Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin
Olga V. Tsepaeva
1, 2
,
Andrey V. Nemtarev
1, 2, 3
,
Timur I Abdullin
3
,
Leysan R. Grigor`eva
3
,
Elena V Kuznetsova
3
,
Rezeda A Akhmadishina
3
,
Hanh H Cong
3
,
Valery L. Mironov
1, 3
,
Vladimir F. Mironov
2, 3
Publication type: Journal Article
Publication date: 2017-08-07
scimago Q1
wos Q1
SJR: 0.629
CiteScore: 6.5
Impact factor: 3.6
ISSN: 01633864, 15206025
PubMed ID:
28782948
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
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.
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Total citations:
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Citations from 2024:
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(22.61%)
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GOST
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Tsepaeva O. V. et al. Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin // Journal of Natural Products. 2017. Vol. 80. No. 8. pp. 2232-2239.
GOST all authors (up to 50)
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Tsepaeva O. V., Nemtarev A. V., Abdullin T. I., Grigor`eva L. R., Kuznetsova E. V., Akhmadishina R. A., Ziganshina L. E., Cong H. H., Mironov V. L., Mironov V. F. Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin // Journal of Natural Products. 2017. Vol. 80. No. 8. pp. 2232-2239.
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TY - JOUR
DO - 10.1021/acs.jnatprod.7b00105
UR - https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00105
TI - Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin
T2 - Journal of Natural Products
AU - Tsepaeva, Olga V.
AU - Nemtarev, Andrey V.
AU - Abdullin, Timur I
AU - Grigor`eva, Leysan R.
AU - Kuznetsova, Elena V
AU - Akhmadishina, Rezeda A
AU - Ziganshina, Lilia E.
AU - Cong, Hanh H
AU - Mironov, Valery L.
AU - Mironov, Vladimir F.
PY - 2017
DA - 2017/08/07
PB - American Chemical Society (ACS)
SP - 2232-2239
IS - 8
VL - 80
PMID - 28782948
SN - 0163-3864
SN - 1520-6025
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Tsepaeva,
author = {Olga V. Tsepaeva and Andrey V. Nemtarev and Timur I Abdullin and Leysan R. Grigor`eva and Elena V Kuznetsova and Rezeda A Akhmadishina and Lilia E. Ziganshina and Hanh H Cong and Valery L. Mironov and Vladimir F. Mironov},
title = {Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin},
journal = {Journal of Natural Products},
year = {2017},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00105},
number = {8},
pages = {2232--2239},
doi = {10.1021/acs.jnatprod.7b00105}
}
Cite this
MLA
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Tsepaeva, Olga V., et al. “Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin.” Journal of Natural Products, vol. 80, no. 8, Aug. 2017, pp. 2232-2239. https://pubs.acs.org/doi/10.1021/acs.jnatprod.7b00105.
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