Synthesis and cancer cell cytotoxicity of 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes
- Author
- Katarina Magdalenic (UGent) , Ulrike Ronse (UGent) , Steven De Jonghe, Leentje Persoons, Dominique Schols, Julie De Munck (UGent) , Charlotte Grootaert (UGent) , John Van Camp (UGent) and Matthias D'hooghe (UGent)
- Organization
- Abstract
- Curcumin is a natural product displaying a broad range of biological activities, including anticancer properties. It is, however, poorly absorbed by the human body and, as a so-called pan-assay interference compound, it exhibits non-specific activity leading to false positive results in biological assays. Nonetheless, different structural modifications of the curcumin scaffold have previously shown to lead to an improved biological and specificity profile without losing antiproliferative activity. In that respect, recent research in our group culminated in unprecedented benzothiazepane-based hit molecules with promising biological and drug-like properties. In the present hit expansion study, 14 new 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)benzothiazepanes were successfully synthesized through the implementation of various aromatic ring modifications and subsequently tested for cancer cell cytotoxicity using eight different cancer cell lines, revealing useful structure-activity relationship insights for this new class of compounds.
- Keywords
- Anticancer agents, Benzothiazepanes, Curcumin, Cytotoxicity, CROSS-COUPLING REACTION, MEDICINAL CHEMISTRY, CURCUMIN, ACID
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01H2AQ08YWBPVN5CJ80G6A7B0A
- MLA
- Magdalenic, Katarina, et al. “Synthesis and Cancer Cell Cytotoxicity of 2-Aryl-4-(4-Aryl-2-Oxobut-3-En-1-Ylidene)-Substituted Benzothiazepanes.” PHYTOCHEMISTRY LETTERS, vol. 55, 2023, pp. 117–23, doi:10.1016/j.phytol.2023.04.008.
- APA
- Magdalenic, K., Ronse, U., De Jonghe, S., Persoons, L., Schols, D., De Munck, J., … D’hooghe, M. (2023). Synthesis and cancer cell cytotoxicity of 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes. PHYTOCHEMISTRY LETTERS, 55, 117–123. https://doi.org/10.1016/j.phytol.2023.04.008
- Chicago author-date
- Magdalenic, Katarina, Ulrike Ronse, Steven De Jonghe, Leentje Persoons, Dominique Schols, Julie De Munck, Charlotte Grootaert, John Van Camp, and Matthias D’hooghe. 2023. “Synthesis and Cancer Cell Cytotoxicity of 2-Aryl-4-(4-Aryl-2-Oxobut-3-En-1-Ylidene)-Substituted Benzothiazepanes.” PHYTOCHEMISTRY LETTERS 55: 117–23. https://doi.org/10.1016/j.phytol.2023.04.008.
- Chicago author-date (all authors)
- Magdalenic, Katarina, Ulrike Ronse, Steven De Jonghe, Leentje Persoons, Dominique Schols, Julie De Munck, Charlotte Grootaert, John Van Camp, and Matthias D’hooghe. 2023. “Synthesis and Cancer Cell Cytotoxicity of 2-Aryl-4-(4-Aryl-2-Oxobut-3-En-1-Ylidene)-Substituted Benzothiazepanes.” PHYTOCHEMISTRY LETTERS 55: 117–123. doi:10.1016/j.phytol.2023.04.008.
- Vancouver
- 1.Magdalenic K, Ronse U, De Jonghe S, Persoons L, Schols D, De Munck J, et al. Synthesis and cancer cell cytotoxicity of 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes. PHYTOCHEMISTRY LETTERS. 2023;55:117–23.
- IEEE
- [1]K. Magdalenic et al., “Synthesis and cancer cell cytotoxicity of 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes,” PHYTOCHEMISTRY LETTERS, vol. 55, pp. 117–123, 2023.
@article{01H2AQ08YWBPVN5CJ80G6A7B0A,
abstract = {{Curcumin is a natural product displaying a broad range of biological activities, including anticancer properties. It is, however, poorly absorbed by the human body and, as a so-called pan-assay interference compound, it exhibits non-specific activity leading to false positive results in biological assays. Nonetheless, different structural modifications of the curcumin scaffold have previously shown to lead to an improved biological and specificity profile without losing antiproliferative activity. In that respect, recent research in our group culminated in unprecedented benzothiazepane-based hit molecules with promising biological and drug-like properties. In the present hit expansion study, 14 new 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)benzothiazepanes were successfully synthesized through the implementation of various aromatic ring modifications and subsequently tested for cancer cell cytotoxicity using eight different cancer cell lines, revealing useful structure-activity relationship insights for this new class of compounds.}},
author = {{Magdalenic, Katarina and Ronse, Ulrike and De Jonghe, Steven and Persoons, Leentje and Schols, Dominique and De Munck, Julie and Grootaert, Charlotte and Van Camp, John and D'hooghe, Matthias}},
issn = {{1874-3900}},
journal = {{PHYTOCHEMISTRY LETTERS}},
keywords = {{Anticancer agents,Benzothiazepanes,Curcumin,Cytotoxicity,CROSS-COUPLING REACTION,MEDICINAL CHEMISTRY,CURCUMIN,ACID}},
language = {{eng}},
pages = {{117--123}},
title = {{Synthesis and cancer cell cytotoxicity of 2-aryl-4-(4-aryl-2-oxobut-3-en-1-ylidene)-substituted benzothiazepanes}},
url = {{http://doi.org/10.1016/j.phytol.2023.04.008}},
volume = {{55}},
year = {{2023}},
}
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