KFU. Card publication. Design, synthesis, and cancer cell growth inhibitory activity of triphenylphosphonium derivatives of the triterpenoid betulin.

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DESIGN, SYNTHESIS, AND CANCER CELL GROWTH INHIBITORY ACTIVITY OF TRIPHENYLPHOSPHONIUM DERIVATIVES OF THE TRITERPENOID BETULIN.

Form of presentation

Articles in international journals and collections

Year of publication

2017

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Authors, employees of KFU

Mironov Vladimir Fedorovich, author

Bibliographic description in the original language

O.V.Tsepaeva, A.V.Nemtarev, T.I.Abdullin, L.R.Grigor'eva, E.V.Kuznetsova, R.A.Akhmadishina, L.E.Ziganshina, H.H.Cong, V.F.Mironov. Design, synthesis, and cancer cell growth inhibitory activity of triphenylphosphonium derivatives of the triterpenoid betulin. // J. Nat. Prod. 2017. Vol. 80. No 8. P. 2232-2239. Doi 10.1021/acs.jnatprod.7b00105.

Annotation

A series of new triphenylphosphonium (TPP) derivatives of the triterpenoid betulin (1, 3-lup-20(29)-ene-3β,28-diol) have been synthesized and evaluated for cytotoxic effects against human breast cancer (MCF-7), prostate adenocarcinoma (PC-3), vinblastine-resistant human breast cancer (MCF-7/Vinb), and human skin fibroblast (HSF) cells. The TPP moiety was applied as a carrier group through the acyl linker at the 28- or 3- and 28-positions of betulin to promote cellular and mitochondrial accumulation of the resultant compounds. A structure−activity relationship study has revealed the essential role of the TPP group in the biological properties of the betulin derivatives produced. The present results showed that a conjugate of betulin with TPP (3) enhanced antiproliferative activity toward vinblastine-resistant MCF-7 cells, with an IC50 value as low as 0.045 μM.

Keywords

triphenylphosphonium, betulin, anticancer drug

The name of the journal

J Nat Prod

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

https://repository.kpfu.ru/eng/?p_id=174851&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Mironov Vladimir Fedorovich	ru_RU
dc.date.accessioned	2017-01-01T00:00:00Z	ru_RU
dc.date.available	2017-01-01T00:00:00Z	ru_RU
dc.date.issued	2017	ru_RU
dc.identifier.citation	O.V.Tsepaeva, A.V.Nemtarev, T.I.Abdullin, L.R.Grigor'eva, E.V.Kuznetsova, R.A.Akhmadishina, L.E.Ziganshina, H.H.Cong, V.F.Mironov. Design, synthesis, and cancer cell growth inhibitory activity of triphenylphosphonium derivatives of the triterpenoid betulin. // J. Nat. Prod. 2017. Vol. 80. No 8. P. 2232-2239. Doi 10.1021/acs.jnatprod.7b00105.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=174851&p_lang=2	ru_RU
dc.description.abstract	J Nat Prod	ru_RU
dc.description.abstract	A series of new triphenylphosphonium (TPP) derivatives of the triterpenoid betulin (1, 3-lup-20(29)-ene-3β,28-diol) have been synthesized and evaluated for cytotoxic effects against human breast cancer (MCF-7), prostate adenocarcinoma (PC-3), vinblastine-resistant human breast cancer (MCF-7/Vinb), and human skin fibroblast (HSF) cells. The TPP moiety was applied as a carrier group through the acyl linker at the 28- or 3- and 28-positions of betulin to promote cellular and mitochondrial accumulation of the resultant compounds. A structure−activity relationship study has revealed the essential role of the TPP group in the biological properties of the betulin derivatives produced. The present results showed that a conjugate of betulin with TPP (3) enhanced antiproliferative activity toward vinblastine-resistant MCF-7 cells, with an IC50 value as low as 0.045 μM.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	triphenylphosphonium	ru_RU
dc.subject	betulin	ru_RU
dc.subject	anticancer drug	ru_RU
dc.title	Design, synthesis, and cancer cell growth inhibitory activity of triphenylphosphonium derivatives of the triterpenoid betulin.	ru_RU
dc.type	Articles in international journals and collections	ru_RU