Naslov
Formation of quinone methides via photochemical deamination

Autori
Basarić, Nikola

Izvornik
Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budimpešta

Vrsta, podvrsta
Ostale vrste radova, ostalo

Godina
2016

Ključne riječi
quinone methides ; photodehydration ; photodeamination ; curcubit[n]uril inclusion complexes

Sažetak
Quinone methides (QM) are reactive intermediates in photochemistry of phenols.1 Interest in their chemistry was primarily initiated due to their biological activity. It has been demonstrated that QMs react with proteins, 2 and DNA.3 Moreover, some classes of antitumor antibiotics exert their action on metabolic formation of QMs. Consequently, simple QMs which can be photo-generated from suitably substituted phenols are potentially viable anticancer agents.4 We have been interested in the photochemistry of phenols, naphthols and anthrols that undergo photodehydration and deliver different classes of QMs that have been characterized by laser flash photolysis (LFP).5 Moreover, we conducted antiproliferative testing of photogenerated QMs on human cancer cell lines, and found lead compounds for potential drug development. Recently, we have turned our attention to photodeamination.6 An investigation of photochemical reactivity in a series of cresol derivatives 1-4 was carried out by preparative irradiations, fluorescence and LFP. The results unraveled possible pathways in the excited state leading to the overall deamination and formation of QMs. However, preliminary antiproliferative investigation of 1 and 3 showed that compounds exhibit no enhancement of the antiproliferative effect on irradiation of cancer cells. The objective of the on-going research is to show that 1 and 3 form inclusion complexes with cucurbit[n]urils (CB[n]s) which might facilitate their transport through cell membranes. Therefore, photochemical formation of QMs in a CB[n] complex and subsequent dissociation can have potential to be developed into a new drug delivery method.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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