Amberlite IR-120 (H) mediated “on water” synthesis of fluorescent Ruthenium(II)-arene 8-hydroxyquinoline complexes for cancer therapy and live cell imaging

Mondal, Ashaparna; De, Sourav; Maiti, Swatilekha; Sarkar, Bidisha; Sk, Ashok Kumar; Jacob, Rini; Moorthy, Anbalagan; Paira, Priyankar

doi:10.1016/j.jphotobiol.2017.11.033

Cited by 24 publications

(5 citation statements)

References 54 publications

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“…Ruthenium (II) metal complexes, on the other hand, have been associated with anticancer activity against a variety of human cell lines, including Caco-2. Recent studies have in fact reported moderate to high (higher than cisplatin) in vitro toxicity of ruthenium arene complexes against Caco-2 cell line 60,61 . In these ruthenium complexes exhibiting anticancer properties, the metal in the molecule is active and therefore the tested concentrations are metal-dependent.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterisation and In Vitro Permeation, Dissolution and Cytotoxic Evaluation of Ruthenium(II)-Liganded Sulpiride and Amino Alcohol

M’bitsi-Ibouily

Marimuthu

Kumar

et al. 2019

Sci Rep

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Sulpiride (SPR) is a selective antagonist of central dopamine receptors but has limited clinical use due to its poor pharmacokinetics. The aim of this study was to investigate how metal ligation to SPR may improve its solubility, intestinal permeability and prolong its half-life. The synthesis and characterisation of ternary metal complexes [Ru(p -cymene)(L)(SPR)]PF6 (L1 = (R)-(+)-2-amino-3-phenyl-1-propanol, L2 = ethanolamine, L3 = (S)-(+)-2-amino-1-propanol, L4 = 3-amino-1-propanol, L5 = (S)-(+)-2-pyrrolidinemethanol) are described in this work. The stability constant of the [Ru(p -cymene)(SPR)] complex was determined using Job’s method. The obtained value revealed higher stability of the metal complex in the physiological pH than in an acidic environment such as the stomach. The ternary metal complexes were characterised by elemental analysis, Fourier transform infrared spectroscopy (FT-IR), 1H and 13C nuclear magnetic resonance (NMR), differential scanning calorimetry (DSC), thermal analyses, Ultraviolet-Visible (UV-Vis). Solubility studies showed higher aqueous solubility for complexed SPR than the free drug. Dissolution profiles of SPR from the metal complexes exhibited slower dissolution rate of the drug. Permeation studies through the pig’s intestine revealed enhanced membrane permeation of the complexed drug. In vitro methyl thiazolyl tetrazolium (MTT) assay showed no noticeable toxic effects of the ternary metal complexes on Caco-2 cell line.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterisation and In Vitro Permeation, Dissolution and Cytotoxic Evaluation of Ruthenium(II)-Liganded Sulpiride and Amino Alcohol

M’bitsi-Ibouily

Marimuthu

Kumar

et al. 2019

Sci Rep

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“…Electronic absorption titration and EtBr displacement assay are the two widely used methods opted to catch the type of interaction observed in compounds and DNA ,…”

Section: Resultsmentioning

confidence: 99%

Experimental and Theoretical Study on the Biomolecular Interaction of Novel Acenaphtho Quinoxaline and Dipyridophenazine Analogues

Sarkar

Jadhav

et al. 2018

ChemistrySelect

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In this report, two different types of quinoxaline derivatives have been developed with an idea that these molecules are composed of planar structure with extensive π‐delocalization. Accordingly, compounds such as 9‐bromoacenaphtho [1,2‐b]quinoxaline (3), 4‐(acenaphtho [1,2‐b] quinoxalin‐9‐yl) benzaldehyde (5), 11‐bromodipyrido [3,2‐a:2′,3′‐c] phenazine (3′) and 4‐(dipyrido [3,2‐a:2′,3′‐c] phenazin‐11‐yl) benzaldehyde (5′) were prepared by a sonication method. In order to prove these compounds as potential anticancer agents, binding studies with calf thymus deoxyribonucleic acid (CT‐DNA) and bovine serum albumin (BSA) have been established by absorption and fluorescence studies. The DNA interaction with prepared compounds shows that quinoxaline (3 and 5) and phenazine derivatives (3′ and 5′) are bind to DNA through intercalation and electrostatic modes. The binding strength of 3′ and 5′ with DNA found to be stronger than other two derivatives (3 and 5). The magnitude of 5 and 5′ exhibits 10‐fold more binding efficacy with protein BSA than compound 3′ but compound 3 did not show any binding efficacy with BSA. The MTT (3‐(4,5‐Dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) analysis reveals that 5′ exhibits highly selective cytotoxicity profile in HeLa cell line and moderate cytoselectivity in human epithelial colorectal adenocarcinoma cells (Caco‐2) cell line with respect to the normal cell line. However, compound 3 showed best potency and selectivity in Caco‐2 cells.

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“…12,[32][33][34][35][36][37][38][39][40][41][42][43][44] Some of them have also been tested for their ability to interact with BSA, protein kinases, lysine-specific demethylase 1, DNA, ATP-competitive neural precursor, mitochondria, and other enzymes. 12,[32][33][34][35][36][37][38][39][40][41][42][43][44] Recently, (iso)quinolone derivative metal complexes have been examined as specific probes and photodynamic therapy reagents, such as 8-hydroxyquinoline Ru(II)arene complexes, 45 8-oxychinolin cyclometalated Ir(III) complexes, 46 zinc(II) phthalocyanine-quinoline derivatives, 47 phenylisoquinoline Ir(III) phosphorescent probe, 48,49 near-infraredemitting Ir(III) complexes, 50 luminescent di-2-picolylamine Ir(III) complexes, 51 and quinoline-coumarin organoplatinum(II) derivatives. 52a Although a few metal-(iso)quinolone compounds have recently been used in mitochondrial and other imaging experiments, rhodium(III) metal complexes bearing quinolinebenzopyran ligands (QB1-QB4) have not yet been studied for such imaging and anticancer therapeutics in cell nucleus fractions, to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

Cell nucleus localization and high anticancer activity of quinoline–benzopyran rhodium(iii) metal complexes as therapeutic and fluorescence imaging agents

Wang

Nai

et al. 2022

Dalton Trans.

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Amberlite IR-120 (H) mediated “on water” synthesis of fluorescent Ruthenium(II)-arene 8-hydroxyquinoline complexes for cancer therapy and live cell imaging

Cited by 24 publications

References 54 publications

Synthesis, Characterisation and In Vitro Permeation, Dissolution and Cytotoxic Evaluation of Ruthenium(II)-Liganded Sulpiride and Amino Alcohol

Synthesis, Characterisation and In Vitro Permeation, Dissolution and Cytotoxic Evaluation of Ruthenium(II)-Liganded Sulpiride and Amino Alcohol

Experimental and Theoretical Study on the Biomolecular Interaction of Novel Acenaphtho Quinoxaline and Dipyridophenazine Analogues

Cell nucleus localization and high anticancer activity of quinoline–benzopyran rhodium(iii) metal complexes as therapeutic and fluorescence imaging agents

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