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Chiral Resolution of Transition Metal Polypyridyl Complexes via HPLC As a Gateway to Enantiopure DNA Targeting Probes

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EUROPEAN j.URNAL OF INORGANIC CHEMISTRY 2025年第11期28卷

作者： Smith, Simon N. Graczyk, Daniel Stitch, Mark Auville, Amelia Stadler, Victoria quinn, susan j. Univ Coll Dublin UCD Sch Chem Dublin D04 V1 W8 Ireland

The intrinsic structural and photophysical properties of octahedral tris-(bidentate) transition metal polypyridyl complexes make them attractive DNA probes whose binding affinity and specificity for DNA can be greatly influenced by the Delta- and Lambda-enantiomer forms. Strategies for chiral resolution include chiral precursors, fractional crystallisation with chiral salts as well as chromatographic methods. The present work details the optimisation of a chiral resolution process to facilitate the isolation of metal complex enantiomers via chiral stationary phase HPLC using a semi-preparative column. The scope of the study includes both Ru(II) and Os(II) polypyridyl enantiomers containing commonly encountered coordination environments as well as a range of more exotic ligand scaffolds that illustrate the generality of the method. Notably, this work also describes the ability to separate enantiomers of a mixture of two complexes prepared as a result of 'ligand-scrambling' during synthesis.

关键词： transition metal polypyridyl complex chirality chromatography HPLC

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Role of Secondary Structure and Time-Dependent Binding on Disruption of Phthalocyanine Aggregates by Guanine-Rich Nucleic Acids

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CHEMISTRY-A EUROPEAN j.URNAL 2025年第2期31卷 e202403095页

作者： Windle, Eleanor R. Rennie, Christopher C. Edkins, Robert M. quinn, susan j. Univ Coll Dublin Sch Chem Dublin Ireland Univ Strathclyde Dept Pure & Appl Chem Glasgow Scotland

Phthalocyanines are versatile photodynamic therapy agents whose biological activity depends on their aggregation state, which is expected to be influenced by binding to biomolecules. Here, guanine-rich nucleic acid binding of a water-soluble cationic, regiopure C4h zinc phthalocyanine bearing four triethylene glycol methyl ether and four N-methyl-4-pyridinium substituents (1) is reported. In contrast to double-stranded DNA, guanine systems GpG, (GG)10, poly(G) and quadruplex DNA are shown to effectively disrupt phthalocyanine aggregates in buffered solution. This process is accompanied by evolution of the Q-band absorbance and enhanced emission. Increasing the sequence length from GpG to (GG)10 increases the binding and confirms the importance of multiple binding interactions. Enhanced binding in the presence of KCl suggests the importance of nucleobase hydrogen-bonded mosaics in phthalocyanine binding. Notably, the (GT)10 sequence is even more effective than quadruplex and pure guanine systems at disrupting the aggregates of 1. Significant time-dependent binding of 1 with poly(G) reveals biexponential binding over minutes and hours, which is linked to local conformations of poly(G) that accommodate monomers of 1 over time. The study highlights the ability of biomacromolecules to disrupt phthalocyanines aggregates over time, which is an important consideration when rationalizing photoactivity of photosensitizers in-vivo.

关键词： phthalocyanines DNA time-dependent disaggregation guanine-rich

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Synthesis of carbon dots from spent coffee grounds: transforming waste into potential biomedical tools

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NANOSCALE 2025年第16期17卷 9947-9962页

作者： Zhou, Yingru Camisasca, Adalberto Dominguez-Gil, Sofia Bartkowski, Michal Rochfort, Keith D. Piletti, Martina White, Anita Krizsan, Dorottya O'Connor, Robert quinn, susan j. Iacopino, Daniela Eustace, Alex j. Giordani, Silvia Dublin City Univ Sch Chem Sci Dublin Ireland Dublin City Univ Life Sci Inst Dublin Ireland Dublin City Univ Sch Biotechnol Dublin Ireland Univ Coll Cork Tyndall Natl Inst Cork Ireland Univ Coll Dublin Sch Chem Dublin Ireland Dublin City Univ Sch Phys Sci Dublin Ireland

Carbon dots (CDs) are small-sized, spherical nanoparticles presenting amorphous carbon cores with nanocrystalline regions of a graphitic structure. They show unique properties such as high aqueous solubility, robust chemical inertness, and non-toxicity and can be manufactured at a relatively low cost. They are also well known for outstanding fluorescence tunability and resistance to photobleaching. Together, these properties boost their potential to act as drug delivery systems (DDSs). This work presents a low-cost synthesis of CDs by upcycling spent coffee grounds (SCGs) and transforming them into value-added products. This synthetic route eliminates the use of highly toxic heavy metals, high energy-consuming reactions and long reaction times, which can improve biocompatibility while benefiting the environment. A series of physico-chemical characterisation techniques demonstrated that these SCG-derived CDs are small-sized nanoparticles with tunable fluorescence. In vitro studies with 120 h of incubation of SCG-derived CDs demonstrated their specific antiproliferative effect on the breast cancer CAL-51 cell line, accompanied by increased reactive oxygen species (ROS) production. Importantly, no impact was observed on healthy breast, kidney, and liver cells. Confocal laser scanning microscopy confirmed the intracellular accumulation of SCG-derived CDs. Furthermore, the drug efflux pumps P-glycoprotein (P-gp) and the breast cancer resistance protein (BCRP) did not impact CD accumulation in the cancer cells.

关键词： Photobleaching

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Hook, Line, and Sinker! Spectroscopic Studies of Bi-Modular Mono- and Bis-1,8-naphthalimide-Ru(bpy)3-conj.gates as DNA "Light Switches"

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INORGANIC CHEMISTRY 2022年第31期61卷 12073-12086页

作者： Ryan, Gary j. Gunnlaugsson, Thorfinnur quinn, susan j. Univ Dublin Trinity Biomed Sci Inst TBSI Trinity Coll Dublin Sch Chem Dublin 2 Ireland Synth & Solid State Pharmaceut Ctr SSPC Bernal Inst Limerick V94 T9PX Ireland Univ Coll Dublin Sch Chem Dublin 4 Ireland

Bi-chromophoric ruthenium polypyridyl complexes comprising one or two nitro-1,8-naphthalimide groups are shown to be effective DNA binders with off-on light switching properties. The binding to DNA was investigated using a combination of studies such as UV-visible absorption and emission titrations, thermal denaturation, and circular dichroism spectroscopy. The DNA affinity was shown to be sensitive to both the linker length and the number of naphthalimides (one vs two) contained in these systems and binding constants ranging from 10(6) to 10(7) M-1 for salmon testes DNA. The strong DNA binding is attributed to the combination of naphthalimide intercalation and the electrostatic interaction of the ruthenium complex. Large emission enhancements from the metal to ligand charge transfer (MLCT) emission arising from the metal complex were observed upon DNA binding, which was attributed to the interruption of intramolecular electron transfer quenching processes. Moving the nitro substitution from the 4-position to the 3-position is found to result in modification of the DNA binding and the resulting optical properties. The off-on light switch phenomena reported demonstrate the potential of these complexes to act as DNA probes.

关键词： Absorption Genetics Ligands Metal to ligand charge transfer Peptides and proteins

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Lanthanide luminescent displacement assays: The sensing of phosphate anions using Eu(III)-cyclen-conj.gated gold nanoparticles in aqueous solution

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j.URNAL OF THE AMERICAN CHEMICAL SOCIETY 2008年第22期130卷 6900-+页

作者： Massue, j.lien quinn, susan j. Gunnlaugsson, Thorfinnur Trinity Coll Dublin Ctr Synth & Chem Biol Sch Chem Dublin 2 Ireland

***, a cyclen based Eu(III)-thiol conj.gate, was incorporated onto the surface of water-soluble gold nanoparticles to give ***. The self-assembly between *** and the antenna 2 resulted in the formation of the highly luminescent lanthanide system, ***-2, at pH 7-4. The sensing of U flavin monophosphate 3 is demonstrated, whereby 3 displaced the antenna 2 in ***-2, resulting in the formation of ***-3 and quenching of the Eu(III) emission.

关键词： Europium/chemistry* Gold/chemistry* Heterocyclic Compounds/chemistry* Luminescent Measurements Metal Nanoparticles/chemistry* Organometallic Compounds/chemical synthesis Organometallic Compounds/chemistry* Phosphates/analysis* Phosphates/analysis* Solutions Water/chemistry

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Photochemically active DNA-intercalating ruthenium and related complexes - insights by combining crystallography and transient spectroscopy

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CHEMICAL SCIENCE 2017年第7期8卷 4705-4723页

作者： Cardin, Christine j. Kelly, j.hn M. quinn, susan j. Univ Reading Sch Chem Whiteknights RG6 6AD England Trinity Coll Dublin Sch Chem Dublin 2 Ireland Univ Coll Dublin Sch Chem Dublin 4 Ireland

Recent research on the study of the interaction of ruthenium polypyridyl compounds and defined sequence nucleic acids is reviewed. Particular emphasis is paid to complexes [Ru(LL)(2)(Int)](2+) containing potentially intercalating ligands (Int) such as dipyridophenazine (dppz), which are known to display light-switching or photo-oxidising behaviour, depending on the nature of the ancillary ligands. X-ray crystallography has made a key contribution to our understanding, and the first complete survey of structural results is presented. These include sequence, enantiomeric, substituent and structural specificities. The use of ultrafast transient spectroscopic methods to probe the ultrafast processes for complexes such as [Ru(TAP)(2)(dppz)](2+) and [Ru(phen)(2)(dppz)](2+) when bound to mixed sequence oligonucleotides are reviewed with particular attention being paid to the complementary advantages of transient (visible) absorption and time-resolved (mid) infra-red techniques to probe spectral changes in the metal complex and in the nucleic acid. The observed photophysical properties are considered in light of the structural information obtained from X-ray crystallography. In solution, metal complexes can be expected to bind at more than one DNA step, so that a perfect correlation of the photophysical properties and factors such as the orientation or penetration of the ligand into the intercalation pocket should not be expected. This difficulty can be obviated by carrying out TRIR studies in the crystals. Dppz complexes also undergo insertion, especially with mismatched sequences. Future areas for study such as those involving non-canonical forms of DNA, such as G-quadruplexes or i-motifs are also briefly considered.

关键词： DNA

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Elderly in hospice: Older patients need unique kinds of physical, psychosocial and religious support

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American j.urnal of Hospice and Palliative Medicine 1984年第1期1卷 27-30页

作者： quinn, susan j. Riverview Hospital Program Riverview Hospital Red Bank New Jersey United States

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Polymer-Supported Gold Nanoparticle Radiosensitizers with Enhanced Cellular Uptake Efficiency and Increased Cell Death in Human Prostate Cancer Cells

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ACS APPLIED NANO MATERIALS 2020年第4期3卷 3157-3162页

作者： Bennie, Lindsey Belhout, Samir A. quinn, susan j. Coulter, j.nathan A. Univ Coll Dublin UCD Sch Chem Dublin 4 D04 V1W8 Ireland Queens Univ Belfast Sch Pharm Belfast BT9 7BL Antrim North Ireland

Polymer-supported gold nanoparticles (AuNPs) show increased stability to biological and physiological conditions compared to free AuNPs. Here, we demonstrate an increase in the cellular uptake efficiency of Au by the DU145 human prostate cancer cell line for 4.5 nm AuNPs loaded onto 100 nm (13%) and 200 nm (18%) polystyrene particles compared to free AuNPs (4%). Composite formulations were well tolerated by the cell with minimal direct toxicity. Under X-ray irradiation, significant radiation dose enhancement of 1.23 at 4 Gy was observed, outperforming previously reported radiosensitization experiments using free AuNPs, demonstrating the potential application of polymer-supported AuNPs as radiosensitizers.

关键词： gold nanoparticles radiosensitization cancer cellular uptake polymer composites

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Lanthanide luminescent gold nanoparticles: pH-driven self-assembly formation between Eu(III)-cyclen conj.gated AuNPs and sensitising β-diketonate antenna in water

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ORGANIC & BIOMOLECULAR CHEMISTRY 2009年第15期7卷 3074-3078页

作者： Bonnet, Celia S. Massue, j.lien quinn, susan j. Gunnlaugsson, Thorfinnur Univ Dublin Trinity Coll Sch Chem Ctr Synth & Chem Biol Dublin D2 Ireland

The formation of a self-assembly between water soluble gold nanoparticles ***, functionalised with a heptadentate macrocyclic Eu(III) cyclen conj.gate via an alkyl thiol spacer, and a naphthalene beta-diketone antenna was investigated as a function of pH in water. In the study, the changes in the absorption spectra of the antenna and the gold surface plasmon resonance band, the fluorescence and the delayed Eu( III) emission of the self-assembly were all monitored. We demonstrate that the Eu( III) emission arising from the self-assembly formation on AuNP is significantly modulated as a function of pH, where within the physiological pH range, the emission is 'switched on' and that a direct connection can be made between theses changes and the quenching in the antenna as a function of pH.

关键词： PH Theses Lanthanides Surface Plasmon Resonance DIRECT DRIVE Rare earths Europium Self-assembly Absorption spectra

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Mixed f-d Coordination Complexes as Dual Visible- and Near-Infrared-Emitting Probes for Targeting DNA

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INORGANIC CHEMISTRY 2009年第11期48卷 4646-4648页

作者： Nonat, Aline M. quinn, susan j. Gunnlaugsson, Thorfinnur Univ Dublin Trinity Coll Sch Chem Ctr Synth & Chem Biol Dublin 2 Ireland

A new family of mixed-lanthanide (Yb-III and Nd-III) transition-metal (f-d) cyclen-Ru-II(phen)(3) (phen = 1,10-phenanthroline) complexes were synthesized as dual visible- and near-infrared (NIR)-emitting DNA probes/sensors. Significant changes were seen in both the Ru-II visible and the Yb-III-centered NIR emission, which was switched off upon binding to DNA at pH 7.4. In contrast, no changes were seen in the Nd-III emission of the analogue f-d conj.gate.

关键词： RARE earth metal compounds COMPLEX compounds -- Synthesis DNA probes GENE targeting FIELD emission CONj.GATED polymers NEAR infrared spectroscopy

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