Mono-substituted corroles containing morpholinyl, piperidyl and pyrrolidinyl units: Photophysics, photobiology and biomolecular interaction studies

IF 5.3 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2025-07-16 DOI:10.1016/j.molliq.2025.128168

Morgana M. Oliveira , Carlos C. Diniz , Luiz Antônio S. Costa , Nicolle A.P. dos Santos , Sofia Nikolaou , Magali P. Moreira , Tiago E. de Oliveira , Bernardo A. Iglesias

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Abstract

A classical approach is reported to design meso-mono-substituted corroles with bioactive heterocycle units. The studied corroles were obtained by the classical Gryko methodology, with yields ranging from 18 to 33 %. Corroles were fully characterized by elemental analysis, high-resolution mass analysis, nuclear magnetic resonance and electrochemical analysis. Spectroscopic assays by ultraviolet-visible absorption, steady-state fluorescence and time-resolved fluorescence emission, with density functional theory (DFT) calculations are conducted. In this sense, the obtained corroles presented absorption spectra typical of tetrapyrrolic macrocycles and emission peaks centered in the red region, with low fluorescence quantum yields and short lifetimes (between 3.0 and 4.05 ns).

Photobiological parameters such as photostability and reactive oxygen species (ROS) generation were also assessed, showing good photostability of the derivatives and generation of singlet oxygen (¹O₂) and superoxide radicals (O₂^•–) species. Finally, spectroscopic, viscometer studies and molecular docking calculations revealed the ability of each corrole derivative to interact with salmon-sperm DNA (SS-DNA) and human serum albumin (HSA) biomacromolecules, suggesting better interactions in the minor grooves of DNA and interaction in site III of albumin.

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含有morpholinyl， pepperidyl和pyrolidinyl单位的单取代的corroroles：光物理，光生物学和生物分子相互作用的研究

报道了一种经典的方法来设计具有生物活性的杂环单元的中介单取代衍生物。用经典的Gryko方法得到了所研究的对应关系，产率从18%到33%不等。通过元素分析、高分辨率质谱分析、核磁共振和电化学分析等手段对原料进行了表征。利用密度泛函理论（DFT）进行了紫外可见吸收、稳态荧光和时间分辨荧光发射光谱分析。从这个意义上说，得到的共聚物呈现出典型的四吡咯大环吸收光谱，发射峰集中在红色区域，荧光量子产率低，寿命短（在3.0 ~ 4.05 ns之间）。光稳定性和光活性氧（ROS）生成等光生物学参数也进行了评估，表明衍生物具有良好的光稳定性和单线态氧（1O2）和超氧自由基（O2•-）的生成。最后，光谱、粘度计研究和分子对接计算表明，每个corrole衍生物都能与鲑鱼精子DNA （SS-DNA）和人血清白蛋白（HSA）生物大分子相互作用，表明在DNA的小凹槽和白蛋白的III位点相互作用更好。

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来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.