Light-induced interaction of anthraquinone derivative with Guanosine monophosphate: molecular mechanism and implication in cytotoxicity

Light-induced interaction of anthraquinone derivative with Guanosine monophosphate: molecular mechanism and implication in cytotoxicity Full article

Journal

Photochemical and Photobiological Sciences
ISSN: 1474-905X

Output data

Year: 2025, Volume: 24, Number: 12, Pages: 2083–2094 Pages count : 12 DOI: 10.1007/s43630-025-00813-9

Tags

Anthraquinone derivatives, Guanosine monophosphate, Electron transfer, Anti-proliferative activity, NMR, CIDNP, Molecular dynamics

Authors

Ulyanova Maya ¹ , Arkhipova Alina ¹ , Babenko Simon ^1,2 , Kartina Olga ^1,3 , Selyutina Olga ¹ , Polyakov Nikolay ¹

Affiliations

1	Institute of Chemical Kinetics and Combustion, Institutskaya St., 3, 630090, Novosibirsk, Russia.
2	International Tomography Center, Novosibirsk, Russia.
3	Institute of Chemical Biology and Fundamental Medicine SB RAS, Lavrentyev av. 8, 630090, Novosibirsk, Russia.

Photoinduced reactions between photosensitizers and nucleic acids represent a fundamental mechanism in photodynamic therapy (PDT), primarily involving light-mediated oxidative damage to DNA. This study elucidates the interaction of a novel anthraquinone derivative, 2-phenyl-4-(butylamino)naphtho[2,3-h]quinoline-7,12-dione (Q1), with nucleotides using a combination of NMR spectroscopy, chemically induced dynamic nuclear polarization (CIDNP), and molecular dynamics simulations. We demonstrate that Q1 forms complexes with guanosine (GMP), adenosine (AMP), and cytidine (CMP) monophosphates in the dark, with the highest stability constant observed for the Q1/GMP complex. Upon photoexcitation, electron transfer occurs exclusively from GMP to Q1, generating a semiquinone radical anion and a neutral guanyl radical. The CIDNP data allowed for an estimation of the triplet state energy of Q1, ET(Q1) = 2.1 ± 0.1 eV. Also, irradiation at 520 nm enhances the cytotoxicity of Q1 against MDA-MB-231 (human breast adenocarcinoma) and A549 (lung carcinoma) cell lines. We conclude that the specific photoinduced radical reaction between Q1 and guanine bases is a component of its cytotoxic mechanism, establishing Q1 as a promising candidate for further development in PDT applications.

Ulyanova M. , Arkhipova A. , Babenko S. , Kartina O. , Selyutina O. , Polyakov N.
Light-induced interaction of anthraquinone derivative with Guanosine monophosphate: molecular mechanism and implication in cytotoxicity
Photochemical and Photobiological Sciences. 2025. V.24. N12. P.2083–2094. DOI: 10.1007/s43630-025-00813-9 WOS Scopus OpenAlex

Published online:	Nov 17, 2025
Published print:	Dec 1, 2025

Web of science:	WOS:001615657800001
Scopus:	2-s2.0-105022294973
OpenAlex:	W7105846709

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