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

doi:10.3390/molecules26113355

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Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity

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Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

Fidelta Ltd., Prilaz Baruna Filipovića 29, 10000 Zagreb, Croatia

Division of Molecular Medicine, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

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Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstr. 25, 79104 Freiburg, Germany

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Division of Material Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

Author to whom correspondence should be addressed.

Academic Editors: Raul Perez and M. Consuelo Jiménez

Molecules 2021, 26(11), 3355; https://doi.org/10.3390/molecules26113355

Received: 5 May 2021 / Revised: 21 May 2021 / Accepted: 28 May 2021 / Published: 2 June 2021

(This article belongs to the Special Issue Photochemical Reactions in Organic Synthesis)

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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 (Φ_F ≈ 10⁻²). Due to FRET, photodehydration of naphthols to QMs takes place inefficiently (Φ_R ≈ 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 K_a ≈ 10⁵–10⁶ M⁻¹, as well as with bovine serum albumin (BSA) K_a ≈ 10⁵ M⁻¹ (1:1 complex). The irradiation of the complex [email protected] 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. View Full-Text

Keywords: naphthols; naphthalimides; FRET; PET; quinone methides; antiproliferative activity

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MDPI and ACS Style

Sambol, M.; Benčić, P.; Erben, A.; Matković, M.; Mihaljević, B.; Piantanida, I.; Kralj, M.; Basarić, N. Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity. Molecules 2021, 26, 3355. https://doi.org/10.3390/molecules26113355

AMA Style

Sambol M, Benčić P, Erben A, Matković M, Mihaljević B, Piantanida I, Kralj M, Basarić N. Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity. Molecules. 2021; 26(11):3355. https://doi.org/10.3390/molecules26113355

Chicago/Turabian Style

Sambol, Matija, Patricia Benčić, Antonija Erben, Marija Matković, Branka Mihaljević, Ivo Piantanida, Marijeta Kralj, and Nikola Basarić. 2021. "Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity" Molecules 26, no. 11: 3355. https://doi.org/10.3390/molecules26113355

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Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity

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