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Synthesis of Novel Aza‐aromatic Curcuminoids with Improved Biological Activities towards Various Cancer Cell Lines

Atiruj Theppawong UGent, Tim Van de Walle UGent, Charlotte Grootaert UGent, Margot Bultinck, Tom Desmet UGent, John Van Camp UGent and Matthias D'hooghe UGent (2018) ChemistryOpen. 7(5). p.381-392
abstract
Abstract Curcumin, a natural compound extracted from the rhizomes of Curcuma longa, displays pronounced anticancer properties but lacks good bioavailability and stability. In a previous study, we initiated structure modification of the curcumin scaffold by imination of the labile β‐diketone moiety to produce novel β‐enaminone derivatives. These compounds showed promising properties for elaborate follow‐up studies. In this work, we focused on another class of nitrogen‐containing curcuminoids with a similar objective: to address the bioavailability and stability issues and to improve the biological activity of curcumin. This paper thus reports on the synthesis of new pyridine‐, indole‐, and pyrrole‐based curcumin analogues (aza‐aromatic curcuminoids) and discusses their water solubility, antioxidant activity, and antiproliferative properties. In addition, multivariate statistics, including hierarchical clustering analysis and principal component analysis, were performed on a broad set of nitrogen‐containing curcuminoids. Compared to their respective mother structures, that is, curcumin and bisdemethoxycurcumin, all compounds, and especially the pyridin‐3‐yl β‐enaminone analogues, showed better water solubility profiles. Interestingly, the pyridine‐, indole‐, and pyrrole‐based curcumin derivatives demonstrated improved biological effects in terms of mitochondrial activity impairment and protein content, in addition to comparable or decreased antioxidant properties. Overall, the biologically active N‐alkyl β‐enaminone aza‐aromatic curcuminoids were shown to offer a desirable balance between good solubility and significant bioactivity.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle
publication status
published
keyword
biological activity, cytotoxicity, enaminones, nitrogen heterocycles, oxidative stress
journal title
ChemistryOpen
volume
7
issue
5
pages
381 - 392
DOI
10.1002/open.201800029
UGent publication?
yes
classification
U
copyright statement
I have transferred the copyright for this publication to the publisher
id
8565182
handle
http://hdl.handle.net/1854/LU-8565182
date created
2018-06-13 08:44:10
date last changed
2018-06-13 08:46:12
@article{8565182,
  abstract     = {Abstract Curcumin, a natural compound extracted from the rhizomes of Curcuma longa, displays pronounced anticancer properties but lacks good bioavailability and stability. In a previous study, we initiated structure modification of the curcumin scaffold by imination of the labile \ensuremath{\beta}\unmatched{2010}diketone moiety to produce novel \ensuremath{\beta}\unmatched{2010}enaminone derivatives. These compounds showed promising properties for elaborate follow\unmatched{2010}up studies. In this work, we focused on another class of nitrogen\unmatched{2010}containing curcuminoids with a similar objective: to address the bioavailability and stability issues and to improve the biological activity of curcumin. This paper thus reports on the synthesis of new pyridine\unmatched{2010}, indole\unmatched{2010}, and pyrrole\unmatched{2010}based curcumin analogues (aza\unmatched{2010}aromatic curcuminoids) and discusses their water solubility, antioxidant activity, and antiproliferative properties. In addition, multivariate statistics, including hierarchical clustering analysis and principal component analysis, were performed on a broad set of nitrogen\unmatched{2010}containing curcuminoids. Compared to their respective mother structures, that is, curcumin and bisdemethoxycurcumin, all compounds, and especially the pyridin\unmatched{2010}3\unmatched{2010}yl \ensuremath{\beta}\unmatched{2010}enaminone analogues, showed better water solubility profiles. Interestingly, the pyridine\unmatched{2010}, indole\unmatched{2010}, and pyrrole\unmatched{2010}based curcumin derivatives demonstrated improved biological effects in terms of mitochondrial activity impairment and protein content, in addition to comparable or decreased antioxidant properties. Overall, the biologically active N\unmatched{2010}alkyl \ensuremath{\beta}\unmatched{2010}enaminone aza\unmatched{2010}aromatic curcuminoids were shown to offer a desirable balance between good solubility and significant bioactivity.},
  author       = {Theppawong, Atiruj and Van de Walle, Tim and Grootaert, Charlotte and Bultinck, Margot and Desmet, Tom and Van Camp, John and D'hooghe, Matthias},
  journal      = {ChemistryOpen},
  keyword      = {biological activity,cytotoxicity,enaminones,nitrogen heterocycles,oxidative stress},
  number       = {5},
  pages        = {381--392},
  title        = {Synthesis of Novel Aza\unmatched{2010}aromatic Curcuminoids with Improved Biological Activities towards Various Cancer Cell Lines},
  url          = {http://dx.doi.org/10.1002/open.201800029},
  volume       = {7},
  year         = {2018},
}

Chicago
Theppawong, Atiruj, Tim Van de Walle, Charlotte Grootaert, Margot Bultinck, Tom Desmet, John Van Camp, and Matthias D’hooghe. 2018. “Synthesis of Novel Aza‐aromatic Curcuminoids with Improved Biological Activities Towards Various Cancer Cell Lines.” ChemistryOpen 7 (5): 381–392.
APA
Theppawong, A., Van de Walle, T., Grootaert, C., Bultinck, M., Desmet, T., Van Camp, J., & D’hooghe, M. (2018). Synthesis of Novel Aza‐aromatic Curcuminoids with Improved Biological Activities towards Various Cancer Cell Lines. ChemistryOpen, 7(5), 381–392.
Vancouver
1.
Theppawong A, Van de Walle T, Grootaert C, Bultinck M, Desmet T, Van Camp J, et al. Synthesis of Novel Aza‐aromatic Curcuminoids with Improved Biological Activities towards Various Cancer Cell Lines. ChemistryOpen. 2018;7(5):381–92.
MLA
Theppawong, Atiruj, Tim Van de Walle, Charlotte Grootaert, et al. “Synthesis of Novel Aza‐aromatic Curcuminoids with Improved Biological Activities Towards Various Cancer Cell Lines.” ChemistryOpen 7.5 (2018): 381–392. Print.