Novel imidazo[4,5-b]pyridine and triaza-benzo[c]fluorene derivatives: Synthesis, antiproliferative activity and DNA binding studies

Hranjec, Marijana; Lučić, Borka; Ratkaj, Ivana; Pavelić, Sandra Kraljević; Piantanida, Ivo; Pavelić, Krešimir; Karminski‐Zamola, Grace

doi:10.1016/j.ejmech.2011.03.062

Cited by 48 publications

(27 citation statements)

References 30 publications

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“…100 base pairs) rod-like B-helical DNA frag-ments. [54] The polynucleotide concentration was determined spectroscopically [55] as the concentration of phosphates (corresponds to c(nucleobase)). Bovine Serum Albumin (BSA) (Sigma-Aldrich) was dissolved in sodium cacodylate buffer, I = 0.05 m,p H7.0 and its concentration determined spectroscopically using aN anoDrop spectrophotometer at 280 nm using its molar extinction coefficient of 43 824 m À1 cm À1 .…”

Section: Methodsmentioning

confidence: 99%

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A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

Ban

Griesbeck

Tomić

et al. 2020

Chemistry A European J

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A water‐soluble tetracationic quadrupolar bis‐triarylborane chromophore showed strong binding to ds‐DNA, ds‐RNA, ss‐RNA, as well as to the naturally most abundant protein, BSA. The novel dye can distinguish between DNA/RNA and BSA by fluorescence emission separated by Δtrueν˜ =3600 cm−1, allowing for the simultaneous quantification of DNA/RNA and protein (BSA) in a mixture. The applicability of such fluorimetric differentiation in vitro was demonstrated, strongly supporting a protein‐like target as a dominant binding site of 1 in cells. Moreover, our dye also bound strongly to ss‐RNA, with the unusual rod‐like structure of the dye, decorated by four positive charges at its termini and having a hydrophobic core, acting as a spindle for wrapping A, C and U ss‐RNAs, but not poly G, the latter preserving its secondary structure. To the best of our knowledge, such unmatched, multifaceted binding activity of a small molecule toward DNA, RNA, and proteins and the selectivity of its fluorimetric and chirooptic response makes the quadrupolar bis‐triarylborane a novel chromophore/fluorophore moiety for biochemical applications.

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Section: Methodsmentioning

confidence: 99%

“…100 base pairs) rod‐like B‐helical DNA fragments . The polynucleotide concentration was determined spectroscopically as the concentration of phosphates (corresponds to c (nucleobase)).…”

Section: Methodsmentioning

confidence: 99%

A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

Ban

Griesbeck

Tomić

et al. 2020

Chemistry A European J

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“…Imidazopyridines have the ability to influence many cellular pathways necessary for the proper functioning of cancerous cells. The inhibited proteins include, inter alia, matrix metalloproteinase-2, RNA-dependent RNA polymerase, hepatocyte growth factor receptor (c-MET), serine/threonine-protein kinase or cell division cycle 25 phosphatases [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ].…”

Section: Biological Properties Of Imidazo[45- B mentioning

confidence: 99%

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

2017

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The structural resemblance between the fused imidazopyridine heterocyclic ring system and purines has prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The discovery of their first bioactivity as GABAA receptor positive allosteric modulators divulged their medicinal potential. Proton pump inhibitors, aromatase inhibitors, and NSAIDs were also found in this chemical group. Imidazopyridines have the ability to influence many cellular pathways necessary for the proper functioning of cancerous cells, pathogens, components of the immune system, enzymes involved in carbohydrate metabolism, etc. The collective results of biochemical and biophysical properties foregrounded their medicinal significance in central nervous system, digestive system, cancer, inflammation, etc. In recent years, new preparative methods for the synthesis of imidazopyridines using various catalysts have been described. The present manuscript to the best of our knowledge is the complete compilation on the synthesis and medicinal aspects of imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines reported from the year 2000 to date, including structure–activity relationships.

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“…The majority of compounds related to benzimidazoles and benzimidazo[1,2-a]quinolines were previously synthesised and spectroscopically characterised by our research group [7][8][9] . Amidino substituted E-acyclic benzimidazole derivatives 3a-3i were prepared in the condensation of aromatic propenales 1a-1d, 1e and 1f with 4-N-amidino-substituted 1,2-phenylenediamines 2a-2d.…”

Section: Chemistrymentioning

confidence: 99%

“…Synthesis and biological activity of several groups of benzimidazo[1,2-a]quinolines, including positively charged amidino-substituted benzimidazo[1,2-a]quinolines and their heteroaromatic analogues was previously reported [7][8][9] . Also biological studies that confirmed the anticancer potential of this class of compounds, especially that of positively charged amidinosubstituted analogues of benzimidazo[1,2-a]quinolines which may intercalate into double-stranded DNA or RNA 10 .…”

Section: Introductionmentioning

confidence: 99%

Antitumor activity of amidino-substituted benzimidazole and benzimidazo[1,2-a]quinoline derivatives tested in 2D and 3D cell culture systems

Brajša¹,

Vujasinović²,

Jelić³

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Due to a poor clinical predictive power of 2D cell cultures, standard tool for in vitro assays in drug discovery process, there is increasing interest in developing 3D in vitro cell cultures, biologically relevant assay feasible for the development of robust preclinical anti-cancer drug screening platforms. Herein, we tested amidino-substituted benzimidazoles and benzimidazo[1,2-a]quinolines as a small platform for comparison of antitumor activity in 2D and 3D cell culture systems and correlation with structure-activity relationship. 3D cell culture method was applied on a human cancer breast (SK-BR-3, MDA-MB-231, T-47D) and pancreatic cancer cells (MIA PaCa-2, PANC-1). Results obtained in 2D and 3D models were highly comparable, but in some cases we have observed significant disagreement indicating that some prominent compounds can be discarded in early phase of researching because of compounds with false positive result. To confirm which of cell culture systems is more accurate, in vivo profiling is needed. Keywords

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Novel imidazo[4,5-b]pyridine and triaza-benzo[c]fluorene derivatives: Synthesis, antiproliferative activity and DNA binding studies

Cited by 48 publications

References 30 publications

A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

Pharmacological Potential and Synthetic Approaches of Imidazo[4,5-b]pyridine and Imidazo[4,5-c]pyridine Derivatives

Antitumor activity of amidino-substituted benzimidazole and benzimidazo[1,2-a]quinoline derivatives tested in 2D and 3D cell culture systems

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