Lanthanides complexes – Chiral sensing of biomolecules

Staszak, Katarzyna; Wieszczycka, Karolina; Marturano, Valentina; Tylkowski, Bartosz

doi:10.1016/j.ccr.2019.06.017

Cited by 146 publications

(77 citation statements)

References 107 publications

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“…Organic materials presenting circularly polarized luminescence (CPL) (Riehl and Richardson, 1977;Kumar et al, 2015;Sanchez-Carnerero et al, 2015;Longhi et al, 2016;Tanaka et al, 2018) have recently emerged as promising candidates for advanced optical applications (Zinna et al, 2015;Han et al, 2018;Shi et al, 2018;Zheng et al, 2018;Burrezo et al, 2019;David et al, 2019;Jiménez et al, 2019;Pop et al, 2019;Yang and Zhong, 2019). Thus for example, CPL emitters have been proposed as chiroptical sensors (Staszak et al, 2019), for smart sensing methodologies (Imai et al, 2018;Reine et al, 2018a,b;Zinna et al, 2019), to encode information in light (Andréassons and Pischel, 2018), in patterning processes using security inks (Andres et al, 2014), or constituents of CPL organic lightemitting diodes OLEDs (Brandt et al, 2016;Di Nuzzo et al, 2017). This property is characterized by the preferential emission of left (I L ) or right handed (I R ) circularly polarized light with respect to the entire emission (I L +I R )/2, being usually described by the dimensionless Kuhn factor of the emission, g lum = 2(I L -I R )/(I L +I R ).…”

Section: Introductionmentioning

confidence: 99%

Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties

et al. 2020

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In this work we describe the linear and non-linear (chiro)optical properties of an enantiopure bis-perylenediimide (PDI) cyclohexane derivative. This compound exhibits upconversion based on a two-photon absorption (TPA) process with a cross-section value of 70 GM together with emission of circularly polarized luminescence (CPL), showing a g lum in the range of 10 −3 . This simple structure represents one of the scarce examples of purely organic compounds combining both TPA and CPL responses, together with large values of molar absorptivity and fluorescence quantum yield with emission in the 500-600 nm. Self-assembly induced by introduction of a poor solvent allows for a spectacular shift of the emission into the near-infrared (NIR, 650-750 nm) by formation of well-defined rotationally displaced dimers. Therefore, we are here presenting a versatile platform whose optical properties can be simply tuned by self-assembly or by functionalization of the electron-deficient aromatic core of PDIs.

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Section: Introductionmentioning

confidence: 99%

Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties

et al. 2020

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“…Finally, the H3 signal in La-L1 is shifted downfield with respect to the L1 ligand, whereas NH 2 protons resonances are shielded (Figure 2). 13 C { 1 H} NMR spectra showed the expected carbon signals for the ligands. For La(III) complexes, the hydroxilic carbon signal was recorded at δ % 141 ppm and 160 ppm for La-L1 and La-L2, respectively, while the carbon of the amine group was observed at 140 ppm and 153 ppm, respectively.…”

Section: Synthesis and Characterization Of Lanthanide Complexesmentioning

confidence: 99%

“…However, the studies of complexes of 2-arylbenzimidazoles with rare earth elements are scarce [11]. Lanthanide (Ln) coordination complexes are of interest due to their biological activities [12,13,14], specific physicochemical properties, unusual electronic configurations, and distinctive multielectron redox chemistry. These properties being ideal for the design and development of novel metal-based pharmaceutical drugs [15,16,17,18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation and model membrane studies on metal complexes containing aromatic N,O-chelate ligands

Aragón-Muriel

Liscano

Rufino‐Felipe

et al. 2020

Heliyon

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Novel lanthanide (Ln) compounds [Ln(L) 2 ]Cl . xH 2 O (Ln ¼ La 3þ , Ce 3þ , Sm 3þ ) containing aromatic N,O-chelate ligands [HL1 ¼ 4-amino-2-(1H-benzimidazol-2-yl)phenol; HL2 ¼ 5-amino-2-(1H-benzimidazol-2-yl)phenol] have been synthesized and structurally characterized by elemental analysis, NMR and IR spectroscopy, molar conductance measurements, and mass spectrometry (MS). The spectroscopic data suggested that the benzimidazolyl-phenol ligands act as N,O-chelate ligands through the iminic nitrogen and phenolic oxygen atoms. Elemental analysis indicated that lanthanide compounds were formed in a 1:2 stoichiometry (metal:ligand). In vitro biological evaluation was carried out using these complexes, exhibiting moderate cytotoxicity against six different human tumor cell lines (U251, human glioblastoma; HCT-15, colorectal carcinoma; MCF-7, breast epithelial adenocarcinoma; PC-3, prostate cancer; K562, myelogenous leukemia; SKLU-1, lung carcinoma) and lower toxicity against a non-cancerous cell line (COS-7, primate kidney). In addition, the antibacterial activity of the compounds was assessed against two gram-positive strains (Staphylococcus aureus ATCC 25923, Listeria monocytogenes ATCC 19115) and two gram-negative strains (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27583) using the microdilution method. The results obtained show that the metal complexes exhibit higher biological activity than the free ligands, confirming a synergistic effect. Further benzimidazolyl-phenol derivatives were explored for the detection of bacteria using fluorescence imaging studies. Interestingly, the fluorescent properties of these compounds make them potential candidates to monitor the morphology of bacteria at different compound concentrations. Hence, the interaction of the ligand and complexes with model membranes mimicking those of bacteria was studied by using differential scanning calorimetry (DSC) and molecular dynamics (MD), showing that both compounds decreased the enthalpy of transition in two model membranes as the concentration of the compounds increased. In addition, the main transition temperature was slightly reduced as a result of these interactions.

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“…Chiral chromophores displaying efficient circularly polarized luminescence (CPL) are promising candidates for bioapplications (e.g. molecular probes and bio-imaging), [1][2][3] photonics (e.g.C P-OLEDs) [4][5][6][7] and advanced security inks. [8] To quantify the degree of "enantiorichness" of aC PL emission the dissymmetry factor g lum has been defined.…”

Section: Introductionmentioning

confidence: 99%

Bright Long‐Lived Circularly Polarized Luminescence in Chiral Chromium(III) Complexes

et al. 2021

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As eries of highly emissive inert and chiral Cr III complexes displaying dual circularly polarized luminescence (CPL) within the NIR region have been prepared and characterized.The helical [Cr(dqpR) 2 ] 3+ (dqp = 2,6-di(quinolin-8-yl)pyridine;R= OCH 3 ,B ro rC CH) complexes were synthesized as racemic mixtures and resolved into their respective PP and MM enantiomers by chiral stationary phase HPLC.T he corresponding enantiomers show large g lum % 0.2 and high quantum yield of up to 17 %, whichaffordimportant CPL brightness of up to 170 m À1 cm À1 ,akey point for applications as chiral luminescent probes.M oreover,t he long-lived CP-NIR emission provided by these chromophores (ms range) in aqueous solution opens the way towardt he quantification of chiral targets in biological systems with timegated detection. Thus,s uch chiral chromophores based on earth abundant and inert 3d metals open new perspectives in the field of CPL and represent an alternative to precious 4d, 5d and to labile 4f metal-based complexes.

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Lanthanides complexes – Chiral sensing of biomolecules

Cited by 146 publications

References 107 publications

Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties

Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties

Synthesis, biological evaluation and model membrane studies on metal complexes containing aromatic N,O-chelate ligands

Bright Long‐Lived Circularly Polarized Luminescence in Chiral Chromium(III) Complexes

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