Scientists synthesize new molecules with anticancer and antioxidant activity

March 15, 2016
Selenohydantoins
General formula of selenohydantoins. Credit: Y. Ivanenkov et.al. Bioorganic & Medical Chemistry (2016)

A group of scientists from Moscow universities led by Yan Ivanenkov, the head of Laboratory of Medical Chemistry and Bioinformatics in MIPT, has succeeded in synthesizing a set of novel selenohydantoins with anticancer and antioxidant activity. The corresponding paper has been published in the scientific journal Bioorganic & Medicinal Chemistry.

It was found that synthesized could potentially be used as agents with good selectivity index. Hydantoin moiety and its derivatives can be found in many drug molecules, including nilutamide, which is used in chemotherapy for prostate cancer, and dantrolene, which helps to relax skeletal muscles and prevent cramps.

Selenohydantoins are derivatives of hydantoins in which one of the oxygen atoms is replaced by selenium. It was found that drug molecules containing selenium possess anticancer activity and can be used as effective antioxidants. Selenium can be found in a number of known , such as Ebselen, an antioxidant with a broad spectrum of therapeutic activity.

In the study, the scientists have synthesized novel selenium-containing hydantoin derivatives. The structures of the molecules obtained were confirmed by NMR (Nuclear Magnetic Resonance) spectroscopy, high resolution mass spectrometry, and X-ray analysis. It was found that in the presence of Cu2+ copper cations, a spatial transformation is observed and a stable isomer is formed.

Diagram of cis-trans isomerism
In the cis-configuration, the radicals (green) are on one side of the plane of the molecule, in the trans-configuration they are on opposite sides. Credit: orgchem.ru

Isomers are molecules with the same atomic composition, but different spatial structure. The interest lies in the fact that the isomers differ in terms of their properties and activity. The scientists used quantum-chemical calculations to explain the mechanism of the transformation they had discovered.

The results of electromechanical studies showed that the synthesized molecules possess , which means they are able to slow down the process of oxidation. They are also able to bind to receptors that protect the body from oxidation.

"We have examined the effect of selenium on the activity of the synthesized molecules. The next step is to investigate the pharmacological potential of the most active molecules in vivo and in vitro," said Yan Ivanenkov, the head of the Laboratory of Medical Chemistry and Bioinformatics, when commenting on the prospects of the research.

The results of the study highlighted the important role of in the structure of hydantoin derivatives. Structural modification such as this has a significant influence on the spectrum of biological activity and properties of the molecules.

Explore further: Scientists develope unique in silico model to predict agrochemical activity of small-molecule organic compounds

More information: Yan A. Ivanenkov et al. Synthesis, isomerization and biological activity of novel 2-selenohydantoin derivatives, Bioorganic & Medicinal Chemistry (2016). DOI: 10.1016/j.bmc.2015.12.050

Related Stories

The antioxidant role of proteins containing selenium

April 28, 2014

The prestigious journal Proceedings of the National Academy of Sciences of the United States of America this week published an article by a research team led by University of Delaware biochemist Sharon Rozovsky, examining ...

Rice scientists synthesize anti-cancer agent

March 10, 2016

A team led by Rice University synthetic organic chemist K.C. Nicolaou has developed a new process for the synthesis of a series of potent anti-cancer agents originally found in bacteria.

Recommended for you

Scientific advances can make it easier to recycle plastics

November 17, 2017

Most of the 150 million tons of plastics produced around the world every year end up in landfills, the oceans and elsewhere. Less than 9 percent of plastics are recycled in the United States, rising to about 30 percent in ...

The spliceosome—now available in high definition

November 17, 2017

UCLA researchers have solved the high-resolution structure of a massive cellular machine, the spliceosome, filling the last major gap in our understanding of the RNA splicing process that was previously unclear.

Ionic 'solar cell' could provide on-demand water desalination

November 15, 2017

Modern solar cells, which use energy from light to generate electrons and holes that are then transported out of semiconducting materials and into external circuits for human use, have existed in one form or another for over ...

0 comments

Please sign in to add a comment. Registration is free, and takes less than a minute. Read more

Click here to reset your password.
Sign in to get notified via email when new comments are made.