Article
Chemistry, Medicinal
Nathalie M. Grob, Roger Schibli, Martin Behe, Ibai E. Valverde, Thomas L. Mindt
Summary: 1,5-Disubstituted 1,2,3-triazoles are bioisosteres of cis-amide bonds and have been shown to enhance pharmacological properties of peptides, particularly in improving receptor binding affinity and tumor uptake as illustrated in this study.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Physical
Felipe S. Stefanello, Yuri G. Kappenberg, Alex Ketzer, Steffany Z. Franceschini, Paulo R. S. Salbego, Thiago Acunha, Pablo A. Nogara, Joao B. T. Rocha, Marcos A. P. Martins, Nilo Zanatta, Bernardo A. Iglesias, Helio G. Bonacorso
Summary: This study synthesized and characterized a series of new SCTz derivatives, investigated their binding properties to DNA and HSA, and found strong binding forces to CT-DNA. UV-Vis and X-ray diffraction analyses revealed a static interaction between the derivatives and DNA, as well as the formation of stable complexes with DNA and HSA.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Review
Chemistry, Multidisciplinary
Agnieszka Staskiewicz, Patrycja Ledwon, Paolo Rovero, Anna Maria Papini, Rafal Latajka
Summary: Triazolyl-containing peptidomimetics play a crucial role in drug design by decreasing the susceptibility of molecules to enzymatic degradation. These compounds exhibit diverse biological properties and can be obtained through various synthetic strategies.
FRONTIERS IN CHEMISTRY
(2021)
Review
Chemistry, Organic
Akash Anand, Rajneesh Kumar, Jyotirmoy Maity, Vipin K. K. Maikhuri
Summary: The synthesis of 1,4-disubstituted 1,2,3-triazoles through copper-catalyzed multicomponent reactions is an efficient and versatile method for the synthesis of bioactive compounds.
SYNTHETIC COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Francesca Nuti, Maud Larregola, Agnieszka Staskiewicz, Bernhard Retzl, Natasa Tomasevic, Lorenzo Macchia, Maria E. Street, Michal Jewginski, Olivier Lequin, Rafal Latajka, Paolo Rovero, Christian W. Gruber, Michael Chorev, Anna Maria Papini
Summary: In this study, a series of C alpha(1)-to-C alpha(6) side chain-to-side chain [1,2,3]triazol-1-yl-containing oxytocin analogues were designed and synthesized. Through in vitro experiments, the conformational analysis and pharmacological activity of these analogues were explored. The macrocyclization approach was employed to increase the stability of oxytocin, and interesting insights into the structure-conformation-function relationship of oxytocin were obtained.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Manisha Chahal, Chander Prakash Kaushik, Raj Luxmi, Devinder Kumar, Ashwani Kumar
Summary: A series of 1,4-disubstituted 1,2,3-triazoles with amide-hydroxyl functionality were synthesized and screened for their antioxidant and antimicrobial activities. Compound 5s exhibited the best antioxidant activity, while compounds 5h and 5l showed good antibacterial and antifungal activities, respectively. Docking studies revealed various binding interactions of the protein-ligand complex. In silico ADME study was conducted to evaluate their drug likeness.
MEDICINAL CHEMISTRY RESEARCH
(2023)
Article
Chemistry, Organic
Elisabeth Sitte, Brendan Twamley, Nitika Grover, Mathias O. Senge
Summary: In this study, methodologies for the synthesis of different BCP triazole building blocks were developed from one precursor, allowing for the synthesis of multiply substituted BCP triazoles. These methodologies were also utilized for appending porphyrin moieties onto the BCP core.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Anna K. Puszko, Piotr Sosnowski, Rachel Rignault-Bricard, Olivier Hermine, Gerard Hopfgartner, Karolina Pulka-Ziach, Yves Lepelletier, Aleksandra Misicka
Summary: The study investigated the synthesis, affinity, enzymatic stability, molecular modeling, and in vitro binding evaluation of branched urea-peptide hybrids as potential compounds for blocking VEGF-A165/NRP-1 interaction. One hybrid showed a more than 10-fold increase in affinity for NRP-1 and improved resistance to proteolytic stability, making it a promising candidate for further development as a VEGF(165)/NRP-1 inhibitor.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Materials Science, Multidisciplinary
T. Krishnaveni, K. Kadirvelu, M. Kaveri
Summary: CuO nanoparticles prepared with quercetin as a capping agent can serve as efficient and cost-effective catalysts for the synthesis of 1,4-disubstituted 1,2,3-triazoles. The catalyst exhibits smaller particle size and provides reasonable product yields under mild reaction conditions.
MATERIALS SCIENCE AND ENGINEERING B-ADVANCED FUNCTIONAL SOLID-STATE MATERIALS
(2022)
Article
Chemistry, Organic
Ramchandra Thorat, Sushil Khot, Manali Nikam, Anil Karnik
Summary: A novel S-BINOL-based 1, 2, 3-triazole was successfully synthesized using an efficient synthetic protocol, and it demonstrated selective sensing of iodide and magnesium ions. The binding affinity of the sensor towards iodide and magnesium ions is remarkably strong, with association constants among the best reported so far. This can be attributed to the structural features of the sensor, such as the helical BINOL backbone and the presence of acidic proton and electron-rich nitrogen atoms in the 1, 2, 3-triazole.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Abid H. Banday, Victor J. Hruby
Summary: The study focuses on metal and solvent-free organo-catalyzed reactions, achieving unprecedented one-pot regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. The approach is straightforward, greener, and avoids tedious workups and chromatographic separation.
CURRENT ORGANOCATALYSIS
(2021)
Article
Chemistry, Organic
Dmitrii S. Vasilchenko, Mikhail S. Novikov, Nikolai V. Rostovskii
Summary: In this study, stable ethene-1,2-diamines were synthesized using dirhodium tetrapivalate as a catalyst. These compounds can serve as new bidentate ligands and substrates for the synthesis of N,N-heterocycles.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2023)
Article
Chemistry, Organic
Nazariy T. Pokhodylo, Yuriy Slyvka, Evgeny A. Goreshnik, Mykola D. Obushak
Summary: This article reports a two-step synthesis of 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate and studies its intermolecular interactions through crystal structure analysis and Hirshfeld surface analysis.
Article
Radiology, Nuclear Medicine & Medical Imaging
Marion Chomet, Maxime Schreurs, Maria J. Bolijn, Mariska Verlaan, Wissam Beaino, Kari Brown, Alex J. Poot, Albert D. Windhorst, Herman Gill, Jan Marik, Simon Williams, Joseph Cowell, Gilles Gasser, Thomas L. Mindt, Guus A. M. S. van Dongen, Danielle J. Vugts
Summary: Novel analogues DFO*-NCS and DFOSq showed superior stability compared to traditional DFO in in vitro and in vivo experiments. Conjugates with DFO* exhibited lower bone uptake and provided superior detection of tumor-specific signal in a bone metastasis model. DFO* proves to be a more stable and effective candidate for preclinical and clinical (89)Zr-immuno-PET.
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2021)
Article
Chemistry, Medicinal
Nathalie M. Grob, Roger Schibli, Martin Behe, Ibai E. Valverde, Thomas L. Mindt
Summary: 1,5-Disubstituted 1,2,3-triazoles are bioisosteres of cis-amide bonds and have been shown to enhance pharmacological properties of peptides, particularly in improving receptor binding affinity and tumor uptake as illustrated in this study.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Carolina Giammei, Nedra Jouini, Marie R. Brandt, Stefanie Frey, Thomas L. Mindt, Jens Cardinale
Summary: During multiple indium-111 labeling of DOTA-modified peptides from a single batch of [In-111]InCl3, inconsistent radiochemical yields were observed due to the formation of a radioactive impurity. This unknown In-111 species could be successfully suppressed by increasing the concentration of chloride ions in the stock solution, resulting in acceptable radiochemical yields. Additionally, convenient iTLC systems were reported for distinguishing between different species during radiolabeling.
APPLIED RADIATION AND ISOTOPES
(2022)
Article
Radiology, Nuclear Medicine & Medical Imaging
Lucas Rischka, Chrysoula Vraka, Verena Pichler, Sazan Rasul, Lukas Nics, Gregor Gryglewski, Patricia Handschuh, Matej Murgas, Godber M. Godbersen, Leo R. Silberbauer, Jakob Unterholzner, Christoph Wotawa, Ahmed Haider, Hazem Ahmed, Roger Schibli, Thomas Mindt, Markus Mitterhauser, Wolfgang Wadsak, Andreas Hahn, Rupert Lanzenberger, Marcus Hacker, Simon M. Ametamey
Summary: This study reports on the performance characteristics of (R)-C-11-Me-NB1, a radioligand used to map GluN2B-enriched NMDARs in the human brain. The radioligand demonstrated high and heterogeneous uptake and a high test-retest reliability. It shows promise in deepening our understanding of the role of GluN2B-containing NMDARs in neurodegenerative and neuropsychiatric diseases such Alzheimer's disease and major depression.
JOURNAL OF NUCLEAR MEDICINE
(2022)
Article
Chemistry, Inorganic & Nuclear
Wolfgang Kandioller, Johannes Theiner, Bernhard K. Keppler, Christian R. Kowol
Summary: Elemental analysis is a powerful tool for purity determination of compounds, but vulnerable to manipulations. The article discusses the relationship between measured deviations and theoretical compositions, and presents an approach to provide original elemental analysis data to support experimental values.
INORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Medicinal
Nedra Jouini, Jens Cardinale, Thomas L. Mindt
Summary: The interaction between PD-1 and PD-L1 affects T-cell deactivation and cancer proliferation. Radiotracers provide information on the expression of PD-L1, allowing personalized treatment. This study aimed to develop a PD-L1-specific PET radiotracer but found that the previous peptide was not suitable.
Article
Chemistry, Multidisciplinary
Heiko Geisler, Sophia Harringer, Dominik Wenisch, Richard Urban, Michael A. Jakupec, Wolfgang Kandioller, Bernhard K. Keppler
Summary: The cytotoxicities of seven dimeric metal species, including rhodium(III) and iridium(III), have been investigated in human cancer cell lines, revealing surprising activity in ovarian malignancies.
Article
Radiology, Nuclear Medicine & Medical Imaging
Lucas Rischka, Matej Murgas, Verena Pichler, Chrysoula Vraka, Ivo Rausch, Dietmar Winkler, Lukas Nics, Sazan Rasul, Leo Robert Silberbauer, Murray Bruce Reed, Godber Mathis Godbersen, Jakob Unterholzner, Patricia Handschuh, Gregor Gryglewski, Thomas Mindt, Markus Mitterhauser, Andreas Hahn, Simon Mensah Ametamey, Wolfgang Wadsak, Rupert Lanzenberger, Marcus Hacker
Summary: This study evaluated the safety, biodistribution, and dosimetry of the GluN2B-specific PET radioligand (R)-[C-11]Me-NB1. The radioligand was found to be safe and well-tolerated, with a low effective dose coefficient. This makes it suitable for longitudinal studies in drug development and treatment monitoring of neuropsychiatric disorders including neurodegenerative diseases.
Article
Pharmacology & Pharmacy
Klaudia Cseh, Heiko Geisler, Kristina Stanojkovska, Julia Westermayr, Philipp Brunmayr, Dominik Wenisch, Natalie Gajic, Michaela Hejl, Martin Schaier, Gunda Koellensperger, Michael A. A. Jakupec, Philipp Marquetand, Wolfgang Kandioller
Summary: The main purpose of this study was to synthesize a new set of naphthoquinone-based ruthenium(II) arene complexes and understand their mode of action. The chemical structures and biological activities of these compounds were examined, and a positive correlation was found between cytotoxicity, lipophilicity, and cellular accumulation. This study provides important insights into the effects of these arene complexes.
Article
Pharmacology & Pharmacy
Janos P. Meszaros, Wolfgang Kandioller, Gabriella Spengler, Alexander Prado-Roller, Bernhard K. Keppler, Eva A. Enyedy
Summary: This study introduces half-sandwich Rh complexes that can be activated in the acidic, extracellular pH of tumor tissue, reducing the side effects and improving the efficacy of chemotherapy.
Article
Biochemistry & Molecular Biology
Xabier Guarrochena, Barbara Kaudela, Thomas L. Mindt
Summary: The use of 1,4-disubstituted 1,2,3-triazoles as trans-amide bond surrogates has become an important tool for the synthesis of metabolically stabilized peptidomimetics. An automated synthesis method using peptide synthesizers is described. The optimized procedure allows for the efficient synthesis of diverse triazolo-peptidomimetics with moderate to good purities.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Article
Biochemistry & Molecular Biology
Youchao Wang, Patrick S. S. Felder, Pierre Mesdom, Olivier Blacque, Thomas L. L. Mindt, Kevin Cariou, Gilles Gasser
Summary: The synthesis and characterization of a ruthenium-rhenium binuclear complex, combining the photophysical properties of a rhenium(I) tricarbonyl complex and a ruthenium(II) polypyridyl complex, is presented in this study for its potential use as a photosensitizer in anticancer photodynamic therapy. One of the complexes synthesized, which localized in mitochondria, showed selectivity towards human lung carcinoma A549 and human colon colorectal adenocarcinoma HT29 cells, with interesting photo-index (PI) values of 135.1 and 256.4, respectively, compared to noncancerous retinal pigment epithelium RPE1 cells (22.4).
Article
Chemistry, Multidisciplinary
Andreas Gradwohl, Jakob Windisch, Matthias Weissensteiner, Bernhard K. Keppler, Wolfgang Kandioller, Franz Jirsa
Summary: The task-specific ionic liquid trihexyltetradecylphosphonium 3-hydroxy-2-naphthoate is a suitable extraction agent for rare earth elements, achieving high extraction efficacies and minimal precipitation of the metals. The extraction efficiency is influenced by pH, temperature, and extraction time, and anion exchange is the extraction mechanism. The leaching into the used matrices is in line with literature values and is not significantly affected by temperature.
Article
Biochemistry & Molecular Biology
Stefan Schmitl, Julia Raitanen, Stephan Witoszynskyj, Eva-Maria Patronas, Lukas Nics, Marius Ozenil, Victoria Weissenboeck, Thomas L. Mindt, Marcus Hacker, Wolfgang Wadsak, Marie R. Brandt, Markus Mitterhauser
Summary: Lu-177Lu-PSMA(I&T) is widely used for the therapy of metastatic castration-resistant prostate cancer. The specific activity is correlated with the formation of deiodinated side products and other cyclization products, which contribute to radiochemical impurities.
Meeting Abstract
Radiology, Nuclear Medicine & Medical Imaging
L. Rischka, C. Vraka, V. Pichler, S. Rasul, L. Nics, G. Gryglewski, P. Handschuh, M. Murgas, G. M. Godbersen, L. R. Silberbauer, J. Unterholzner, C. Wotawa, A. Haider, H. Ahmed, R. Schibli, T. Mindt, M. Mitterhauser, W. Wadsak, A. Hahn, R. Lanzenberger, M. Hacker, S. M. Ametamey
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2021)