New synthetic method could open doors to novel drugs and dyes

Method enables synthesis of many different natural products and their variations, which are useful in drug discovery

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Researchers from Rice University (TX, USA) have developed a method to synthesize the chemical components used in drug discovery research, and in the manufacture of drugs and dyes. The target of this new method is uncialamycin, a compound found in nature and synthesized by lead researcher of the study KC Nicolaou, and is based on modifying the compound’s central three-ring structure.

The new method from the Nicolaou laboratory was designed to facilitate discovery and development of cancer-fighting drugs, and as an efficient means of producing novel molecular structures for use in biology and medicine.

The primary product of the method is anthraquinone, a structure found in many red dyes and some drugs. It has a three-ringed structure of carbon, hydrogen and oxygen atoms. The researchers discovered a practical method to synthesize amino- and methoxyphenolic anthraquinones, more complex structures necessary for the development of novel compounds.

The Nicolaou laboratory specializes in researching the synthesis of naturally occurring, scarce substances too difficult or rare to extract from their source. The researchers are using the new technique to synthesize natural and designed biologically active molecules.

“This is a practical, very general method that allows us a way to make all kinds of natural products and their variations, which is important in drug discovery,” Nicolaou explained. “Uncialamycin and its analogs are examples of the many applications we envision for this method.”

If uncialamycin can be successfully attached to antibodies that target tumor cells, it could potentially invade cancerous cells and destroy their DNA, elaborated Nicolaou. “This is one of the most important anti-cancer agents found in nature in recent times. The antibodies can deliver this toxin specifically to cancer cells, and they become Trojan horses,” he continued. “They’re sucked inside and kill the cell. So there’s a lot of interest in these compounds.”

“If we can’t find a method in the chemical repertoire to solve a problem, we’re forced to create a new one,” Nicolaou concluded. “Every molecule provides a different challenge to a synthetic chemist. We see these challenges as opportunities to develop methods that everybody can use.”

Stella Bennett


Rice method opens pathway to new drugs and dyes; Nicolaou K. C, Lu M, Chen P, Shah AA.. Practical Synthesis of p- and o-Amino- and Methoxyphenolic Anthraquinones. Angew Chem Int Ed Engl. doi:10.1002/anie.201507007 (2015) (Epub ahead of print).

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Stella Bennett

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