СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ
Reactions of azide-alkilic cycloaddition are well known since 1893. At the same time, with the elaboration of click chemistry, the techniques of labelling biological objects, particularly by fluorescent dyes, were widely developed. The use of fluorescent labels provides the ability to visually monit...
Saved in:
| Date: | 2020 |
|---|---|
| Main Authors: | , , |
| Format: | Article |
| Language: | English |
| Published: |
V.I.Vernadsky Institute of General and Inorganic Chemistry
2020
|
| Online Access: | https://ucj.org.ua/index.php/journal/article/view/131 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Journal Title: | Ukrainian Chemistry Journal |
Institution
Ukrainian Chemistry Journal| id |
oai:ojs2.1444248.nisspano.web.hosting-test.net:article-131 |
|---|---|
| record_format |
ojs |
| spelling |
oai:ojs2.1444248.nisspano.web.hosting-test.net:article-1312020-05-27T11:34:11Z SYNTHESIS OF MODYFIED FLUORESCEINE FOR CLICK REACTIONS СИНТЕЗ МОДИФИЦИРОВАННЫХ ФЛУОРЕСЦЕИНОВ ДЛЯ ИСПОЛЬЗОВАНИЯ В КЛИК-РЕКАЦИЯХ СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ Selin, Roman Chernii, Viktor Mokhir, Andriy modified fluorescein, fluorescein, click reaction Reactions of azide-alkilic cycloaddition are well known since 1893. At the same time, with the elaboration of click chemistry, the techniques of labelling biological objects, particularly by fluorescent dyes, were widely developed. The use of fluorescent labels provides the ability to visually monitor the process streamlines hardware load and reduces research time. Fluorescein is among the fluorophores mostly used for labelling of biomolecules due to its high quantum yields and good stability in biological media. However, despite of commercial availability of fluorescein derivatives functionalized for use in click reactions, methods for their synthesis are virtually absent in the literature. Therefore, we have developed a reliable and effective methodic for the synthesis of functionalized fluoresceines for the use in the click reactions. Synthesis of diacetyl N-(4-azidobutyl)-fluoresceine-5(6)-carboxamide was performed in six stages, starting form resorcinol and trimellitic acid anhydride. The diacetylated analogue was synthesized for the click modifications in the “soft” conditions, since N-(4-azidobutyl)-fluorescein-5(6)-carboxamide is poorly soluble in the classic organic solvents. Proposed synthetic protocol allows to increase the yield of the final and intermediate compounds and to optimized the procedure of their isolation and purification. V.I.Vernadsky Institute of General and Inorganic Chemistry 2020-04-07 Article Article Inorganic Chemistry Неорганическая химия Неорганічна хімія application/pdf https://ucj.org.ua/index.php/journal/article/view/131 10.33609/0041-6045.86.3.2020.3-8 Ukrainian Chemistry Journal; Vol. 86 No. 3 (2020): Ukrainian Chemistry Journal; 3-8 Украинский химический журнал; Том 86 № 3 (2020): Украинский химический журнал; 3-8 Український хімічний журнал; Том 86 № 3 (2020): Український хімічний журнал; 3-8 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/131/83 |
| institution |
Ukrainian Chemistry Journal |
| baseUrl_str |
|
| datestamp_date |
2020-05-27T11:34:11Z |
| collection |
OJS |
| language |
English |
| topic_facet |
modified fluorescein fluorescein click reaction |
| format |
Article |
| author |
Selin, Roman Chernii, Viktor Mokhir, Andriy |
| spellingShingle |
Selin, Roman Chernii, Viktor Mokhir, Andriy СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ |
| author_facet |
Selin, Roman Chernii, Viktor Mokhir, Andriy |
| author_sort |
Selin, Roman |
| title |
СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ |
| title_short |
СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ |
| title_full |
СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ |
| title_fullStr |
СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ |
| title_full_unstemmed |
СИНТЕЗ МОДИФІКОВАНИХ ФЛУОРЕСЦЕЇНІВ ДЛЯ ВИКОРИСТАННЯ У КЛІК-РЕАКЦІЯХ |
| title_sort |
синтез модифікованих флуоресцеїнів для використання у клік-реакціях |
| title_alt |
SYNTHESIS OF MODYFIED FLUORESCEINE FOR CLICK REACTIONS СИНТЕЗ МОДИФИЦИРОВАННЫХ ФЛУОРЕСЦЕИНОВ ДЛЯ ИСПОЛЬЗОВАНИЯ В КЛИК-РЕКАЦИЯХ |
| description |
Reactions of azide-alkilic cycloaddition are well known since 1893. At the same time, with the elaboration of click chemistry, the techniques of labelling biological objects, particularly by fluorescent dyes, were widely developed. The use of fluorescent labels provides the ability to visually monitor the process streamlines hardware load and reduces research time. Fluorescein is among the fluorophores mostly used for labelling of biomolecules due to its high quantum yields and good stability in biological media. However, despite of commercial availability of fluorescein derivatives functionalized for use in click reactions, methods for their synthesis are virtually absent in the literature. Therefore, we have developed a reliable and effective methodic for the synthesis of functionalized fluoresceines for the use in the click reactions. Synthesis of diacetyl N-(4-azidobutyl)-fluoresceine-5(6)-carboxamide was performed in six stages, starting form resorcinol and trimellitic acid anhydride. The diacetylated analogue was synthesized for the click modifications in the “soft” conditions, since N-(4-azidobutyl)-fluorescein-5(6)-carboxamide is poorly soluble in the classic organic solvents. Proposed synthetic protocol allows to increase the yield of the final and intermediate compounds and to optimized the procedure of their isolation and purification. |
| publisher |
V.I.Vernadsky Institute of General and Inorganic Chemistry |
| publishDate |
2020 |
| url |
https://ucj.org.ua/index.php/journal/article/view/131 |
| work_keys_str_mv |
AT selinroman synthesisofmodyfiedfluoresceineforclickreactions AT cherniiviktor synthesisofmodyfiedfluoresceineforclickreactions AT mokhirandriy synthesisofmodyfiedfluoresceineforclickreactions AT selinroman sintezmodificirovannyhfluoresceinovdlâispolʹzovaniâvklikrekaciâh AT cherniiviktor sintezmodificirovannyhfluoresceinovdlâispolʹzovaniâvklikrekaciâh AT mokhirandriy sintezmodificirovannyhfluoresceinovdlâispolʹzovaniâvklikrekaciâh AT selinroman sintezmodifíkovanihfluoresceínívdlâvikoristannâuklíkreakcíâh AT cherniiviktor sintezmodifíkovanihfluoresceínívdlâvikoristannâuklíkreakcíâh AT mokhirandriy sintezmodifíkovanihfluoresceínívdlâvikoristannâuklíkreakcíâh |
| first_indexed |
2025-09-24T17:43:24Z |
| last_indexed |
2025-09-24T17:43:24Z |
| _version_ |
1849658073745981440 |