/PMC9583079/ /pubmed/36278048 http://dx.doi.org/10.1021/acsomega.2c04173 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Yakub, Guldjan
Manolova, Nevena E.
Rashkov, Iliya B.
Markova, Nadya
Toshkova, Reneta
Georgieva, Ani
Mincheva, Rosica
Toncheva, Antoniya
Raquez, Jean-Marie
Dubois, Philippe
Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity
title Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity
title_full Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity
title_fullStr Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity
title_full_unstemmed Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity
title_short Pegylated Curcumin Derivative: Water-Soluble Conjugates with Antitumor and Antibacterial Activity
title_sort pegylated curcumin derivative: water-soluble conjugates with antitumor and antibacterial activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9583079/
https://www.ncbi.nlm.nih.gov/pubmed/36278048
http://dx.doi.org/10.1021/acsomega.2c04173
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