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Aromatic secondary amine-functionalized fluorescent NO probes: improved detection sensitivity for NO and potential applications in cancer immunotherapy studies
摘要： Tumor-associated macrophages (TAMs), constituting up to 50% of the solid tumor mass and commonly having a pro-tumoral M2 phenotype, are closely associated with decreased survival in patients. Based on the highly dynamic properties of macrophages, in recent years the repolarization of TAMs from pro-tumoral M2 phenotype to anti-tumoral M1 phenotype by various strategies has emerged as a promising cancer immunotherapy approach for improving cancer therapy. Herein, we present an aromatic secondary amine-functionalized Bodipy dye 1 and its mitochondria-targetable derivative Mito1 as fluorescent NO probes for discriminating M1 macrophages from M2 macrophages in terms of their difference in inducible NO synthase (iNOS) levels. The two probes possess the unique ability to simultaneously respond to two secondary oxides of NO, i.e., N2O3 and ONOO-, thus being more sensitive and reliable for reflecting intracellular NO than most of the existing fluorescent NO probes that usually respond to N2O3 only. With 1 as a representative, the discrimination between M1 and M2 macrophages, evaluation of the repolarization of TAMs from pro-tumoral M2 phenotype to anti-tumoral M1 phenotype, and visualization of NO communication during the immune-mediated phagocytosis of cancer cells by M1 macrophages have been realized. These results indicate that our probes should hold great potential for imaging applications in cancer immunotherapy studies and relevant anti-cancer drug screening.
关键词： fluorescent NO probes,Bodipy dye,cancer immunotherapy,NO detection,macrophage polarization
更新于2025-09-19 17:15:36
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[Advances in Heterocyclic Chemistry] || Recent developments in the synthesis of the BODIPY dyes
摘要： The BODIPYs are a very widely used class of fluorescent dyes, based around a heterocyclic organic framework, which have found applications across a broad range of research areas and real-world applications. Their popularity and utility derive from a winning combination of easily controllable photophysical properties and synthetic accessibility. Since their inception in 1968, considerable research has been directed toward the understanding, improvement, and development of flexible synthetic methodologies toward this privileged class of organic molecules. In this review we seek both to present an overview of commonly used synthetic methods and to highlight recent developments in the synthesis and modification of BODIPY dyes.
关键词： Dipyrromethene,Boron-chelated,Organic fluorophores,dipyrromethene,BODIPY,Synthesis,Dipyrromethane,4,40-Difluoro-4-bora-3a,4a-diaza-s-indacene
更新于2025-09-19 17:15:36
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Pyrazole appended quinoline-BODIPY based arene ruthenium complexes: their anticancer activity and potential applications in cellular imaging
摘要： Synthesis of an entirely new series of arene ruthenium complexes [Ru(η6-C6H6)(L1)Cl]PF6, (1), [Ru(η6-C10H14)(L1)Cl]PF6 (2), [Ru(η6-C6H6)(L2)Cl]PF6 (3) and [Ru(η6-C10H14)(L2)Cl]PF6 (4) involving 5-[2-(1H-pyrazol-1-yl)quinoline]-BODIPY (L1) and 5-[6-methoxy-2-(1H-pyrazol-1-yl)quinoline]-BODIPY (L2) was described. The ligands and complexes were thoroughly characterized by various physicochemical techniques and the structures of L1, 1 and 4 were determined by X-ray single crystal analyses. Photo-/ and electrochemical property, DNA binding, cytotoxicity, cellular uptake and apoptotic studies on 1–4 were performed by various methods, while singlet oxygen-mediated cytotoxicity via photo-irradiation by visible light was supported by 1,3-diphenylisobenzofuran titration studies. Binding of the complexes in the minor groove of CT-DNA via van der Waals forces and electrostatic interactions was affirmed by molecular docking studies. In vitro antiproliferative activity and photocytotoxicity of 1–4 were examined against the human cervical cancer cell line (HeLa) which clearly showed that these are extremely photocytotoxic under visible light (400–700 nm, 10 J cm?2; IC50 49.15, 1; 25.18, 2; 15.85, 3; 12.87, 4), less toxic in the dark (IC50 > 100 μM) and preferentially accumulate in the lysosome of the HeLa cells. Further, these complexes behave as a potential theranostic agent and their ability to kill cancer cells under visible light lies in the order 4 > 3 > 2 > 1.
关键词： singlet oxygen,arene ruthenium complexes,DNA binding,cellular imaging,BODIPY,photodynamic therapy,anticancer activity
更新于2025-09-19 17:15:36
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AIE active piperazine appended naphthalimide-BODIPYs: photophysical properties and applications in live cell lysosomal tracking
摘要： Piperazine appended naphthalimide-BODIPYs (NPB1–NPB4) exhibiting solvatochromism and aggregation-induced emission with a large Stokes shift (up to 146 nm) have been described. Separation of naphthalimide and BODIPY fluorophores by piperazine in these conjugates creates a donor–acceptor system and induces twisted intramolecular charge transfer, in addition to photoinduced electron transfer. The crucial role of naphthalimide, the alkyl chain length, the piperazine ring, and the solid-state packing on AIE has been extensively investigated by various studies. Superior cell permeability coupled with bio-compatibility of these conjugates offers a unique opportunity for their potential applications in live cell lysosomal tracking.
关键词： solvatochromism,piperazine,naphthalimide,lysosomal tracking,BODIPY,AIE
更新于2025-09-19 17:15:36
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BCl3-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions
摘要： A general and straightforward method for the synthesis of COO-BODIPYs from F-BODIPYs and carboxylic acids is established. The method is based on the use of boron trichloride to activate the involved substitution of fluorine, which leads to high yields through rapid reactions under soft conditions. This mild method opens the way to unprecedented laser dyes with outstanding efficiencies and photostabilities, which are difficult to obtain by the current methods.
关键词： COO-BODIPY,Laser Dyes,Mild Conditions,High Yields,BCl3-Activated Synthesis
更新于2025-09-19 17:13:59
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Aggregate Formation of BODIPY-Tethered Oligonucleotides That Led to Efficient Intracellular Penetration and Gene Regulation
摘要： Exogenous nucleic acids showed low e?ciency regarding cellular uptake and low stability in biological conditions; therefore, a number of techniques have been developed to improve their basic properties. One of the best solutions is the application of nanosized particles consisting of oligonucleotides that penetrate the cell membrane without any additives and exhibit high stability in cells. In this report, we employed a simple approach to address the basic properties of nanoparticles of oligonucleotides in biological systems. We prepared BODIPY-labeled oligonucleotides that carried an exclusive modi?cation at the strand end. BODIPY shows high hydrophobicity and ?uorescent emission; therefore, the oligonucleotides formed nanosized aggregates in aqueous solution and their behaviors in cells or tissues were easily revealed that aggregate formation was tracked. Detailed experiments indispensable for the oligonucleotides via scavenger-receptor-mediated endocytosis. In addition, the aggregates provided an e?cient gene regulation in living cells and tumor tissues transplanted into mice.
关键词： gene regulation,aggregate formation,BODIPY,cellular uptake,amphiphilic oligonucleotides
更新于2025-09-16 10:30:52
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BODIPY (meso-phenyl-meso) Dimer as Photovoltaic Material
摘要： Derivatives of boron-dipyrromethene (BODIPY) constitute an important class of chromophores. The BODIPY dyes can be applied in an extensive variety of applications, such as cellular imaging, photodynamic therapy, drug-delivery or organic photovoltaics [1–4]. BODIPYs are also excellent compounds to be applied as electron-donor materials in organic photovoltaic cells as they have a strong absorption in the visible spectra region, a photochemical and chemical stability, good solubility and a general suitable HOMO/LUMO frontier orbital energy levels (Figure 1). Following our work on the use of BODIPYs as photovoltaic materials [5], in this communication we present the synthesis and characterization of a meso-meso BODIPY dimer. This BODIPY dimer has all the main properties to work efficiently as electron-donor material since it exhibits strong absorbance in the visible spectrum, good solubility and suitable HOMO and LUMO energy orbitals to work as donor material in the bulky heterojunction BODIPY/PCBM layer, based solar cells.
关键词： organic chemistry,synthesis,BODIPY
更新于2025-09-16 10:30:52
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BODIPY Substituted Zinc(II) Phthalocyanine and Its Bulk Heterojunction Application in the solar cells
摘要： A novel asymmetrical zinc(II) phthalocyanine-BODIPY conjugate (ZnPc-BODIPY) bearing three iodine directly substituted to the macrocycle and one BODIPY connected to macrocycle with amide bond was synthesized by the reaction of carboxylic acid substituted asymmetrical zinc(II) phthalocyanine (ZnPc) with BODIPY derivative bearing amino group (BODIPY-NH2). This conjugate was fully characterized by spectroscopic methods (FT-IR, UV-Vis, 1H NMR, 11B NMR, 19F NMR and mass) and elemental analysis. The fluorescence behavior of ZnPc-BODIPY was studied for determination of energy transfer process. The voltammetry measurements (CV and SWV) were performed for specifying of the HOMO-LUMO energy levels and band gaps of ZnPc-BODIPY and starting compounds ZnPc and BODIPY-NH2 for comparison. In addition, the band gaps of these compounds were also determined by UV-Vis absorption onset (λonset) and theoretical calculations. Bulk heterojunction solar cell containing ZnPc-BODIPY were fabricated in the structure of ITO/PEDOT:PSS/ZnPc-BODIPY:PCBM/Al. The photovoltaic parameters of the solar cell were obtained and ZnPc-BODIPY conjugate was found to bring spectral contribution to IPCE at a peak of 510 nm.
关键词： BODIPY,Organic solar cell,Suzuki coupling,Phthalocyanine
更新于2025-09-12 10:27:22
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Enhanced triplet state generation through radical pair intermediates in BODIPY-quantum dot complexes
摘要： Generation of triplet excited states through radical pair intermediates has been extensively studied in molecular complexes. Similar schemes remain rare in hybrid structures of quantum dot-organic molecules, despite intense recent interest of quantum dot sensitized triplet excited state generation. Herein, we demonstrate that the efficiency of the intersystem crossing from the singlet to the triplet state in boron dipyrromethene (BODIPY) can be enhanced in CdSe quantum dot-BODIPY complexes through a radical pair intermediate state consisting of an unpaired electron in the quantum dot conduction band and that in oxidized BODIPY. By transient absorption spectroscopy, we show that the excitation of BODIPY with 650 nm light leads to the formation of a charge separated state by electron transfer from BODIPY to CdSe (with a time constant of 6.33 ± 1.13 ns), competing with internal conversion to the ground state within BODIPY, and the radical pair state decays subsequently by back charge recombination to generate a triplet excited state (with a time constant of 158 ± 28 ns) or the ground state of BODIPY. The overall quantum efficiency of BODIPY triplet excited state generation was determined to be (27.2 ± 3.0)%. The findings of efficient triplet state formation and intermediate radical pair states in this hybrid system suggest that quantum dot-molecule complexes may be a promising platform for spintronics applications.
关键词： CdSe quantum dot,radical pair intermediates,transient absorption spectroscopy,intersystem crossing,spintronics,triplet excited states,BODIPY,quantum dot-organic molecules
更新于2025-09-12 10:27:22
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BODIPY platform: a tunable tool for green to NIR OLEDs
摘要： The rapid appearance of organic optoelectronics as a promising alternative to conventional optoelectronics has been largely achieved through the design and development of new conjugated systems. The 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based materials have recently emerged as platforms for many types of applications such as sensors, organic thin-film transistors and organic photovoltaics; however, their application as active materials in organic light-emitting diodes (OLEDs) has only been poorly explored. This review article provides an overview of the most important developments in the structural design and synthesis of BODIPY-based organic semiconductors for application in OLED devices. The results summarised and discussed here include the most relevant results starting from the first application of BODIPY-based materials in OLEDs in 2002 up to the recent discoveries as near-IR emitters also promoted by aggregation-induced emission (AIE). Therefore, this review should inspire new research for future developments of BODIPY-based materials, in particular as ‘metal-free’ infrared emitters.
关键词： optoelectronic devices,BODIPY,OLED
更新于2025-09-11 14:15:04