Search Results (199)

One of the promising research areas involving carborane derivatives is boron neutron capture therapy (BNCT). Due to the high boron atom content in carborane molecules, these compounds are considered potential candidates for BNCT-based cancer treatment. Despite ongoing studies on various biologically active carboranyl-containing compounds, the search continues for substances that meet the stringent requirements of effective BNCT agents. In this study, the synthesis of carboranyl-containing derivatives of β-arylaliphatic acids is described, along with the investigation of their reactivity with primary and secondary amines, as well as with metals and their hydroxides. The molecular structures of the synthesized compounds were confirmed using Fourier-transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, elemental analysis, and mass spectrometry (LC-MS). Cytotoxicity of the water-soluble compound potassium 3-(2-isopropyl-1,2-dicarba-closo-dodecaboran-1-yl)-3-phenylpropanoate was evaluated using several cell lines, including HdFn and MCF-7. Full article

1,3,4-Oxadiazoles containing boronic acid moieties are promising as a highly versatile class of compounds with significant utility across various scientific domains. The diverse synthetic methodologies for their preparation make these compounds valuable precursors for developing novel entities with tailored properties in medicinal chemistry, agrochemistry, and materials science. This review systematically compiles and discusses synthetic methods for the direct and indirect incorporation of boronic acid derivatives into 1,3,4-oxadiazole scaffolds. Understanding these strategies is particularly important because of their key role in modern synthetic transformations, especially Suzuki–Miyaura cross-coupling reactions, which enable easy access to a new generation of structurally diverse 1,3,4-oxadiazole-based compounds. The synthetic procedures and reactions discussed are based on the currently available literature, offering a comprehensive overview of this rapidly evolving field. Full article

Head and neck cancer (HNC) is a highly aggressive malignancy with limited treatment options and poor prognosis. Inflammation plays a critical role in HNC progression, with elevated levels of pro-inflammatory cytokines such as TNF, IL-6, IL-8, and IL-1β contributing to tumor development. In this study, a novel series of boronic chalcones was designed and synthesized as potential dual-action anticancer and anti-inflammatory agents. The most potent compounds were evaluated for their cytotoxicity against Squamous Cell Carcinoma (SCC-25), and their selectivity index (SI) was determined. Compound 5 emerged as the most promising, displaying cytotoxicity against cancer cells, with IC₅₀ values of 17.9 µM and a favorable SI (>3). Mechanistic studies revealed that its anticancer activity was independent of p53 status, and annexin V/PI staining indicated cell death via necrosis. Interestingly, compound 5 also significantly reduced pro-inflammatory cytokine levels, as TNF and IL-6. Furthermore, drug metabolism and pharmacokinetics (DMPK) studies demonstrated that compound 5 exhibited moderate solubility and high permeability. These findings underscore the crucial role of the boronic acid moiety in enhancing both anticancer and anti-inflammatory properties. Full article

Since the approval of Bortezomib (Velcade^®) by the U.S. Food and Drug Administration (FDA) in 2003, boron-containing drugs have successfully entered the global market, spanning therapeutic areas such as anticancer, antibacterial, and antifungal agents. Meanwhile, boron is an essential trace element for plant growth, and boronic acid has been widely used as plant resistance inducers and growth promoters. In 2024, the Fungicide Resistance Action Committee (FRAC) introduced benzoxaboroles as a new category of fungicides, which fully demonstrates the significant application potential of boron-containing compounds (BCCs) in the field of agricultural fungicides. Recently, studies on BCCs in agriculture have emerged continuously. Compared with the systematic reviews in the pharmaceutical field, those focusing on BCCs in agriculture remain absent. This review systematically collates BCCs with reported biological activities from the literature over the past 20 years, from the perspective of boron-containing building blocks. It mainly focuses on the potential of boronic acid derivatization and its activities in agrochemicals. Additionally, it covers the applications of boron-containing building blocks in pharmaceuticals, including their action mechanisms. Full article

Boronic acids are an important class of molecules diversely used in organic synthesis, catalysis, medicinal chemistry, and for the design of functional materials. Particularly, aryl boronic acids in the solid state are known to exhibit pharmaceutical and photoluminescent properties for antimicrobial, sensing, and drug delivery applications. Furthermore, the phenazine molecule is known for its diverse pharmacological properties, including antibiotic activity. In the case of molecular crystalline solids, it is well established that understanding noncovalent interactions remains key to designing or engineering their functional properties. While both aryl boronic acids and phenazine molecules individually represent an important class of compounds, their co-assembly in the crystalline state is of interest within the context of supramolecular chemistry and crystal engineering. Herein, we report the supramolecular features of two newly synthesized cocrystals, which are composed of para-F/CF₃-substituted phenylboronic acids, respectively, and phenazine, as demonstrated by structure analysis by single-crystal X-ray diffraction. Full article

Fluorescent chemosensors are increasingly becoming relevant in recognition chemistry due to their sensitivity, selectivity, fast response time, real-time detection capability, and low cost. Boronic acids have been reported for the recognition of mycolactone, the cytotoxin responsible for tissue damage in Buruli ulcer disease. A library of fluorescent arylboronic acid chemosensors with various signaling moieties with certain beneficial photophysical characteristics (i.e., aminoacridine, aminoquinoline, azo, BODIPY, coumarin, fluorescein, and rhodamine variants) and a recognition moiety (i.e., boronic acid unit) were rationally designed and synthesised using combinatorial approaches, purified, and fully characterised using a set of complementary spectrometric and spectroscopic techniques such as NMR, LC-MS, FT-IR, and X-ray crystallography. In addition, a complete set of basic photophysical quantities such as absorption maxima (λ_abs^max), emission maxima (λ_em^max), Stokes shift (∆λ), molar extinction coefficient (ε), fluorescence quantum yield (Φ_F), and brightness were determined using UV-vis absorption and fluorescence emission spectroscopy techniques. The synthesised arylboronic acid chemosensors were investigated as chemosensors for mycolactone detection using the fluorescent-thin layer chromatography (f-TLC) method. Compound 7 (with a coumarin core) emerged the best (λ_abs^max = 456 nm, λ_em^max = 590 nm, ∆λ = 134 nm, ε = 52816 M⁻¹cm⁻¹, Φ_F = 0.78, and brightness = 41,197 M⁻¹cm⁻¹). Full article

Boron-containing compounds, known for their high calorific value, can significantly enhance the energy density of traditional liquid propellants. Through precise chemical modification of the C-H bonds in ortho-carborane, a novel liquid cluster material was synthesized: C,C′-Bis(2-ethylhexanoylmethyl)-o-carborane (BEHMC). This compound exhibits excellent stability, density, and energy properties. By combining BEHMC with mixed amine-50, a cluster liquid propellant was formulated, and its key performance metrics such as density, freezing point, mass calorific value, and volumetric calorific value were evaluated. The propellant achieved a density of 0.884 g·cm⁻³, a freezing point below −55 °C, a mass calorific value of 41.13 kJ·g⁻¹, and a volumetric calorific value of 36.36 kJ·cm⁻³. The theoretical specific impulse reached 346 s, and the theoretical density impulse was 2.99 × 10⁶ N·s·m⁻³. Compared to the traditional mixed amine-50/red fuming nitric acid propellant, the cluster liquid propellant developed in this study maintains a similar calorific value while improving the theoretical specific impulse and density impulse by 2.3% and 3.8%, respectively. Full article

In this study, we evaluated in situ click chemistry as a platform for discovering boronic acid-based β-lactamase inhibitors (BLIs). Unlike conventional drug discovery approaches requiring multi-step synthesis, protection strategies, and extensive screening, the in situ method can allow for the generation and identification of potent β-lactamase inhibitors in a rapid, economic, and efficient way. Using KPC-2 (class A carbapenemase) and AmpC (class C cephalosporinase) as templates, we demonstrated their ability to catalyse azide-alkyne cycloaddition, facilitating the formation of triazole-based β-lactamase inhibitors. Initial screening of various β-lactamases and boronic warheads identified compound 3 (3-azidomethylphenyl boronic acid) as the most effective scaffold for kinetic target-guided synthesis (KTGS). KTGS experiments with AmpC and KPC-2 yielded triazole inhibitors with K_i values as low as 140 nM (compound 10a, AmpC) and 730 nM (compound 5, KPC-2). Competitive inhibition studies confirmed triazole formation within the active site, while an LC–MS analysis verified that the reversible covalent interaction of boronic acids did not affect detection of the in situ-synthesised product. While KTGS successfully identified potent inhibitors, limitations in amplification coefficients and spatial constraints highlight the need for optimised warhead designs. This study validates KTGS as a promising strategy for BLI discovery and provides insights for further refinement in fighting β-lactamase-mediated antibiotic resistance. Full article

The corrosion of metal substrates is closely associated with the permeability of the corrosive medium in which they are immersed. To enhance the protection of metal materials and improve anti-corrosion performance from an epoxy resin perspective, the diffusion path complexity can be increased and porosity reduced within the epoxy resin coating to effectively block the invasion of corrosive media. Simultaneously, reducing the affinity between the corrosive media and the epoxy resin coating makes it difficult for corrosive substances to adhere. Based on this principle, this study introduces two-dimensional boron nitride nanosheets (BNNS) and fluoropolymers-modified one-dimensional nano-silica (SiO₂) and organic tannic acid as fillers to jointly enhance the protective effect of waterborne epoxy-resin-based composites. Experimental results demonstrate that when the BNNS content is 0.5 wt.%, the 0.5-BNNS/WEP composite coating exhibits superior anti-corrosion performance, achieving an electrochemical impedance of 2.90 × 10⁷ Ω∙cm². Moreover, when BNNS is compounded with fluorinated SiO₂ or fluorinated tannic acid as fillers and incorporated into waterborne epoxy resin, the resulting composite coatings maintain excellent long-term anti-corrosion performance even after 20 days of salt spray testing. Full article

This paper describes the first detailed NMR analysis of the borylated intermediates and target compounds for a small library of pyrrolidine iminosugars of l-gulose absolute stereochemical configuration. The iminosugars were functionalised via N-alkylation to bear a boronate ester or boronic acid groups. The addition of the organic boron pharmacophore allows to further explore the chemical space around and in the active sites, where the boron atom has the capability to make reversible covalent bonds with enzyme nucleophiles and other nucleophiles. We discuss the concurrent complex equilibrium processes of mutarotation and borarotation as studied by NMR. Full article

Boron-containing compounds (BCCs) have been proposed for the treatment of diabetes and its complications. Recent studies have reported an improvement in the design and development of pharmaceutical formulations (often gels) containing boric acid applied to the foot ulcers of humans diagnosed with diabetes. The proposed mechanisms of action of boric acid include antimicrobial effects, the modulation of inflammation and metabolism, and the induction of cell differentiation. On the other hand, recent studies have suggested that boronic acids are potent antibacterial and antifungal compounds, effective modulators of inflammation, and inducers of vascular regeneration as well as inducers of healing, and they confer attractive properties such as adhesion, interaction, and the formation of complexes in formulations. Moreover, only a handful of studies conducted in animals have suggested the effective role of some BCCs as potent enhancers of wound healing, including their actions on induced and/or infected wounds in animals with disrupted metabolism. Also, it should be mentioned that no strong interactions between boric acid and the boronic acids present in formulations have been described. The developed combination could act as an additive and complementary therapy in the treatment of diabetic ulcers in humans. Further studies are required to support the hypothesis that this combination acts through diverse mechanisms to improve healing while avoiding or limiting a local or disseminated infection. Furthermore, the safety of BCCs used for foot ulcers should be established, as should the role of these formulations as a complementary therapy in current protocols for treating patients with diabetic foot ulcers. Full article

We have fabricated a new highly reproducible, stable, and sensitive cellulose paper-based Surfaced-enhanced Raman scattering (SERS) sensor substrate for non-enzymatic label-free glucose detection. To enhance reproducibility, stability, and sensitivity, the cellulose paper (CP) substrate has been modified with a naturally derived biocompatible polymer, chitosan (CS), followed by depositing enormous amount of plasmonic silver nanoparticles (AgNPs) on CP/CS and finally forming a self-assembling monolayer of 4-mercaptophenyl boronic acid (MPBA) on CP/CS/AgNPs (CP/CS/AgNPs/MPBA). The SERS sensor substrate is characterized by scanning electron microscopy (SEM), energy dispersive X-ray (EDX), Fourier transform infrared (FT-IR), and X-ray diffraction (XRD) spectroscopy techniques. The glucose sensing is achieved by monitoring the SERS intensity of C-S and B-O stretching vibrations at 1072 cm⁻¹ in MPBA, which is gradually increased with increasing concentration of glucose due to the increasing orientation change of MPBA on AgNPs. The results show that the proposed glucose paper-based SERS sensor exhibits a high analytical enhancement factor (AEF) (3.4 × 10⁷), enhanced reproducibility (<7%), improved stability (>5 weeks), excellent selectivity towards other metabolic compounds, and high sensitivity with a limit of detection (LOD) of 0.74 mM and a linear dynamic range between 1.0 and 7.0 mM. The practical application of this SERS sensor is examined in real spiked and non-spiked human blood serum samples for the detection of glucose, and satisfactory recovery results have been obtained, demonstrating the potentiality of the present paper-based SERS sensor for non-enzymatic label-free glucose detection in real biological samples. Full article

Organoboron compounds, especially those containing boronic acid and benzoxaborole in their structure, have been gaining prominence in medicinal chemistry, following the FDA approval of tavaborole for the treatment of onychomycosis and bortezomib for multiple myeloma. The antimicrobial and anticancer effects of organoboron compounds motivate the investigation of the effects of the novel derivatives described here. A total of fourteen new boronic derivatives were synthesized and characterized using analytical methods. The antimicrobial activities were evaluated against M. tuberculosis (Mtb) H37Rv strains and fungal dermatophytes (C. albicans, ATCC 90028; T. rubrum, ATCC 28189; and T. mentagrophytes, ATCC 11481), while the anticancer effect was evaluated against oral squamous cell carcinoma (SCC) cell lines. Several promising boron-containing prototypes were identified, providing a foundation for further molecular optimization in the development of new antimicrobial and anticancer compounds. Full article

High boron (B) concentrations in the soil can cause toxic effects to plants, so herbaceous cotton (Gossypium hirsutum latifolium Hucth) is a crop sensitive to such stress. Thus, this study aimed to evaluate the emergence, partitioning, and allocation of metabolic compounds of two herbaceous cotton cultivars subjected to B treatments. The experiment was carried out in a greenhouse, under a completely randomized design in a 2 × 4 factorial scheme, using two cultivars and four concentrations of B in the form of boric acid: 0.5 (control), 30, 60, and 120 mg dm⁻³ B. The increase in the concentration of B in the soil generated a significant toxic effect on the growth and biomass of the cotton plant. Cultivar 1—TMG 50 WS3 obtained greater emergence and shoot growth, while cultivar 2—FM 911 GLTP invested in roots; however, in both cultivars, B remained accumulated in the shoot. There was an increase in amino acids in the roots and a decrease in proteins and phenolic compounds in leaves and cotyledons. It was concluded that the seedlings presented satisfactory emergence up to 60 mg dm⁻³ B, and that among the cultivars there are distinct responses to B application. Full article

The synthesis of three biaryl systems containing the benzo[1,2-b:4,3-b’] framework was accomplished through the Suzuki–Miyaura cross-coupling reaction between 1-bromobenzo[1,2-b:4,3-b’]dithiophene and easily available polycyclic aromatic hydrocarbon boronic acid pinacol esters containing pyrene, fluorene, and fluorenone. The spectroscopic characterization of these molecules was carried out by means of NMR experiments and high-resolution mass spectrometry. UV-vis absorption measurements at different concentrations of the newly synthesized compounds were also performed. Full article