A Novel Ethylenediamine Bridged Indole-BODIPY Schiff Base Applied for Selective Response to Fe, Cu and Al Detection.

In this work, fluorescent compounds with Schiff base functional groups were obtained by using ethylenediamine bridged indole-BODIPY. The fluorescent probe Indole-ethylenediamine-BODIPY (ID-E-BP) and its performance in recognizing metal ions were investigated by UV and fluorescence spectroscopy, which showed that the fluorescent probe had a maximum absorption wavelength of 536 nm and a maximum emission wavelength of 557 nm. The fluorescent probe exhibited a fast and sensitive fluorescence quenching response effect in ethanol solution for Fe3+, Cu2+ and Al3+, and the detection limits were 0.24 µM, 0.19 µM and 0.15 µM, respectively. The ID-E-BP sensor is basically not affected by metal ions and environmental pH, and can be successfully applied to test strips and real water samples to detect metal ions. In addition, density functional theory (DFT) was calculated, and the results showed that the fluorescence probe combined with Fe3+, Cu2+ and Al3+ had a stable configuration. In summary, the sensor synthesized in this paper can be stably combined with metal ions and used to identify special metal ions.

Strategies based on nido-carborane embedded indole fluorescent polymers: their synthesis, spectral properties and cell imaging studies.

The continuous preparation scheme EPO-Poly-indol-nido-carborane (E-P-INDOLCAB), L100-55-Poly-indol-nido-carborane (L-P-INDOLCAB), RS-Poly-indol-nido-carborane (S-P-INDOLCAB), and RL-Poly-indol-nido-carborane (R-P-INDOLCAB) were used to prepare the four types of acrylic resin-coated nido-carborane indole fluorescent polymers. After testing their spectral properties and the fluorescence stability curve trend at various acidic pH values (3.4 and 5.5, respectively), L-P-INDOLCAB and S-P-INDOLCAB were determined to be the best polymers. The stable states of the two polymers and the dispersion of the nanoparticles on the system's surface during Atomic Force Microscope (AFM) test are shown by the zeta potentials of -23 and -42 mV. The dispersion of nanoparticles on the system's surface and the stable condition of the two polymers were examined using zeta potential and atomic force microscopy (AFM). Transmission electron microscopy (TEM) can also confirm these findings, showing that the acrylic resin securely encases the interior to form an eyeball. Both polymers' biocompatibility with HELA cells was enhanced in cell imaging, closely enclosing the target cells. The two complexes displayed strong inhibitory effects on PC-3 and HeLa cells when the concentration was 20 ug/mL, as validated by subsequent cell proliferation toxicity studies.

Design, synthesis, and antitumor activity evaluation of BF3-o, m, p-phenylenediamine bridged with pyrimidine-indole BF3 adduction derivatives.

Fluorescent drugs and pyrimidine-indole scaffolds have been shown to have advantages in cancer treatment. Fluorescent antitumor drugs BF3-o, m, p-phenylenediamine pyrimidine-indole derivatives (PYB1, PYB2, and PYB3) were synthesized by linking pyrimidine and indole groups with aniline through a simple step and introducing BF3. The drugs exhibit promising antitumor activity and their fluorescent properties make them useful for imaging purposes. The optical properties of the three compounds have been investigated. All of them have fluorescent properties and compound PYB2 has good fluorescent properties. Additionally, the in vitro cytotoxicity of these compounds was evaluated against the human cancer cell line HeLa and the human normal cell line L02. The inhibition rates of HeLa cells treated with PYB1, PYB2, and PYB3 at a concentration of 19.2 µg/mL were 80.91%, 77.72%, and 65.94%, respectively. These results indicate a strong inhibitory effect on cancer cells. Further through the cell imaging experiment, we can see that PYB2 can enter the cell through the cell membrane through the fluorescence scattering diagram, which has good biocompatibility. In addition, the possible interactions between the compounds and Ras protein active sites were analyzed by molecular docking. The three compounds can bind well to Ras protein through hydrogen bonding. This study provides a basis for the development and modification of pyrimidine-indole fluorescent anticancer drugs. Compound PYB2 shows potential as a fluorescent anticancer drug.

A novel strategy to bind pyrimidine sulfonamide derivatives with odd even chains: exploration of their design, synthesis and biological activity evaluation.

Based on the hybridization strategy of dominant fragments, a series of pyrimidine sulfonamide (PS) derivatives were obtained by combining the pharmacophore fragments (sulfonamide group and pyrimidine group) with different biological activities, and evaluated as a new type of anticancer drug. The compounds were evaluated for in vitro cytotoxicity against four human cancer cell lines (HeLa, HCT-116, A-549 and HepG2) and the normal human cell line L02. Compared with the anti-cancer drug 5-fluorouracil (5-FU), the antiproliferative activity of compound PS14 was close to 5-FU and it has good antitumor activity. The IC50 values were 15.13 ± 2.20, 19.87 ± 2.01, 12.64 ± 3.22, 22.20 ± 1.34 and 102.46 ± 2.27 µM, respectively. The structure activity relationship was analyzed. The antitumor activity of the compound tended to increase. When the substituents of the branch chain of sulfonamides were odd. In addition, the oil-water partition coefficient was also investigated. The logP value of PS14 was between 0 and 3, indicating that PS14 was a compound with good lipophilic property, poor water solubility and easy to be absorbed and transported through cell membrane. The anti-cancer mechanism was further studied by flow cytometry. After PS14 treated HeLa, HCT-116, A-549 and HepG2, the percentage of apoptotic cells was 45.30%, 28.2%, 31.00% and 35.20%, respectively, which was higher than that of the control 5-FU. The results of cell cycle showed that PRD2 mainly blocked the cell cycle in the S phase, thereby inhibiting cell proliferation. Furthermore, molecular docking analyzed possible interactions between the compound and the PI3Kα active site, this compound has good binding with PI3Kα. Overall, this study laid the groundwork for the development and structural modification of new pyrimidine sulfonamide drugs, and PS14 could be further developed into a cancer treatment drug.

A porous form Coomassie brilliant blue G250-isorhamnetin fluorescent composite coated with acrylic resin for tumor cell imaging.

Four distinct fluorescence complexes, the fluorescent complex-1 (FC-1), fluorescent complex-2 (FC-2), fluorescent complex third (FC-3) and fluorescent complex fourth (FC-4), were created using isorhamnetin and Coomassie brilliant blue G250 as raw materials. The issue of isorhamnetin's low solubility has been resolved, and isorhamnetin-coomassie brilliant blue G250 now has better biocompatibility. Four different forms of fluorescence compounds' ultraviolet absorption spectra were identified. It was discovered that FC-2, FC-3, and FC-4, respectively, had double peaks at 483-620 nm. FC-4 had the highest ultraviolet absorption intensity, whereas FC-1 exhibited the most consistent and longest wavelength of ultraviolet absorption. Transmission electron microscopy revealed that the acrylic resin evenly disseminated the Coomassie brilliant blue G250-isorhamnetin complex in an amorphous flocculent form. Human prostate cancer cells (PC3) and human cervical cancer cells (HeLa) were investigated in the (Cell Counting Kit-8) CCK8 experiment under 10 different concentration circumstances, and the proliferation impact was 64.30% and 68.06%, respectively. Shown the complex's strong anti-tumor properties and minimal cytotoxicity. Through in vitro imaging of tumor cells, it was found that FC-1's fluorescent complex has high selectivity and can accurately infiltrate tumor cells, proving that it is biocompatible. The design not only addresses the issue of isorhamnein-Coomassie Bright Blue G250's bioavailability, but it also has an effective visual fluorescence targeting effect.

Strategy of eudragit coated curcumin nanoparticles delivery system: Release and cell imaging studies in simulated gastrointestinal microenvironments.

Curcumin has a broad-spectrum anti-tumor effect and has no toxic side effects. However, the unique diketone structure of curcumin will undergo diketo-enol tautomerism under different acid-base conditions, resulting in its instability under physiological conditions. In addition, the low biocompatibility and absorption rate of curcumin also limit the use of curcumin drugs. In this paper, curcumin was modified by substitution of acryloyl and acrylsulfonyl groups, and four kinds of nanoparticles with regular morphology were prepared using non-toxic and non-irritating acrylic resin as coating material to improve the stability and bioavailability of the compounds. Zeta potential testing shows that the composites surface carries positive charges and have good stability. In the release experiment, four complexes have the potential for slow and controlled release. Imaging of Hela cells with different channels was performed, and the imaging results showed that the complexes could enter the cells and be absorbed by them, demonstrating good imaging performance. MTT experiments have shown that the complexes have certain anti-tumor activity and low cytotoxicity. In general, the complexes synthesized in this paper have potential in the field of drug fluorescence imaging detection. At the same time, this experiment provides a new idea for the design of slow and controlled release of drugs.

Blue Emission of Tetrafluorobenzocarbazole Under the Interactions of Nitrogen-oxygen Saturated hydrogen Bonds with Aggregated Proton Acid.

Two novel tetrafluorobenzocarbazole and containing the amino branch introduced at the end of the molecule are synthesized by a simple method. The tetrafluorobenzocarbazole as the electron donor with electron-rich fluoride ions connected by π-benzyl ring conjugation structure, which affects the overall electron cloud density. Moreover, the amino branch introduced at the end of the molecule, which makes it easy to form intermolecular hydrogen bonds and affected photophysical properties. Meanwhile, the photophysical property of both compounds are discussed under different acidic conditions. The UV-absorption show that around ~286 nm is mainly attributed to the strong structural absorption band peak of the π-π ∗ transition of the carbazole moiety, and the irregular absorption band around ~314 nm and ~326 nm are mainly attributed to the n-π ∗ transition of the carbazole group conjugate with the adjacent molecule. The emission spectrum of both compounds showed that the intensity of fluorescence decreased in different degrees after the addition of the acidic solution. Furthermore, the electrochemical properties were evidenced by cyclic voltammetry (CV) and density functional theory (DFT) calculations, and the orbital conformation (HOMOs-LUMOs) was simulated by Gaussian 09 software and its crystal structure was observed by X-ray diffraction (XRD). The results exhibited that both compounds are electrochemically stable blue small-molecule fluorescent substances, and expected that both compounds can be novel and stable acid-sensitive organic blue-light materials.

Spectral-envelope modulated double-phase method for computer-generated holography.

Computer-generated holography provides an approach to modulate the optical wavefront with computationally synthesized holograms. Since the hardware implementation for complex wavefronts is not yet available, double-phase decomposition is utilized as a complex encoding method of converting a complex wavefront to a double-phase hologram. The double-phase hologram adapts a complex wavefront for the phase-type devices, but the reconstruction is plagued by the noise caused by spatial-shifting errors. Here, a spectral-envelope modulated double-phase method is proposed to suppress the spatial-shifting noise with an off-axis envelope modulation on the Fourier spectrum of a double-phase hologram. This proposed method out-performs conventional on-axis double-phase method in optical reconstructing accuracy with indicated 9.54% improvement in PSNR and 196.86% improvement in SSIM.

Symmetry dual functional pyrimidine-BODIPY probes for imaging targeting and activity study.

Nondestructive diagnosis of tumor has always been the goal of scientists. Fluorescent dyes have become the rising star in the field of cancer diagnosis because of their excellent characteristics. Therefore, in this work, fluorescence probes d-Y-B and dO-Y-B with anti-tumor activity were constructed by introducing pyrimidine groups with high anti-tumor activity using fluorescence dye BODIPY as parent nucleus. The modified BODIPY group in the structure had the advantage of fluorescent dye, ensuring the strong fluorescence and photosensitivity of the target compound. That ethylenediamine acts as a bridge with two -NH- groups to increase molecular hydrogen bonding, and can bind firmly to multiple proteins. Co-localization of the target compounds d-Y-B and dO-Y-B with the hoechst dye for labeling living cells showed that these compounds had high biocompatibility and photostability for localization to HeLa cells. In vivo imaging in mice can realize specific localization and real-time visualization of tumor cells. The results of cytotoxicity experiments in vitro and computer software simulating molecular docking confirmed the potential of the target compounds as an anticancer agents. The bifunctional probe realized visualization of cancer cells in mice, and can kill cancer cells by anti-proliferation, which may provide a direction for future anticancer drug development.

Bioactivity and Cell Imaging of Antitumor Fluorescent Agents (Curcumin Derivatives) Coated by Two-Way Embedded Cyclodextrin Strategy.

Curcumin has a wide range of pharmacological activities, which can be used to treat tumors, inflammation and other diseases. However, curcumin's poor solubility and low bioavailability limit its application. In this article, the structure of curcumin was modified with boron trifluoride ether to change fluorescent labeling. The compounds were then embedded into the hydrophobic cavity of α-cyclodextrin and hydroxypropyl ß-cyclodextrin to form inclusion complexes. The two inclusion complexes have excellent photophysical properties, and the maximum emission wavelength is in the range of 550-565 nm. In addition, the two compounds were applied to the fluorescence imaging of HCT-116 cells and HeLa cells, and the proliferation toxicity of the compounds was detected. Both compounds showed certain inhibitory effects on the proliferation of cancer cells. In short, the fluorescent drug molecule synthesized in this article has great reference value for the development of new dosage forms of curcumin.

Water-soluble BODIPY-nido-carborane nanoparticles applied to biocompatibility tumor cell imaging.

In this article, o-carborane has a high boron content, high hydrophobicity, and good chemical stability. It has been widely used in the fields of biology and medicine, especially in the application of boron neutron capture therapy (BNCT). However, o-carborane is a fat-soluble compound, its hydrophobicity is too strong, and its bioavailability is poor. This project aims to improve the water solubility of o-carborane drugs, so that the drugs can reach specific sites. For this reason, this article provides a one-pot reaction for the synthesis of water-soluble boron-containing drugs. 2-Chloro-1-(difluoroboranyl)-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl) methyl)-1H-pyrrole and ethylenediamine are used as raw materials to synthesize fluorescent molecular probe BODIPY-NH2, and the fluorescent molecular probe is reacted with P-CBMA (poly(carboxybetaine methacrylate)) to produce a water-soluble gel polymer. Water-soluble o-carborane polymers were synthesized by hydrogen bonding of the polymers with bis(4-azaspiro[3.4]octan-4-ium)-nido-ortho-carborane and bis(5-azaspiro[4.5]decan-5-ium)-nido-ortho-caborane. The two polymers were characterized and the results showed that the maximum UV absorption wavelength of the two boron polymers in different polar solutions was 530-540 nm. In the fluorescence spectrum, the maximum emission wavelengths of the two boron polymers are concentrated between 550 and 560 nm. Through electron microscopy imaging, the fluoroboron pyrrole polymers wrap the boron clusters to form a spherical stacked. Through fluorescent cell imaging, both boron polymers can enter target cells.

Design, synthesis and biological activity of bis-sulfonyl-BODIPY probes for tumor cell imaging.

In recent years, BODIPY derivatives have become one of the research hotspots in the field of bioprobes, but most of them have the problems of poor hydrophilicity, low biocompatibility and no targeting. In this paper, novel ethylenediamine bridging bis-sulfonyl-BODIPY fluorescent probes were successfully designed and synthesized to solve these problems; What's more, the cytotoxicity analysis, cell imaging, in vivo imaging and apoptosis experiments were carried out. Ethylenediamine bridges and oxygen-rich sulfonyl groups made such probes had certain hydrophilicity, so they could be dissolved in dimethylsulfoxide and methanol. The IC50 value of compound 9 in HCT-116 cells was 93.12 ± 6.33 µM, and in HeLa cells was 89.09 ± 11.84 µM, which indicating that the probe had certain inhibitory effect on cancer cells. The excellent biocompatibility and potential tumor targeting properties of the compound were clearly observed in cell and mice imaging. This study is of great significance for the rational design of novel targeted BODIPY probes with good hydrophilicity and biocompatibility.

High activity, high selectivity and high biocompatibility BODIPY-pyrimidine derivatives for fluorescence target recognition and evaluation of inhibitory activity.

BODIPY-Pyrimidine (BP) is a highly selective, highly active, and highly biocompatible fluorescent drug, which is characterized by its own activity combined with a fluorophore. The combination of pyrimidines with good biological activity and fluorophores to obtain new compounds with both anti-tumor activity and fluorescent targeting probe functions is the focus of this research. In terms of biological activity, in vitro cytotoxicity of the compounds on four human cancer cells (HepG2, HeLa, A-459, and HCT-116) and the human normal cell line L-02 was studied. BP-4 has good antiproliferative activity, and its IC50 values are 19.12 ± 2.29, 13.47 ± 3.80, 18.59 ± 7.42, 14.57 ± 2.44 and 92.48 ± 6.03 µM, respectively. Good biocompatibility with tumor cells can be observed in cell imaging. The anti-tumor mechanism of the compound was further studied by flow cytometry. After BP-2, BP-3 and BP-4 treated HeLa cells, the percentage of apoptotic cells was 19.07%, 22.09% and 27.3%, respectively. The cell cycle study found that, compared with the positive control 5-FU (48.05%), the compounds BP-2, BP-3 and BP-4 all increased the proportion of HeLa cells in the G1 phase, reaching 57.65%, 55.46% and 53.58%, respectively. In vivo bioimaging results show that all three compounds can be targeted and accurately expressed in tumor tissues. In addition, molecular docking analyzes the possible interaction between the compound and the active site of thymidylate synthase.

Combination of Structured Illumination Microscopy with Hyperspectral Imaging for Cell Analysis.

Existing structured illumination microscopy (SIM) allows super-resolution live-cell imaging in few color channels that provide merely morphological information but cannot acquire the sample spectrum that is strongly relevant to the underlying physicochemical property. We develop hyperspectral SIM which enables high-speed spectral super-resolution imaging in SIM for the first time. Through optically mapping the three-dimensional (x, y, and λ) datacube of the sample to the detector plane, hyperspectral SIM allows snapshot spectral imaging of the SIM raw image, detecting the sample spectrum while retaining the high-speed and super-resolution characteristics of SIM. We demonstrate hyperspectral SIM imaging and reconstruct a datacube containing 31 super-resolution images of different wavelengths from only 9 exposures, achieving a 15 nm spectral resolution. We show time-lapse hyperspectral SIM imaging that achieves an imaging speed of 2.7 s per datacube-31-fold faster than the existing wavelength scanning strategy. To demonstrate the great prospects for further combining hyperspectral SIM with various spectral analysis methods, we also perform spectral unmixing of the hyperspectral SIM result while imaging the spectrally overlapped sample.

Imaging spectrometer with single component of freeform concave grating.

In this Letter, an imaging spectrometer in which a freeform concave grating is the only optical component in the system is introduced. The degrees of freedom of optical freeform surfaces and a variable line-spacing (VLS) grating are used to realize imaging spectrometers. A point-by-point system design method is proposed that can generate a good initial solution rapidly. By exploring the limitations of the system specifications, it is demonstrated that the spectral dispersion, spectral resolving power, and system length can be improved significantly by using the freeform VLS concave grating. It is also found that freeform surfaces with higher degrees of freedom than a toroid can further improve system performance when using a VLS grating.

Design, synthesis and photophysical studies of BODIPY-o, m, p-phenylenediamine-based probes: Insights into their responsiveness under different pH conditions.

In this paper, a series of novel phenylenediamine-fluoroboron pyrrole fluorescent derivatives were prepared which have distinct responsiveness under different hydrogen ion concentration (pH) conditions. It is noticed that the products showed excellent fluorescence properties in different solvents, especially in tetrahydrofuran and dichloromethane, with the most prominent fluorescence intensity, while the fluorescence in methanol, acetonitrile, and dimethyl sulfoxide was weaker. Responsiveness under different hydrogen ion concentration conditions in aqueous solutions were also observed, where the fluorescence intensity is quenching when the pH is 4.0. With regard to cells imaging investigation, the products showed the prominent fluorescence in HeLa cells. Further acidic cell imaging results showed that under acidic conditions made of formic acid or acetic acid, the intracellular fluorescence of the compounds was clustered around the cells and intensive enough different from without acidity control group. Especially, the compounds have unique fluorescence in acidic environment and has great potential and research value as acidic probes.

Phase hologram optimization with bandwidth constraint strategy for speckle-free optical reconstruction.

An iterative method with bandwidth constraint strategy is proposed to design phase holograms for high-quality speckle-free optical reconstruction. The bandwidth properties of the reconstructed field are analyzed theoretically based on the sampling theory, which helps in properly allocating the sampling resources for efficiently describing the speckles and artifacts in the reconstructed field. Iterative calculation with bandwidth constraint strategy of the reconstructed field and quadratic initial phase can optimize the phase hologram without stagnation problem, which provides effective controls of the reconstructed intensity fluctuations and helps to suppress the speckles and artifacts. Numerical and optical experiments have been performed to validate the proposed method can achieve excellent image fidelity.

Shifted band-extended angular spectrum method for off-axis diffraction calculation.

The shifted band-extended angular spectrum method (Shift-BEASM) is proposed to calculate free-space diffraction between two parallel planes with an off-axis offset. Off-axis numerical propagation is useful for simulating non-paraxial and large-scale fields. The proposed Shift-BEASM allow us to calculate the off-axis diffraction in a wide propagation range by extending the effective bandwidth using the nonuniform fast Fourier transform. The calculation accuracy is higher than that of existing techniques, such as the shifted-Fresnel method and shifted band-limited angular spectrum method, not only in the near field but also in the far field. Numerical examples and accuracy as well as theoretical formulation are presented to confirm validity of the proposed method.

Simultaneous improvement of field-of-view and resolution in an imaging optical system.

A novel imaging system design is proposed, in which the FOV and maximum resolution are improved simultaneously while the detector remains fixed. These improvements are realized using freeform optical surfaces and field-dependent characteristic parameters. The resulting imaging system design has optical properties that vary continuously with the field angle. In the central FOV, the system is equivalent to a long-focal-length camera, while in the marginal FOV, it is equivalent to a short-focal-length camera; however, the system has a constant F-number across the FOV. A 2× variation in the field-dependent characteristic parameters across the FOV is achieved.

A Novel BODIPY Quaternary Ammonium Salt-Based Fluorescent Probe: Synthesis, Physical Properties, and Live-Cell Imaging.

The development of biological fluorescent probes is of great significance to the field of cancer bio-imaging. However, most current probes within the bulky hydrophobic group have limited application in aqueous medium and restricted imaging under physiological conditions. Herein, we proposed two efficient molecules to study their physical properties and imaging work, and the absorption and fluorescence intensity were collected with varying ions attending in aqueous medium. We enhance the water solubility through the quaternization reaction and form a balance between hydrophilic and hydrophobicity with dipyrrome-theneboron difluoride (BODIPY) fluorophore. We introduced pyridine and dimethylaminopyridine (DMAP) by quaternization and connected the BODIPY fluorophore by ethylenediamine. The final synthesized probes have achieved ideal affinity with HeLa cells (human cervical carcinoma cell line) in live-cell imaging which could be observed by Confocal Microscope. The probes also have a good affinity with subcutaneous tumor cells in mice in in vivo imaging, which may make them candidates as oncology imaging probes.