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Biological Chemistry

Marian Grman, Muhammad Jawad Nasim, Roman Leontiev, Anton Misak, Veronika Jakusova, Karol Ondrias, Claus Jacob
Since the heydays of Reactive Sulfur Species (RSS) research during the first decade of the Millennium, numerous sulfur species involved in cellular regulation and signalling have been discovered. Yet despite the general predominance of organic species in organisms, recent years have also seen the emergence of inorganic reactive sulfur species, ranging from inorganic polysulfides (HSx(-)/Sx(2-)) to thionitrous acid (HSNO) and nitrosopersulfide (SSNO(-)). These inorganic species engage in a complex interplay of reactions in vitro and possibly also in vivo...
February 15, 2017: Antioxidants (Basel, Switzerland)
Nauman Khalid, Isao Kobayashi, Mitsutoshi Nakajima
Microelectromechanical systems (MEMS) and micro total analysis systems (μTAS) revolutionized the biochemical and electronic industries, and this miniaturization process became a key driver for many markets. Now, it is a driving force for innovations in life sciences, diagnostics, analytical sciences, and chemistry, which are called 'lab-on-a-chip, (LOC)' devices. The use of these devices allows the development of fast, portable, and easy-to-use systems with a high level of functional integration for applications such as point-of-care diagnostics, forensics, the analysis of biomolecules, environmental or food analysis, and drug development...
February 17, 2017: Wiley Interdisciplinary Reviews. Systems Biology and Medicine
Amit Kumar Chattopadhyay, Stephen Hanessian
Daphniphyllum is an evergreen species known since 1826. After initial systematic investigations, more than 320 members of this family have been isolated, which comprise complex and fascinating structures. Unique azapolycyclic architectures containing one or more quaternary stereocenters render these alkaloids synthetically challenging. This review covers efforts toward the synthesis of Daphniphyllum alkaloids spanning the period from 2005 to the beginning of 2016, including reported biological activities as well as the isolation of new members of this genus...
February 16, 2017: Chemical Reviews
Teli Liu, Qianqian Gan, Junbo Zhang
[(99m) Tc(CO)3 (H2 O)3 ](+) has attracted great attention among (99m) Tc-labeling techniques, due to its ease of preparation, readily substituted water molecules of the precursor fac-[(99m) Tc(CO)3 (H2 O)3 ](+) by a variety of functional groups, small size and inertness. Bifunctional chelator based on a macrocyclic polyamine framework shows easy complexation with [(99m) Tc(CO)3 (H2 O)3 ](+) to produce stable complex. In this study, two novel 1, 5, 9-triazacyclododecane derivatives containing a glucose group (6 and 7) were successfully synthesized by reacting different glucose-azides with alkyne-[12]aneN3 via the so-called click chemistry and radiolabeled with [(99m) Tc(CO)3 (H2 O)3 ](+) to form (99m) Tc(CO)3 -6 (C-1-substituted complex) and (99m) Tc(CO)3 -7 (C-2-substituted complex) in high yields...
February 2017: Chemical Biology & Drug Design
Muhammad Moazzam Naseer, Mukhtiar Ahmed, Shahid Hameed
Calixarenes, composed of phenolic units linked by methylene bridges at the 2,6-positions, represent a versatile class of macrocyclic compounds in supramolecular chemistry that can host small molecules or ions in their well-defined hydrophobic cavities. In recent years, it has been recognized that this class of compounds has the potential to serve as platform for the design of biological active compounds. Therefore, the calixarenes functionalized with different pharmacophoric groups have been synthesized as target structure by many researchers and were further evaluated for their biological activities...
February 2017: Chemical Biology & Drug Design
A Ribar, K Fink, Z Li, S Ptasińska, I Carmichael, L Feketeová, S Denifl
Imidazole [C3H4N2] is ubiquitous in nature as an important biological building block of amino acids, purine nucleobases or antibiotics. In the present study, dissociative electron attachment to imidazole shows low energy shape resonances at 1.52 and 2.29 eV leading to the most abundant dehydrogenated anion [imidazole - H](-) through dehydrogenation at the N1 position. All the other anions formed exhibit core excited resonances observed dominantly at similar electron energies of ∼7 and 11 eV, suggesting an initial formation through two temporary negative ion states...
February 15, 2017: Physical Chemistry Chemical Physics: PCCP
Emilie Mathieu, Anne-Sophie Bernard, Nicolas Delsuc, Elodie Quévrain, Géraldine Gazzah, Barry Lai, Florian Chain, Philippe Langella, Maria Bachelet, Joelle Masliah, Philippe Seksik, Clotilde Policar
Inorganic complexes are increasingly used for biological and medicinal applications, and the question of the cell penetration and distribution of metallodrugs is key to understanding their biological activity. Oxidative stress is known to be involved in inflammation and in inflammatory bowel diseases for which antioxidative defenses are weakened. We report here the study of the manganese complex Mn1 mimicking superoxide dismutase (SOD), a protein involved in cell protection against oxidative stress, using an approach in inorganic cellular chemistry combining the investigation of Mn1 intracellular speciation using mass spectrometry and of its quantification and distribution using electron paramagnetic resonance and spatially resolved X-ray fluorescence with evaluation of its biological activity...
February 15, 2017: Inorganic Chemistry
Fabrizio Giordanetto, Christian Tyrchan, Johan Ulander
Design strategies centered on intramolecular hydrogen bonds are sometime used in drug discovery, but their general applicability has not been addressed beyond scattered examples or circumstantial evidence. A total of 1053 matched molecular pairs where only one of the two molecules is able to form an intramolecular hydrogen bond via monatomic transformations have been identified across the ChEMBL database. These pairs were used to investigate the effect of intramolecular hydrogen bonds on biological activity...
February 9, 2017: ACS Medicinal Chemistry Letters
David S Hewings, John A Flygare, Matthew Bogyo, Ingrid E Wertz
The reversible post-translational modification of proteins by ubiquitin and ubiquitin-like proteins regulates almost all cellular processes, by affecting protein degradation, localization, and complex formation. Deubiquitinases (DUBs) are proteases that remove ubiquitin modifications or cleave ubiquitin chains. Most DUBs are cysteine proteases, which makes them well suited for study by activity-based probes. These DUB probes report on deubiquitinase activity by reacting covalently with the active site in an enzyme-catalyzed manner...
February 14, 2017: FEBS Journal
Dorian M Cheff, Matthew D Hall
The platinum-based anti-cancer agents cisplatin, carboplatin and oxaliplatin, represent a spectacular translational science achievement. The basic research observations that led to the discovery of Pt complexes as DNA-binding agents that elicit cell arrest, the pre-clinical tumor regression studies, and the inorganic medicinal chemistry that led to clinical implementation of effective platinum complexes in the clinic, have fueled multi-disciplinary research into platinum-based drugs. While the successes are clear and the research activity continues, a significant window of time has passed since a new Pt drug has been approved for clinical use...
February 14, 2017: Journal of Medicinal Chemistry
Dake Hao, Wenwu Xiao, Ruiwu Liu, Priyadarsini Kumar, YuanPei Li, Ping Zhou, Fuzheng Guo, Diana L Farmer, Kit S Lam, Fengshan Wang, Aijun Wang
Endothelial progenitor cells (EPCs) and endothelial cells (ECs) play a vital role in endothelialization and vascularization for tissue regeneration. Various EPC/EC targeting biomolecules have been investigated to improve tissue regeneration with limited success often due to their limited functional specificity and structural stability. One-Bead-One-Compound (OBOC) combinatorial technology is an ultra-high throughput chemical library synthesis and screening method suitable for ligand discovery against a wide range of biological targets, such as integrins...
February 14, 2017: ACS Chemical Biology
Steve Ullmann, Rene Schnorr, Marcel Handke, Christian Laube, Bernd Abel, Jörg Matysik, Matthias Findeisen, Robert Rüger, Thomas Heine, Berthold Kersting
A new macrocycle H2L comprising fluorescent bis(iminomethyl)phenol and calix[4]arene head units has been synthesized and its coordination chemistry examined. H2L allows the sensitive optical detection of Zn2+ among a series of biologically relevant metal ions by a dual fluorescence enhancement / quenching effect in solution.
February 13, 2017: Chemistry: a European Journal
Wenjuan Yuan, Ying Zhang, Yun Xiong, Tao Tao, Yi Wang, Jun Yao, Lei Zhang, Guoquan Yan, Huimin Bao, Haojie Lu
Modification of proteins with 4-hydroxynonenal (HNE) is known to alter the function of proteins and regulate the associated biological processes in eukaryotic cells. The development of mass spectrometry (MS) makes high-throughput analysis of HNE modification accessible. However, the identification of HNE modification is still hampered by the low frequency of this modification. Therefore, only a limited number of HNE modification sites have been identified. The enrichment of HNE-modified peptides is critical for the MS analysis of this modification because of its low abundance...
February 13, 2017: Analytical Chemistry
Xilei Xie, Mengmeng Li, Fuyan Tang, Yong Li, Leilei Zhang, Xiaoyun Jiao, Xu Wang, Bo Tang
We present a feasible paradigm of developing original fluorescent probes for target biomolecules via combinatorial chemistry. In this developmental program, pyrimidine moieties were investigated and optimized as unique recognition units for thiols for the first time through a parallel synthesis in combination with a rapid screening process. This time-efficient and cost-saving process effectively facilitated the developmental progress and provided detailed structure-reactivity relationships. As a result, Res-Biot and Flu-Pht were identified as optimal fluorescent probes for biothiol and thiophenol, respectively...
February 15, 2017: Analytical Chemistry
Bebiana C Sousa, Andrew R Pitt, Corinne M Spickett
The process of lipid oxidation generates a diverse array of small aldehydes and carbonyl-containing compounds, which may occur in free form or esterified within phospholipids and cholesterol esters. These aldehydes mostly result from fragmentation of fatty acyl chains following radical oxidation, and the products can be subdivided into alkanals, alkenals (usually α,β-unsaturated), γ-substituted alkenals and bis-aldehydes. Isolevuglandins are non-fragmented di-carbonyl compounds derived from H2-isoprostanes, and oxidation of the ω-3-fatty acid docosahexenoic acid yield analogous 22 carbon neuroketals...
February 10, 2017: Free Radical Biology & Medicine
Dongshi Zhang, Bilal Gökce, Stephan Barcikowski
Driven by functionality and purity demand for applications of inorganic nanoparticle colloids in optics, biology, and energy, their surface chemistry has become a topic of intensive research interest. Consequently, ligand-free colloids are ideal reference materials for evaluating the effects of surface adsorbates from the initial state for application-oriented nanointegration purposes. After two decades of development, laser synthesis and processing of colloids (LSPC) has emerged as a convenient and scalable technique for the synthesis of ligand-free nanomaterials in sealed environments...
February 13, 2017: Chemical Reviews
Guoting Qin, Zhiling Zhu, Siheng Li, Alison M McDermott, Chengzhi Cai
In this work, we developed a simple method to load drugs into commercially available contact lenses utilizing fluorous chemistry. We demonstrated this method using model compounds including fluorous-tagged fluorescein and antibiotic ciprofloxacin. We showed that fluorous interactions facilitated the loading of model molecules into fluorocarbon-containing contact lenses, and that the release profiles exhibited sustained release. Contact lenses loaded with fluorous-tagged ciprofloxacin exhibited antimicrobial activity against Pseudomonas aeruginosa in vitro, while no cytotoxicity towards human corneal epithelial cells was observed...
January 31, 2017: Biomaterials
Jing Tang, Karen A Kirby, Andrew D Huber, Mary C Casey, Juan Ji, Daniel J Wilson, Stefan G Sarafianos, Zhengqiang Wang
3-Hydroxypyrimidine-2,4-dione (HPD) represents a versatile chemical core in the design of inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H and integrase strand transfer (INST). We report herein the design, synthesis and biological evaluation of an HPD subtype (4) featuring a cyclohexylmethyl group at the C-6 position. Antiviral testing showed that most analogues of 4 inhibited HIV-1 in the low nanomolar to submicromolar range, without cytotoxicity at concentrations up to 100 μM...
January 30, 2017: European Journal of Medicinal Chemistry
Marc H M Thelen, Rob T P Jansen, Cas W Weykamp, Herman Steigstra, Ron Meijer, Christa M Cobbaert
BACKGROUND: To provide its participants with an external quality assessment system (EQAS) that can be used to check trueness, the Dutch EQAS organizer, Organization for Quality Assessment of Laboratory Diagnostics (SKML), has innovated its general chemistry scheme over the last decade by introducing fresh frozen commutable samples whose values were assigned by Joint Committee for Traceability in Laboratory Medicine (JCTLM)-listed reference laboratories using reference methods where possible...
February 9, 2017: Clinical Chemistry and Laboratory Medicine: CCLM
Peng Zhang, Ernst Wagner
As an option for genetic disease treatment and an alternative for traditional cancer chemotherapy, gene therapy achieves significant attention. Nucleic acid delivery, however, remains a main challenge in human gene therapy. Polymer-based delivery systems offer a safer and promising route for therapeutic gene delivery. Over the past five decades, various cationic polymers have been optimized for increasingly effective nucleic acid transfer. This resulted in a chemical evolution of cationic polymers from the first-generation polycations towards bioinspired multifunctional sequence-defined polymers and nanocomposites...
April 2017: Topics in Current Chemistry (Journal)
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