ВЗАИМОДЕЙСТВИЕ ИНДОЦИАНИНОВОГО ЗЕЛЕНОГО НОВОГО С N- И О-НУКЛЕОФИЛАМИ: СИНТЕЗ И ФИЗИКО-ХИМИЧЕСКИЕ СВОЙСТВА КРАСИТЕЛЕЙ ДЛЯ ФОТОТЕРМОТЕРАПИИ
Аннотация
ИК-фотосенсибилизаторы (ФС) не только обеспечивают лучшее проникновение излучения в ткани при фототерапии глубокозалегающих опухолей, но и способствуют эффективному преобразованию поглощенной энергии фотонов в тепловую энергию, вызывая локальный разогрев опухолевой ткани и ее деградацию. Нами с применением реакции нуклеофильного замещения атома хлора в молекуле ИК-фотосенсибилизатора Индоцианинового зеленого нового (IGN) синтезированы и спектрально идентифицированы пять его амино- и эфирных производных с концевыми карбокси- и аминогруппами, которые могут рассматриваться как перспективные средства фототермической терапии (ФТТ) опухолей, а также как компоненты для получения препаратов для комбинированного лечения путем их ковалентного связывания с ФС фотодинамического принципа действия. Замещение атома хлора в молекуле красителя IGN приводит к значительному уширению и гипсохромному (до 150 нм) смещению полос в электронном спектре поглощения (ЭСП), величина которого изменяется в зависимости от природы линкера, что позволяет вести целенаправленный синтез ФС с требуемыми спектральными характеристиками. Анализ ЭСП водных растворов красителей показал, что в этих условиях ФС находятся в агрегированной форме и могут быть дезагрегированы экзогенными пассивными носителями мицеллярного типа. Расчет констант связывания продемонстрировал невысокую степень взаимодействия IGN и его производного с ПАВ Твин 80 и Плюроник Р123, приводящего, тем не менее, к полному разрушению наноагрегатов красителя. В результате проведения прямых и косвенных фотофизических исследований IGN было обнаружено отсутствие генерации этим красителем синглетного кислорода в фосфатно-солевом буферном растворе. В сочетании со слабой флуоресценцией красителя это позволяет с уверенностью ожидать, что основным каналом релаксации молекулы в результате ее фотовозбуждения будет безызлучательная трансформация энергии в тепловую энергию, что характерно для других ИК-фотосенсибилизаторов этого класса.
Для цитирования:
Березин Д.Б., Паламар А.В., Бондарева Т.В., Шухто О.В., Разговоров П.Б., Терентьев А.А. Взаимодействие индоцианинового зеленого нового с N- и О-нуклеофилами: синтез и физико-химические свойства красителей для фототермотерапии. Изв. вузов. Химия и хим. технология. 2026. Т. 69. Вып. 9. С. 6-23. DOI: 10.6060/ivkkt.20266909.7132.
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