Pregled bibliografske jedinice broj: 1170470
Anti-Kasha Photochemical Deamination from BODIPY Compounds
Anti-Kasha Photochemical Deamination from BODIPY Compounds // Pacifichem 2021: A Creative Vision for the Future
Honolulu (HI), Sjedinjene Američke Države, 2021. (predavanje, međunarodna recenzija, neobjavljeni rad, znanstveni)
CROSBI ID: 1170470 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Anti-Kasha Photochemical Deamination from BODIPY Compounds
Autori
Basarić, Nikola ; Zlatić, Katarina ; Antol, Ivana ; Uzelac, Lidija ; Kralj, Marijeta
Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, neobjavljeni rad, znanstveni
Skup
Pacifichem 2021: A Creative Vision for the Future
Mjesto i datum
Honolulu (HI), Sjedinjene Američke Države, 16.12.2021. - 21.12.2021
Vrsta sudjelovanja
Predavanje
Vrsta recenzije
Međunarodna recenzija
Ključne riječi
BODIPY ; Anti-Kasha Photochemistry ; Quinone methides
Sažetak
Photochemical reactions usually take place from the lowest excited state due to competing fast nonradiative processes. However, photoreactions from higher excited states, known as anti-Kasha photochemistry, are also possible [1]. For example, we have recently unraveled the mechanism of photoelimination of nitrogen from diazo compounds, which takes place efficiently only if initiated from higher excited singlet states [2]. Furthermore, we have demonstrated the anti-Kasha photochemical reactivity in photodeamination of BODIPY-quinone methide (QM) precursors [3]. BODIPY compounds are versatile chromophores that have been in intensive use over several decades owing to their exceptional photophysical properties. We have connected BODIPY compounds to QMs with the aim of finding novel anticancer photo-therapeutics. QMs are reactive intermediates known for their reactivity with polynucleotides and proteins. Some anticancer drugs such as mitomycin base their antiproliferative activity on metabolic formation of QMs, which alkylate DNA. Here we report anti-Kasha photochemical reactivity of BODIPY-QM precursors, such as derivatives 1 and 2 [4]. Upon excitation by visible light they deactivate radiatively from the singlet excited state, or they undergo excited state proton transfer, but the deamination to QMs does not occur due to an energy barrier. However, upon excitation by light of higher energy (λ<350 nm), deamination to QMs takes place. The photodeamination reaction mechanism has been investigated by preparative irradiations, fluorescence spectroscopy, laser flash photolysis and computations. Furthermore, we demonstrate the applicability of compounds as potential anticancer photo-therapeutics and in fluorescent labeling of proteins.
Izvorni jezik
Engleski
Znanstvena područja
Kemija, Biotehnologija u biomedicini (prirodno područje, biomedicina i zdravstvo, biotehničko područje)
POVEZANOST RADA
Projekti:
--IP-2019-04-8008 - Fotokemija: Reakcijski mehanizmi i primjene u organskoj sintezi i biologiji (PhotoApp) (Basarić, Nikola) ( CroRIS)
Ustanove:
Institut "Ruđer Bošković", Zagreb
Profili:
Lidija Uzelac
(autor)
Marijeta Kralj
(autor)
Ivana Antol
(autor)
Katarina Zlatić
(autor)
Nikola Basarić
(autor)