New triazole-bearing gramine derivatives – synthesis, structural analysis and protective effect against oxidative haemolysis

Kozanecka-Okupnik, Weronika; Sierakowska, Arleta; Berdzik, Natalia; Kowalczyk, Iwona; Mrówczyńska, Lucyna; Jasiewicz, Beata

doi:10.1080/14786419.2020.1864364

Cited by 7 publications

(19 citation statements)

References 20 publications

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“…Exogenous antioxidants have received much attention in recent years, as they may play an important role in preventing oxidative damage in cells. Indole derivatives are known for their antioxidant properties, including protection of cells from ROS detrimental effects [ 18 , 19 , 20 ]. The high reactivity of indole antioxidants is probably due to the electron-rich aromatic ring system, which enables them to act as electron donors for the formation of cationic radicals or by the addition of electrophilic radicals at the C-3 position of the indole [ 16 ].…”

Section: Resultsmentioning

confidence: 99%

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Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities

et al. 2023

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In the search for new bioactive compounds, a methodology based on combining two molecules with biological properties into a new hybrid molecule was used to design and synthesize of a series of ten indole derivatives bearing imidazole, benzothiazole-2-thione, or benzoxazole-2-thione moieties at the C-3 position. The compounds were spectroscopically characterized and tested for their antioxidant, antibacterial, and fungicidal activities. The crystal structures were determined for five of them. Comparison of the closely related structures containing either benzothiazole-2-thione or benzoxazole-2-thione clearly shows that the replacement of -S- and -O- ring atoms modify molecular conformation in the crystal, changes intermolecular interactions, and has a severe impact on biological activity. The results indicate that indole-imidazole derivatives with alkyl substituent exhibit an excellent cytoprotective effect against AAPH-induced oxidative hemolysis and act as effective ferrous ion chelating agents. The indole-imidazole compound with chlorine atoms inhibited the growth of fungal strains: Coriolus versicolor (Cv), Poria placenta (Pp), Coniophora puteana (Cp), and Gloeophyllum trabeum (Gt). The indole-imidazole derivatives showed the highest antibacterial activity, for which the largest growth-inhibition zones were noted in M. luteus and P. fluorescens cultures. The obtained results may be helpful in the development of selective indole derivatives as effective antioxidants and/or antimicrobial agents.

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Section: Resultsmentioning

confidence: 99%

“…Our previous study showed that gramine substituted by the pyrrolidinedithiocarbamate moiety has significant antioxidant properties [ 18 ]. Moreover, selected C-3 substituted indole-uracils [ 19 ] and indole-triazole [ 20 ] conjugates were able to inhibit AAPH-induced oxidative hemolysis effectively.…”

Section: Introductionmentioning

confidence: 99%

Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities

et al. 2023

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“…Although zinc does not directly interact with the oxidant, it may indirectly reduce its effect by protecting cells from the oxidative damage and stabilizing the molecular structure of the cell membrane [ 44 ]. Our previous work has shown that indole derivatives with a substituent at the C-3 position protect human erythrocytes against oxidative hemolysis in vitro [ 8 , 16 , 45 , 46 ]. In addition, indole–imidazole compounds exhibit excellent iron complexing properties [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

“…The cytoprotective activity of the derivatives was evaluated in vitro by determining the inhibition of oxidative-hemolysis, which is induced by free radicals generated by 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH). Human erythrocytes (red blood cells, RBCs), due to the lack of any intracellular membrane systems, are widely used as model cells to assess the protective activity of the cell membrane-incorporating compounds under oxidative stress conditions [ 8 , 16 , 45 , 46 ]. In addition, the complexes were screened for antibacterial and antifungal properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl2: Can Coordination Enhance the Functionality of Bioactive Ligands?

et al. 2023

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The ability of the indole–imidazole hybrid ligands to coordinate with the Zn(II) ion and the resulting structures of this new class of coordination compounds were analyzed in order to determine their structural properties and biological functionalities. For this purpose, six novel Zn(II) complexes, [Zn(InIm)2Cl2] (1), [Zn(InMeIm)2Cl2] (2), [Zn(IniPrIm)2Cl2] (3), [Zn(InEtMeIm)2Cl2] (4), [Zn(InPhIm)2Cl2] (5) and [Zn2(InBzIm)2Cl2] (6) (where InIm is 3-((1H-imidazol-1-yl)methyl)-1H-indole), were synthesized by the reactions of ZnCl2 and the corresponding ligand in a 1:2 molar ratio in methanol solvent at an ambient temperature. The structural and spectral characterization of these complexes was performed using NMR, FT–IR and ESI–MS spectrometry and elemental analysis, and the crystal structures of 1–5 were determined using single-crystal X-ray diffraction. Complexes 1–5 form polar supramolecular aggregates by utilizing, for this purpose, the N-H(indole)∙∙∙Cl(chloride) intermolecular hydrogen bonds. The assemblies thus formed differ depending on the distinctive molecular shape, which can be either compact or extended. All complexes were screened for their hemolytic, cytoprotective, antifungal, and antibacterial activities. The results show that the cytoprotective activity of the indole/imidazole ligand significantly increases upon its complexation with ZnCl2 up to a value comparable with the standard antioxidant Trolox, while the response of its substituted analogues is diverse and less pronounced.

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“…22 Bioconjugates of indole, such as indole-phthalimide or indole-uracil, exhibit high cytoprotective effects against AAPHinduced oxidative hemolysis. 25,26 Some indole-containing pyrazole analogs showed significant activity against leukemia, whereas substituted-3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole derivatives act as an antibacterial agent. 27,28 In recent years, compounds containing a triazole ring have gained more attention.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Hemolytic Activity of Bile Acid-Indole Bioconjugates Linked by Triazole

Berdzik,

Koenig,

Mrówczyńska

et al. 2023

J. Org. Chem.

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New formyl and acetyl derivatives of bile acid propargyl esters and their bioconjugates with modified gramine molecules have been obtained using the click chemistry method to study their hemolytic potency. The structures of all compounds were confirmed by spectral ( 1 H- and 13 C NMR and FT-IR) analysis and mass spectrometry (ESI-MS) as well as PM5 semiempirical methods. According to the results, the structural modification of formyl and acetyl bile acid derivatives, leading to the formation of new propargyl esters and indole bioconjugates, reduces their hemolytic activity. According to molecular docking studies, the tested ligands are highly likely to exhibit a similar affinity, as native ligands, for the active sites of specific protein domains (PDB IDs: 2Q85 and 5V5Z ). The obtained results may be helpful for the development of selective bile acid bioconjugates as effective antibacterial, antifungal, or antioxidant agents.

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New triazole-bearing gramine derivatives – synthesis, structural analysis and protective effect against oxidative haemolysis

Cited by 7 publications

References 20 publications

Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities

Indole Derivatives Bearing Imidazole, Benzothiazole-2-Thione or Benzoxazole-2-Thione Moieties—Synthesis, Structure and Evaluation of Their Cytoprotective, Antioxidant, Antibacterial and Fungicidal Activities

Synthesis, Structure and Biological Activity of Indole–Imidazole Complexes with ZnCl2: Can Coordination Enhance the Functionality of Bioactive Ligands?

Synthesis and Hemolytic Activity of Bile Acid-Indole Bioconjugates Linked by Triazole

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