scholarly journals Dirhenium(III) complex with beta-alanine ligand: anticancer, antioxidant and DNA-binding properties

Earlier we have shown that dirhenium(III) dicarboxylate complex with γ-aminobutyric acid possessed higher antitumor activity, than those of the previously investigated alkylcarboxylates, also may act as a modulator of cisplatin mechanism of action and as a stabilizer of red blood cells in tumor-bearing organisms. Thus, the task of the work was to investigate anticancer activity of the complex cis-[Re2(β-Ala)2Cl6] (I) in the model of tumor growth in vivo and to realize if the amino acid residue influences the DNA-binding activity of the amino acid derivatives of the cluster rhenium(III) compounds. Antitumor properties of the complex I were studied in the model of tumor growth with the use of Wistar rats inoculated by tumor carcinoma Guerink cells. The introduction of the compound alone in free and liposomal forms inhibited the tumor growth by 36 % and 45 % correspondingly, that is more than for dirhenium(III) clusters with alkyl ligands. The combined introduction of I and cisplatin had a significant impact on the tumor growth and showed the disappearance of the tumors in most of the animals. No considerable differences were found between introduction of liposomal and free form of I. The electronic absorption spectra of Calf Thymus DNA (CT-DNA) exhibit hyperchromism in the presence of increasing amounts of I. The DNA band at ~ 260 nm arises from the π-π* transitions of the nucleic acid bases and changes in the intensity and slight wavelength shifts of this characteristic band reflect the corresponding structural modifications of the DNA, which include changes in stacking, disruption of the hydrogen bonds between complementary strands, covalent binding of the DNA bases, intercalation of aromatic rings and others. The binding constant Kb(I) = 2.43 × 103 M-1 to CT-DNA was obtained that was lower than the values reported for the classical DNA intercalators and compares well with the magnitude of the binding constants for other complexes of dirhenium(III); titration of СT-DNA with cisPt and hydrogen peroxide also leads to a hypochromic effect, weak at low concentrations and more significant at high concentrations of I; the DNA binding constants increased in several times when using H2O2 or cisplatin that confirms a mechanism for redox activation of interaction of I with DNA in a cancer cell. The obtained results demonstrate the possibility of application of the amino acid derivatives of dirhenium(III) clusters in antitumor therapy.

2016 ◽  
Vol 81 (12) ◽  
pp. 1345-1358 ◽  
Author(s):  
Jovana Vilipic ◽  
Irena Novakovic ◽  
Mario Zlatovic ◽  
Miroslava Vujcic ◽  
Srdjan Tufegdzic ◽  
...  

The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. SDS electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e. existence of interactions between the quinones and CT-DNA. Determination of binding constant by absorption titration indicates weak interactions between quinone derivatives and CT-DNA. The quenching of fluorescence of intercalator ethidium bromide from EB-CT-DNA system and of minor groove binder Hoechst 33258 from H-CT-DNA system by the synthesized derivatives indicates interactions of compounds and CT-DNA. CD spectra demonstrate non-intercalative binding mode of quinone derivaties to CT-DNA. Molecular docking results confirm binding to the minor groove. Electrophoretic pattern showed no cleavage of pUC19 plasmid in the presence of any of the synthesized compounds. The ability of the derivatives to scavenge radicals was confirmed by DPPH test. All the presented results suggest that the DNA minor groove binding is the principal mechanism of action of the examined amino acid derivatives.


2014 ◽  
Vol 14 (7) ◽  
pp. 984-993 ◽  
Author(s):  
Gabriela Luna-Palencia ◽  
Federico Martinez-Ramos ◽  
Ismael Vasquez-Moctezuma ◽  
Manuel Fragoso-Vazquez ◽  
Jessica Mendieta-Wejebe ◽  
...  

2020 ◽  
Vol 88 (4) ◽  
pp. 57
Author(s):  
Oussama Moussaoui ◽  
Rajendra Bhadane ◽  
Riham Sghyar ◽  
El Mestafa El Hadrami ◽  
Soukaina El Amrani ◽  
...  

A new series of amino acid derivatives of quinolines was synthesized through the hydrolysis of amino acid methyl esters of quinoline carboxamides with alkali hydroxide. The compounds were purified on silica gel by column chromatography and further characterized by TLC, NMR and ESI-TOF mass spectrometry. All compounds were screened for in vitro antimicrobial activity against different bacterial strains using the microdilution method. Most of the synthesized amino acid-quinolines show more potent or equipotent inhibitory action against the tested bacteria than their correspond esters. In addition, many of them exhibit fluorescent properties and could possibly be utilized as fluorophores. Molecular docking and simulation studies of the compounds at putative bacterial target enzymes suggest that the antimicrobial potency of these synthesized analogues could be due to enzyme inhibition via their favorable binding at the fluoroquinolone binding site at the GyrA subunit of DNA gyrase and/or the ParC subunit of topoisomerase-IV.


1959 ◽  
Vol 81 (2) ◽  
pp. 377-382 ◽  
Author(s):  
L. R. Morris ◽  
R. A. Mock ◽  
C. A. Marshall ◽  
J. H. Howe

2005 ◽  
Vol 2005 (10) ◽  
pp. 640-642 ◽  
Author(s):  
Ying Liu ◽  
Liang Zhao ◽  
Liang Liu ◽  
Lin-Yi Wei ◽  
Lu-Hua Lai

Amino acid derivatives of a modified indole-3-acetic acid have been synthesised. Fourteen new dipeptide-like compounds 3–4 were obtained and their structures were elucidated based on the IR, 1H NMR, MS spectra.


2013 ◽  
Vol 450 (2) ◽  
pp. 149-151 ◽  
Author(s):  
I. V. Serkov ◽  
E. A. Chugunova ◽  
A. R. Burilov ◽  
S. O. Bachurin

2021 ◽  
Vol 11 (6) ◽  
pp. 13903-13910

As a result of the carried out research it was synthesized an order of new potentially biologically active modified N-,O-contained heterocycles on the base of amino acid derivatives of 2,6,7-nitrogen substituted-3-chloro-1,4-naphthoquinone. It was established that among synthesized compounds, there are potential antimicrobial substances with high activity.


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