Tokyo University of Science


2020.11.17 Tuesday

Killing Cancer Naturally: New Process to Produce Compounds with Anti-Cancer Properties

Scientists have uncovered a method of combining natural organic compounds which can create anticancer drugs with minimal side effects.

Scientists from the Tokyo University of Science have made a breakthrough in the development of potential drugs that can kill cancer cells. They have discovered a method of synthesizing organic compounds that are four times more fatal to cancer cells and leave non-cancerous cells unharmed. Published in the American Chemical Society Omega, their research can assist in the creation of new anticancer drugs with minimal side effects.

Water Predictions: Telling when a Nanolithography Mold will Break Through Droplets

In the past decades, cancer has surpassed many other diseases to become the current second leading cause of death globally, with one in six people dying from it. This concerning position has given it a unique and ubiquitous position in global culture, so much so that finding a cure for cancer is considered one of the most noble things any person can do. Sadly, humanity hasn't arrived at this cure yet; tons of research is being conducted to explore every angle of cancer, trying to find a weakness.

A group of scientists from the Tokyo University of Science, led by Prof Kouji Kuramochi, has also been dedicated to this mission. In their search for a weapon against cancer, they turned to a specific set of organic compounds called "phenazines." Phenazines are a large group of nitrogen-containing "heterocycles" (or compounds with a ring structure composed of at least two different elements). More than a hundred phenazine compounds are found naturally, and over 6000 can be "synthesized." Of these, N-alkylphenazin-1-ones (phenazinones) are a minor group of phenazines that are known to have antibacterial, antifungal, and cytotoxic activities. Cytotoxicity is an exciting property in cancer research, because, if we can "direct" cytotoxic compounds to work against cancer cells, we can eliminate the cancer.

"Pyocyanin, lavanducyanin, lavanducyanin-derived WS-9659 A, WS-9659 B, and marinocyanins A and B, all different types of phenazines, show cytotoxic activities, against cancer cells. However, these compounds are difficult to derive from their natural sources such as bacteria," reports Prof Kuramochi.

Determined to shed more light on them and harness their properties for good, the scientists experimented with synthesizing these compounds through several methods. They performed "halogenation" (the process of adding halogens like chlorine and bromine) and "oxidative condensation" (or addition of an oxidant and a water molecule) on various compounds.

Their strategy succeeded in the highly efficient and selective synthesis of N-alkyl-2-halophenazin-1-ones. Of all the synthesized compounds, they found that 2-chloropyocyanin exhibited high cytotoxicity toward the lung cancer cells. Their findings published in American Chemical Society Omega, explain the logistics of their study in full technical detail.

Prof Kuramochi believes that their discovery also has a beneficial effect on the living world. "We have established a highly versatile synthetic method that is simple and can be applied to the synthesis of many natural products," he says. "Since the oxidative coupling reaction proceeds only with oxygen, it is an environmentally friendly synthetic method."

What's more, this novel technique overcomes one of the main drawbacks of the existing techniques. The traditional chlorination of N-alkylphenazin-1-ones with selectively occurs at the 4-position, meaning that the compounds that form out of that reaction are the undesired N-alkyl-4-chlorophenazin-1-ones. This novel synthesis technique overcomes this issue, and allows, for the first time, the synthetic production of WS-9659 B!

Prof Kuramochi and his team look forward to verifying the effects of phenazinones in animal studies and clinical trials. In the development of anticancer drugs, drugs that have little effect on normal cells and act selectively on cancer cells are ideal drug candidates with few side effects.

These new compounds are more than four times more selectively toxic to cancer cells than normal cells. Only time will truly tell if this is the new door opening to the elusive cure for cancer, but this is a sure and definite step in the right direction.

Title of original paper  : Synthesis and Cytotoxic Evaluation of N-Alkyl-2-halophenazin-1-ones
Journal  : ACS Omega
DOI  : 10.1021/acsomega.0c04253
About The Tokyo University of Science

Tokyo University of Science (TUS) is a well-known and respected university, and the largest science-specialized private research university in Japan, with four campuses in central Tokyo and its suburbs and in Hokkaido. Established in 1881, the university has continually contributed to Japan's development in science through inculcating the love for science in researchers, technicians, and educators.

With a mission of "Creating science and technology for the harmonious development of nature, human beings, and society", TUS has undertaken a wide range of research from basic to applied science. TUS has embraced a multidisciplinary approach to research and undertaken intensive study in some of today's most vital fields. TUS is a meritocracy where the best in science is recognized and nurtured. It is the only private university in Japan that has produced a Nobel Prize winner and the only private university in Asia to produce Nobel Prize winners within the natural sciences field.

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About Professor Kouji Kuramochi from Tokyo University of Science

Professor Kouji Kuramochi works at the Faculty of Science and Technology, Tokyo University of Science (TUS). He received his PhD from the University of Tokyo and was a postdoctoral fellow at TUS and Yale University. His research interests are focused on bioorganic chemistry and he has published nearly 40 papers in esteemed journals like the Journal of Synthetic Organic Chemistry and the American Chemical Society.


Professor Tokyo University of Science, Faculty of Science and Technology, Department of Applied Biological Science

Funding information

This study was partly funded by JSPS KAKENHI.


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