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Article

Stacking Effects on Anthraquinone/DNA Charge-Transfer Electronically Excited States

1
Chemistry Department, Universidad Autónoma de Madrid, Calle Francisco Tomás y Valiente, 7, 28049 Madrid, Spain
2
IADCHEM, Institute for Advanced Research in Chemistry, Universidad Autónoma de Madrid, Calle Francisco Tomás y Valiente, 7, 28049 Madrid, Spain
*
Author to whom correspondence should be addressed.
Academic Editors: Daniel Roca-Sanjuán, Virginie L. Lhiaubet-Vallet and Iñaki Tuñón
Molecules 2020, 25(24), 5927; https://doi.org/10.3390/molecules25245927
Received: 29 October 2020 / Revised: 3 December 2020 / Accepted: 13 December 2020 / Published: 15 December 2020
(This article belongs to the Special Issue DNA Damage and Repair)
The design of more efficient photosensitizers is a matter of great importance in the field of cancer treatment by means of photodynamic therapy. One of the main processes involved in the activation of apoptosis in cancer cells is the oxidative stress on DNA once a photosensitizer is excited by light. As a consequence, it is very relevant to investigate in detail the binding modes of the chromophore with DNA, and the nature of the electronically excited states that participate in the induction of DNA damage, for example, charge-transfer states. In this work, we investigate the electronic structure of the anthraquinone photosensitizer intercalated into a double-stranded poly(dG-dC) decamer model of DNA. First, the different geometric configurations are analyzed by means of classical molecular dynamics simulations. Then, the excited states for the most relevant poses of anthraquinone inside the binding pocket are computed by an electrostatic-embedding quantum mechanics/molecular mechanics approach, where anthraquinone and one of the nearby guanine residues are described quantum mechanically to take into account intermolecular charge-transfer states. The excited states are characterized as monomer, exciton, excimer, and charge-transfer states based on the analysis of the transition density matrix, and each of these contributions to the total density of states and absorption spectrum is discussed in terms of the stacking interactions. These results are relevant as they represent the footing for future studies on the reactivity of anthraquinone derivatives with DNA and give insights on possible geometrical configurations that potentially favor the oxidative stress of DNA. View Full-Text
Keywords: photodynamic therapy; charge transfer; electronically excited states; anthraquinone; DNA; molecular dynamics; TD-DFT; transition-density analysis photodynamic therapy; charge transfer; electronically excited states; anthraquinone; DNA; molecular dynamics; TD-DFT; transition-density analysis
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MDPI and ACS Style

Cárdenas, G.; Nogueira, J.J. Stacking Effects on Anthraquinone/DNA Charge-Transfer Electronically Excited States. Molecules 2020, 25, 5927. https://doi.org/10.3390/molecules25245927

AMA Style

Cárdenas G, Nogueira JJ. Stacking Effects on Anthraquinone/DNA Charge-Transfer Electronically Excited States. Molecules. 2020; 25(24):5927. https://doi.org/10.3390/molecules25245927

Chicago/Turabian Style

Cárdenas, Gustavo, and Juan J. Nogueira 2020. "Stacking Effects on Anthraquinone/DNA Charge-Transfer Electronically Excited States" Molecules 25, no. 24: 5927. https://doi.org/10.3390/molecules25245927

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