The discovery of half-sandwich iridium complexes containing lidocaine and (pyren-1-yl)ethynyl derivatives of phenylcyanamide ligands for photodynamic therapy

Tabrizi, Leila

doi:10.1039/c7dt01091e

Cited by 12 publications

(9 citation statements)

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“…22 Recently, the syntheses and biological properties on the Ni(II), Co(II), Ru(II), Ir(III), Pt(II) and Pd(II) complexes with lidocaine have been reported for traditional chemotherapy and photodynamic therapy. [23][24][25][26][27] Ibuprofen is a propionic acid derivative and nonsteroidal anti-inammatory drug with anti-inammatory, analgesic and antipyretic effects. Ibuprofen inhibits the activity of cyclo-oxygenase I and II (COX-1 and COX-2), causing a reduced formation of precursors of prostaglandins and thromboxanes.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical evaluation on the antioxidant activity of a copper(ii) complex based on lidocaine and ibuprofen amide-phenanthroline agents

Tabrizi

Dao

2019

RSC Adv.

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A new copper(II) complex, [Cu(LC)(Ibu-phen)(H 2 O) 2 ](ClO 4 ) 2 (LC: lidocaine, Ibu-phen: ibuprofen amidephenanthroline), was synthesized and characterized. The antioxidant activities of the free ligands and the copper(II) complex were evaluated by in vitro experiments and theoretical calculations using density functional theory (DFT). Structures of the ligand Ibu-phen and the complex were identified by 1 H and 13 C NMR, FT-IR spectroscopies, mass spectrometry, thermogravimetric analysis and elemental analysis. The antioxidant potentials of LC and Ibu-phen ligands as well as copper(II) complex were also evaluated by DPPHc, ABTSc + , HOc essays and EPR spectroscopy. The experimental results show that the radical scavenging activity (RSA) at various concentrations is decreased in the following order: copper(II) complex > ascorbic acid > LC > Ibu-phen. Structural and electronic properties of the studied compounds were also analyzed by DFT approach at the M05-2X/6-311++g(2df,2p)//M05-2X/LanL2DZ level of theory. ESP maps and NPA charge distributions show that the highly negative charge regions found on the N and O heteroatoms make these sites more favorable to bind with the central copper ion.Frontier orbital distributions of copper(II) complex indicate that HOMOs are mainly localized at Ibu-phen, while its LUMOs are distributed at LC. Based on natural bond orbitals (NBO) analyses, Cu(II) ion plays as electron acceptor in binding with the two ligands and two water molecules. Thermochemical properties including bond dissociation enthalpy (BDE), ionization energy (IE), electron affinity (EA), proton affinity (PA) characterizing three common antioxidant mechanisms i.e. hydrogen transfer (HT), single electron transfer (SET) and proton loss (PL) were finally calculated in the gas phase and water solvent for two ligands and the copper(II) complex at the same level of theory. As a result, the higher EA and lower BDE and PA values obtained for copper(II) complex show that the complex shows higher antioxidant potential than the free ligands. † Electronic supplementary information (ESI) available: 1 H, 13 C NMR spectra of ligand Ibu-phen, mass spectra of ligand Ibu-phen and copper(II) complex. Cartesian coordinates and molecular enthalpies of copper(II) complex structures for different multiplicities from 2 to 8 optimized at M05-2X/LanL2DZ level of theory in the gas phase. See View Article Online a IC 50 (50% concentration of inhibition for radical scavenging activity). Values are mean AE SD of triplicates.3326 | RSC Adv., 2019,9,[3320][3321][3322][3323][3324][3325][3326][3327][3328][3329][3330][3331][3332][3333][3334][3335] This journal is

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Section: Introductionmentioning

confidence: 99%

Experimental and theoretical evaluation on the antioxidant activity of a copper(ii) complex based on lidocaine and ibuprofen amide-phenanthroline agents

Tabrizi

Dao

2019

RSC Adv.

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“…The study of interaction of these complexes with DNA is carried out since DNA is considered as a primary pharmacological target of anticancer drugs. As the pyrenyl derivatives are capable of being act as a photosensitizer for complexes, the photo‐induced DNA and protein cleavage activity of the complexes has been explored. In addition, because of the crucial role of plasma protein in drug transport, efficacy and metabolism, the BSA binding properties of complexes have been carried out to understand drug‐protein interaction.…”

Section: Introductionmentioning

confidence: 99%

Biological and catalytic evaluation of Ru(II)‐p‐cymene complexes of Schiff base ligands: Impact of ligand appended moiety on photo‐induced DNA and protein cleavage, cytotoxicity and C‐H activation

Gopalakrishnan

Srinath

Baskar

et al. 2018

Applied Organom Chemis

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Two organometallic Ru(II)‐p‐cymene complexes of the type [Ru(η6‐p‐cymene)(L)Cl]PF6 1 and 2, where L is N,N‐bis(4‐isopropylbenzylidene)ethane‐1,2‐diamine (bien, L1) or N,N‐bis (pyren‐2‐ylmethylene)ethane‐1,2‐diamine (bpen, L2) have been prepared and characterized well. Because of appended pyrenyl groups in coordinated bpen ligand, the complex 2 exhibits higher DNA and protein binding than complex 1 in which isopropylbenzyl groups are incorporated. Interestingly, the luminescent characteristic complex 2 is unique in displaying DNA cleavage after light activation by UVA light at 365 nm through oxygen dependent mechanism. AFM analysis attests the photo‐induced DNA fragmentation ability of complex 2. Also, the complex 2 cleaves the protein after light exposure in a non‐specific manner suggesting that it can act as a protein photo cleaving agent. In contrast to the trend of DNA and protein interaction of complexes, the complex 1 exhibits cytotoxic activity against human breast carcinoma (MCF‐7) and liver carcinoma (HepG2) with potency higher than that of complex 2 due to enhanced hydrophobicity of isopropyl groups present in p‐cymene and bien ligands. Indeed, complex 2 is inactive against MCF‐7 and HepG2 cancer cell lines even up to 200 μM concentration. The AO/EB staining assay reveals that the complex 1 is able to induce late apoptotic mode of cell death in breast cancer cells, which is further confirmed by inter‐nucleosomal DNA cleavage. Furthermore, the complexes 1 and 2 are evaluated for their catalytic activities and found to be working well for the β‐carboline directed C–H arylation to afford the desired products in good yield (40–47%).

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“…Among these interactions, it is remarkable that the π-π stacking was between the Cp* and the benzene ring of benzothiazole moiety in complex 8[CO,S-Cl], which is reinforced by the C-H•••π interactions of the methyl groups of Cp* and the same benzene ring (Figure S5 and Table S6). Although these interactions involving Cp* are unusual and weak, some examples in complexes with other metal ions have been reported in the literature [70][71][72][73].…”

Section: Resultsmentioning

confidence: 99%

Targets, Mechanisms and Cytotoxicity of Half-Sandwich Ir(III) Complexes Are Modulated by Structural Modifications on the Benzazole Ancillary Ligand

Acuña

Rubio

Martı́nez-Alonso

et al. 2022

Cancers

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Cancers are driven by multiple genetic mutations but evolve to evade treatments targeting specific mutations. Nonetheless, cancers cannot evade a treatment that targets mitochondria, which are essential for tumor progression. Iridium complexes have shown anticancer properties, but they lack specificity for their intracellular targets, leading to undesirable side effects. Herein we present a systematic study on structure-activity relationships of eight arylbenzazole-based Iridium(III) complexes of type [IrCl(Cp*)], that have revealed the role of each atom of the ancillary ligand in the physical chemistry properties, cytotoxicity and mechanism of biological action. Neutral complexes, especially those bearing phenylbenzimidazole (HL1 and HL2), restrict the binding to DNA and albumin. One of them, complex 1[C,NH-Cl], is the most selective one, does not bind DNA, targets exclusively the mitochondria, disturbs the mitochondria membrane permeability inducing proton leak and increases ROS levels, triggering the molecular machinery of regulated cell death. In mice with orthotopic lung tumors, the administration of complex 1[C,NH-Cl] reduced the tumor burden. Cancers are more vulnerable than normal tissues to a treatment that harnesses mitochondrial dysfunction. Thus, complex 1[C,NH-Cl] characterization opens the way to the development of new compounds to exploit this vulnerability.

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The discovery of half-sandwich iridium complexes containing lidocaine and (pyren-1-yl)ethynyl derivatives of phenylcyanamide ligands for photodynamic therapy

Cited by 12 publications

References 72 publications

Experimental and theoretical evaluation on the antioxidant activity of a copper(ii) complex based on lidocaine and ibuprofen amide-phenanthroline agents

Experimental and theoretical evaluation on the antioxidant activity of a copper(ii) complex based on lidocaine and ibuprofen amide-phenanthroline agents

Biological and catalytic evaluation of Ru(II)‐p‐cymene complexes of Schiff base ligands: Impact of ligand appended moiety on photo‐induced DNA and protein cleavage, cytotoxicity and C‐H activation

Targets, Mechanisms and Cytotoxicity of Half-Sandwich Ir(III) Complexes Are Modulated by Structural Modifications on the Benzazole Ancillary Ligand

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