Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates

Racané, Livio; Stojković, Ranko; Tralić‐Kulenović, Vesna; Cerić, Helena; Đaković, Marijana; Ester, Katja; Krpan, Ana Mišir; Stojković, Marijana Radić

doi:10.1016/j.ejmech.2014.08.072

Cited by 21 publications

(14 citation statements)

References 57 publications

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“…Being one of the well-known privileged building substructures in medicinal chemistry, benzimidazoles and benzothiazoles have important roles as the constituents of various biologically important systems [1,2]. Among versatile pharmacological features, the most important ones for the rational design of novel bioactive compounds are antitumor, antimicrobial, antiviral, anti-inflammatory activities [3,4,5,6,7,8]. We have described the antitumor potential of various benzimidazole and/or benzothiazole derivatives bearing amidino, carboxamido, amino, halogen, cyano, amino, or nitro substituents placed at different positions on the mentioned scaffolds.…”

Section: Introductionmentioning

confidence: 99%

Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2-Carboxamides with Antiproliferative Activity

et al. 2019

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We present the synthesis of a range of benzimidazole/benzothiazole-2-carboxamides with a variable number of methoxy and hydroxy groups, substituted with nitro, amino, or amino protonated moieties, which were evaluated for their antiproliferative activity in vitro and the antioxidant capacity. Antiproliferative features were tested on three human cancer cells, while the antioxidative activity was measured using 1,1-diphenyl-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) assays. Trimethoxy substituted benzimidazole-2-carboxamide 8 showed the most promising antiproliferative activity (IC50 = 0.6–2.0 µM), while trihydroxy substituted benzothiazole-2-carboxamide 29 was identified as the most promising antioxidant, being significantly more potent than the reference butylated hydroxytoluene BHT in both assays. Moreover, the latter also displays antioxidative activity in tumor cells. The measured antioxidative capacities were rationalized through density functional theory (DFT) calculations, showing that 29 owes its activity to the formation of two [O•∙∙∙H–O] hydrogen bonds in the formed radical. Systems 8 and 29 were both chosen as lead compounds for further optimization of the benzazole-2-carboxamide scaffold in order to develop more efficient antioxidants and/or systems with the antiproliferative activity.

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Section: Introductionmentioning

confidence: 99%

Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2-Carboxamides with Antiproliferative Activity

et al. 2019

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“…[7,8] Among all amidino substituted benzazole derivatives, the ones with the cyclic amidino substituent, namely 2-imidazolinyl group, showed the most significant antiproliferative activity in vitro with IC50 values in submicromolar range of concentrations. [9] Almost all previously synthesized active derivatives have been designed to have cationic amidino substituents which have significantly improve their biological activity. Amidine substituents placed at the termini of the molecule have great importance in the molecule -biological target interactions allowing the formation of the stable complex with biologically important molecules.…”

Section: Introductionmentioning

confidence: 99%

“…Regarding the 2-phenylbenzothiazole derivatives, we have shown that their antiproliferative activity strongly depends on the type of amidino group as well as on their position on the targeted molecule. [7,9] Nowadays, the attention of medicinal chemists is focused also on the development of the novel antioxidative agents, especially after it has been evidenced that oxidative damage of important biomacromolecules is directly connected with the pathogenesis of various diseases. [11,12] Thus, the reactive oxygen species (ROS) through the damage of cellular biomacromolecules like proteins, lipids or DNA/RNA may be playing an important role in the development of cancer, atherosclerosis, aging or rheumatoid arthritis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidative Potency of Novel Amidino Substituted Benzimidazole and Benzothiazole Derivatives

Racané¹,

Cindrić²,

Perin³

et al. 2017

Croat. Chem. Acta

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Herein we present the synthesis of versatile amidino substituted benzothiazole 3-10 and benzimidazole 12-19 derivatives substituted with the variable number of hydroxy and methoxy groups. Furthermore, the synthesized compounds were explored for their antioxidative activity in vitro by using three biological assays, namely DPPH, ABTS and FRAP. The obtained results indicated that the variable number of hydroxy groups together with the type of the amidino substituent strongly influenced the antioxidative activity and reducing power of tested compounds. The most promising antioxidative activity showed trihydroxy substituted compounds 6, 10, 15 and 19. In general, it was noticed that unsubstituted amidino group induced the more pronounced activity in comparison to derivatives bearing 2-imidazolinyl group.

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“…2). Furthermore, benzothiazoles also interact with ss-RNA, but only 2imidazolinyl 2-phenylbenzothiazole displayed well defined orientation and dominant binding mode (by induced CD signals) with poly A and poly G. [25] Amidino substituted benzimidazole-2-carboxamide as groove binder evidenced sequence-selective binding in the A-T rich side (Fig. 2).…”

Section: Introductionmentioning

confidence: 97%

Synthesis and Antiproliferative activity in vitro of Amidino Substituted 2-phenylbenzazoles

Racané

Butković

Kleiner

et al. 2019

Croat. chem. acta (Online)

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Within this work we describe the synthesis of versatile substituted 2-phenyl benzothiazole 3–10 and 2-phenylbenzimidazole 12–19 derivatives bearing amidino groups. Furthermore, the synthesized compounds were explored for their antiproliferative activity in vitro on three cancer cell lines. Tested compounds showed moderate to strong antiproliferative activity. Furthermore, the type of the attached amidino group on benzazole nuclei has the significant impact on the antiproliferative activity only within benzimidazole derivatives with 2-imidazolinyl substituted derivatives being more active in comparison to amidino substituted analogues. All obtained results revealed that this type of benzothiazole derivatives have a great potential for further optimization and development of more efficient potential antiproliferative agents.

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Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates

Cited by 21 publications

References 57 publications

Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2-Carboxamides with Antiproliferative Activity

Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2-Carboxamides with Antiproliferative Activity

Synthesis and Antioxidative Potency of Novel Amidino Substituted Benzimidazole and Benzothiazole Derivatives

Synthesis and Antiproliferative activity in vitro of Amidino Substituted 2-phenylbenzazoles

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