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Antiproliferative activity of quinone methides with bodipy chromophore


Cindrić, Matej; Mlinarić-Majerski, Kata; Basarić, Nikola; Martin Kleiner, Irena; Uzelac, Lidija; Kralj, Marijeta
Antiproliferative activity of quinone methides with bodipy chromophore // 10th Joint Meeting of Medicinal Chemistry / Dubrovnik, Hrvatska
Dubrovnik, Hrvatska, 2017. str. 97-97 (poster, međunarodna recenzija, sažetak, znanstveni)


Naslov
Antiproliferative activity of quinone methides with bodipy chromophore

Autori
Cindrić, Matej ; Mlinarić-Majerski, Kata ; Basarić, Nikola ; Martin Kleiner, Irena ; Uzelac, Lidija ; Kralj, Marijeta

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

Izvornik
10th Joint Meeting of Medicinal Chemistry / Dubrovnik, Hrvatska / - , 2017, 97-97

ISBN
978-953-55232-8-4

Skup
10th Joint Meeting of Medicinal Chemistry / Dubrovnik, Hrvatska

Mjesto i datum
Dubrovnik, Hrvatska, 25-28.06. 2017

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
BODIPY, quinone methide, photodeamination, antiproliferative activity

Sažetak
BODIPY is a trade name for the well known fluorescent dyes comprising different 4, 4-Difluoro-4-bora-3a, 4a-diaza-s-indacene derivatives.[1] These chromophores absorb in the visible region of spectrum and have excellent photophysical and spectral properties characterized by sharp fluorescence peaks with high fluorescence quantum yields.[2] Small modifications of molecular structure lead to fine-tuning of their spectroscopic and photophysical properties.[3] Therefore, a large number of different BODIPY derivatives has been synthesized and their spectroscopic properties have been investigated. We have become interested in the photochemistry of appropriately substituted phenols that undergo photodehydration and deliver quinone methides (QMs) [4]. The interest in the chemistry of QMs has been initiated due to their biological properties. It has been demonstrated that QMs react with amino acids, proteins, nucleotides and DNA. Moreover, ability of QMs to cross-link DNA has been associated to biological action of some anticancer antibiotics such as mitomycin C. Consequently, QMs represent potential new class of anticancer drugs. However, QMs are reactive intermediates that cannot be stored, they have to be generated in situ. The best method for the generation of QMs is photodehydration of phenol derivatives. To have molecules applicable as drugs in human medicine it is of pivotal importance to make QM precursors on the chromophoric system absorbing in the visible part of the spectrum (at > 600 nm) to assure penetration of light through tissue. Herein we present synthesis of QM precursors that bear BODIPY chromophore, investigation of their photochemical reactivity and aptitude to deliver QMs, as well as antiproliferative activity of photogenerated QMs. To test the effect of irradiation, the antiproliferative activity is tested on human cancer cell lines that are treated with compounds and kept in dark or irradiated with visible light.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
HRZZ-IP-2013-5660
HRZZ-IP-2014-09-6312 - Supramolekulska kontrola fotokemijskih reakcija eliminacije (Nikola Basarić, )

Ustanove
Institut "Ruđer Bošković", Zagreb