Naslov
Synthesis of quinone methide precursors containing BODIPY fluorophore and characterization as potential anticancer drugs

Autori
Zlatić, Katarina ; Basarić, Nikola

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
E-WISPOC 19 - European Winter School on Physical Organic Reactivity / - , 2019, 23-23

Skup
E-WISPOC 19 / European Winter School on Physical Organic Reactivity

Mjesto i datum
Bressanone, Italija, 27.01.2019. - 01.02.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
BODIPY ; quinone methide ; photodeamination ; antiproliferative activity

Sažetak
Quinone methides (QMs) are reactive intermediates that have been shown as useful synthons in organic synthesis, 1 as well as biologically active agents applicable in biochemistry and medicine.1, 2 In the groups of S. Rokita3 and M. Freccero3 it has been demonstrated that QMs react with nucleotides and induce DNA alkylation and cross-linking, leading to cytotoxicity.5 The generation of QMs under mild conditions can be facilitated by photochemical dehydration6 and deamination, 7, 8 which are particularly interesting in biological systems.9 Consequently, photochemical generation of QMs may be developed into a new cancer phototreatment. To have molecules applicable in medicine, it is important to design new QM precursor molecules that have chromophores absorbing light at λ > 600 nm to assure penetration through tissues. Therefore, we incorporated BODIPY10 chromophore into the QM precursor units.11 For example BODIPY derivative 1 undergoes photodeamination and delivers QM that reacts with nucleophiles in a Michael addition. We have synthesized several BODIPY-QM precursors and investigated their photochemical reactivity and photophysical properties. Non-covalent interactions of BODIPY-QM precursors with DNA and proteins by several spectroscopic methods are investigated, as well as ability of photochemically formed QMs to covalently alkylate biomacromolecules.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA