КФУ. Карточка публикации. Bifunctionalized Betulinic Acid Conjugates with C-3-Monodesmoside and C-28-Triphenylphosphonium Moieties with Increased Cancer Cell Targetability

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BIFUNCTIONALIZED BETULINIC ACID CONJUGATES WITH C-3-MONODESMOSIDE AND C-28-TRIPHENYLPHOSPHONIUM MOIETIES WITH INCREASED CANCER CELL TARGETABILITY

Форма представления

Статьи в зарубежных журналах и сборниках

Год публикации

2023

Язык

английский

Авторы, сотрудники КФУ

Ишкаева Резеда Анасовна, автор

Лайков Александр Владимирович, автор

Библиографическое описание на языке оригинала

Tsepaeva O.V, Salikhova T.I, Ishkaeva R.A, Bifunctionalized Betulinic Acid Conjugates with C-3-Monodesmoside and C-28-Triphenylphosphonium Moieties with Increased Cancer Cell Targetability//Journal of Natural Products. - 2023. - Vol.86, Is.8. - P.1939-1949.

Аннотация

A convenient synthesis is presented for a new class of bioactive bifunctionalized conjugates of lupane-type triterpenoids with triphenylphosphonium (TPP) and glycopyranosyl targeting moieties. The main synthesis steps include glycosylation of haloalkyl esters of the triterpene acid at the C-3 position by the imidate derivatives of glycopyranose followed by the product modification at the C-28 position with triphenylphosphine. The conjugates of betulinic acid (BetA) with TPP and d-glucose, l-rhamnose, or d-mannose moieties were thus synthesized as potential next-generation BetA-derived anticancer compounds. LC-MS/MS analysis in glucose-free physiological solution indicated that the glycosides showed better accumulation in PC-3 prostate cancer cells than both BetA and TPP–BetA conjugate, while the transporting effect of monosaccharide residues increased as follows: d-mannose < l-rhamnose ≈ d-glucose.

Ключевые слова

anticancer conjugates, lupane-type triterpenes, betulinic acid, glucose, rhamnose, mannose, phosphonium salts, cytotoxicity, cellular availability, mitochondrial effects

Название журнала

Journal of Natural Products

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85167812521&doi=10.1021%2facs.jnatprod.3c00304&partnerID=40&md5=26fea4d061e578ed627aea4ffdeb9d32

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https://repository.kpfu.ru/?p_id=293799

Полная запись метаданных

Поле DC	Значение	Язык
dc.contributor.author	Ишкаева Резеда Анасовна	ru_RU
dc.contributor.author	Лайков Александр Владимирович	ru_RU
dc.date.accessioned	2023-01-01T00:00:00Z	ru_RU
dc.date.available	2023-01-01T00:00:00Z	ru_RU
dc.date.issued	2023	ru_RU
dc.identifier.citation	Tsepaeva O.V, Salikhova T.I, Ishkaeva R.A, Bifunctionalized Betulinic Acid Conjugates with C-3-Monodesmoside and C-28-Triphenylphosphonium Moieties with Increased Cancer Cell Targetability//Journal of Natural Products. - 2023. - Vol.86, Is.8. - P.1939-1949.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/?p_id=293799	ru_RU
dc.description.abstract	Journal of Natural Products	ru_RU
dc.description.abstract	A convenient synthesis is presented for a new class of bioactive bifunctionalized conjugates of lupane-type triterpenoids with triphenylphosphonium (TPP) and glycopyranosyl targeting moieties. The main synthesis steps include glycosylation of haloalkyl esters of the triterpene acid at the C-3 position by the imidate derivatives of glycopyranose followed by the product modification at the C-28 position with triphenylphosphine. The conjugates of betulinic acid (BetA) with TPP and d-glucose, l-rhamnose, or d-mannose moieties were thus synthesized as potential next-generation BetA-derived anticancer compounds. LC-MS/MS analysis in glucose-free physiological solution indicated that the glycosides showed better accumulation in PC-3 prostate cancer cells than both BetA and TPP–BetA conjugate, while the transporting effect of monosaccharide residues increased as follows: d-mannose < l-rhamnose ≈ d-glucose.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	anticancer conjugates	ru_RU
dc.subject	lupane-type triterpenes	ru_RU
dc.subject	betulinic acid	ru_RU
dc.subject	glucose	ru_RU
dc.subject	rhamnose	ru_RU
dc.subject	mannose	ru_RU
dc.subject	phosphonium salts	ru_RU
dc.subject	cytotoxicity	ru_RU
dc.subject	cellular availability	ru_RU
dc.subject	mitochondrial effects	ru_RU
dc.title	Bifunctionalized Betulinic Acid Conjugates with C-3-Monodesmoside and C-28-Triphenylphosphonium Moieties with Increased Cancer Cell Targetability	ru_RU
dc.type	Статьи в зарубежных журналах и сборниках	ru_RU