Физико-химические свойства хромофора GFP и флуоресцентные красители на его основе тема диссертации и автореферата по ВАК РФ 02.00.10, кандидат химических наук Баранов, Михаил Сергеевич

• Баранов, Михаил Сергеевич
• кандидат химических наук
• 2013

Оглавление диссертации кандидат химических наук Баранов, Михаил Сергеевич

Содержание

Содержание

Введение

Глава I. Литературный обзор

1. Основные структурные классы флуоресцентных красителей

1.1 Полиароматические соединения

1.2 Производные нафталинсульфоновой и нафталинкарбоновой кислот

1.3 Кумариновые красители

1.4 Производные родамина и флуоресцеина (ксантеновые красители)

1.5 Метановые красители

1.5.1 Цианиновые красители

1.5.2 ВСЮГРУ

1.6 Заключение

2. Хромофоры флуоресцентных белков. Синтетический взгляд

2.1 Синтез оксазолонов

2.1.1 Конденсация карбонильных соединений с производными 1Ч-ацилглицина

2.1.2 Прочие методы синтеза оксазолонов

2.2 Синтез производных Ы-ацилдегидроаминокислот

2.2.1 Нуклеофильное раскрытие оксазолонов

2.2.2 Прочие методы синтеза амидов К-ацилдегидроаминокислот

2.3 Методы синтеза имидазолонов

2.3.1 Циклизация амидов М-ацилдегидроаминокислот

2.3.2 Прочие методы синтеза имидазолонов

2.4 Заключение

Глава II. Экспериментальная часть

1. Материалы и оборудование

2. Синтез

2.1 Получение имидазолонов на основе производных 2-азидокоричных кислот

2.2 Производные оксазол-4-карбоновых кислот

2.3 Конденсация ароматических альдегидов с эфирами нитроуксусной кислоты

2.4. Получение борированных производных без линкеров

2.5. Получение борированных производных с линкерами

Глава III. Результаты и обсуждение

Подходы к созданию флуоресцентных аналогов хромофора вРР

1. Роль заместителей во 2 положении

2. Производные оксазол-4-карбоновых кислот

3. Производные 1,2-оксазин-З-карбоновых кислот

4. Борированный аналог хромофора GFP с фиксированной геометрией

4.1 Синтез

4.2 Свойства

Флуоресцентные красители на основе борированного аналога хромофора GFP

5. Аминопроизводные

5.1 Синтез

5.2 Свойства

5.3 Применение

6. Фторпроизводные

6.1 Синтез

6.2 Свойства

7. Флуоресцентные красители с линкерными заместителями

7.1 Синтез

7.2 Применение

7.2.1 Флуоресцентно-меченый ингибитор катепсинов человека

7.2.1 Флуоресцентно-меченый диолеилфосфатидилэтаноламин

Выводы

Благодарности

Список сокращений и условных обозначений

Список литературы

Введение диссертации (часть автореферата) на тему «Физико-химические свойства хромофора GFP и флуоресцентные красители на его основе»

Введение

Современные технологии флуоресцентной микроскопии позволили визуализировать многие биологические процессы. Одним из важнейших инструментов подобных исследований, применимых как для прикладных биомедицинских анализов, так и для научных задач, являются флуоресцентные красители, дающие возможность проводить наблюдение за целевыми молекулами и средами в режиме реального времени.

Использование живых систем наложило множество дополнительных ограничений на строение подобных веществ. Такие красители должны быть достаточно гидрофильны (для исключения неспецифических гидрофобных взаимодействий), их спектр поглощения и испускания должен лежать в видимой, по возможности более красной области (для уменьшения фототоксичности и фоновой авто флуоресценции), а молекулярный вес должен быть наименьшим (для уменьшения влияния на меченые биомолекулы).

Очевидно, что не существует веществ, идеально удовлетворяющих всем этим условиям. В связи с этим, важной задачей, стоящей перед современными химиками является разработка новых флуоресцентных красителей.

Одним из потенциальных претендентов на эту роль является хромофор зеленого флуоресцентного белка (ОБР). Это соединение обладает достаточно высоким коэффициентом молярного поглощения, а также имеет небольшую молекулярную массу и высокую гидрофильность. Однако, в отличие от флуоресцентных белков, синтетический хромофор вГР совершенно лишен флуоресцентных свойств.

Настоящая работа посвящена выявлению взаимосвязи между строением и флуоресцентными свойствами ряда аналогов хромофора зеленого флуоресцентного белка, а также синтезу новых высокофлуоресцентных производных и созданию серии флуоресцентных красителей на их основе. В рамках исследования были предложены методы синтеза различных аналогов хромофора ОБР, изучены свойства полученных соединений и показано ключевое влияние подвижности бензилиденового фрагмента на флуоресцентные свойства хромофора.

Предложенный в работе метод создания борированных аналогов позволил впервые получить близкие производные хромофора йРР, обладающие высокими квантовыми выходами флуоресценции. С использованием разработанной методики был синтезирован ряд высокофлуоресцентных аналогов хромофора, различающихся по своим оптическим свойствам, а также способных связываться с различными биологическими субстратами. Изучение полученных веществ, а также их конъюгатов, показало перспективность использования подобных соединений в роли флуоресцентных маркеров.

Заключение диссертации по теме «Биоорганическая химия», Баранов, Михаил Сергеевич

Выводы

1. Разработан новый метод синтеза 5-арилиден-3,5-дигидро-4Я-имидазол-4-онов, на основе 2-азидо-коричных кислот. С использованием этого метода получена серия производных, содержащих различные заместители в положении 2 имидазолонового ядра. Показано отсутствие заметного влияния размера заместителя на величину квантового выхода флуоресценции.

2. Разработан новый подход к синтезу производных оксазол-4-карбоновых кислот. Изучены спектральные свойства полученных этим методом соединений.

3. Разработан новый высокоэффективный метод синтеза эфиров 4-арил-5-гидрокси-6-оксо-1,2-оксазин-З-карбоновых кислот.

4. Впервые разработан метод синтеза (2)-4-(2-(дифторборил)-арилиден)-1Я-имидазол-5(4//)-онов, представляющих собой аналоги хромофора ОРР с фиксированным бензилиденовым фрагментом.

5. Показано ключевое влияние подвижности бензилиденового фрагмента на флуоресцентные свойства хромофора СБР.

6. Показана перспективность использования (2)-4-(2-(дифторборил)-4-аминобензилиден)-1,2-диметил-1 Я-имидазол-5(4//)-онов в роли флуоресцентных красителей.

7. Показано существенное уменьшение рКа основного и возбужденного состояний и возникновение "супер" фотокислотности для борированных аналогов хромофора ОРР при введении в их структуру атомов фтора.

8. Разработан метод синтеза флуоресцентных борированных аналогов хромофора вРР, содержащих функциональные группы, позволяющие проводить конъюгацию с биомолекулами. Показана возможность использования полученных соединений в роли флуоресцентных маркеров.

Благодарности

Автор выражает благодарность своему научному руководителю к.х.н. Ямпольскому И.В. за помощь в работе, полезные советы и поддержку на протяжении всех этапов исследования. Автор благодарит руководителя Лаборатории биофотоники д.б.н Лукьянова К.А. (ИБХ РАН, Москва) за поддержку при публикации работ, полезные советы, а также проведение экспериментов на клеточных линиях. Автор выражает свою благодарность коллективу группы к.х.н. Солнцева K.M. (Технологический институт, Джорджия, США) за выполнение экспериментов с привлечением спектроскопии, разрешенной по времени. Автор благодарит коллектив Лаборатории углеводов и ее руководителя д.х.н. Профессора Бовина Н.В. (ИБХ РАН, Москва), а также коллектив лаборатории Профессора Михаэля Гютщова (Боннский университет, Бонн, Германия) и отдельно Фризлера М. за изучение флуоресцентных конъюгатов. Отдельную благодарность автор выражает к.х.н Борисовой А.О. (Центр рентгеноструктурных исследований ИНЭОС РАН, Москва) за проведение рентгеноструктурного анализа, а также сотрудникам Лаборатории биомолекулярной ЯМР-спектроскопии (ИБХ РАН, Москва), в том числе к.ф-м.н. Минееву К.С., за регистрацию спектров ядерного магнитного резонанса.

Список сокращений и условных обозначений

Вое трет-бутоксикарбонил

СЪг бензилоксикарбонил

ББО 2,3-дихлоро-5,6-дициано-1,4-бензохинон

БОРЕ диолеилфосфатидилэтаноламин

СП' зеленый флуоресцентный белок

НОВ! К-гидроксибензотриазол

РМВ пара-м етоксибензил

Ру пиридин сукцинимид

ТВБМ8 трет-бутилдиметилсилил

ТВБМв трет-бутилдифенилсилил

ГАМК гшша-аминомасляная кислота дабко, БАВСО 1,4-диазобицикло [2.2,2]октан

ДБУ, БВи диазобициклоундецен

ДИПЭА, ШРЕЛ диизопропилэтиламин

ДМСО, БМвО диметилсульфоксид

ДМФ, БМЕ диметилформамид

ДЦК, БСС дициклогексилкарбодиимид

ДЭАД, ПЕЛО диэтилазодикарбоксилат

Имидазолон 5-арилиден-3,5-дигидро-477-имидазол-4-он

КВ квантовый выход

КДИ, СБ1 карбонилдиимидазол

ЛДА, ЬБА дизопропиламид лития мс, мв молекулярные сита

НБС, N68 ^бром сукцинимид

Оксазолон 5-арилиден-3,5-дигидро-4#-оксазол-4-он

РСА рентгеноструктурный анализ

ТБАФ тэтрабутиламмоний фторид

ТГФ, ЮТ тетрагидрофуран тех тонкослойная хроматография

ФБ флуоресцентный белок

ЯМР ядерный магнитный резонанс

Также применяются типичные сокращения для названий аминокислот (С1у, РЬе и т.п.), карбонильных (Е^ Рг и т.п.) и прочих (Вп, РЬ, Аг, Те и т.п.) радикалов.

Список литературы диссертационного исследования кандидат химических наук Баранов, Михаил Сергеевич, 2013 год

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