4.5 Article

NHC-Ir(I) complexes derived from 5,6-dinitrobenzimidazole. Synthesis, characterization and preliminary evaluation of their in vitro anticancer activity

期刊

INORGANICA CHIMICA ACTA
卷 496, 期 -, 页码 -

出版社

ELSEVIER SCIENCE SA
DOI: 10.1016/j.ica.2019.119061

关键词

Cancer; Cytotoxic activity; N-heterocyclic carbene; Iridium complexes; Fluorinated complexes; Antioxidant properties

资金

  1. Programa de Becas Posdoctorales-DGAPA-UNAM [CJIC/CTIC/4751/2018]
  2. CONACYT [A1-S-33933, 629466]
  3. Programa de Catedras CONACYT-PRY
  4. PAPIIT-DGAPA-UNAM [PAPIIT IN207317]

向作者/读者索取更多资源

The design, synthesis, characterization and in vitro anticancer activity of a series of Ir(I) NHC complexes derived from 5,6-dinitrobenzimidazole is reported. The evaluation was performed in five human cancer cell-lines, namely glioblastoma (U-251), prostatic adenocarcinoma (PC-3), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7) and lung adenocarcinoma (SKLU-7), including healthy cells of African green monkey kidney (COS-7) for comparative purposes. The complexes exhibited better activity in comparison with the corresponding NHC ligand precursors. In particular, complex (4a) exhibited a good performance against PC-3 and SKLU-1 with IC50 values of 10.6 +/- 0.9 mu M and 10.4 +/- 1.5 mu M, respectively.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.5
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Chemistry, Inorganic & Nuclear

Antibacterial activity and molecular studies of non-symmetric POCOP-Pd (II) pincer complexes derived from 2,4-dihydroxybenzaldehyde (2,4-DHBA)

Alberto Aragon-Muriel, Bethsy A. Aguilar-Castillo, Ernesto Rufino-Felipe, Hugo Valdes, Lucero Gonzalez-Sebastian, Rebeca Nayely Osorio-Yanez, Yamil Liscano, Valente Gomez-Benitez, Dorian Polo-Ceron, David Morales-Morales

Summary: A series of non-symmetric POCOP-Pd(II) pincer complexes with aldehyde group were prepared and evaluated for their antibacterial activities. Complex 3-Pd, containing the aldehyde functionality, showed the highest activity against S. aureus ATCC 25923 strain.

POLYHEDRON (2022)

Article Chemistry, Multidisciplinary

Electronic properties and supramolecular study of selenoureas with fluorinated-NHC ligands derived from imidazo[1,5-a]pyridines

Luis Angel Turcio-Garcia, Hugo Valdes, Antonino Arenaza-Corona, Simon Hernandez-Ortega, David Morales-Morales

Summary: A series of selenourea compounds with fluorinated fragments were synthesized and their Se-77 NMR chemical shifts were studied. The presence of more fluorine atoms in the structure caused a downfield shift of the Se-77 signal, indicating higher pi-acidity in the N-heterocycle. The position of the fluorine atom also influenced the chemical shift, with the 3-position showing the highest downfield shift.

NEW JOURNAL OF CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Role of Metal Cations of Copper, Iron, and Aluminum and Multifunctional Ligands in Alzheimer's Disease: Experimental and Computational Insights

Nicolas Puentes-Diaz, Diego Chaparro, David Morales-Morales, Areli Flores-Gaspar, Jorge Ali-Torres

Summary: Alzheimer's disease (AD) is a common form of dementia and its causes are not fully understood. High concentration of certain metal cations has been linked to the development of AD and the production of reactive oxygen species that cause neuronal damage. Multifunctional ligands have been proposed as a potential treatment to prevent or reverse the damaging effects of these metal cations. This review discusses recent advances in understanding the role of metal cations and the development of multifunctional ligands for AD.

ACS OMEGA (2023)

Article Chemistry, Medicinal

Facile, Single-Step Synthesis of a Series of D-Ring Ethisterones Substituted with 1,4-1,2,3-Triazoles: Preliminary Evaluation of Cytotoxic Activities

Daniel Canseco-Gonzalez, Isaac Rodriguez-Victoria, Teresa Apan-Ramirez, Alejandro O. Viviano-Posadas, Juan S. Serrano-Garcia, Antonino Arenaza-Corona, Adrian L. Orjuela, Jorge Ali-Torres, Alejandro Dorazco-Gonzalez, David Morales-Morales

Summary: A series of D-ring ethisterones substituted with 1,4-1,2,3-triazoles were synthesized through click chemistry reactions. The new compounds were characterized by various spectroscopic techniques and their crystal structures were determined. The cytotoxic activities of these derivatives were evaluated against several human cancer cell lines, and compounds (3, X=Cl) and (5, X=I) exhibited promising activity against leukemia adenocarcinoma (K562) and lung adenocarcinoma (SKLU). DNA docking simulations suggested that all compounds interacted with DNA through crosslink intrstrand p-alkyl-like interactions.

CHEMMEDCHEM (2023)

Article Chemistry, Inorganic & Nuclear

Novel hybrid phosphinite-theophylline ligands and their Pd(II) complexes. Synthesis, characterization and catalytic evaluation in Suzuki-Miyaura couplings

Edgar Marin-Carrillo, Hugo Valdes, Simon Hernandez-Ortega, David Morales-Morales

Summary: Two Pd(II) complexes with bidentated [R'2(OR)P<^>P(OR)R'2] (OR = 7-(2,3-dihydroxypropyl)theophylline and R' = Ph for (1) and R' = iPr for (2)) ligands were synthesized and characterized. Their molecular structures were determined by single crystal X-ray diffraction analysis, confirming the chelating coordination of the phosphinite-theophylline ligand to the Pd(II) center. Complex (2) showed excellent catalytic activity in Suzuki-Miyaura Couplings, achieving yields of > 99% for the formation of C-C bonds under mild reaction conditions (50 degrees C, 50 W, 5 min, and 0.05 mol % of catalyst).

INORGANICA CHIMICA ACTA (2023)

Article Chemistry, Inorganic & Nuclear

Synthesis and preliminary in vitro cytotoxic activity of Pd(II) complexes including Salen- or Salphen-Ligands

Rafael Lopez-Sanchez, J. Roberto Pioquinto-Mendoza, Lucero Gonzalez-Sebastian, Ruben A. Toscano, Marcos Flores-Alamo, Maria Teresa Ramirez-Apan, Adrian L. Orjuela, Jorge Ali-Torres, David Morales-Morales

Summary: This study describes the synthesis of a series of Pd(II) (Pd-1-3) complexes with salen or salphen ligands. The complexes were characterized using standard spectroscopic techniques. The crystal structure analysis of complex Pd-3 revealed a distorted square planar environment for the palladium center. In addition, the in vitro cytotoxic activity of the palladium complexes Pd-1-3 against five human cancer cell lines was evaluated, and Pd-2 showed the best inhibitory activity against human prostatic adenocarcinoma (PC-3) with an IC50 of 3.8 +/- 0.4 µM. Docking calculations were also performed to support these results.

INORGANICA CHIMICA ACTA (2023)

Article Chemistry, Physical

New organotin(IV) complexes with a bis-acyl-hydrazone ligand: Synthesis, crystal structure and immobilization on magnetic mesoporous silica nanoparticles as a strategy in cancer therapy

Tahereh Sedaghat, Marjan Aminian, Soheila Abaee, Elham Hoveizi, Abbas Tarassoli, Azizollah Beheshti, David Morales-Morales

Summary: The new binuclear organotin(IV) complexes, (Me2Sn)2L ( 1 ) and (Ph2Sn)2L ( 2 ), were synthesized by reacting R2SnCl2 (R = Me or Ph) with bis(2-hydroxy-1-naphthaldehyde) succinic dihydrazone (H4L). The synthesized compounds were characterized by elemental analysis and IR, 1 H NMR, and 119Sn NMR spectroscopy. The crystal structure of complex 1 was determined by X-ray crystallography. Additionally, the dihydrazone ligand and its diphenyltin(IV) complex were immobilized on functionalized magnetic mesoporous silica nanoparticles and characterized using various techniques. The cytotoxicity of the synthesized compounds against A549 cancer cell lines was evaluated, and it was found that diphenyltin(IV)-loaded magnetic mesoporous silica nanoparticles showed the highest cytotoxic activity.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Article Pharmacology & Pharmacy

Ball-Milling Preparation of the Drug-Drug Solid Form of Pioglitazone-Rosuvastatin at Different Molar Ratios: Characterization and Intrinsic Dissolution Rates Evaluation

M. Fernanda Munoz Tecocoatzi, Jose C. Paez-Franco, Kenneth Rubio-Carrasco, Alejandra Nunez-Pineda, Alejandro Dorazco-Gonzalez, Ines Fuentes-Noriega, Alfredo R. Vilchis-Nestor, Lilian I. Olvera, David Morales-Morales, Juan Manuel German-Acacio

Summary: Ball-milling using neat grinding or liquid-assisted grinding with different solvents allowed the formation of various solid forms of pioglitazone hydrochloride (PGZ·HCl) and rosuvastatin calcium (RSV). By adjusting the molar ratios of the reactants, coamorphous forms with different stoichiometries were obtained. In addition, mixtures of solid forms coexisted with the coamorphous forms when the drug ratio was not stoichiometric. The dissolution profiles of these solid forms were evaluated, and a synchronized release of both drugs was observed. The coamorphous 2:1 form showed an improved dissolution rate compared to pure PGZ·HCl, which may be attributed to pH changes caused by the degradation processes of RSV.

PHARMACEUTICS (2023)

Article Chemistry, Medicinal

Diversity of Solid Forms Promoted by Ball Milling: Characterization and Intrinsic Dissolution Studies of Pioglitazone Hydrochloride and Fluvastatin Sodium Drug-Drug Systems

Marco Villeda-Villegas, Jose C. Paez-Franco, Guadalupe Coyote-Dotor, Alejandra Nunez-Pineda, Alejandro Dorazco-Gonzalez, Ines Fuentes-Noriega, Kenneth Rubio-Carrasco, Helen Toledo P. Jaldin, David Morales-Morales, Juan Manuel German-Acacio

Summary: A coamorphous salt in a 1:1 ratio of Fluvastatin sodium (FLV) and Pioglitazone hydrochloride (PGZ center dot HCl) can be prepared by ball milling through neat grinding (NG), while the salt-cocrystal continuum is preferably formed by liquid-assisted grinding (LAG) using ethanol (EtOH). Attempts to prepare the coamorphous salt from the salt-cocrystal continuum by neat grinding were unsuccessful. Ball milling by NG or LAG can access a great variety of solid forms (PGZ center dot HCl-FLV 1:1): coamorphous with hexane; physical mixture with ethyl acetate; salt-cocrystal continuum with EtOH; and immiscible components with water.

PHARMACEUTICALS (2023)

Review Chemistry, Inorganic & Nuclear

Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

Raul Colorado-Peralta, Jose Luis Olivares-Romero, Sharon Rosete-Luna, Oscar Garcia-Barradas, Viviana Reyes-Marquez, Delia Hernandez-Romero, David Morales-Morales

Summary: This article summarizes the efficient antimicrobial activity of copper complexes using thiazole and benzothiazole as ligands against different bacteria and fungi.

INORGANICS (2023)

Article Chemistry, Physical

Heptacoordinated lanthanide(III) complexes based on 2,6-bis(1H-benzo[d]imidazol-2-yl)pyridine ligands (bbp, bmbp and bdmbp): Computational calculations, luminescent properties and cytotoxic evaluation.

Antonio Cruz-Navarro, Sharon Rosete-Luna, Jose Maria Rivera, Mario Rodriguez, Angelina Flores-Parra, Silvia Castillo-Blum, David Morales-Morales, Raul Colorado-Peralta

Summary: Two new series of heptacoordinated lanthanide(III) nitrates complexes with bbp and bdmbp were synthesized and characterized. The complexes exhibited luminescent properties and coordinated with the lanthanide(III) ion in a bidentate manner. Cytotoxic activity studies showed moderate activity of bdmbp-based complexes against HeLa cell line. (c) 2023 Elsevier B.V. All rights reserved.

JOURNAL OF MOLECULAR STRUCTURE (2023)

Article Chemistry, Multidisciplinary

Pincer Ligands as Multifunctional Agents for Alzheimer's Copper Dysregulation and Oxidative Stress: A Computational Evaluation

Nicolas Puentes-Diaz, Diego Chaparro, David Morales-Morales, Jorge Ali-Torres, Areli Flores-Gaspar

Summary: Alzheimer's disease, characterized by β-amyloid plaque formation, metal ion dysregulation, and oxidative stress, is the most common type of dementia. This study evaluated the potential pharmaceutical activity of 26 pincer compounds in the context of AD's copper ion-related oxidative stress framework. The results suggest that two compounds have potential antioxidant activity, while five compounds show promise as distributor-like compounds for AD.

CHEMPLUSCHEM (2023)

Article Chemistry, Multidisciplinary

Arylation of aldehydes catalyzed by fluorinated NHC-Rh(i) complexes

Luis angel Turcio-Garcia, Hugo Valdes, Simon Hernandez-Ortega, Daniel Canseco-Gonzalez, David Morales-Morales

Summary: The synthesis and characterization of twelve Rh(i) complexes with fluorinated NHC ligands were described. The catalytic activity of these complexes in the arylation of aldehydes was found to be related to the number of fluorine atoms present in their structures. More fluorine atoms in the NHC ligand led to higher catalytic activity, likely due to the reduced electron-donating properties of the ligand.

NEW JOURNAL OF CHEMISTRY (2022)

Article Chemistry, Inorganic & Nuclear

Indirect photolysis of cysteine and thiourea in the presence of metal ions in the aquatic environment

Angela Lis, Viorica Gladchi, Gheorghe Duca, Sergey Travin

Summary: This work presents studies on the photochemical transformations of TU and Cys with the addition of Cu(II) or Fe(III) ions. The results show that the oxidation rate of the thiols increases significantly when Cu(II) or Fe(III) ions are added to the system. It has also been found that TU and Cys can form stable complex compounds with the studied metal ions. The oxidation rates of the thiols are found to depend on the radiation intensity and emission spectrum of the irradiation sources.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

New binuclear copper(I) complexes with dual bioactivity: Synthesis, structural characterization and biological assays against bacteria and cancer

Cristiane F. A. Teixeira, Estefane I. Teixeira, J. P. C. Nascimento, M. Amilcar Junior, L. M. C. Pinto, Anderson R. L. Caires, G. B. Alcantara, Ana C. Micheletti, Victor M. Deflon, Davi F. Back, Heveline Silva, Lucas Pizzuti, Gleison Antonio Casagrande

Summary: Novel binuclear heteroleptic copper(I) complexes based on mixed DPPE/thiocarbamoyl-pyrazoline ligands were synthesized and structurally characterized. These complexes exhibited similar structural behavior around the Copper(I) atoms and showed promising antimicrobial and anticancer activities.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Mononuclear Cu(I) halide complexes containing asymmetric diphosphine and diphenyl pyridyl monophosphine: Structures and photophysical properties

Chen Chen, Li Liu, Xin-Xin Zhong, Fa-Bao Li, Hai-Mei Qin

Summary: Thermally activated delayed fluorescent (TADF) Cu(I) halide complexes with short lifetimes and intense emissions were synthesized and characterized. These complexes exhibit intense green to yellow-green delayed fluorescence and are suitable for OLED devices.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Efficient alcohol electro-oxidation based on a 3D Ni(II)-MOF with centrosymmetric Ni6 cluster

Tian-Yu Zhang, Xue-Qian Wu, Heng-Yu Ruan, Yi Yuan, Le Wang, Ya-Pan Wu, Qing-Wen Han, Ruan Chi, Dong-Sheng Li

Summary: In this study, a novel Ni(II)-based metal-organic framework with good electrocatalytic oxidation performance was successfully synthesized, showing potential for direct alcohol fuel cells.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

X-ray structures, density functional theory study, DNA binding ability and micellization behaviour of decavanadates anions containing cationic organic moieties

Susanta Das Baishnab, R. N. Dutta Purkayastha, Waldemar Maniukiewicz, Rosa M. Gomila, Antonio Frontera

Summary: The synthesis, structure, and DNA binding ability of three decavanadate complexes containing cationic organic moieties were reported. The complexes were characterized by various techniques and their solid-state structures were analyzed. The complexes showed interesting assembly patterns and exhibited moderately strong intercalative binding with CTDNA. Additionally, their micellization behavior in the presence of the surfactant CTAB was studied.

INORGANICA CHIMICA ACTA (2024)

Review Chemistry, Inorganic & Nuclear

Isomorphous series of inorganic complexes and composite materials

Jubaraj B. Baruah

Summary: Isomorphous series are generated by replacing atoms or molecules to form materials with similar compositions. They allow modulation of structure and properties, and generate equivalent compositions with novel material properties. The study of stereo-electronic aspects of different equivalent compositions can improve the utility of the original composition.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Dna-binding and antiproliferative properties of Palladium(II) complexes with tridentate ligands

Kamelah S. Al-Rashdi, Bandar A. Babgi, Ehab M. M. Ali, Bambar Davaasuren, Abdul-Hamid M. Emwas, Mariusz Jaremko, Mark G. Humphrey, Mostafa A. Hussien

Summary: Tridentate ligands were used to synthesize a set of palladium complexes, which were characterized and found to have DNA and BSA binding abilities. The complexes also showed differences in anticancer activities.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Synthesis, structure and electrochemical properties of tris (3-phenylpyrazolyl)borato zinc(II) adducts with o-semiquinonate ligands

Diane Isaacs, Chandler Cox, Mark A. Bezpalko, W. Scott Kassel, William G. Dougherty

Summary: The structure and electrochemical properties of zinc(II) complexes with a face-capping ligand have been investigated, revealing the effect of the ligand on bound semiquinonate (SQ) radicals. The substitution pattern of the SQ ring plays a crucial role in determining the fate of the bound SQ radicals. Additionally, the protective pocket formed by the ligand's phenyl substituents is unable to prevent decomposition of SQ radicals with minimal steric bulk, suggesting that substitution of the SQ ring is the main contributor to their stabilization.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Self-adjusting coordination of carboxylate for constructing stable 4-con-nected tetrazolate porous frameworks with luminescence

Xingliang Chen, Zhiqiang Jiang

Summary: Here, a series of zinc tetrahedral tetrazolate frameworks (Zn-TTFs) are presented, and it is demonstrated that rotation of carboxyl group can generate structural diversity. Compound 3 exhibits a unique zeolite-like structure, while compound 4 shows both super acid and alkali resistance.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Geometric control of Cu, Ni and Pd complexes in the solid state via intramolecular H-bonding interactions

Ankita Puri, Allison Mcaninch, Sheng Shu, Khashayar Rajabimoghadam, Maxime A. Siegler, Marcel Swart, Isaac Garcia-Bosch

Summary: In this article, the synthesis and characterization of copper, nickel, and palladium complexes bound by bidentate ligands derived from ortho-phenylenediamine are described. The complexes contain tunable H-bond donors and their crystal structures reveal intramolecular H-bonding interactions between the ligand scaffolds. Variations in the coordination sphere led to the isolation of the complexes in square-planar or twisted pseudo-tetrahedral geometries. Structural analysis showed that intramolecular H-bonding interactions can be altered by disrupting the bonds between countercations, solvent of crystallization, and ligand scaffold, resulting in changes in the geometry of the complexes. DFT calculations confirmed that Cu complexes prefer twisted geometries while Ni and Pd complexes favor square-planar geometries.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Exploring the copper(II) coordination to 2′-hydroxy-4-benzyloxychalcone analogues and their potential pharmacological applications

Laiane dos Santos Oliveira, Pedro Henrique de Souza Guarda, Leticia Bazilio Rosa, Gustavo Clauss Rodrigues, Daniele Daiane Affonso, Joao Ernesto de Carvalho, Igor Andrade Santos, Mark Harris, Douglas Hideki Nakahata, Jose Ricardo Sabino, Danilo Ciccone Miguel, Ana Lucia Tasca Gois Ruiz, Ana Carolina Gomes Jardim, Camilla Abbehausen

Summary: Chalcones are chemical precursors of flavonoids that have various biological properties. In this study, novel copper(II)-2'-hydroxy-4-benzyloxychalcone complexes were synthesized and evaluated for their antileishmanial, antiproliferative, and antiviral activities. The results demonstrated that these complexes showed potential effects against tumor cells, leishmania parasites, and SARS-CoV-2 virus. The study also highlighted the influence of ligand structure on biological activity.

INORGANICA CHIMICA ACTA (2024)

Review Chemistry, Inorganic & Nuclear

Investigating the interactions of carbon nuclei in di- and tri-butyltin carboxylates: A comprehensive review of 13C NMR spectra

Archana Thakur, Harpreet Kaur, Vishal Tyagi

Summary: This review article discusses the findings of research on the 13C NMR spectra of di- and tri-butyltin carboxylates, highlighting the importance of 13C NMR chemical shifts in determining the chemical surroundings of carbon nuclei and their role in structure elucidation.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Studies on Structure, optical and magnetic properties of Cd, Zn, Mn and Co complexes of terpyridine ligand

Qiang Zhao, Qi-Yang Li, Zhi Shen, Guo Zang, Wen-Jun Lv

Summary: In this study, five metal complexes were synthesized using a solvothermal reaction and their structures were analyzed by single crystal X-ray diffraction. Fluorescence and magnetic properties of some complexes were also investigated.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

BODIPY-ruthenium(II) polypyridyl complexes: Synthesis, computational, spectroscopic, electrochemical, and singlet oxygen studies

Jeremy Erb, Darcy Setter, Jake Swavey, Frederick Willits, Shawn Swavey

Summary: Three BODIPY-Ru(II) complexes were synthesized by coordinating [Ru(bpy)2Cl]+ complexes to BODIPY ligands. The spectroscopic and electrochemical properties of the complexes were characterized. The complexes exhibited intense absorption peaks due to the pi pi* transitions localized on the BODIPY core, and additional charge transfer transitions associated with the metal center. The complexes showed significant singlet oxygen generation and were able to induce photo-nicking of DNA.

INORGANICA CHIMICA ACTA (2024)

Article Chemistry, Inorganic & Nuclear

Functional mimic for catechol oxidase and phenoxazinone synthase: Structural, spectral, electrochemical and catalytic properties of mononuclear copper(II) complex

Sahin Reja, Dilip Sarkar, Kaushik Sarkar, Deboshmita Mukherjee, T. K. S. Fayaz, Palash Sanphui, Rajesh Kumar Das

Summary: A promising bioinspired metallocatalyst has been produced and characterized, showing high catalytic activity in oxygen dependant enzymatic radical pathway. The catalyst also exhibits inter and intra molecular H-bonding and C-H-pi interactions.

INORGANICA CHIMICA ACTA (2024)