Search Results (86)

The effects of Δ⁹-tetrahydrocannabinol (THC) on adipocyte function under obesogenic, free-fatty-acid (FFA)-rich conditions remain poorly characterized, particularly regarding adipogenesis, FFA buffering, and downstream hepatocyte lipid handling. We investigated THC’s effect on adipogenic differentiation, temporal FFA buffering in mature adipocytes under lipid stress, and hepatocyte lipid accumulation driven by extracellular FFAs. The 3T3-L1 preadipocytes were differentiated in 0.5 mM oleate: palmitate (2:1) medium with vehicle (EtOH), THC (1 μM), or rosiglitazone (30 μM). Adipogenesis was assessed using BODIPY/NucSpot 650 staining followed by lipid droplet (LD) analysis. Adipocytes (days 10–18) were monitored for lipid accumulation, LD morphology, lipolysis, extracellular non-esterified fatty acids (NEFA), and lipid-handling gene expression. Conditioned media (CM) were applied to AML12 hepatocytes to assess lipid uptake. By day 6, THC enhanced adipogenesis, increasing lipid accumulation. In mature adipocytes, THC induced a biphasic buffering response: on day 10, NEFA levels were elevated despite unchanged lipid content, with increased isoproterenol-stimulated lipolysis. By day 18, buffering improved, with enhanced lipid storage, elevated stimulated lipolysis, smaller LDs, and altered gene expression. AML12 lipid accumulation corresponded with residual NEFA in CM, indicating that adipocyte FFA sequestration modulates hepatocyte lipid uptake. These findings reveal that under FFA-rich conditions, THC promotes late-stage adipogenesis and remodels adipocyte lipid handling, regulating extracellular FFA availability and hepatocyte lipid loading. Full article

The detection of aliphatic and aromatic biogenic amines (BAs) is important in food spoilage, environmental monitoring, and disease diagnosis and treatment. Existing fluorescent probes predominantly detect aliphatic BAs with single signal variation and low sensitivity, impairing the adaptability of discriminative sensing platforms. Herein, we present a visual chemosensor (galactose-functionalized pyrrolopyrrole aza-BODIPY, PPAB-Gal) that simultaneously detects eight aliphatic and aromatic BAs in a real-time and intuitive way based on their unique electronic and structural features. Our findings reveal that the dual colorimetric and ratiometric emission changes are rapidly produced in presence of eight BAs through a noncovalent interaction (π–π stacking and hydrogen bond)-assisted chromophore reaction. Specifically, other lone-pair electrons containing compounds, such as secondary amines, tertiary amines, NH₃, and thiol, fail to exhibit these changes. As a result, superior sensing performances with distinctly dual signals (Δλ_ab = 130 nm, Δλ_em = 150 nm), a low LOD (~25 nM), and fast response time (<2 min) were obtained. Based on these advantages, a qualitative and smartphone-assisted sensing platform with a PPAB-Gal-loaded TLC plate is developed for visual detection of putrescine and cadaverine vapor. More importantly, we construct a connection between a standard quantitative index for the TVBN value and fluorescence signals to quantitatively determine the freshness of tuna and shrimp, and the method is facile and convenient for real-time and on-site detection in practical application. Furthermore, since the overexpressed spermine is an important biomarker of cancer diagnosis and treatment, PPAB-Gal NPs can be used to ratiometrically image spermine in living cells. This work provides a promising sensing method for BAs with a novel fluorescent material in food safety fields and biomedical assays. Full article

Estradiol (E2) plays an important role in cell proliferation and certain brain functions. To reveal its mechanism of action, its detectability is essential. Only a few fluorescent-labeled hormonally active E2s exist in the literature, and their mechanism of action usually remains unclear. It would be of particular interest to develop novel labeled estradiol derivatives with retained biological activity and improved optical properties. Due to their superior optical characteristics, aza-BODIPY dyes are frequently used labeling agents in biomedical applications. E2 was labeled with the aza-BODIPY dye at its phenolic hydroxy function via an alkyl linker and a triazole coupling moiety. The estrogenic activity of the newly synthesized fluorescent conjugate was evaluated via transcriptional luciferase assay. Docking calculations were performed for the classical and alternative binding sites (CBS and ABS) of human estrogen receptor α. The terminal alkyne function was introduced into the tetraphenyl aza-BODIPY core via selective formylation, oxidation, and subsequent amidation with propargyl amine. The conjugation was achieved via Cu(I)-catalyzed azide–alkyne click reaction of the aza-BODIPY-alkyne with the 3-O-(4-azidobut-1-yl) derivative of E2. The labeled estrogen induced a dose-dependent transcriptional activity of human estrogen receptor α with a submicromolar EC₅₀ value. Docking calculations revealed that the steroid part has a perfect overlap with E2 in ABS. In CBS, however, a head-tail binding deviation was observed. A facile, fluorescent labeling methodology has been elaborated for the development of a novel red-emitting E2 conjugate with substantial estrogenic activity. Docking experiments uncovered the binding mode of the conjugate in both ABS and CBS. Full article

Phosphorus-containing fluorophores provide a versatile framework for tailoring photophysical properties, enabling the design of advanced fluorogenic materials for various applications. Boron dipyrromethene (BODIPY) and squaraine dyes are of interest due to their multifaceted modularity and synthetic accessibility. Incorporating phosphorus-based functional groups into BODIPY or squaraine scaffolds has been achieved through a plethora of synthetic methods, including post-dye assembly functionalization. These modifications often influence key spectroscopic properties and molecular functionality by expanding their utility in bioimaging, sensing, photosensitization, and theranostic applications. By leveraging the tunable nature of phosphorus-containing moieties, these dyes hold immense promise for addressing current challenges in spectroscopy, imaging, and material designs while unlocking new opportunities for advanced functional systems in chemistry, biology, and medicine. Full article

The lipid content of nine dinoflagellates was analyzed using flow cytometry to compare lipid levels. Additionally, the correlation between lipid content, cell size, and carbon content in dinoflagellates was evaluated using BODIPY 505/515 staining. The flow cytometry side scatter (SSC) effectively represented relative cell size, showing a linear relationship with the equivalent spherical diameter (ESD). Larger cells exhibited higher relative lipid content; however, lipid accumulation was influenced by nutritional modes and habitats, with mixorophic and benthic species displaying higher lipid content than heterotrophic species. A comparison of fluorescent dyes revealed that Nile Red overestimated lipid content, suggesting overlap with chlorophyll autofluorescence. Flow cytometry analysis with BODIPY 505/515 demonstrated a linear correlation with the sulfo-phospho-vanillin (SPV) method, enabling determination of actual lipid content using FL1 fluorescence and the slope value. As the carbon content increased, the lipid content initially increased rapidly but plateaued at higher carbon levels, indicating saturation. These findings suggest that relative fluorescence via flow cytometry provides an effective means to estimate the lipid content and carbon content as a function of cell size. Full article

This study explored the synthesis and application of BODIPY-functionalized gold nanoparticles (AuNPs) for the sensitive detection of biothiols via an indicator displacement assay coupled with surface-enhanced Raman scattering (SERS) techniques, alongside their efficacy for in vitro cancer cell imaging. Moreover, the assay allowed for the visible colorimetric detection of biothiols under normal and ultraviolet light conditions. The BODIPY (boron-dipyrromethene) fluorophores were strategically conjugated to the surface of gold nanoparticles, forming a robust nanohybrid that leverages the plasmonic properties of AuNPs for enhanced spectroscopic sensitivity. The detection mechanism exploited the displacement of the BODIPY indicator upon interaction with biothiols, triggering a measurable change in fluorescence and SERS signals. This dual-mode sensing approach provides high selectivity and sensitivity for biothiol detection, with detection limits reaching nanomolar concentrations using fluorescence and femtomolar concentration for cysteine using SERS. Furthermore, the BODIPY-AuNP complexes demonstrated excellent biocompatibility and photostability, facilitating their use in the fluorescence imaging of biothiol presence within cellular environments and highlighting their potential for diagnostic and therapeutic applications in biomedical research. Full article

The human body synthesizes catecholamine neurotransmitters, such as dopamine and noradrenaline. Monitoring the levels of these molecules is crucial for the prevention of important diseases, such as Alzheimer’s, schizophrenia, Parkinson’s, Huntington’s, attention-deficit hyperactivity disorder, and paragangliomas. Here, we have synthesized, characterized, and functionalized the BODIPY core with picolylamine (BDPy-pico) in order to create a sensor capable of detecting these biomarkers. The sensing properties of the BDPy-pico probe in solution were studied using fluorescence titrations and supported by DFT studies. Catecholamine sensing was also performed in the solid state by a simple strip test, using an optical fiber as the detector of emissions. In addition, the selectivity and recovery of the sensor were assessed, suggesting the possibility of using this receptor to detect dopamine and norepinephrine in human saliva. Full article

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based molecules have emerged as interesting materials for optoelectronic applications due to the possibility to easily fine-tune their photophysical and optical properties, dominated by two main absorption bands in the visible range. However, no studies have been reported on the nature of these spectral features. By means of ultrafast spectroscopy, we detect intramolecular energy transfer in a spin-coated film of di-thieno-phenyl BODIPY (DTPBDP) dispersed in a polystyrene matrix after pumping the high-energy absorption band. The same effect is not present upon pumping the lowest-energy band, which instead allows the achievement of efficient amplified spontaneous emission. Density functional calculations indicate the different nature of the two main absorption bands, explaining their different photophysical behavior. Full article

The reversibility of the covalent interaction between boronic acids and 1,2- or 1,3-diols has put the spotlight on this reaction for its potential in the development of sensors and for the fishing of bioactive glycoconjugates. In this work, we describe the investigation of this reaction for the reversible functionalization of the surface of CdSe/ZnS Quantum Rods (QRs). With this in mind, we have designed a turn-off Förster resonance energy transfer (FRET) system that ensures monitoring the extent of the reaction between the phenyl boronic residue at the meso position of a BODIPY probe and the solvent-exposed 1,2-diols on QRs’ surface. The reversibility of the corresponding boronate ester under oxidant conditions has also been assessed, thus envisioning the potential sensing ability of this system. Full article

Leishmaniasis and Human African trypanosomiasis pose significant public health threats in resource-limited regions, accentuated by the drawbacks of the current antiprotozoal treatments and the lack of approved vaccines. Considering the demand for novel therapeutic drugs, a series of BODIPY derivatives with several functionalizations at the meso, 2 and/or 6 positions of the core were synthesized and characterized. The in vitro activity against Trypanosoma brucei and Leishmania major parasites was carried out alongside a human healthy cell line (MRC-5) to establish selectivity indices (SIs). Notably, the meso-substituted BODIPY, with 1-dimethylaminonaphthalene (1b) and anthracene moiety (1c), were the most active against L. major, displaying IC₅₀ = 4.84 and 5.41 μM, with a 16 and 18-fold selectivity over MRC-5 cells, respectively. In contrast, the mono-formylated analogues 2b and 2c exhibited the highest toxicity (IC₅₀ = 2.84 and 6.17 μM, respectively) and selectivity (SI = 24 and 11, respectively) against T. brucei. Further insights on the activity of these compounds were gathered from molecular docking studies. The results suggest that these BODIPYs act as competitive inhibitors targeting the NADPH/NADP⁺ linkage site of the pteridine reductase (PR) enzyme. Additionally, these findings unveil a range of quasi-degenerate binding complexes formed between the PRs and the investigated BODIPY derivatives. These results suggest a potential correlation between the anti-parasitic activity and the presence of multiple configurations that block the same site of the enzyme. Full article

α7 nicotinic acetylcholine receptors (nAChRs) are mainly distributed in the central nervous system (CNS), including the hippocampus, striatum, and cortex of the brain. The α7 nAChR has high Ca²⁺ permeability and can be quickly activated and desensitized, and is closely related to Alzheimer’s disease (AD), epilepsy, schizophrenia, lung cancer, Parkinson’s disease (PD), inflammation, and other diseases. α-conotoxins from marine cone snail venom are typically short, disulfide-rich neuropeptides targeting nAChRs and can distinguish various subtypes, providing vital pharmacological tools for the functional research of nAChRs. [Q1G, ΔR14]LvΙB is a rat α7 nAChRs selective antagonist, modified from α-conotoxin LvΙB. In this study, we utilized three types of fluorescein after N-Hydroxy succinimide (NHS) activation treatment: 6-TAMRA-SE, Cy3 NHS, and BODIPY-FL NHS, labeling the N-Terminal of [Q1G, ΔR14]LvΙB under weak alkaline conditions, obtaining three fluorescent analogs: LvIB-R, LvIB-C, and LvIB-B, respectively. The potency of [Q1G, ΔR14]LvΙB fluorescent analogs was evaluated at rat α7 nAChRs expressed in Xenopus laevis oocytes. Using a two-electrode voltage clamp (TEVC), the half-maximal inhibitory concentration (IC₅₀) values of LvIB-R, LvIB-C, and LvIB-B were 643.3 nM, 298.0 nM, and 186.9 nM, respectively. The stability of cerebrospinal fluid analysis showed that after incubation for 12 h, the retention rates of the three fluorescent analogs were 52.2%, 22.1%, and 0%, respectively. [Q1G, ΔR14]LvΙB fluorescent analogs were applied to explore the distribution of α7 nAChRs in the hippocampus and striatum of rat brain tissue and it was found that Cy3- and BODIPY FL-labeled [Q1G, ΔR14]LvΙB exhibited better imaging characteristics than 6-TAMARA-. It was also found that α7 nAChRs are widely distributed in the cerebral cortex and cerebellar lobules. Taking into account potency, imaging, and stability, [Q1G, ΔR14]LvΙB -BODIPY FL is an ideal pharmacological tool to investigate the tissue distribution and function of α7 nAChRs. Our findings not only provide a foundation for the development of conotoxins as visual pharmacological probes, but also demonstrate the distribution of α7 nAChRs in the rat brain. Full article

The modulation of biological processes with light-sensitive chemical probes promises precise temporal and spatial control. Yet, the design and synthesis of suitable probes is a challenge for medicinal chemists. This article introduces a photocaging strategy designed to modulate the pharmacology of histamine H₃ receptors (H₃R) and H₄ receptors (H₄R). Employing the photoremovable group BODIPY as the caging entity for two agonist scaffolds—immepip and 4-methylhistamine—for H₃R and H₄R, respectively, we synthesized two BODIPY-caged compounds, 5 (VUF25657) and 6 (VUF25678), demonstrating 10–100-fold reduction in affinity for their respective receptors. Notably, the caged H₃R agonist, VUF25657, exhibits approximately a 100-fold reduction in functional activity. The photo-uncaging of VUF25657 at 560 nm resulted in the release of immepip, thereby restoring binding affinity and potency in functional assays. This approach presents a promising method to achieve optical control of H₃R receptor pharmacology. Full article

The optical properties of light-absorbing materials in optical shutter devices are critical to the use of such platforms for optical applications. We demonstrate switchable optical properties of dyes and nanoparticles in liquid-based electrowetting-on-dielectric (EWOD) devices. Our work uses narrow-band-absorbing dyes and nanoparticles, which are appealing for spectral-filtering applications targeting specific wavelengths while maintaining device transparency at other wavelengths. Low-voltage actuation of boron dipyromethene (BODIPY) dyes and nanoparticles (Ag and CdSe) was demonstrated without degradation of the light-absorbing materials. Three BODIPY dyes were used, namely Abs 503 nm, 535 nm and 560 nm for dye 1 (BODIPY-core), 2 (I₂BODIPY) and 3 (BODIPY-TMS), respectively. Reversible and low-voltage (≤20 V) switching of dye optical properties was observed as a function of device pixel dimensions (300 × 900, 200 × 600 and 150 × 450 µm). Low-voltage and reversible switching was also demonstrated for plasmonic and semiconductor nanoparticles, such as CdSe nanotetrapods (abs 508 nm), CdSe nanoplatelets (Abs 461 and 432 nm) and Ag nanoparticles (Abs 430 nm). Nanoparticle-based devices showed minimal hysteresis as well as faster relaxation times. The study presented can thus be extended to a variety of nanomaterials and dyes having the desired optical properties. Full article

Dihydroorotate dehydrogenase (DHODH) is a rate-limiting enzyme of de novo biosynthesis of pyrimidine. Although the involvement of DHODH in resisting ferroptosis has been successively reported in recent years, which greatly advanced the understanding of the mechanism of programmed cell death (PCD), the genetic sequence of the yak DHODH gene and its roles in ferroptosis are still unknown. For this purpose, we firstly cloned the coding region sequence of DHODH (1188 bp) from yak liver and conducted a characterization analysis of its predictive protein that consists of 395 amino acids. We found that the coding region of the yak DHODH gene presented high conservation among species. Second, the expression profile of the DHODH gene in various yak tissues was investigated using RT-qPCR. The results demonstrated that DHODH was widely expressed in different yak tissues, with particularly high levels in the spleen, heart, and liver. Third, to investigate the involvement of DHODH in regulating ferroptosis in cells, yak skin fibroblasts (YSFs) were isolated from fetuses. And then, bisphenol S (BPS) was used to induce the in vitro ferroptosis model of YSFs. We observed that BPS decreased the cell viability (CCK8) and membrane potential (JC-1) of YSFs in a dose-dependent manner and induced oxidative stress by elevating reactive oxygen species (ROS). Simultaneously, it was evident that BPS effectively augmented the indicators associated with ferroptosis (MDA and BODIPY staining) and reduced GSH levels. Importantly, the co-administration of Ferrostatin-1 (Fer), a potent inhibitor of ferroptosis, significantly alleviated the aforementioned markers, thereby confirming the successful induction of ferroptosis in YSFs by BPS. Finally, overexpression plasmids and siRNAs of the yak DHODH gene were designed and transfected respectively into BPS-cultured YSFs to modulate DHODH expression. The findings revealed that DHODH overexpression alleviated the occurrence of BPS-induced ferroptosis, while interference of DHODH intensified the ferroptosis process in YSFs. In summary, we successfully cloned the coding region of the yak DHODH gene, demonstrating its remarkable conservation across species. Moreover, using BPS-induced ferroptosis in YSFs as the model, the study confirmed the role of the DHODH gene in resisting ferroptosis in yaks. These results offer valuable theoretical foundations for future investigations into the functionality of the yak DHODH gene and the underlying mechanisms of ferroptosis in this species. Full article

BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) derivatives have attracted attention as probes in applications like imaging and sensing due to their unique properties like (1) strong absorption and emission in the visible and near-infrared regions of the electromagnetic spectrum, (2) strong fluorescence and (3) supreme photostability. They have also been employed in areas like photodynamic therapy. Over the last decade, BODIPY-based molecules have even emerged as candidates for cancer treatments. Cancer remains a significant health issue world-wide, necessitating a continuing search for novel therapeutic options. BODIPY is a flexible fluorophore with distinct photophysical characteristics and is a fascinating drug development platform. This review provides a comprehensive overview of the most recent breakthroughs in BODIPY-based small molecules for cancer or disease detection and therapy, including their functional potential. Full article