Scientists synthesize new compound with anticarcinogenic properties

Jul 5 2018

The patent has been registered from the University of Seville and licensed by the British company Evgen Pharma, which is currently developing programs aimed at breast cancer, subarachnoid hemorrhage and multiple sclerosis, among others

The Stereochemistry and Asymmetric Synthesis Group at the Faculty of Pharmacy at the University of Seville, in collaboration with the Asymmetric Synthesis and Functional Nanosystems Group at the Chemical Research Institute of cicCartuja, have managed to synthesize active, stable derivatives with high bioavailability of a compound with anticarcinogenic properties, also used in the treatment of other diseases.

This compound is an analogue of sulforaphane (SFN), a compound which was isolated for the first time in 1992 from broccoli extracts and which is considered by the National Cancer Institute in the United States as one of the forty most promising anti-cancer agents. SFN is currently the best naturally-occurring phase II detoxification enzyme inductor, inhibits phase I metabolism, and, also, is capable of regulating gene expression via epigenetics using multiple mechanisms. All this makes it one of the epigenetic agents that offers the greatest protection in the treatment of many diseases.

So far, there have been no adverse effects detected after its application in the studies that have been carried out, which means that SFN and its analogues could be used in the prevention and treatment of countless diseases, as well as different types of cancer. This is a list which includes cardiovascular diseases, diabetes, skin aging, COPD, bacterial infections, atopic diseases, etc. It has been demonstrated that sulforaphane is capable of crossing the blood-brain barrier and exercising its protective effect on the central nervous system, which has seen the beginning of its use in the treatment of Parkinson's disease and Alzheimer's. In addition, SFN has recently shown great promise as a future treatment of autism and Hutchinson-Gilford progeria syndrome.

Despite the great potential of SFN for preventative or curative therapy for many diseases, for the moment, there is no medicine on the market that features it as an active ingredient. Currently, the entire market connected to SFN is related to broccoli extracts, anti-aging creams, food supplements, and other products sold by herbalists. However, all these supplements contain an inactive precursor of SFN, which puts into question their ability to add SFN to the diet.

The main reason that no medicine used for any specific disease is available on the market today is the instability of the SFN molecule, as this isothiocyanate is susceptible to being degraded by the action of oxygen, heat and alkaline conditions.

Therefore, today we can only enjoy the benefits of the properties of SFN via continued and abundant consumption of vegetables that are rich in this phytochemical, although during the normal cooking methods for broccoli and crucifers, the bioavailability of SFN is reduced considerably. Heating to 90°C for only 20 minutes sees the degradation of more than 90% of the SFN content. In addition, these vegetable need to be stored in specific conditions to maintain their chemopreventive properties.

The patent
The patent "Compounds derived from sulforaphane, extraction method and its medical, dietary and cosmetic uses" was presented in March 2012 by the University of Seville teachers, Inmaculada Fernández and Rocío Recio and the researcher Noureddine Khiar, of the Higher Council of Scientific Research (CSIC). It has been licensed by the British company Evgen Pharma (http://evgen.com/technology/), which is currently directing programs aimed at breast cancer (phase II studies), subarachnoid hemorrhage (phase II studies) and Multiple Sclerosis (pre-clinical studies), among others.

Thanks to the financing of this pharmaceutical company, it has been possible to extend the patent via the Patent Cooperation Treaty (PCT) and start to acquire international patent protection. Already approved in Australia, and recently in the United States and Europe, decisions are now awaited from the health authorities in China and Japan.

In this patent, the three researchers have developed new stable analogues of sulforaphane, with the aim of improving its biological activity and its bioavailability and, by means of a contract with Evgen Pharma, the last year as seen a medicinal chemical program aimed at finding the best analogue.