Spiro-bicyclo[2.2.2]octane derivatives as paclitaxel mimetics. Synthesis and toxicity evaluation in breast cancer cell lines.
Manner, Sophie LU ; Oltner, Viveca ; Oredsson, Stina LU ; Ellervik, Ulf LU
and Frejd, Torbjörn
LU
(2013)
In Organic and Biomolecular Chemistry
11(41).
p.7134-7144
- Abstract
- Paclitaxel is one of the most important anti-cancer agents introduced during the last 20 years. However, the use of paclitaxel is limited by undesirable side effects as well as the development of drug resistance. Here, we report a synthetic strategy towards spiro-bicyclo[2.2.2]octane derivatives, which includes double Michael addition and ring-closing metathesis as key synthetic steps. This strategy was used to synthesize a series of spiro-bicyclic compounds designed to be paclitaxel mimetics, which were evaluated in human breast-derived cell lines. One of these paclitaxel mimetics showed toxicity, although at higher concentrations than paclitaxel itself. In addition, two other spiro-bicyclic compounds, lacking the paclitaxel side chain,... (More)
- Paclitaxel is one of the most important anti-cancer agents introduced during the last 20 years. However, the use of paclitaxel is limited by undesirable side effects as well as the development of drug resistance. Here, we report a synthetic strategy towards spiro-bicyclo[2.2.2]octane derivatives, which includes double Michael addition and ring-closing metathesis as key synthetic steps. This strategy was used to synthesize a series of spiro-bicyclic compounds designed to be paclitaxel mimetics, which were evaluated in human breast-derived cell lines. One of these paclitaxel mimetics showed toxicity, although at higher concentrations than paclitaxel itself. In addition, two other spiro-bicyclic compounds, lacking the paclitaxel side chain, showed toxicity. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/4065510
- author
- Manner, Sophie
LU
; Oltner, Viveca
; Oredsson, Stina
LU
; Ellervik, Ulf
LU
and Frejd, Torbjörn
LU
- organization
- publishing date
- 2013
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Organic and Biomolecular Chemistry
- volume
- 11
- issue
- 41
- pages
- 7134 - 7144
- publisher
- Royal Society of Chemistry
- external identifiers
-
- wos:000326010300015
- pmid:24057031
- scopus:84885087746
- ISSN
- 1477-0539
- DOI
- 10.1039/c3ob41417e
- language
- English
- LU publication?
- yes
- id
- 15e2d3f7-0371-43b8-ad1c-78b531e99a7d (old id 4065510)
- date added to LUP
- 2016-04-01 11:09:08
- date last changed
- 2025-10-14 10:45:22
@article{15e2d3f7-0371-43b8-ad1c-78b531e99a7d,
abstract = {{Paclitaxel is one of the most important anti-cancer agents introduced during the last 20 years. However, the use of paclitaxel is limited by undesirable side effects as well as the development of drug resistance. Here, we report a synthetic strategy towards spiro-bicyclo[2.2.2]octane derivatives, which includes double Michael addition and ring-closing metathesis as key synthetic steps. This strategy was used to synthesize a series of spiro-bicyclic compounds designed to be paclitaxel mimetics, which were evaluated in human breast-derived cell lines. One of these paclitaxel mimetics showed toxicity, although at higher concentrations than paclitaxel itself. In addition, two other spiro-bicyclic compounds, lacking the paclitaxel side chain, showed toxicity.}},
author = {{Manner, Sophie and Oltner, Viveca and Oredsson, Stina and Ellervik, Ulf and Frejd, Torbjörn}},
issn = {{1477-0539}},
language = {{eng}},
number = {{41}},
pages = {{7134--7144}},
publisher = {{Royal Society of Chemistry}},
series = {{Organic and Biomolecular Chemistry}},
title = {{Spiro-bicyclo[2.2.2]octane derivatives as paclitaxel mimetics. Synthesis and toxicity evaluation in breast cancer cell lines.}},
url = {{http://dx.doi.org/10.1039/c3ob41417e}},
doi = {{10.1039/c3ob41417e}},
volume = {{11}},
year = {{2013}},
}