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Solution to long-standing chemistry riddle has implications for drug development

February 1, 2018
Trinity College Dublin
Scientists have solved a decades-old challenge by working out how to craft functional residues onto a molecular cube. Cubane now has a plethora of additional applications in the fields of drug development, materials science and molecular engineering.

Scientists have solved a decades-old chemistry riddle by developing new tools for a synthetic (human-made) molecule -- cubane -- that is widely used in the pharma industry. By circumventing the inherent reactivity of this molecule, they have opened up a new world of possibilities as cubane derivatives have a plethora of applications in drug development, materials science, and molecular engineering.

Cubane molecules consist of eight carbon atoms arranged at the corners of a perfect cube. Yet despite the simplicity of the shape, modern chemistry has, until now, had a very tough time handling its unique reactivity.

Although it is absent in nature, cubane mimics the effect of the very abundant benzene-motif, by improving the effects of drugs and/or reducing their side effects. Despite this ability, which makes it of potential use in medicinal drug development, or as a rigid, isolating linker that can join and organise different molecules in materials science, the range of applications was greatly limited as more complex systems were out of bounds.

However, this lack of a synthetic handle has now been tackled by a team from Trinity College Dublin's School of Chemistry. Their discovery has recently been published in the international journal Chemistry -- A European Journal, in which it features as a VIP paper and on the journal front cover.

A team of six researchers under the supervision of Professor of Organic Chemistry at Trinity, Mathias O. Senge, discovered how to circumvent the inherent reactivity of the cubane core. Senior Research Fellow, Dr Bernhard, and the other team members essentially filled the empty cubane toolbox, which allowed them to establish new connections and craft important residues onto the cubane scaffold. As a result, they have opened new vistas in drug development and material sciences.

Professor Senge said: "I often challenge my students to think outside the box so I was really surprised when they pitched me the idea of literally making a box! However, it is the apparent simplicity of the cubane core that really underlies the impact of the present accomplishment."

"We have a structurally unique building block which has been neglected by the majority of synthetic chemists up to now precisely because of how difficult this cube is to work with. However, with great risk comes great reward. I am delighted with our present success and intrigued about the avenues it will open in fields ranging from new drug discovery to 21st century computer chip generation!"

"Science has known for a long time that cubanes held great potential for medicinal drug development, and for shifting the barriers of materials science, and that much of that potential was still to be unlocked. To perform that lock-picking, we just needed the right tools, and having found them, we are really excited for what the future holds."

"The results from this long-term, fundamental research project will have significant benefits in the years to come as we can now prepare a greater variety of tailored compounds. We are very grateful to have received continuous long-term funding from Science Foundation Ireland to support this work, without which we would not have made this important discovery."

Story Source:

Materials provided by Trinity College Dublin. Note: Content may be edited for style and length.

Journal Reference:

  1. Stefan S. R. Bernhard, Gemma M. Locke, Shane Plunkett, Alina Meindl, Keith J. Flanagan, Mathias O. Senge. Cubane Cross-Coupling and Cubane-Porphyrin Arrays. Chemistry - A European Journal, 2018; 24 (5): 1026 DOI: 10.1002/chem.201704344

Cite This Page:

Trinity College Dublin. "Solution to long-standing chemistry riddle has implications for drug development." ScienceDaily. ScienceDaily, 1 February 2018. <>.
Trinity College Dublin. (2018, February 1). Solution to long-standing chemistry riddle has implications for drug development. ScienceDaily. Retrieved April 22, 2024 from
Trinity College Dublin. "Solution to long-standing chemistry riddle has implications for drug development." ScienceDaily. (accessed April 22, 2024).

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