1H and 13C NMR spectra, structure and physicochemical features of phenyl acridine-9-carboxylates and 10-methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulphonates – alkyl substituted in the phenyl fragment

Krzymiński, Karol; Malecha, Piotr; Zadykowicz, Beata; Wróblewska, Agnieszka; Błażejowski, Jerzy

doi:10.1016/j.saa.2010.10.029

Cited by 17 publications

(16 citation statements)

References 41 publications

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“…Acridine-based ligands, being polyaromatic compounds, constitute an effective system of charge carrier transfer. The HOMO and LUMO energy levels of 4,5-acridine derivatives are comparable with these energy levels of semiconductor NCs [ 23 , 34 , 35 ], which allows these derivatives to be used as hole-transporting materials in designing photovoltaic [ 35 ] and optoelectronic devices [ 36 ]. On the other hand, this charge transfer leads to the problem of quenching of the QD PL [ 37 , 38 ] due to photoinduced electron transfer (PET) [ 39 ].…”

Section: Resultsmentioning

confidence: 99%

Conjugates of Ultrasmall Quantum Dots and Acridine Derivatives as Prospective Nanoprobes for Intracellular Investigations

et al. 2021

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Designing nanoprobes in which quantum dots (QDs) are used as photoluminescent labels is an especially promising line of research due to their possible medical applications ranging from disease diagnosis to drug delivery. In spite of the significant progress made in designing such nanoprobes, the properties of their individual components, i.e., photoluminescent QDs, vectorization moieties, and pharmacological agents, still require further optimization to enhance the efficiency of diagnostic or therapeutic procedures. Here, we have developed a method of engineering compact multifunctional nanoprobes based on functional components with optimized properties: bright photoluminescence of CdSe/ZnS (core/shell) QDs, a compact and effective antitumor agent (an acridine derivative), and direct conjugation of the components via electrostatic interaction, which provides a final hydrodynamic diameter of nanoprobes smaller than 15 nm. Due to the possibility of conjugating various biomolecules with hydroxyl and carboxyl moieties to QDs, the method represents a versatile approach to the biomarker-recognizing molecule imaging of the delivery of the active substance as part of compact nanoprobes.

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Section: Resultsmentioning

confidence: 99%

Conjugates of Ultrasmall Quantum Dots and Acridine Derivatives as Prospective Nanoprobes for Intracellular Investigations

et al. 2021

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“…Acridine ligands and QDs form an effective charge-carrier transfer system because of the polyaromatic structure of the former. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of acridine derivatives are comparable to those of semiconductor nanocrystals, − which makes it possible for excited electrons and holes to move between these components. This charge transfer may lead to QD fluorescence quenching , by photoinduced electron transfer (PET) and loss of colloidal stability.…”

Section: Resultsmentioning

confidence: 99%

Selection of the Optimal Chromatography Medium for Purification of Quantum Dots and Their Bioconjugates

et al. 2020

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Photoluminescent quantum dots (QDs) due to their unique optical properties and capacity for conjugation with biomolecules are widely used in biomedicine. However, numerous by-products of bioconjugation can seriously influence the interaction of these nanoprobes and their targets. The use of size exclusion chromatography (SEC) for the separation of QDs and byproducts of bioconjugation is rather challenging because of the difference in chemical and physical nature of nanoparticles and biomolecules, which makes the choice of stationary phases for SEC a complicated task. Here we have investigated the efficiency of SEC purification of water-soluble CdSe/ZnS QDs and QD-based conjugates from polyethylene glycol derivatives serving as stabilizing ligands, as well as bis-netropsin and 4,5,9-trisubstituted acridine derivative serving as DNA ligands using Sephadex resins with different porosities. We have found that multiple SEC cycles using popular pre-packed Sephadex G25 columns does not provide efficient purification of QDs, whereas Sephadex G100 and G200 are much more efficient after a single SEC run because of the optimal peak resolution and allow preserving the colloidal stability of QDs. Our results show that the use of less common chromatographic media in the group of Sephadex resins allows efficient purification of QD bioconjugates from contaminants for their subsequent use in bioimaging or diagnostics.

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“…Taking into consideration the previous assignments of 1 H-NMR of the indole system [15], protons at δ 7.34 and δ 7.59 were assigned as protons on C-11 and C-12, respectively. Furthermore, based on preceding literature in which the peaks observed at about 125 and 145 ppm were designated as C-9 and C-10 carbon adjacent to nitrogen atom, respectively [16][17][18], the peak at δ 144.7 was assigned as carbons at C-10. Through two-dimensional NMR analysis, we were also able to assign the 13 C-NMR peak of C-9 (δ 120.8) that could not be assigned in the previous study [4].…”

Section: Scheme 1 Synthesis Of Proposed Structure Of Aaptoline B (1)mentioning

confidence: 99%

Synthesis of Proposed Structure of Aaptoline B via Transition Metal-Catalyzed Cycloisomerization and Evaluation of Its Neuroprotective Properties in C. Elegans

et al. 2021

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A concise synthesis of the proposed structure of aaptoline B, a pyrroloquinoline derived from a marine sponge, was accomplished. A key feature of this synthesis is the versatile transition metal-catalyzed cycloisomerization of N-propargylaniline to construct a quinoline skeleton. However, the spectral data of the synthesized aaptoline B did not agree with those of previous studies. The structure of the synthesized aaptoline B was confirmed using a combined 2D NMR analysis. Furthermore, we assessed the possible neuroprotective potential of aaptoline B using the C. elegans model system. In this study, aaptoline B significantly improved the viability and the morphology of dopaminergic neurons of nematodes under MPP+ exposure conditions. We also found that MPP+-induced motor deficits in nematodes were efficiently restored by aaptoline B treatment. Our findings demonstrate the neuroprotective effects of aaptoline B against MPP+-induced dopaminergic neuronal damage. Further studies are underway to explain its pharmacological mechanism.

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1H and 13C NMR spectra, structure and physicochemical features of phenyl acridine-9-carboxylates and 10-methyl-9-(phenoxycarbonyl)acridinium trifluoromethanesulphonates – alkyl substituted in the phenyl fragment

Cited by 17 publications

References 41 publications

Conjugates of Ultrasmall Quantum Dots and Acridine Derivatives as Prospective Nanoprobes for Intracellular Investigations

Conjugates of Ultrasmall Quantum Dots and Acridine Derivatives as Prospective Nanoprobes for Intracellular Investigations

Selection of the Optimal Chromatography Medium for Purification of Quantum Dots and Their Bioconjugates

Synthesis of Proposed Structure of Aaptoline B via Transition Metal-Catalyzed Cycloisomerization and Evaluation of Its Neuroprotective Properties in C. Elegans

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