Article
Pharmacology & Pharmacy
Patricia Fernandez de Larrinoa, Jordan Parmentier, Antoine Kichler, Thierry Achard, Monique Dontenwill, Christel Herold-Mende, Sylvie Fournel, Benoit Frisch, Beatrice Heurtault, Stephane Bellemin-Laponnaz
Summary: A novel series of platinum(II) complexes modified with the mitochondria targeting group triphenylphosphonium were synthesized, which showed significantly higher anticancer activity on cancer stem cell line compared to oxaliplatin. Mechanistic studies revealed that these complexes altered mitochondrial function and induced atypical cell death.
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2023)
Article
Chemistry, Applied
Vanessa Vethacke, Vanessa Claus, Martin C. Dietl, Daniel Ehjeij, Arne Meister, Jonas F. Huber, Leon K. Paschai Darian, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
Summary: A variety of unsymmetric diaryl gold N-acyclic carbene (NAC) complexes were successfully synthesized by three different methods, allowing access to new complexes and overcoming previous limitations in the isonitrile route. These new complexes also proved to be successful as pre-catalysts in gold-catalyzed phenol synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Pharmacology & Pharmacy
Jose C. Paez-Franco, Miriam R. Zermeno-Ortega, Carmen Myriam de la O-contreras, Daniel Canseco-Gonzalez, Jesus R. Parra-Unda, Alcives Avila-Sorrosa, Raul G. Enriquez, Juan M. German-Acacio, David Morales-Morales
Summary: Fluorination of pharmaceutical agents is crucial for modifying their pharmacological profiles and addressing the limitations of metallodrugs, ultimately enhancing their potential anticancer activity.
Article
Chemistry, Organic
Killari Satyam, Jakkula Ramarao, Surisetti Suresh
Summary: The NHC-catalyzed intramolecular benzoin condensation-oxidation allows for the expedient synthesis of diverse cyclic 1,2-diketones incorporated in dibenzo-fused seven-membered heterocycles in good to excellent yields under ambient conditions. The transformation appears to proceed through the benzoin intermediate followed by aerobic oxidation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Physical
Ricardo J. Alves, Laize Zaramello, Elvis N. Nishida, Frank H. Quina, Bruno S. Souza
Summary: In this study, we investigated the transient formation of N-heterocyclic carbenes (NHCs) in zwitterionic imidazolium sulfonate surfactants in a water environment. The formation of NHCs was accelerated above the critical micelle concentration, due to increased local concentration of hydroxide or deuteroxide ions. The rate of NHC formation could be controlled by the anions of added salts, which also affected the selectivity of anion binding to the micelle surface. The NHCs generated at the micelle surface promoted the selective oxidation of 4-nitrobenzaldehyde, demonstrating the importance of micellar microenvironment in controlling reactivity and selectivity in aqueous media.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Article
Oncology
Lara Massai, Luigi Messori, Andrea Carpentieri, Angela Amoresano, Chiara Melchiorre, Tania Fiaschi, Alessandra Modesti, Tania Gamberi, Francesca Magherini
Summary: In this study, the mode of action of Au(NHC) and Au(NHC)(2)PF6 was investigated, identifying common cellular targets while confirming their different influence on mitochondrial function.
CANCER CHEMOTHERAPY AND PHARMACOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Ashmita Singh, A. K. Narula
Summary: A facile method for the amidation of aldehydes by a cascade approach has been developed using NHC as the catalyst and NHS as the mediator. The method utilizes TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS to form active esters, which were easily converted into amides. The drug moclobemide was successfully synthesized using this methodology to demonstrate its practical utility.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Biochemical Research Methods
Fady Nahra, Nikolaos Tzouras, Alba Collado, Steven P. Nolan
Summary: N-heterocyclic carbene gold(I) chloride and hydroxide complexes are commonly used as synthetic reagents and efficient catalysts. This study describes a straightforward and practical method for synthesizing mononuclear gold complexes with high yields, as well as the synthesis of a mononuclear gold(I) hydroxide complex and an improved synthesis method for a dinuclear gold(I) hydroxide complex. This methodology offers advantages such as the use of sustainable reaction solvents and commercially available starting materials.
Article
Chemistry, Multidisciplinary
Yunquan Man, Xiaojun Zeng, Bo Xu
Summary: We have developed an efficient N-heterocyclic carbene (NHC)-catalyzed thioesterification of aldehydes using N-thiosuccinimides as the thiolation reagent. This method allows easy access to highly functionalized thioesters and demonstrates good chemical yields and functional group tolerance.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Lakshmikanta Maity, Sahadev Barik, Raju Biswas, Ramalingam Natarajan, Joydev Dinda
Summary: In this study, the synthesis, structures, luminescent properties, and electrochemistry of gold(III)-N-heterocyclic carbene (NHC) complexes with 2,2'-bipyridine (bpy) or 1,10'-phenanthroline (phen) were investigated. The presence of NHC significantly enhanced the emission properties of the complexes.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Rahat Gupta, Priya Sahni, Salil K. Jana, Anshul Negi, Amlan K. Pal
Summary: In this study, two novel deep-blue Ir-NHC emitters were synthesized with strategically designed pro-carbenic imidazolium ligands incorporating a heavy bromine atom. These emitters exhibited enhanced emission properties in both solution and film forms, with a 15 times higher photoluminescence quantum yield compared to benchmark complexes.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Sofie M. P. Vanden Broeck, Catherine S. J. Cazin
Summary: This review focuses on manganese complexes bearing N-heterocyclic carbene (NHC) ligands. The complexes exhibit different properties in various oxidation states and are widely used in catalytic reactions, particularly in CO2 reduction, hydrosilylation and alkylation.
Article
Chemistry, Inorganic & Nuclear
Thomas Scattolin, Andrea Piccin, Matteo Mauceri, Flavio Rizzolio, Nicola Demitri, Vincenzo Canzonieri, Fabiano Visentin
Summary: Newly synthesized palladium allyl complexes exhibit lower antiproliferative activity, with similar anticancer activity in two ovarian cancer cell lines, suggesting a different mechanism of action compared to platinum-based anticancer drugs. Some compounds show lower cytotoxicity on normal cells and higher selectivity towards cancer cells. Comparing the IC50 values of NHC/PTA complexes and their trifluoromethyl congeners indicates similar antiproliferative activity against cancer cells, but the absence of the CF3 group decreases selectivity towards them.
Article
Biochemistry & Molecular Biology
Carla Rizzo, Sara Amata, Ivana Pibiri, Andrea Pace, Silvestre Buscemi, Antonio Palumbo Piccionello
Summary: The incorporation of fluorine atoms or heterocyclic moieties into drug structures is a common pattern in medicinal chemistry. The combination of these two features is consistently observed in newly synthesized molecular entities with diverse biological activities, as evidenced by the increasing number of Fluorinated heterocyclic compounds approved by the FDA as drugs. This review highlights the biological activity and synthetic aspects of 33 recently FDA-approved fluorinated heterocyclic drugs from 2016 to 2022.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Maria Gil-Moles, Cillian O'Beirne, Igor V. V. Esarev, Petra Lippmann, Matthias Tacke, Jindrich Cinatl, Denisa Bojkova, Ingo Ott
Summary: The ongoing SARS-CoV-2 pandemic has led to a high demand for innovative antiviral drugs. In this study, silver NHC complexes with chloride or iodide ligands were found to be potent inhibitors of the SARS-CoV-2 papain-like protease (PLpro), but inactive against another SARS-CoV-2 protease, 3C-like protease (3CL(pro)). Mechanistic studies showed that the complexes could remove zinc from the zinc binding domain of PLpro, which was a relevant factor for their activity. In addition, enzyme kinetic experiments revealed that the complexes were uncompetitive inhibitors, offering advantages in selectivity. The silver NHC complexes with iodide ligands showed low or no host cell toxicity and showed strong effects on viral replication in SARS-CoV-2-infected cells, making them promising candidates for future antiviral drugs.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
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, Medicinal
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.
Article
Chemistry, Inorganic & Nuclear
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
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
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
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.
Article
Chemistry, Medicinal
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.
Review
Chemistry, Inorganic & Nuclear
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.
Article
Chemistry, Physical
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
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.
Article
Chemistry, Organic
Raul Colorado-Peralta, Sonia Araceli Sanchez-Ruiz, Angelina Flores-Parra
Summary: This paper reports the structure and reactivity of a series of compounds derived from easily accessible molecules, and characterizes them using various analytical and spectrometric techniques. The results show that small variations in stoichiometry and reaction conditions significantly influence the obtained products.
