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Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity

Sambol, Matija; Benčić, Patricia; Erben, Antonija; Matković, Marija; Mihaljević, Branka; Piantanida, Ivo; Kralj, Marijeta; Basarić, Nikola (2021) Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity. Molecules, 26 (11). ISSN 1420-3049

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Abstract

Quinone methide precursors 1a–e, with different alkyl linkers between the naphthol and the naphthalimide chromophore, were synthesized. Their photophysical properties and photochemical reactivity were investigated and connected with biological activity. Upon excitation of the naphthol, Förster resonance energy transfer (FRET) to the naphthalimide takes place and the quantum yields of fluorescence are low (ΦF ≈ 10−2). Due to FRET, photodehydration of naphthols to QMs takes place inefficiently (ΦR ≈ 10−5). However, the formation of QMs can also be initiated upon excitation of naphthalimide, the lower energy chromophore, in a process that involves photoinduced electron transfer (PET) from the naphthol to the naphthalimide. Fluorescence titrations revealed that 1a and 1e form complexes with ct-DNA with moderate association constants Ka ≈ 105–106 M−1, as well as with bovine serum albumin (BSA) Ka ≈ 105 M−1 (1:1 complex). The irradiation of the complex 1e@BSA resulted in the alkylation of the protein, probably via QM. The antiproliferative activity of 1a–e against two human cancer cell lines (H460 and MCF 7) was investigated with the cells kept in the dark or irradiated at 350 nm, whereupon cytotoxicity increased, particularly for 1e (>100 times). Although the enhancement of this activity upon UV irradiation has no imminent therapeutic application, the results presented have importance in the rational design of new generations of anticancer phototherapeutics that absorb visible light.

Item Type: Article
Uncontrolled Keywords: Naphthols ; Naphthalimides ; FRET ; PET ; Quinone Methides ; Antiproliferative Activity
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Materials Chemistry
Division of Molecular Medicine
Division of Organic Chemistry and Biochemistry
Projects:
Project titleProject leaderProject codeProject type
Supramolekulska kontrola fotokemijskih reakcija eliminacijeBasarić, NikolaIP-2014-09-6312HRZZ
Fotokemija: Reakcijski mehanizmi i primjene u organskoj sintezi i biologijiBasarić, NikolaIP-2019-04-8008HRZZ
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteinaPiantanida, IvoIP-2018-01-5475HRZZ
Depositing User: Branka Mihaljević
Date Deposited: 05 Jul 2021 14:00
Last Modified: 05 Jul 2021 14:01
URI: http://fulir.irb.hr/id/eprint/6479
DOI: 10.3390/molecules26113355

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