KFU. Card publication. 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

Form of presentation

Articles in international journals and collections

Year of publication

2023

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Authors, employees of KFU

Ishkaeva Rezeda Anasovna, author

Laykov Aleksandr Vladimirovich, author

Bibliographic description in the original language

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.

Annotation

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.

Keywords

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

The name of the journal

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

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=293799&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Ishkaeva Rezeda Anasovna	ru_RU
dc.contributor.author	Laykov Aleksandr Vladimirovich	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/eng/?p_id=293799&p_lang=2	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	Articles in international journals and collections	ru_RU