Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens

Imrich, Ján; Bedlovičová, Zdenka; Kristián, Pavol; Danihel, Ivan; Böhm, Stanislav; Sabolová, Danica; Kožurková, Mária; Paulíková, Helena; Klika, Karel D.

doi:10.3987/com-09-s(s)83

Cited by 6 publications

(1 citation statement)

References 37 publications

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“…It is known that hydrazides of carboxylic acids, due to their reactivity, are widely used for the synthesis of various nitrogen-containing heterocyclic systems [29][30][31][32]. The most common way to obtaine hydrazides of carboxylic acids is the hydrazinolysis reaction of complex esters of the corresponding acids [29][30][31]33]. Therefore, we used butyric esters of 2-(2R-9-oxoacridine-10(9H)yl)ethane acids (2, 2a) for the synthesis of hydrazides (3, 3a).…”

Section: Synthesis Of 10-((5-mercapto-134-oxadiazole-2yl)methyl)-2rmentioning

confidence: 99%

Experimental and Theoretical Spectroscopic Study of Thione-Thiol Tautomerism of New Hybrides 1,3,4-Oxadiazole-2-thion with Acridine-9(10H)-one

Karpenko¹,

Omelyanchik²,

Panasenko³

2018

ChChT

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The synthesis of new hybrides 1,3,4-oxadiazol-2-thione with acridine 9(10H)-one is carried out. Their structure is confirmed by LC-MS, IR-, 1 H and 13 C NMRspectroscopy. The thione-thiol equilibrium was investigated in eight solvents with different relative permittivity with the help of UV-spectroscopy and quantum chemistry methods using DFT/B3LYP and HF bases. The results of the experimental calculations are in agreement with theoretical ones and have shown the prevalence of the thione. There were established centers for reactions with the mechanism S E and A E , taking into account the electronic structural formulas and the results of calculating the atom charges of compounds.

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Section: Synthesis Of 10-((5-mercapto-134-oxadiazole-2yl)methyl)-2rmentioning

confidence: 99%

Experimental and Theoretical Spectroscopic Study of Thione-Thiol Tautomerism of New Hybrides 1,3,4-Oxadiazole-2-thion with Acridine-9(10H)-one

Karpenko¹,

Omelyanchik²,

Panasenko³

2018

ChChT

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Syntheses

Ježek¹,

Hlaváček²,

Šebestı́k³

2017

Progress in Drug Research

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DNA binding, anti-tumour activity and reactivity toward cell thiols of acridin-9-ylalkenoic derivatives

et al. 2015

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In this paper, we describe the synthesis, biochemical properties and biological activity of a series of new 9-substituted acridine derivatives with a reactive alkene moiety: 9-[(E)-2-phenylethenyl] acridine (1) and methyl (2E)-3-(acridin-9-yl)-prop-2-enoate (2). The interaction of derivatives 1 and 2 with calf thymus DNA was investigated using UV-Vis, fluorescence and circular dichroism spectroscopy. The binding constants K were estimated as being in the range of 1.9 to 7.1 × 10 5 M −1 , and the percentage of hypochromism was found to be 40-57% (from spectral titration). UV-Vis, fluorescence, and CD measurements indicate that the compounds were effective DNA-intercalating agents. Electrophoretic separation proved that ligands 1 and 2 relaxed topoisomerase I at a concentration of 5 μM. Ester 2 was shown to have a stronger cytostatic effect on leukemia cell line L1210 than alkene 1. The incubation of ligands 1 and 2 with the ovarian carcinoma cell line A2780 confirmed their extensive cytotoxic effects, an effect which was particularly pronounced in the case of ligand 2. Cytotoxicity tests against A2780 cells demonstrate that a conjugate of compound 2 with L-cysteine (3) is less cytotoxic than compound 2, especially at concentrations greater than 10 μM.

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Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens

Cited by 6 publications

References 37 publications

Experimental and Theoretical Spectroscopic Study of Thione-Thiol Tautomerism of New Hybrides 1,3,4-Oxadiazole-2-thion with Acridine-9(10H)-one

Experimental and Theoretical Spectroscopic Study of Thione-Thiol Tautomerism of New Hybrides 1,3,4-Oxadiazole-2-thion with Acridine-9(10H)-one

Syntheses

DNA binding, anti-tumour activity and reactivity toward cell thiols of acridin-9-ylalkenoic derivatives

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