Methods for Introdusing Fluorescent Labels into Polysaccharides

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Abstract

Polysaccharides are widely represented in plants and bacteria, where they are distinguished by their extraordinary structural diversity and the performance of various functions. To study the functions of polysaccharides, their fluorescent labeling is needed. This review discusses methods for introducing fluorescent labels into polysaccharides by chemical modification of certain functional groups of these complex biopolymers, as well as using the so-called bioorthogonal reactions, which allow labeling in a cell without affecting its viability. In addition to modification with organic dyes, the possibility of using quantum dots and coordination compounds of lanthanides is also discussed.

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About the authors

A. Yu. Nokel

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences; National Medical Research Center for Obstetrics, Gynecology and Perinatology named after Academician V.I. Kulakov of the Ministry of Health of Russian Federation

Email: professorbovin@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Oparina 4, Moscow, 117997

N. V. Bovin

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: professorbovin@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. B. Tuzikov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences

Email: professorbovin@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

T. V. Ovchinnikova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences

Email: professorbovin@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

N. V. Shilova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences; National Medical Research Center for Obstetrics, Gynecology and Perinatology named after Academician V.I. Kulakov of the Ministry of Health of Russian Federation

Email: professorbovin@yandex.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Oparina 4, Moscow, 117997

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Supplementary files

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2. Fig. 1. Introduction of a fluorescent label to the aldehyde group (hereinafter, the green diamond is a fluorescent label): reducing polysaccharide (a), Schiff base (b), reduced Schiff base (c), hydrazone – reaction product with hydrazine (d), hydrazone – reaction product with hydrazide (d).

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3. Fig. 2. Introduction of an amino group using a hydroxylamine derivative using the disaccharide N-acetyllactosamine as an example.

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4. Fig. 3. Introduction of a fluorescent label at the hydroxyl group: reaction with isocyanates (a), isothiocyanates (b), dichlorodiazine (c) and vinyl sulfone (d).

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5. Fig. 4. Introduction of a fluorescent label at the amino group: reaction with succinimide ester (a), sulfochloride (b) and isothiocyanate (c).

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6. Fig. 5. Introduction of a fluorescent label at the carboxyl group: by activation with carbodiimide (a), reaction with diazomethane (b).

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7. Fig. 6. Labeling using azide-alkyne cycloaddition.

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8. Fig. 7. Introduction of functional groups for click reaction using carbonyldiimidazole: (a) – synthesis of propargyl carbonate dextran, (b) – synthesis of azidopropyl carbonate dextran.

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9. Fig. 8. Preparation of cellulose with an azide group using 1-azido-2,3-epoxypropane.

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10. Fig. 9. Scheme of photoclick reaction with tetrazole.

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11. Fig. 10. Staudinger reaction: (a) – Staudinger ligation, (b) – traceless ligation according to Staudinger.

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12. Fig. 11. Bifunctional ligands for lanthanide labels: isothiocyanatophenylethylenediaminetetraacetic acid (EDTA) [126, 127] (a), isothiocyanatobenzyldiethylenetriaminetetraacetic acid (DTTA) [126, 127] (b), isothiocyanatobenzyldiethylenetriaminepentaacetic acid (DTPA) [126–128] (c), isothiocyanatobenzyltetraazacislododecaneacetic acid (DOTA) [126, 129] (d), isothiocyanatobenzyltetraazacislotetradecaneacetic acid (TETA) [126, 129] (d), isothiocyanatobenzyltriazacislononacetic acid (NOTA) [129] (e), dichlorotriazinoaminobenzyl diethylenetriaminetetraacetic acid (DTTA) [128] (f).

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