Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model
Irina Yu. Strobykina
1
,
M G Belenok
1
,
Marina Semenova
2, 3
,
Victor Semenov
4
,
Vasiliy M Babaev
1
,
Vladimir E. Kataev
1
3
Chemical Block Ltd., 3 Kyriacou Matsi, 3723 Limassol, Cyprus
|
Publication type: Journal Article
Publication date: 2015-06-04
scimago Q1
wos Q1
SJR: 0.629
CiteScore: 6.5
Impact factor: 3.6
ISSN: 01633864, 15206025
PubMed ID:
26042548
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
Abstract
A series of novel triphenylphosphonium (TPP) cations of the diterpenoid isosteviol (1, 16-oxo-ent-beyeran-19-oic acid) have been synthesized and evaluated in an in vivo phenotypic sea urchin embryo assay for antimitotic activity. The TPP moiety was applied as a carrier to provide selective accumulation of a connected compound into mitochondria. When applied to fertilized eggs, the targeted isosteviol TPP conjugates induced mitotic arrest with the formation of aberrant multipolar mitotic spindles, whereas both isosteviol and the methyltriphenylphosphonium cation were inactive. The structure-activity relationship study revealed the essential role of the TPP group for the realization of the isosteviol effect, while the chemical structure and the length of the linker only slightly influenced the antimitotic potency. The results obtained using the sea urchin embryo model suggested that TPP conjugates of isosteviol induced mitotic spindle defects and mitotic arrest presumably by affecting mitochondrial DNA. Since targeting mitochondria is considered as an encouraging strategy for cancer therapy, TPP-isosteviol conjugates may represent promising candidates for further design as anticancer agents.
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55
Total citations:
55
Citations from 2024:
5
(9.09%)
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GOST
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Strobykina I. Y. et al. Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model // Journal of Natural Products. 2015. Vol. 78. No. 6. pp. 1300-1308.
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Strobykina I. Y., Belenok M. G., Semenova M., Semenov V., Babaev V. M., Rizvanov I. Kh., Mironov V. L., Kataev V. E. Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model // Journal of Natural Products. 2015. Vol. 78. No. 6. pp. 1300-1308.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.jnatprod.5b00124
UR - https://doi.org/10.1021/acs.jnatprod.5b00124
TI - Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model
T2 - Journal of Natural Products
AU - Strobykina, Irina Yu.
AU - Belenok, M G
AU - Semenova, Marina
AU - Semenov, Victor
AU - Babaev, Vasiliy M
AU - Rizvanov, Ildar Kh
AU - Mironov, Valery L.
AU - Kataev, Vladimir E.
PY - 2015
DA - 2015/06/04
PB - American Chemical Society (ACS)
SP - 1300-1308
IS - 6
VL - 78
PMID - 26042548
SN - 0163-3864
SN - 1520-6025
ER -
Cite this
BibTex (up to 50 authors)
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@article{2015_Strobykina,
author = {Irina Yu. Strobykina and M G Belenok and Marina Semenova and Victor Semenov and Vasiliy M Babaev and Ildar Kh Rizvanov and Valery L. Mironov and Vladimir E. Kataev},
title = {Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model},
journal = {Journal of Natural Products},
year = {2015},
volume = {78},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.jnatprod.5b00124},
number = {6},
pages = {1300--1308},
doi = {10.1021/acs.jnatprod.5b00124}
}
Cite this
MLA
Copy
Strobykina, Irina Yu., et al. “Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model.” Journal of Natural Products, vol. 78, no. 6, Jun. 2015, pp. 1300-1308. https://doi.org/10.1021/acs.jnatprod.5b00124.
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