Article
Chemistry, Multidisciplinary
Qixing Lu, Tao Wang, Qian Wu, Lijing Cheng, Han Luo, Lei Liu, Guobiao Chu, Lufeng Wang, Baosheng Li
Summary: In this study, a catalyst-free reaction of beta-OTf-substituted enamides with aromatics was developed to achieve aryl-substituted aza-1,4-dicarbonyl compounds, which can be transformed into aryl-imidazole, aryl-thiazole, and aryl-oxazole. This method provides a simple, efficient, clean, and scalable strategy for C-H heteroarylation of aromatics, and is compatible with various aromatics of varying complexities.
Article
Chemistry, Multidisciplinary
Thomas Hansen, Pascal Vermeeren, F. Matthias Bickelhaupt, Trevor A. Hamlin
Summary: The alpha-effect explains the enhanced reactivity of alpha-nucleophiles compared to normal nucleophiles, but the exact origin is still debated. Our analysis found that an alpha-nucleophile needs to have a small HOMO lobe and high energy HOMO to exhibit the alpha-effect.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xiaoxiao Lu, Lulu Li, Xiaoren Zhang, Bina Fu, Xin Xu, Dong H. Zhang
Summary: A comparison of atomistic dynamics between microsolvated and unsolvated reactions can reveal the precise role of solvent molecules and provide insights into how solvation influences chemical reactions. In this study, a full-dimensional analytical potential energy surface was developed for the F-(H2O) + CH3I reaction, enabling efficient dynamics simulations at a quantitatively accurate level. The computed S(N)2 reactivity suppression ratio of the monosolvated F-(H2O) + CH3I reaction exhibits an inverted-V shape as a function of collision energy, indicating the combined dynamical effects of interaction time, steric hindrance, and collision-induced dehydration. Furthermore, analysis suggests that the steric effect of the F-(H2O) + CH3I reaction mainly arises from dragging the F- anion away from the central C atom, rather than shielding F- from C. This study highlights the potential for rigorously investigating the role of solvents in more complex reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Physical
Xiangyu Wu, Chongyang Zhao, Jing Xie
Summary: Quantum chemistry calculations were used to study the competition between the solvent-induced HO--S(N)2 pathway and the normal HOO--S(N)2 pathway in the reaction between HOO- and CH3Cl. The results show that incremental hydration increases the barrier heights and favors the HOO--S(N)2 pathway.
Article
Chemistry, Physical
Xiaoyan Ji, Chongyang Zhao, Jing Xie
Summary: This study investigates a recently discovered S(N)2 reaction mechanism, the front-side complex (FSC) or halogen-bonded complex (XC) mechanism, which combines the traditional front-side attack and back-side attack Walden-inversion mechanisms. The XC pathway has a deeper well depth compared to the back-side attack for certain nucleophiles. The barriers of FSA and BSA paths increase with solvation, while the change in XTS depends on the nucleophile type.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Physical
Ibon Alkorta, Jose Elguero
Summary: The studied reactions represent microscopic analogs of Newton cradle, where the left and right molecules are attacked and leave respectively, while the central molecules remain unchanged. Symmetric and non-symmetric reactions with different molecular combinations and element variations have been explored.
CHEMICAL PHYSICS LETTERS
(2022)
Review
Chemistry, Organic
Brenno A. D. Neto, Marcos N. Eberlin, James Sherwood
Summary: The importance of solvent effects on multicomponent reactions is often overlooked, and understanding the influence of solvents on reactions is crucial for optimizing the reaction process.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Attila A. Dekany, Gyula Z. Kovacs, Gabor Czako
Summary: This study characterizes the stationary points along the Walden inversion, front-side attack, and double-inversion pathways of the S(N)2 reactions of X- + CH3Y and X- + SiH3Y. The research reveals the differences in competitive mechanisms and characteristics of the inversion pathways, front-side attack, and double inversion at the carbon and silicon centers.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Biochemical Research Methods
Rosana M. Lobayan, Roberto C. Bochicchio, Alejandro D. Marturet
Summary: This report deeply explores electron rearrangements in a chemical reaction case study. It focuses on the subtle description of electron distribution at both equilibrium and non-equilibrium conformations, particularly the determination of complex interaction patterns of two or four electrons in three centers. The results highlight the crucial importance of these interaction patterns in the charge transference process.
JOURNAL OF MOLECULAR GRAPHICS & MODELLING
(2022)
Article
Chemistry, Physical
Malte Fugel, Anneke Dittmer, Florian Kleemiss, Simon Grabowsky
Summary: The study reveals that the shape of the potential energy surface (PES) of gas-phase S(N)2 reactions at silicon is determined by the type of nucleophile, the leaving group, and the substituents bonded to silicon. It is also shown that leaving groups are stabilized by hydrogen bonding in certain systems, contributing to the shapes of the PESs of ClSiMe3Cl and CISi(OMe)(3)Cl in the gas phase.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Chemistry, Multidisciplinary
Yue Fu, Leonardo Bernasconi, Peng Liu
Summary: This computational approach utilizes AIMD simulations to evaluate glycosylation reaction mechanisms, providing complementary indicators such as free energy profiles, synchronicity of transition state structures, and time gaps to describe and predict glycosylation mechanisms accurately.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Immunology
Min Xu, Tong Wu, Zhaoxia Li, Guijie Xin
Summary: Using Two-Sample Mendelian randomization analysis, it was found that celiac disease, multiple sclerosis, rheumatoid arthritis, and type 1 diabetes have a causal association with non-alcoholic fatty liver disease (NAFLD), while Crohn's disease does not have a causal effect on NAFLD. The prevalence of NAFLD may be higher in patients with multiple sclerosis, rheumatoid arthritis, and type 1 diabetes than in the general population, highlighting the importance of monitoring NAFLD in these populations.
FRONTIERS IN IMMUNOLOGY
(2023)
Article
Chemistry, Physical
Xiangyu Wu, Shaowen Zhang, Jing Xie
Summary: In this study, the influence of solvent on the competing E2 and S(N)2 reactions was investigated by analyzing the reactions of microsolvated HO (H2O)(n) anions with CH3CH2X (X = Cl, Br, I). The results showed that the barrier heights of the reaction channels increased with incremental hydration and were correlated with several thermodynamic, geometric, and charge parameters. The inv-S(N)2 pathway was found to be favored over the anti-E2 pathway in the E2/S(N)2 competition.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Physical
Siwei Zhao, Gang Fu, Wenqing Zhen, Hongyi Wang, Meiling Liu, Li Yang, Jiaxu Zhang
Summary: In this study, the effects of nucleophiles on the gas-phase E2/SN2 competition were investigated using electronic structure calculations. It was found that as the nucleophile changes from OH- to I-, both SN2 and E2 reactions become more exothermic. Additionally, the study revealed the influence of ion-dipole complex formation on the competition and atomic-level mechanisms of E2/SN2 reactions.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Biochemistry & Molecular Biology
Fernando M. Lisboa, Josefredo R. Pliego
Summary: The reactivity of fluoride ion towards alkyl halides is influenced by the solvent environment. In polar aprotic solvents, it produces substantial E2 product, whereas in polar protic solvents it shows high selectivity for S(N)2 reactions. Addition of tert-butanol to acetonitrile solvent can modulate the reactivity and selectivity of TBAF. The TBAF(tert-butanol) complex plays a key role in increasing the S(N)2 selectivity.
JOURNAL OF MOLECULAR MODELING
(2022)
Article
Biochemistry & Molecular Biology
Urszula Kosikowska, Monika Wujec, Nazar Trotsko, Wojciech Plonka, Piotr Paneth, Agata Paneth
Summary: In this study, a library of fluorobenzoylthiosemicarbazides and their cyclic analogues was created and tested for antibacterial activity. The trifluoromethyl derivatives showed optimum activity against Gram-positive bacteria strains, suggesting their potential as allosteric d-alanyl-d-alanine ligase inhibitors.
Article
Biochemistry & Molecular Biology
Renata Smulik-Izydorczyk, Karolina Debowska, Michal Rostkowski, Jan Adamus, Radoslaw Michalski, Adam Sikora
Summary: This study investigates the pH-dependent kinetics of HNO reactions with glutathione, N-acetylcysteine, bovine serum albumin, and human serum albumin. The results show that the reaction of azanone with the anionic form of thiols is favored over reactions with the protonated form. Quantum mechanical calculations support the data presented in the study.
CELL BIOCHEMISTRY AND BIOPHYSICS
(2021)
Review
Biochemistry & Molecular Biology
Katarzyna Dziduch, Dominika Greniuk, Monika Wujec
Summary: Parasitic diseases remain a significant issue for mankind, becoming a major cause of chronic diseases worldwide. Factors such as population migration, pollution of the natural environment, and climate changes contribute to the rapid spread of these diseases. Efforts are being made to find effective antiparasitic drugs with minimal side effects due to the growing resistance of parasites to current medications.
Article
Biochemistry & Molecular Biology
Sara Janowska, Dmytro Khylyuk, Anna Bielawska, Anna Szymanowska, Agnieszka Gornowicz, Krzysztof Bielawski, Jaroslaw Noworol, Slawomir Mandziuk, Monika Wujec
Summary: We designed and synthesized 1,3,4-thiadiazole derivatives with different substituents at the C2 and C5 positions. The cytotoxic activity of these compounds was evaluated in MCF-7 and MDA-MB-231 breast cancer cells and normal fibroblast cells. The most potent anti-proliferative compound was found to be 2-(2-trifluorometylophenylamino)-5-(3-methoxyphenyl)-1,3,4-thiadiazole, which exhibited IC50 values of 49.6 μM and 53.4 μM against MCF-7 and MDA-MB-231 breast cancer cells, respectively. Importantly, the new compounds showed weaker cytotoxic activity towards normal cells compared to breast cancer cells. In silico studies suggested a potential multitarget mode of action for these compounds, with involvement of Caspase 3, Caspase 8, and BAX proteins.
Article
Biochemistry & Molecular Biology
Agnieszka Krzeminska, Jose-Emilio Sanchez-Aparicio, Jean-Didier Marechal, Agata Paneth, Piotr Paneth
Summary: Disaccharide complexes have shown promise as drug encapsulation and delivery candidates, with strong non-covalent stabilization through electrostatic interactions and hydrogen bonds. They are also biocompatible and biodegradable, making them excellent candidates for self-assembly smart materials.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Sara Janowska, Dmytro Khylyuk, Agnieszka Gornowicz, Anna Bielawska, Michal Janowski, Robert Czarnomysy, Krzysztof Bielawski, Monika Wujec
Summary: Based on previous work, we designed and synthesized 1,3,4-thiadiazole derivatives and evaluated their cytotoxic activity against breast cancer cells. The compounds displayed weak anticancer activity, with SCT-4 showing the most significant effect on MCF-7 breast cancer cells. Further investigation suggested a possible multitarget mode of action for the synthesized compounds, with a potential involvement of caspase 8.
Article
Chemistry, Organic
Monika Wujec, Rafal Typek
Summary: The novel compound 2-{[4-(4-bromophenyl)piperazin-1-yl)]methyl}-4-(3-chlorophenyl)-5-(4-methoxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione is synthesized efficiently using a three-step protocol. The structure of the product is confirmed by HRMS, IR, H-1, and C-13 NMR experiments.
Article
Biochemistry & Molecular Biology
Agata Sowinska, Michal Rostkowski, Agnieszka Krzeminska, Tzofia Englman, Faina Gelman, Agnieszka Dybala-Defratyka
Summary: LinB and DhaA are two well-known haloalkane dehalogenases that can convert various halogenated alkanes, including persistent pollutants. This study aimed to investigate the enzymatic dehalogenation of selected dibromo-and bromochloro-ethanes and propanes by LinB and DhaA using a computational approach. The results indicate that generalizations about the enzymatic process involving different ligands are not possible, even if the ligands are structurally similar. Small structural differences, such as changing the halogen substituent, can result in significant changes in the enzymatic process and the rate-limiting step.
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS
(2023)
Review
Biochemistry & Molecular Biology
Anna Skoczynska, Andrzej Lewinski, Mateusz Pokora, Piotr Paneth, Elzbieta Budzisz
Summary: This review examines the potential applications of Ru(II)/(III) ion complexes in medicine or pharmacy, which have shown greater potential in cancer chemotherapy than Pt(II) complexes with known side effects. Research on cancer cell lines and clinical trials on ruthenium complexes have received much attention. In addition to their antitumor activity, ruthenium complexes have displayed potential in other diseases such as type 2 diabetes, Alzheimer's disease, and HIV. The review also briefly discusses theoretical approaches to studying the interactions of Ru(II)/Ru(III) complexes with biological receptors for the rational design of ruthenium-based drugs.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Sara Janowska, Dmytro Khylyuk, Michal Janowski, Urszula Kosikowska, Paulina Strzyga-Lach, Marta Struga, Monika Wujec
Summary: The treatment of infectious diseases poses a challenge to the medical community due to the emergence of drug-resistant strains. Schiff bases, a promising class of compounds, were synthesized and tested for their antibacterial and antifungal activities. Compound RO4 exhibited the highest antifungal activity against Candida spp., with an MIC value of 62.5 μg/mL. The synthesized compounds were also evaluated for their toxicity on cell lines and their mechanism of action through molecular docking studies.
Article
Biochemistry & Molecular Biology
Pawel Hikisz, Ewelina Namiecinska, Piotr Paneth, Elzbieta Budzisz
Summary: This study aims to investigate the biological aspects and anticancer activity of arene-ruthenium(II) complexes. Additional testing was conducted to better understand the potential mechanism of antitumor activity, including membrane permeability studies, ROS/RNS assays, and DNA analysis. Lipophilicity and molecular docking studies were also conducted. The presented data may have practical implications in cancer treatment.
Article
Biochemistry & Molecular Biology
Sara Janowska, Sylwia Andrzejczuk, Piotr Gawrys, Monika Wujec
Summary: A series of novel Mannich bases were synthesized and evaluated for their antimicrobial activity against bacteria and yeasts. The compounds exhibited significant activity against Gram-positive bacteria, including staphylococci, as well as selected strains of Gram-negative bacteria. They also showed high fungistatic activity against Candida spp. yeasts. In addition, in silico studies suggested that the tested compounds have good oral bioavailability. Overall, these findings provide valuable data for further research on these compounds.
Review
Nutrition & Dietetics
Agnieszka Kopystecka, Ilona Koziol, Dominika Radomska, Krzysztof Bielawski, Anna Bielawska, Monika Wujec
Summary: Bog bilberry and bilberry are plants with antioxidant, anti-inflammatory, anti-cancer, and apoptosis-reducing activities, widely used as dietary supplements and components of sunscreen preparations.
Article
Oncology
Katarzyna Bogusiak, Marcin Kozakiewicz, Aleksandra Puch, Radoslaw Mostowski, Piotr Paneth, Jozef Kobos, Anita Kloss-Brandstaetter
Summary: By analyzing the isotopic composition of oral squamous cell carcinoma (OSCC) tissue, we can gain a better understanding of its biology, which may improve treatment outcomes.
Article
Biochemistry & Molecular Biology
Kinga Paruch, Anna Biernasiuk, Dmytro Khylyuk, Roman Paduch, Monika Wujec, Lukasz Popiolek
Summary: In this research, a series of acylhydrazones and 1,3,4-oxadiazoline derivatives were synthesized and tested for their antimicrobial activity. Some compounds showed promising activity against Gram-positive bacteria without cytotoxicity to normal cell lines. These compounds or their derivatives may be used in the future for the prevention and treatment of infections caused by pathogenic or opportunistic microorganisms.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
