Article
Biochemistry & Molecular Biology
Daniel Pecorari, Andrea Mazzanti, Michele Mancinelli
Summary: In this study, a lactone-atorvastatin prodrug with atropisomeric features was successfully synthesized. Conformational and experimental studies were conducted to assess the stability of the chiral axis, and docking calculations were used to evaluate the continuous inhibition of a library of atorvastatins. The best candidate was fully synthesized, yielding a thermally stable atropisomeric lactone-atorvastatin. Chiroptical ECD spectroscopy coupled with TD-DFT calculations were used to determine the absolute configuration of the chiral axis of the atropisomers.
Article
Chemistry, Multidisciplinary
Michael Gock, Michael Lutter, Anna Pintus, Dieter Schollmeier, Massimiliano Arca, Vito Lippolis, Klaus Jurkschat
Summary: The phosphorus-containing aryllithium compound reacted with various reagents to yield aryldiphenylphosphane chalcogenides and benzoxaphos-phaphospholes, which were characterized structurally.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Shitian Jiang, Yingxue Jin, Rui Yan, Zhiqiang Wang
Summary: In this study, a comprehensive structural search and calculation of the Lorlatinib molecule were carried out using theoretical calculations, showing good agreement between calculated values and experimental results. Furthermore, reliable vibrational assignments of the compound were determined based on potential energy distribution and characteristic vibrational absorption bands in the IR spectra.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Biochemistry & Molecular Biology
Tibor Kovacs, Ildiko Lajter, Norbert Kusz, Zsuzsanna Schelz, Noemi Bozsity-Farago, Aniko Borbas, Istvan Zupko, Georg Krupitza, Richard Frisch, Judit Hohmann, Andrea Vasas, Attila Mandi
Summary: A new flexible germacranolide (1, lobatolide H) was isolated from the aerial parts of Neurolaena lobata. The structure elucidation was performed by classical NMR experiments and DFT NMR calculations. Lobatolide H exhibited remarkable antiproliferative activity against human cervical tumor cell lines with different HPV status (SiHa and C33A), induced cell cycle disturbance, and showed a substantial antimigratory effect in SiHa cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Hannah Siera, Saber Mehrparvar, Jonas Fax, Mathis Kreuzahler, Gebhard Haberhauer
Summary: Size and shape are crucial for the function and properties of a molecular system. However, existing methods for determining distances within a molecule have limitations. In this study, we introduce a molecular spring and demonstrate that C-13 NMR spectroscopy can accurately measure distances within macrocycles in the range of 10 angstrom. We also discover a previously overlooked phenomenon of thermal shrinking, which can potentially be used to alter the function of a system by changing its length.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Iran Rojas-Leon, Gelen Gomez-Jaimes, Pedro Montes-Tolentino, Wolf Hiller, Hazem Alnasr, Braulio Rodriguez-Molina, Iran F. Hernandez-Ahuactzi, Hiram Beltran, Klaus Jurkschat, Herbert Hopfl
Summary: Hydrolysis reactions of di- and trinuclear organotin halides resulted in large novel cage compounds containing Sn-O-Sn bridges, with octanuclear tetraorganodistannoxanes showing double-ladder motifs. Among them, the co-crystal 2.0.48 I-2 exhibited the largest spacing reported to date for distannoxane-based double ladders. DFT calculations were conducted for both hexanuclear cage compound and a related octanuclear congener alongside experimental work.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Martin Dracinsky
Summary: This study thoroughly analyzes the large deviations in predicted hydrogen and carbon chemical shifts of a series of solid pyridinium fumarates. The influence of geometry optimization protocol and computational level on the accuracy of predicted chemical shifts is investigated, with improvements suggested for proton chemical-shift predictions through the use of computationally demanding hybrid functional for geometry optimization.
Article
Biochemistry & Molecular Biology
Alessia Ciogli, Andrea Fochetti, Andrea Sorato, Giancarlo Fabrizi, Nunzio Matera, Andrea Mazzanti, Michele Mancinelli
Summary: The dynamic behavior of di-aryls-pyrano-chromenes was investigated using DFT calculations. The presence of two ortho-substituted aryls substituents and the symmetry of the chromene scaffold result in the formation of two syn/anti diastereoisomers and conformational enantiomers with varying rotational barriers. Experimental energy barriers were determined through techniques such as Dynamic NMR, Dynamic HPLC, or kinetic studies, and the relative conformations and configurations were derived using NOESY-1D experiments. Atropisomeric pairs were resolved in certain scenarios and their absolute configuration was assigned using the ECD/TD-DFT method.
Article
Chemistry, Medicinal
Jared S. Wood, William H. Gordon, Jeremy B. Morgan, R. Thomas Williamson
Summary: Researchers discovered that cannabicitran, a compound found in cannabis, is a mixture of enantiomers, raising questions about its enzymatic origin. This study reports the isolation and absolute configuration of (-)-cannabicitran and (+)-cannabicitran, and discusses several possible scenarios for their production in plants and during extraction processes.
Article
Chemistry, Organic
Soon-Kit Wong, Joanne Soon-Yee Yeap, Chun-Hoe Tan, Kae-Shin Sim, Siew-Huah Lim, Yun-Yee Low, Toh-Seok Kam
Summary: Three new bisindole alkaloids were isolated from the stem bark extract of Malayan Kopsia arborea, with arbolodinine B showing significant cytotoxic effects against various human cancer cell lines.
Article
Biochemistry & Molecular Biology
Patryk Rybczynski, Anna Kaczmarek-Kedziera, Alex Iglesias-Reguant, Damian Plazuk, Borys Osmialowski
Summary: The tautomeric equilibrium of a series of 1-benzamidoisoquinoline derivatives was investigated using NMR spectroscopy and computational chemistry. The substitution effect could control the equilibrium between different tautomers, with the relative content of the amide form varying depending on the substituent. Unlike 2-phenacylquinoline derivatives, the most stable tautomer in the 1-benzamidoisoquinoline series was an amide, except for the two most electron-accepting substituents. The inclusion of explicit solvent was necessary to reproduce the experimental tendencies observed in this system, particularly for the formation of strong intermolecular hydrogen bonds.
Article
Chemistry, Multidisciplinary
Antonio J. LaPorte, Jack E. Feldner, Jan C. Spies, Tom J. Maher, Martin D. Burke
Summary: Multifunctional organoboron compounds enable the generation of complex, Csp(3)-rich small molecules, and boron-containing functional groups can modify the reactivity of α-radicals. Boronic esters with vacant p-orbitals stabilize α-radicals through delocalization of spin density into the empty orbital. This study demonstrates that coordinatively saturated MIDA and TIDA boronates stabilize secondary alkyl α-radicals via σ(B-N) hyperconjugation, allowing for site-selective C-H bromination.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
A. L. Buzlukov, N. Medvedeva, D. Suetin, A. Serdtsev, Y. Baklanova, S. F. Solodovnikov, A. P. Tyutyunnik, T. A. Denisova, O. A. Gulyaeva
Summary: The type and concentration of M element in alluaudite-type compounds play a crucial role in the sodium diffusion process, with higher concentration and charge of M element enhancing sodium mobility. Additionally, sodium dynamics increase with the size of M ion.
JOURNAL OF SOLID STATE CHEMISTRY
(2021)
Article
Chemistry, Physical
Woo-Ok Jung, Binh Khanh Mai, Minjin Yoo, Samuel W. J. Shields, Jason R. Zbieg, Craig E. Stivala, Peng Liu, Michael J. Krische
Summary: The mechanism of pi-allyliridium C,O-benzoate-catalyzed allylic amination was studied using various methods. The reaction showed first-order dependence on catalysts and fractional-order dependence on amines. The intervention of cesium-bridged amine dimers and the formation of cesium amide nucleophiles were observed.
Article
Chemistry, Multidisciplinary
Yongqiang Xu, Zhigang Ni, Yao Xiao, Ziwei Chen, Sisi Wang, Lizhi Gai, You-Xuan Zheng, Zhen Shen, Hua Lu, Zijian Guo
Summary: In this study, a series of helical beta-isoindigo-based B-O-B bridged aza-BODIPY analogs were synthesized conveniently. These compounds exhibited excellent spectroscopic and chiroptical properties, achieving tunable circularly polarized luminescence with the highest luminescence dissymmetry factor (g(lum)) of 1.3x10(-3) and a CPL brightness (B-CPL=11.5 M-1 cm(-1)) in the near-infrared region.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Gloria A. Suarez-Ortiz, Rodrigo Hernandez-Correa, Melissa D. Morales-Moreno, Ruben A. Toscano, Maria Teresa Ramirez-Apan, Armando Hernandez-Garcia, Manuel Amezquita-Valencia, Daniela Araiza-Olivera
Summary: A series of new chiral rhenium complexes were synthesized and fully characterized. The experiments revealed that the chirality of both the metal and ligand significantly influenced the cytotoxicity.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Organic
Elihu Bautista, Sarahi Lozano-Gamboa, Mabel Fragoso-Serrano, Jose Rivera-Chavez, Luis A. Salazar-Olivo
Summary: A new pseudoguaiane sesquiterpenoid was isolated from the roots of Jatropha dioica, along with known diterpenoids. The new compound exhibited no cytotoxicity against cancer cell lines, but a mixture of other compounds enhanced sensitivity to vinblastine.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Lilian Dolores Chel-Guerrero, Matteo Scampicchio, Giovanna Ferrentino, Ingrid Mayanin Rodriguez-Buenfil, Mabel Fragoso-Serrano
Summary: The by-products of Capsicum chinense, a medicinal herb known as habanero pepper, show potential in anti-proliferative activity and cytotoxicity modulation, particularly the extracts from leaves and stems grown on black soil, which exhibit significant effects against colorectal cancer and breast cancer.
APPLIED SCIENCES-BASEL
(2022)
Article
Plant Sciences
Armando Moreno-Velasco, Pedro de Jesu's Flores-Tafoya, Mabel Fragoso-Serrano, Suzana Guimaraes Leitao, Rogelio Pereda-Miranda
Summary: This study isolated and identified three undescribed resin glycosides from Operculina hamiltonii, a plant native to the north and northeast region of Brazil. These compounds were found to significantly enhance cytotoxicity against breast carcinoma cells when combined with the anticancer agent vinblastine, suggesting their potential for drug repurposing in chemotherapy.
JOURNAL OF NATURAL PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Jhon F. Castaneda-Gomez, Suzana Guimaraes Leitao, Rogelio Pereda-Miranda
Summary: Scarlet morning glory is an ornamental vine with numerous beneficial properties including oxytocic, cytotoxic, antipsychotic, anti-inflammatory, antioxidant, and antimicrobial effects. A study on the glycosidic acids isolated from the resin glycosides of the plant revealed the presence of hederifolic acids A-D which are heptaglycosides and hexaglycosides connected to specific fatty acid aglycones. The findings also showed that hederifolic acids B and D are dehydroxylated homologs of hederifolic acids A and C at C-3 of the fatty acid aglycones, respectively.
Review
Chemistry, Medicinal
Rogelio Pereda-Miranda, Elihu Bautista, Lucero Martinez-Fructuoso, Mabel Fragoso-Serrano
Summary: Structural elucidation and absolute stereochemistry determination of natural plant products, specifically chiral bioactive metabolites, is a crucial step in pharmacognosy and phytochemistry research. Various methods, both direct and indirect, have been established to solve the absolute configuration of these compounds. This review provides an overview of the most practical methods used in assigning the absolute stereochemistry of natural plant products, with a focus on multi-chiral center bioactive small molecules from diverse flora in Brazil and Mexico.
REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY
(2023)
Article
Biochemistry & Molecular Biology
Armando Moreno-Velasco, Mabel Fragoso-Serrano, Pedro de Jesus Flores-Tafoya, Sebastian Carrillo-Rojas, Elihu Bautista, Suzana Guimara Leitao, Jhon F. Castaneda-Gomez, Rogelio Pereda-Miranda
Summary: This study investigated the roots of Operculina hamiltonii, a traditional medicinal plant in Brazil. Three new acyl sugars or resin glycosides were identified and their structures elucidated. The combination of these compounds with other drugs showed enhanced cytotoxic effects on breast cancer cells.
Article
Chemistry, Medicinal
Xitlalick Garcia-Nava, Mabel Fragoso-Serrano, Elihu Bautista, Denisse de Loera, Omar Cortezano-Arellano, Fernando Calzada, Brenda Y. Bedolla-Garcia
Summary: The HPLC-PDA profiling of an acetone-soluble extract of the leaves of Salvia circinnata Cay. indicated the presence of the chemotype amarisolide A. Two new diterpenoid glucosides, amarisolide H and 15-epi-amarisolide H, were isolated from the extract, along with other known compounds. The cytotoxicity and anti-multidrug resistance effects of these compounds in MCF-7 cancer cells were tested.
REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY
(2022)
Article
Chemistry, Medicinal
Maria Emma Montiel-Ayala, Nadia Rosalina Jimenez-Barcenas, Jhon Castaneda-Gomez, Armando Moreno-Velasco, Jesus Lira-Ricardez, Mabel Fragoso-Serrano, Suzana Guimaraes Leitao, Rogelio Pereda-Miranda
Summary: Brazilian jalap root, a plant belonging to the morning glory family, is used as a purgative or laxative medicinal plant. Research has revealed the presence of several undescribed glycosidic acids in this plant, and distinctive chromatographic profiles can be generated for each sample through analysis.
REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY
(2021)
Review
Chemistry, Medicinal
Gilda Guimaraes Leitao, Carla Monteiro Leal, Simony Carvalho Mendonca, Rogelio Pereda-Miranda
Summary: Alkaloids are nitrogen-containing compounds found in plants, microorganisms, animals, insects, and marine organisms, soluble in water but not in organic solvents due to the presence of nitrogen atoms. Liquid-liquid partitioning techniques like countercurrent chromatography can be used for their extraction.
REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY
(2021)
Article
Chemistry, Medicinal
Suzana Guimaraes Leitao, Gabriel R. Martins, Lucero Martinez-Fructuoso, Danila de Sousa Silva, Thamirys Silva da Fonseca, Caroline Vianna V. Castilho, Leopoldo Clemente Baratto, Daniela S. Alviano, Celuta Sales Alviano, Gilda Guimaraes Leitao, Rogelio Pereda-Miranda
REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY
(2020)