Application of Organic Fluorophores in the Development of Drug Delivery Systems Based on Synthetic and Natural Polymers

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The application of fluorescent markers in the study of nanoparticle interaction with living matter cells has proven to be a highly effective method. Numerous studies have demonstrated the rapid and efficient uptake of nanoparticles by cells, with the use of fluorescent markers in microscopic observations playing a pivotal role. These methods facilitate not only the observation of qualitative changes in fluorescence intensity but also the quantitative assessment of changes occurring during the introduction of delivery systems into the body. Synthetic dyes can be integrated into the structure of a polymer (polylactide or modified hyaluronic acid) during the production of nanoparticles with a fluorescent marker, without the formation of new chemical bonds between the fluorophore and the nanoparticle. However, the tracking of such systems is often inefficient due to poor solubility and diffusion of the components in the biological environment. Conversely, the incorporation of fluorescent tags via chemical modification of the functional groups of polymers with dyes appears to be a far more promising alternative, as it allows the production of strong conjugates that serve as markers of the system itself. Furthermore, the covalent binding of fluorophores to the polymer addresses problems such as the inaccuracy of localization associated with the release of the tag from the nanoparticle and its further penetration into non-target cells and organelles.

This review presents a detailed critical evaluation of the methods of introduction and the classes of fluorescent markers used to modify polymers, based on lactic, glycolic and hyaluronic acids, for the purpose of drug delivery.

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D. Yuriev

Mendeleev University of Chemical Technology of Russia

编辑信件的主要联系方式.
Email: iurev.d.i@muctr.ru
俄罗斯联邦, Miusskaya pl., 9, Moscow, 125047

S. Tkachenko

Mendeleev University of Chemical Technology of Russia

Email: iurev.d.i@muctr.ru
俄罗斯联邦, Miusskaya pl., 9, Moscow, 125047

A. Polivanova

Mendeleev University of Chemical Technology of Russia

Email: iurev.d.i@muctr.ru
俄罗斯联邦, Miusskaya pl., 9, Moscow, 125047

Y. Kryschenko

Mendeleev University of Chemical Technology of Russia

Email: iurev.d.i@muctr.ru
俄罗斯联邦, Miusskaya pl., 9, Moscow, 125047

M. Oshchepkov

Mendeleev University of Chemical Technology of Russia

Email: iurev.d.i@muctr.ru
俄罗斯联邦, Miusskaya pl., 9, Moscow, 125047

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2. Fig. 1. Copolymerization of PLGA by the cycle opening method.

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3. Fig. 2. Structural formulas of compounds mentioned in the review.

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4. 3. Covalent modification of PLGA with 1,8-naphthalimide derivatives.

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5. 4. Confocal visualization of 4T1 cells after incubation with PLGA-III nanoparticles. (a) – Combined image; (b) – PLGA-III nanoparticles; (c) – lysosomes stained with LysoTracker Red DND-99.

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6. Fig. 5. Methods of covalent modification of HA structure by fluorescent markers.

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7. 6. (a) is the conjugation process of HA with 5b–cholanic acid and Cy5.5 dye (Cy5.5 HA); (b) is the conjugation process of hydrophobic 5b-cholanic acid of HA with Su7.5 dye.

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8. Fig. 7. Modification of GC by ceramide.

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9. 8. Scheme of synthesis of HA conjugate with fluorescent polymer (PFA).

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10. Fig. 9. Scheme of modification of folic acid and fluorescent marker with ethylenediamine, and their introduction into HA.

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11. Fig. 10. Scheme of GC modification for cytochrome C delivery.

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12. Fig. 11. Synthesis scheme of GC containing diiodostyrene-BODIPY.

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13. Fig. 12. Modified HA with cholanic acid (CA).

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14. 13. Scheme of synthesis of HA modified with cyclodextrin (CD) and amantadine-modified agents (Gd–DOTA and cyanine dye Cy7).

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15. 14. Scheme of synthesis of HA modified with oleic acid and cypate.

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16. Fig. 15. Scheme of synthesis of HA conjugates with fluorescent dyes C u 7.5 and IRDye800.

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17. 16. Scheme of synthesis of HA nanoparticles with peptide and doxorubicin.

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18. 17. Preparation of borated fluorescently labeled HA derivative for controlled quercetin delivery.

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19. 18. Preparation of a glutathione-sensitive fluorescently labeled HA derivative.

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20. Fig. 19. (a) – A general scheme for the production of glutathione-sensitive fluorescent nanoparticles based on derivatives of hyaluronic acid, dye Su5.5 and rifampicin for the diagnosis and treatment of tuberculosis. (b) is a UV-induced click reaction between hyaluronic acid derivatives during the formation of composite nanoparticles.

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