Article
Chemistry, Medicinal
Abdelrahman Mohamed, Mohamed Salah, Mariam Tahoun, Manuel Hawner, Ahmed S. Abdelsamie, Martin Frotscher
Summary: A novel approach for simultaneous inhibition of steroid sulfatase and 17 beta-hydroxysteroid dehydrogenase type 1 was explored. The designed compounds showed promising inhibitory effects and potential for the treatment of endometriosis and other estrogen-dependent diseases.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Review
Medicine, Research & Experimental
Anirban Goutam Mukherjee, Uddesh Ramesh Wanjari, Dhanushya Nagarajan, K. K. Vibhaa, V Anagha, P. Joshua Paul, T. Tharani Priya, Rituraj Chakraborty, Kaviyarasi Renu, Abhijit Dey, Balachandar Vellingiri, Abilash Valsala Gopalakrishnan
Summary: The highly active estrogen metabolism and receptor protein expression contribute to the elevated breast cancer rate in post-menopausal women. Letrozole, an aromatase inhibitor, is an effective endocrine medication used in the treatment of breast cancer. It can also stimulate ovulation in infertile pre-menopausal women. However, its potential benefits in fertility treatments have not been fully utilized.
Article
Neurosciences
Alev Selek, Zehra Seda Unal Halbutogullari, Cigdem Inci Aydemir, Berrin Cetinarslan, Zeynep Canturk, Ilhan Tarkun, Gulay Erman, Cansu Subasi, Karaoz Erdal
Summary: This study investigates the potential of using an aromatase inhibitor as a substitute for testosterone in treating prolactinomas. The findings reveal that the aromatase inhibitor can inhibit cell proliferation and induce apoptosis in prolactinoma cells, as well as reduce prolactin and estrogen levels.
MOLECULAR NEUROBIOLOGY
(2023)
Article
Physics, Applied
H. R. Barnard, G. R. Nash
Summary: The characteristics of four-layer chiral metamaterials, optically active in the mid-infrared region, have been studied through simulations and experiments. The spectral response of the materials can be tailored while maintaining the magnitude of circular dichroism relative to standard double layer metamaterials. Analysis shows that these four-layer structures offer greater design freedom in coupling than expected from simple consideration of double layer structures.
APPLIED PHYSICS LETTERS
(2021)
Article
Agriculture, Multidisciplinary
Yingying Gao, Xuejun Zhao, Xiaofang Sun, Zhen Wang, Jing Zhang, Lianshan Li, Haiyan Shi, Minghua Wang
Summary: The study established an effective analytical method for enantioselective detection of oxathiapiprolin and revealed that R-(-)-oxathiapiprolin exhibits higher bioactivity and preferential degradation compared to S-(+)-oxathiapiprolin. This suggests that the R-enantiomer may be a better choice in enhancing bioactivity and reducing pesticide residues at lower application rates.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Jing Ai, Xueliang Zhang, Te Bai, Qing Shen, Peter Oleynikov, Yingying Duan, Osamu Terasaki, Shunai Che, Lu Han
Summary: This study presents a general approach based on three-dimensional electron diffraction tomography for determining chiral hierarchical mesostructures, providing more precise and comprehensive identification.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Luke Hodson, Kevin J. Visagie, Michael-Phillip Smith, Leigh Loots, David Kuter, Tregen M. Snayer, Gareth E. Arnott
Summary: Inherently chiral calix[4]arenes with C-4-symmetry are rare and difficult to synthesise, but this study successfully obtained a high-yield product through a specific reaction. The use of a specific chiral group enabled the separation of the diastereomers formed, leading to the pure enantiomers.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Jie Wen, Lei Feng, Hongmei Zhao, Li Zheng, Pericles Stavropoulos, Lin Ai, Jiaxin Zhang
Summary: This study successfully established an unconventional enantiomeric discrimination method for hydantoin derivatives, representatives of five-membered N,N-heterocycles, and observed non-equivalent chemical shifts through H-1 NMR spectroscopy. Additionally, theoretical calculations were performed to understand the intermolecular interactions between chiral solvating agents and enantiomers.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jessica C. Neville, Michelle Y. Lau, Tilo Sohnel, Jonathan Sperry
Summary: Chitin-derived platforms have emerged as valuable chemical entities for nitrogenous fine chemicals construction independent of the Haber ammonia process. However, much of the research in this field has focused on achiral platforms, limiting the access to enantiopure, bio-based nitrogenous chemical space. In this study, dihydroxyethyl acetamidofuran (Di-HAF), a chiral synthon easily available from chitin, has been transformed into epi-leptosphaerin, a marine alkaloid. This work extends the concept of Haber-independent synthesis to enantiopure chemical space that is not routinely accessible from existing achiral platforms.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Agriculture, Multidisciplinary
Lianshan Li, Xiaofang Sun, Xuejun Zhao, Yudie Xiong, Beibei Gao, Jing Zhang, Haiyan Shi, Minghua Wang
Summary: The study established a new method to investigate the biological activity and degradation of mefentrifluconazole enantiomers against target fungi, revealing that R-(-)-mefentrifluconazole has higher bioactivity compared to S-(+)-mefentrifluconazole and exhibits stronger binding with the target protein.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Pei-Fang Chiu, I-Chun Lin, Yeh-Lin Lu, Chiao-Nien Chang, Hui-Yu Chan, Tzung-Shen Lin, Keng-Chang Tsai, Yves S. Y. Hsieh, Mei-Jou Chen, Mei-Hsiang Lin, Pi-Hui Liang
Summary: Inhibition of steroid sulfatase (STS) can decrease estrogen production, thereby suppressing tumor proliferation. In this study, twenty-one tricyclic and tetraheterocyclic coumarin-based derivatives were explored and evaluated for their STS enzyme kinetic parameters, docking models, and cytotoxicity towards breast cancer and normal cells. The tricyclic derivative 9e and tetracyclic derivative 10c were found to be the most promising irreversible inhibitors, with K-I values of 0.05 and 0.4 nM, and k(inact)/K-I ratios of 28.6 and 19.1 nM(-1)min(-1) on human placenta STS, respectively.
BIOORGANIC CHEMISTRY
(2023)
Review
Biotechnology & Applied Microbiology
Shumei Sun, Hao Zhang, Peicheng Zhong, Zhihong Xu
Summary: The combination of dydrogesterone and letrozole significantly reduces levels of VEGF, CA125, E2, P, IL-6, and TNF-a in patients with endometriosis compared to the control group. Additionally, the total effectiveness is higher in the experiment group. No significant difference was found in FSH and LH levels between the two groups.
BIOMED RESEARCH INTERNATIONAL
(2021)
Article
Chemistry, Medicinal
Hanan S. Anbar, Zahraa Isa, Jana J. Elounais, Mariam A. Jameel, Joudi H. Zib, Aya M. Samer, Aya F. Jawad, Mohammed El-Gamal
Summary: The STS enzyme plays a crucial role in the metabolism of steroid sex hormones and is associated with the pathophysiology of certain diseases. Successful STS inhibitor candidates like Irosustat have shown promise in treating specific cancers and neurodegenerative disorders, with reduced estrogenic side effects. Dual-acting molecules that inhibit STS and another synergistic mechanism may offer therapeutic efficiency.
EXPERT OPINION ON THERAPEUTIC PATENTS
(2021)
Article
Biochemistry & Molecular Biology
Chiao-Nien Chang, I-Chun Lin, Tzung-Sheng Lin, Pei -Fang Chiu, Yeh-Lin Lu, Manmath Narwane, I-Chen Liu, Yue Hng, Keng-Chang Tsai, Mei-Hsiang Lin, Yves S. Y. Hsieh, Mei-Jou Chen, Pi-Hui Liang
Summary: The study focuses on the synthesis and evaluation of compound inhibitors for steroid sulfatase, which showed that the introduction of chlorine substitution enhanced the inhibition of STS. The kinetic analysis revealed the high efficiency of irreversible inhibition for chloride-bearing compounds. The selected compounds also demonstrated safety and anticancer activity.
BIOORGANIC CHEMISTRY
(2022)
Review
Environmental Sciences
Ye Li, Jiyun Nie, Jia Zhang, Guofeng Xu, Hui Zhang, Mingyu Liu, Xiaoqin Gao, Bacha Syde Asim Shah, Ning Yin
Summary: Traditional evaluation methods may not accurately assess the properties of chiral pesticides. This study investigated the absolute configuration, bioactivity, ecotoxicity, and stereoselective degradation of penconazole enantiomers. The results provided new insights and emphasized the importance of risk assessments at the enantiomeric level for chiral pesticides.
SCIENCE OF THE TOTAL ENVIRONMENT
(2022)
Article
Chemistry, Physical
S. Ghidinelli, G. Longhi, S. Abbate, C. Haettig, S. Coriani
Summary: UV-vis absorption and magnetic circular dichroism spectra of naphthalene and its derivatives were simulated using CC2 and TD-DFT methods. CC2 simulations showed the best agreement with experimental data. Analysis of electric dipole and magnetic dipole transition moments helped interpret electronic transitions and Faraday B term inversion among naphthalene derivatives.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Chemistry, Physical
Simone Ghidinelli, Sergio Abbate, Ernesto Santoro, Sandra Belviso, Giovanna Longhi
Summary: This study utilized UV-vis absorption and MCD spectra to investigate the properties of different metal complexes, with TDDFT calculations yielding good matches with experimental spectra. Additionally, the observed red shift effect in thioalkyl compounds and the role of sulfur atoms in molecular orbitals were explained, highlighting the importance of these factors in spectroscopic studies.
JOURNAL OF PHYSICAL CHEMISTRY B
(2021)
Article
Chemistry, Inorganic & Nuclear
Martin Ravutsov, Georgi M. Dobrikov, Miroslav Dangalov, Rositsa Nikolova, Vladimir Dimitrov, Giuseppe Mazzeo, Giovanna Longhi, Sergio Abbate, Lorenzo Paoloni, Marco Fuse, Vincenzo Barone
Summary: A series of 1,2-disubstituted planar chiral ferrocenes were successfully synthesized through ortho-directed lithiation of chiral ferrocenesulfonamides and reaction with electrophilic reactants. The relative configurations of chemical groups were determined by NMR experiments and X-ray crystallography, while experimental ECD and VCD spectra were recorded and interpreted using quantum chemical computations.
Article
Chemistry, Multidisciplinary
Carlo Bravin, Giuseppe Mazzeo, Sergio Abbate, Giulia Licini, Giovanna Longhi, Cristiano Zonta
Summary: This communication focuses on the synthesis of a chiral supramolecular cage to bias the helicity of a perfluorinated carbon chain, monitoring the phenomenon of chiral induction through VCD experiments and DFT calculations.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Michela Lupi, Martina Onori, Stefano Menichetti, Sergio Abbate, Giovanna Longhi, Caterina Viglianisi
Summary: In this study, an efficient chemical resolution method was developed for the separation of racemic hydroxy substituted dithia-aza[4]helicenes. Enantiopure acids were used as resolving agents, leading to better diastereomeric separation. Highly optically pure products were obtained through subsequent manipulations.
Article
Chemistry, Physical
Giuseppe Mazzeo, Simone Ghidinelli, Renzo Ruzziconi, Marco Grandi, Sergio Abbate, Giovanna Longhi
Summary: Testing nine [2]paracyclo[2](5,8)-quinoliphane derivatives to find new simple organic molecules generating circularly polarized luminescence (CPL), the study observes asymmetry ratios g of the order 10^(-3) in luminescence, similar to the absorption case. TD-DFT calculations provide insight into the molecular orbitals responsible for transitions in the observed signals of these molecules, explaining the behaviors of the |g(lum)|/|g(abs)| ratios.
Article
Chemistry, Organic
Francesca Mangiavacchi, Giuseppe Mazzeo, Maria Chiara Graziani, Francesca Marini, Jozef Drabowicz, Ewelina Wielgus, Luca Sancineto, Giovanna Longhi, Riccardo Vivani, Sergio Abbate, Claudio Santi
Summary: In this study, the base induced activation of beta-naphthol was utilized for the synthesis of a novel 1,1'-diselanediylbis(naphthalen-2-ol), which was fully characterized using NMR and X-Ray analysis. The reactivity of this compound was investigated, leading to the discovery of a novel synthesis method for chiral selenium containing heterocycles. Chiroptical methods, specifically VCD and ECD, were successfully employed to determine the absolute configuration of these compounds, representing the first example reported for organoselenium derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Simone Ghidinelli, Marco Fuse, Giuseppe Mazzeo, Sergio Abbate, Giovanna Longhi
Summary: The MCD and induced CD spectra of N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyperylene-3,4:9,10-tetracarboxydiimide, also known as Lumogen Red 300 or ROT-300, have been recorded in both achiral and chiral solvents. The spectroscopic response in CD and MCD experiments is discussed, and DFT calculations satisfactorily predict both spectra.
Article
Chemistry, Physical
Valentina Pelliccioli, Francesca Cardano, Giacomo Renno, Francesca Vasile, Claudia Graiff, Giuseppe Mazzeo, Andrea Fin, Giovanna Longhi, Sergio Abbate, Alessia Rosetti, Claudio Villani, Guido Viscardi, Emanuela Licandro, Silvia Cauteruccio
Summary: This study reports the synthesis of a novel class of functionalized thia[6]helicenes and a thia[5]helicene, and investigates their configurational stability and photophysical properties. Experimental and theoretical studies confirmed the stability of selected thia[6]helicenes, while the pyrene-based thia[5]helicene was found to be unstable. The configuration assignment for one representative thiahelicene was established through the comparison between experimental and theoretical circular dichroism (CD) spectra.
Article
Chemistry, Physical
Marco Fuse, Giovanna Longhi, Giuseppe Mazzeo, Stefano Stranges, Francesca Leonel, Giorgia Aquila, Enrico Bodo, Bruno Brunetti, Carlo Bicchi, Cecilia Cagliero, Julien Bloino, Sergio Abbate
Summary: In this study, the VCD and IR spectra of chiral isomers of methyloxirane and methylthiirane were reinvestigated using experimental and theoretical approaches. Anharmonic corrections were taken into account to better understand the active anharmonic modes and the role of mechanical and electrical anharmonicity in determining the intensities of VCD and IR/NIR data.
JOURNAL OF PHYSICAL CHEMISTRY A
(2022)
Review
Biochemistry & Molecular Biology
Giovanna Longhi, Simone Ghidinelli, Sergio Abbate, Giuseppe Mazzeo, Marco Fuse, Stefan E. Boiadjiev, David A. Lightner
Summary: In this study, we review the research activities on the structural aspects of bilirubin (BR) and biliverdin (BV). The focus is on the exocyclic C=C bonds with mostly Z configurations and the overall conformation difference between BR and BV due to the presence or absence of the double C=C bond at C-10. In both cases, racemic mixtures of M or P configurations are present in achiral solutions, but imbalance between the two configurations can be easily achieved. Chiroptical spectroscopies, including electronic circular dichroism (ECD) and vibrational circular dichroism (VCD), are used to investigate chirally derivatized BR and BV molecules. Deracemization experiments of BR in the presence of serum albumin and anesthetic compounds are also discussed.
Article
Chemistry, Multidisciplinary
Marina Gonzalez-Sanchez, Mariia J. Mayoral, Violeta Vazquez-Gonzalez, Marketa Paloncyova, Irene Sancho-Casado, Fatima Aparicio, Alberto de Juan, Giovanna Longhi, Patrick Norman, Mathieu Linares, David Gonzalez-Rodriguez
Summary: Self-assembled nanotubes with distinct internal arrangements and properties are achieved through different supramolecular scenarios prior to polymerization, driven by chelate cooperativity and self-recognition motifs at the edges. The chosen supramolecular pathway for structurally related molecules with complementary nucleobases is determined by their propensity for specific cyclic structures through Watson-Crick pairing. These findings provide insight into the unpredictability and experimental evaluation of self-assembly pathways, as well as the design of functional nanomaterials with controlled helicity and chiroptical properties.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Giuseppe Mazzeo, Marco Fuse, Antonio Evidente, Sergio Abbate, Giovanna Longhi
Summary: Currently, circularly polarized luminescence (CPL) is mainly studied in the field of materials science, focusing on special organic molecules, polymers, metal complexes, and organic dyes. This study fills the gap by investigating the CPL of lycorine and narciclasine, which are abundant alkaloids and isocarbostyrils from the Amaryllidaceae family. The results reveal the occurrence of an excited-state intramolecular proton transfer (ESIPT) process in narciclasine, explaining the observed Stokes shift and CPL spectra. Computational studies using density functional theory (DFT) further illuminate the properties of lycorine and narciclasine.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Roberto Penasa, Federico Begato, Giulia Licini, Klaus Wurst, Sergio Abbate, Giovanna Longhi, Cristiano Zonta
Summary: The use of chiroptical techniques in chiral sensing is gaining popularity. Circular dichroism (CD) is commonly used, but vibrational CD (VCD), circularly polarized luminescence (CPL), and Raman optical activity (ROA) are emerging as innovative tools. This study reports the use of an anthracene-decorated tris(2-pyridylmethyl)amine zinc complex (TPMA) as a chiral sensor, using either CD or fluorescence detected circular dichroism (FDCD). The FDCD technique allows for determination of enantiomeric excess at low sensor concentrations. The limitations and possibilities of this methodology, particularly regarding probe specificity in the presence of contaminants, are discussed.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Sandra Belviso, Giulia Marsico, Roberta Franzini, Claudio Villani, Sergio Abbate, Giovanna Longhi
Summary: The spectroscopic, electrochemical, and chiroptical properties of chiral Ni(ii) and Pd(ii) complexes of [6]helicene thioethyl porphyrazine have been investigated. These complexes possess an extended aromatic moiety and have helical chirality, which make them suitable for potential pi-pi interactions with nanocarbons and optoelectronic applications. The research provides valuable insights for the development of new optoelectronic materials.
DALTON TRANSACTIONS
(2022)