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Review
. 2023 Nov 28;24(23):16854.
doi: 10.3390/ijms242316854.

The Fundamental Role of Oxime and Oxime Ether Moieties in Improving the Physicochemical and Anticancer Properties of Structurally Diverse Scaffolds

Jean Fotie  1 , Caitlyn M Matherne  1 , Jasmine B Mather  1 , Jordan E Wroblewski  1 , Khaitlynn Johnson  1 , Lara G Boudreaux  1 , Alba A Perez  1
Affiliations
Review

The Fundamental Role of Oxime and Oxime Ether Moieties in Improving the Physicochemical and Anticancer Properties of Structurally Diverse Scaffolds

Jean Fotie et al. Int J Mol Sci. .

Abstract

The present review explores the critical role of oxime and oxime ether moieties in enhancing the physicochemical and anticancer properties of structurally diverse molecular frameworks. Specific examples are carefully selected to illustrate the distinct contributions of these functional groups to general strategies for molecular design, modulation of biological activities, computational modeling, and structure-activity relationship studies. An extensive literature search was conducted across three databases, including PubMed, Google Scholar, and Scifinder, enabling us to create one of the most comprehensive overviews of how oximes and oxime ethers impact antitumor activities within a wide range of structural frameworks. This search focused on various combinations of keywords or their synonyms, related to the anticancer activity of oximes and oxime ethers, structure-activity relationships, mechanism of action, as well as molecular dynamics and docking studies. Each article was evaluated based on its scientific merit and the depth of the study, resulting in 268 cited references and more than 336 illustrative chemical structures carefully selected to support this analysis. As many previous reviews focus on one subclass of this extensive family of compounds, this report represents one of the rare and fully comprehensive assessments of the anticancer potential of this group of molecules across diverse molecular scaffolds.

Keywords: SAR; anticancer activities; docking studies; oxime ethers; oximes; physicochemical properties.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
First synthetic and earliest amino acid-derived oximes from plants [33,34,35,36].
Figure 2
Figure 2
Illustrative examples of anticancer indirubin-3′-oxime derivatives, bearing a diversity of substitution patterns on the core bis-indole scaffold.
Figure 3
Figure 3
Crystal structure of the 37-DYRK2 complex revealing a nontypical binding mode, in which the orientation of the indirubin core is in good accordance with the predicted binding mode [94] (https://pubs.acs.org/doi/10.1021/ml300207a), accessed on 27 August 2023. This image is reused with the express permission of ACS, and any further permissions related to this material should be directed to ACS.
Figure 4
Figure 4
Illustrative examples of anticancer indirubin-3′-oxime ether derivatives.
Figure 5
Figure 5
Illustrative examples of anticancer indirubin-3′-oxime derivative with substituents at N1 of the bisindole core.
Figure 6
Figure 6
Illustrative examples of other antitumor indole derivatives bearing an oxime moiety.
Figure 7
Figure 7
Illustrative examples of anticancer triazole- and pyrazole-based oximes and oxime ethers.
Figure 8
Figure 8
Illustrative examples of miscellaneous small nitrogen-containing hetorocyclic-based oximes with anticancer properties.
Figure 9
Figure 9
Illustrative examples of anticancer quinone-based oximes and oxime ethers.
Figure 10
Figure 10
Illustrative examples of anticancer quinone oxime bond-linked bioconjugates.
Figure 11
Figure 11
Illustrative examples of anticancer flavonoid-based oximes and oxime ethers.
Figure 12
Figure 12
Illustrative examples of anticancer quinolinone-, cyclohexanone-, piperidin-4-one- and tetralone-based oximes.
Figure 13
Figure 13
Illustrative examples of radicicol oxime and oxime ether derivatives with antitumor activities.
Figure 14
Figure 14
Illustrative examples of anticancer small aromatic and phenolic-based oximes and oxime ethers.
Figure 15
Figure 15
Illustrative examples of anticancer steroidal oximes and oxime ethers.
Figure 16
Figure 16
The binding mode of 279 docked into the active site of CYP17, with the red dotted line representing a hydrogen bond [241] (https://doi.org/10.1016/j.steroids.2019.03.003 accessed on 27 August 2023). This image was reused with express permission from Elsevier, and any further permissions related to this material should be directed to Elsevier.
Figure 17
Figure 17
Illustrative examples of anticancer oleanolic acid oxime derivatives and steroidal oxime conjugates.
Figure 18
Figure 18
Illustrative examples of anticancer platinum complexes bearing chelating oxime ligands.
Figure 19
Figure 19
Illustrative examples of miscellaneous oxime-chelated metal complexes as potential chemotherapeutic agents for cancer treatment.
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