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Review
. 2022 Jan 10:24:400-416.
doi: 10.1016/j.omto.2022.01.005. eCollection 2022 Mar 17.

Carboranes as unique pharmacophores in antitumor medicinal chemistry

Yu Chen  1 , Fukuan Du  1 , Liyao Tang  1 , Jinrun Xu  1 , Yueshui Zhao  1 , Xu Wu  1 , Mingxing Li  1 , Jing Shen  1 , Qinglian Wen  2   3 , Chi Hin Cho  1   3   4 , Zhangang Xiao  2   3
Affiliations
Review

Carboranes as unique pharmacophores in antitumor medicinal chemistry

Yu Chen et al. Mol Ther Oncolytics. .

Abstract

Carborane is a carbon-boron molecular cluster that can be viewed as a 3D analog of benzene. It features special physical and chemical properties, and thus has the potential to serve as a new type of pharmacophore for drug design and discovery. Based on the relative positions of two cage carbons, icosahedral closo-carboranes can be classified into three isomers, ortho-carborane (o-carborane, 1,2-C2B10H12), meta-carborane (m-carborane, 1,7-C2B10H12), and para-carborane (p-carborane, 1,12-C2B10H12), and all of them can be deboronated to generate their nido- forms. Cage compound carborane and its derivatives have been demonstrated as useful chemical entities in antitumor medicinal chemistry. The applications of carboranes and their derivatives in the field of antitumor research mainly include boron neutron capture therapy (BNCT), as BNCT/photodynamic therapy dual sensitizers, and as anticancer ligands. This review summarizes the research progress on carboranes achieved up to October 2021, with particular emphasis on signaling transduction pathways, chemical structures, and mechanistic considerations of using carboranes.

Keywords: antitumor; cage; carborane; drug design; pharmacophore.

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Conflict of interest statement

The authors declare no competing interests.

Figures

None
Graphical abstract
Figure 1
Figure 1
Interaction of carborane derivatives and cancer cells (A) Schematic representation of the routes of carborane derivatives entering cancer cells. (B) Carboranes bind to the skeleton of different enzyme inhibitors and interfere with receptors.
Figure 2
Figure 2
How BNCT kills tumor cells
Figure 3
Figure 3
Applications of carboranes in BNCT
Figure 4
Figure 4
Signaling pathways of a carborane-derived COX-2 inhibitor
Figure 5
Figure 5
Synthesis of carborane-derived PDT/BNCT dual sensitizers
Figure 6
Figure 6
Applications of carboranes in anticancer ligands
Figure 7
Figure 7
Mechanisms and signaling pathways (A) Mechanisms of gene regulation by AR. (B) Mechanisms of gene regulation by VDR. (C) Signaling pathways regulated by EGFR.
See this image and copyright information in PMC

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