625-82-1Relevant academic research and scientific papers
Development of a new fluorescent probe: 1,3,5,7-tetramethyl-8-(4′-aminophenyl)-4,4-difluoro-4-bora-3a, 4a-diaza-s-indacence for the determination of trace nitrite
Li, Mengling,Wang, Hong,Zhang, Xian,Zhang, Hua-Shan
, p. 987 - 993 (2004)
A new fluorescent probe, 1,3,5,7-tetramethyl-8-(4′-aminophenyl)-4,4-difluoro-4-bora-3a, 4a-diaza-s-indacence (TMABODIPY) has been developed for the determination of trace nitrite in terms of the reaction of nitrite with TMABODIPY first in acidic solution and then in alkaline solution to form diazotate, a stable and highly fluorescent reagent. The method offered the advantage of specificity, sensitivity and simplicity. The linear calibration range for nitrite was 8-300nmoll-1s with a 3σ detection limit of 0.65nmoll -1. The proposed method has been applied to monitor the trace nitrite in drinking water and vegetable without extraction.
A near-infrared and lysosomal targeting thiophene-BODIPY photosensitizer: Synthesis and its imaging guided photodynamic therapy of cancer cells
Bai, Jin,Zhang, Lei,Qian, Ying
supporting information, (2021/02/16)
In this study, a novel NIR and lysosomal targeting thiophene-BODIPY photosensitizer SBOP-Lyso was synthesized to explore its potential applications in photodynamic therapy of A549 cells. In the strategy of designing SBOP-Lyso, S atom in thiophene as well as heavy atom I were introduced to promote ISC efficiency to ensure high singlet oxygen yield. A common lysosome targeted group (M1: 1-(2-morpholinoethyl)-1H-indole-3-carbaldehyde) was linked to SBOP to extend its wavelength to the NIR region. Its absorption peak was at 660 nm (εmax = 5.2 × 104 cm?1 M?1) and its corresponding emission peak was located at 705 nm. Singlet oxygen could be quickly generated by SBOP-Lyso in the presence of 660 nm LED irradiation and the singlet oxygen yield was up to 44.1%. In addition, it also had good biocompatibility and could enter cells or zebrafish in a short time. SBOP-Lyso had negligible dark cytotoxicity (cell survival rate > 80%) and excellent phototoxicity (IC50 = 0.2 μM). DCFH-DA (ROS indicator) proved that SBOP-Lyso could generate singlet oxygen with 660 nm LED irradiation. Singlet oxygen produced by SBOP-Lyso could kill cancer cells in PDT process and it had the ability to effectively inhibit A549 cells migration. Besides that, lysosomal colocalization assay showed that it had good lysosomal localization ability (Pearson colocation coefficient, R = 0.93). Considering the above results, SBOP-Lyso as a unique lysosome-targeted photosensitizer with excellent properties would exhibit positive results in PDT process of cancer cells.
Novel indole-BODIPY photosensitizers based on iodine promoted intersystem crossing enhancement for lysosome-targeted imaging and photodynamic therapy
Liu, Miao,Qian, Ying,Wang, Chengjun
supporting information, p. 18082 - 18089 (2021/10/12)
In this work, we report the new lysosome-targeting indole-BODIPY derivatives BDP-Lys, IBDP-Lys, and I2BDP-Lys. BDP-Lys dye was designed for fluorescence imaging through introduction of an indole-containing morpholine moiety to a BODIPY core. Monoiodine and diiodine were incorporated into BDP-Lys dye to develop the photosensitizers IBDP-Lys and I2BDP-Lys. The maximum absorption (λabs) for IBDP-Lys and I2BDP-Lys displayed a redshift at approximately 11 nm and 27 nm, respectively, compared with the BDP-Lys dye (λabs= 504 nm). Similarly, the maximum emission also exhibited a redshift. The fluorescence quantum yield (ΦF) of IBDP-Lys (ΦF= 0.37%) and I2BDP-Lys (ΦF= 0.71%) was much lower than that of BDP-Lys dye (ΦF= 7.48%). The singlet oxygen quantum yields were measured as 43.10% for IBDP-Lys and 71.00% for I2BDP-Lys, which were higher than the iodine-free dye BDP-Lys. The theoretical calculation reasonably explains that iodine atoms promoted the intersystem crossing (ISC) process, and di-iodine further enhanced the ISC in indole-BODIPY dyes. Moreover, monoiodine photosensitizer IBDP-Lys was able to balance the generation of singlet oxygen and biocompatibility in cancer treatment. IBDP-Lys exhibited low dark toxicity (cell viability >90%), satisfactory biocompatibility, and precise lysosome targeting, with a Pearson coefficient of 0.93. The IBDP-Lys photosensitizer also was able to kill tumour cells. Considering the above results, the novel structure of indole-BODIPY photosensitizers could serve as a potential platform for lysosome-targeted imaging and photodynamic therapy.
Design and synthesis of perfluoroalkyl decorated BODIPY dye for random laser action in a microfluidic device
Maity, Apurba,Sarkar, Anirban,Bhaktha B.n, Shivakiran,Patra, Sanjib K.
supporting information, p. 14650 - 14661 (2020/10/02)
New and highly emissive 2,6-diacetynyl and 2,6-bis-(phenylacetynyl) functionalized pentamethyldifluoroboron-dipyrromethane (BODIPY) derivatives (FBDP1-2) with perfluorinated pendant groups at the boron center have been synthesized successfully by the combination of two strategies: extending the π-conjugation and functionalization at the boron centre. The newly synthesized dyes have been characterized unambiguously by using various analytical tools such as multinuclear NMR, MALDI-TOF, and single crystal XRD analysis. The dyes (FBDP1-2) exhibit excellent photophysical properties in the yellow to red spectral region (λabs = 530 nm and 555 nm, and λem = 555 nm and 596 nm, respectively) with relatively good Stokes shifts (849 cm-1 and 1240 cm-1), high quantum efficiency (?F = 0.72 and 0.61) and excellent brightness (2.95 × 104 and 2.38 × 104 M-1 cm-1). Most importantly, under a transverse pumping condition at 532 nm, the dyes show efficient and stable laser action, having a good tunable range (20 nm and 13 nm) with a maximum lasing efficiency of 45% and 38% for FBDP1 and FBDP2, respectively. Moreover, the random lasing behavior of FBDP1 has been investigated in a dye-circulated polydimethylsiloxane (PDMS) based disordered microfluidic device. The appearance of randomly positioned sharp spikes with a full width at half maximum (FWHM) of less than 0.3 nm around 555 nm indicates the random laser (RL) emission. The relationship between input pump energy and output random lasing intensity has also been demonstrated, with the random lasing threshold of 0.5 mJ.
A water-soluble BODIPY based ‘OFF/ON' fluorescent probe for the detection of Cd2+ ions with high selectivity and sensitivity
Maity, Apurba,Ghosh, Utsav,Giri, Dipanjan,Mukherjee, Devdeep,Maiti, Tapas Kumar,Patra, Sanjib K.
supporting information, p. 2108 - 2117 (2019/02/12)
A water-soluble dilithium salt BODIPY derivative (LiBDP) with appended dicarboxylate pseudo-crown ether [NO4] coordinating sites has been designed, synthesized and characterized successfully for the selective and sensitive recognition of Cd2+ in aqueous media. The chemosensor exhibits a remarkable increase in fluorescence intensity as well as a distinct color change upon the addition of Cd2+ over other environmentally and biologically relevant metal ions in H2O. The fluorometric response of LiBDP is attributed to the metal chelation-enhanced fluorescence (MCHEF) effect which has been confirmed by a strong association constant of 2.57 ± 1.06 × 105 M?1 and Job's plot, indicating 1?:?1 binding stoichiometry between LiBDP and Cd2+. Frontier molecular orbital analysis (obtained from DFT studies) also illustrates the turn-on fluorescence of the probe by blocking photoinduced electron transfer (PET) after coordination to Cd2+. The probe can detect Cd2+ in a competitive environment up to a submicromolar level in a biologically significant pH range. The sensor is proved to be reversible and reusable by the alternative addition of Cd2+ followed by S2?. The OFF/ON/OFF sensing behavior is utilized to construct an INHIBIT molecular logic gate based on the two inputs of Cd2+ and S2? and a fluorescence intensity at 512 nm as an output. The test paper experiment demonstrates the practical utility of LiBDP to monitor Cd2+ in an aqueous sample. Finally, the sensing probe was utilized to monitor Cd2+ in living cells.
Thermal Behavior Analysis of Two Synthesized Flavor Precursors of N-alkylpyrrole Derivatives
Ai, Lvye,Liu, Mengzhen,Ji, Xiaoming,Lai, Miao,Zhao, Mingqin,Ren, Tianbao
, p. 2389 - 2397 (2019/08/01)
To expand the library of pyrrole-containing flavor precursors, two new flavor precursors—methyl N-benzyl-2-methyl-5-formylpyrrole-3-carboxylate (NBMF) and methyl N-butyl-2-methyl-5-formylpyrrole-3-carboxylate (NUMF)—were synthesized by cyclization, oxidation, and alkylation reactions. Thermogravimetry (TG), differential scanning calorimeter, and pyrolysis–gas chromatography/mass spectrometry were utilized to analyze the thermal degradation behavior and thermal degradation products of NBMF and NUMF. The TG-DTG curve indicated that the maximum mass loss rates of NBMF and NUMF appear at 310 and 268°C, respectively. The largest peaks of NBMF and NUMF showed by the differential scanning calorimeter curve were 315 and 274°C, respectively. Pyrolysis–gas chromatography/mass spectrometry detected small molecule fragrance compounds appeared during thermal degradation, such as 2-methylpyrrole, 1-methylpyrrole-2-carboxylic acid methyl ester, limonene, and methyl formate. Finally, the thermal degradation mechanism of NBMF and NUMF was discussed, which provided a theoretical basis for their application in tobacco flavoring additives.
Synthesis, photophysical and concentration-dependent tunable lasing behavior of 2,6-diacetylenyl-functionalized BODIPY dyes
Maity, Apurba,Sarkar, Anirban,Sil, Amit,B. N., Shivakiran Bhaktha,Patra, Sanjib K.
supporting information, p. 2296 - 2308 (2017/03/22)
2,6-Diacetylenyl- and 2,6-bis(arylacetylenyl)-functionalized pentamethyl-difluoroborondipyrromethene (BODIPY) derivatives, namely, PBDP1 and PBDP2-4 (aryl = phenyl, 4-methoxyphenyl, or 4-cyanophenyl), respectively, which exhibit extended π-conjugation, were synthesized and characterized by various spectroscopic methods. Significant bathochromic shifts in both absorption and emission were observed upon modifying the structure of the BODIPY core via the strategy of extending its π-conjugation. The derivatives displayed efficient emission in the yellow-to-red spectral region, with a high fluorescence quantum yield and a relatively large Stokes shift. Under conditions of transverse pumping in a cuvette, PBDP1 and PBDP2 exhibited highly efficient and stable laser activity for up to 180 and 110 minutes of continuous irradiation, respectively. Amplified spontaneous emission (FWHM of ca. 2.5 nm) with an efficiency of 41% and 36% was achieved for PBDP1 and PBDP2, respectively, in toluene, which had tunable ranges of 561 to 580 nm and 602 to 617 nm, respectively, on irradiation with a Q-switched Nd:YAG laser at 532 nm. The lasing properties of PBDP3 and PBDP4, which contain electron-donating (-OMe) and electron-withdrawing (-CN) arylacetylenyl moieties, respectively, were also investigated. A corresponding digold(i) diacetylide organometallic complex, namely, (PPh3)Au-C≡C-BODIPY-C≡C-Au(PPh3) (PBDP5) was also synthesized and characterized to study the effect of Au(i). PBDP5 exhibited phosphorescence in the vis-NIR region centered at 751 nm at 77 K owing to heavy-atom-induced intersystem crossing.
Synthesis and evaluation of a [18F]BODIPY-labeled caspase-inhibitor
Ortmeyer, Christian Paul,Haufe, Günter,Schwegmann, Katrin,Hermann, Sven,Sch?fers, Michael,B?rgel, Frederik,Wünsch, Bernhard,Wagner, Stefan,Hugenberg, Verena
supporting information, p. 2167 - 2176 (2017/03/23)
BODIPYs (boron dipyrromethenes) are fluorescent dyes which show high stability and quantum yields. They feature the possibility of selective 18F-fluorination at the boron-core. Attached to a bioactive molecule and labeled with [18F]fluorine, the resulting compounds are promising tracers for multimodal imaging in vivo and can be used for PET and fluorescence imaging. A BODIPY containing a phenyl and a hydroxy substituent on boron was synthesized and characterized. Fluorinated and hydroxy substituted dyes were coupled to an isatin-based caspase inhibitor via cycloaddition and the resulting compounds were evaluated in vitro in caspase inhibition assays. The metabolic stability and the formed metabolites were investigated by incubation with mouse liver microsomes and LC-MS analysis. Subsequently the fluorophores were labeled with [18F]fluorine and an in vivo biodistribution study using dynamic PET was performed.
A novel triphenylamine-BODIPY dendron: Click synthesis, near-infrared emission and a multi-channel chemodosimeter for Hg2+ and Fe3+
Shen, Bao-Xing,Qian, Ying
supporting information, p. 7549 - 7559 (2016/12/09)
A novel triphenylamine-BODIPY based Schiff base fluorescent probe (TPA-BODIPY-OH) with an emission in the near-infrared (NIR) region was designed and prepared by click reaction. TPA-BODIPY-OH showed three emission bands at 510 nm, 598 nm and 670 nm, and can detect Fe3+ and Hg2+ ions with remarkable fluorescence enhancement in THF/H2O (v/v, 1:1, buffered with 10 mM HEPES pH = 7.4) based on the hydrolysis reaction of the -CN bond, and naked eye detection was realized with an obvious color change. The stoichiometry between the probe and ions was deduced from a Job's plot, which is 1:3 for TPA-BODIPY-OH/Fe3+ and 1:2 for TPA-BODIPY-OH/Hg2+, respectively. The dissociation constant value was found to be 1.35 × 10-16 M for TPA-BODIPY-OH/Fe3+ and 2.06 × 10-11 M for TPA-BODIPY-OH/Hg2+. The low detection limit was calculated from the titration results with the values of 5.15 × 10-7 M for TPA-BODIPY-OH/Fe3+ and 6.81 × 10-7 M for TPA-BODIPY-OH/Hg2+, respectively. In order to investigate the biological applications of TPA-BODIPY-OH, a living cell imaging experiment was carried out. The results demonstrate that TPA-BODIPY-OH can be successfully applied as a bioimaging agent in living cells. In addition, amino-group-functionalized silica fluorescent nanoparticles (FNPs) encapsulating the TPA-BODIPY-OH dyes were prepared and characterized by transmission electron microscopy. TPA-BODIPY-OH/SiO2 nanoparticles exhibit good dispersibility, and the quantum yield of FNPs at 657 nm was 42.3%.
A novel BODIPY -Schiff base-based colorimetric and fluorometric dosimeter for Hg2+, Fe3+ and Au3+
Cheng, Huan-Ren,Qian, Ying
, p. 82887 - 82893 (2015/10/19)
A novel Schiff base-based multi-target dosimeter for Hg2+, Fe3+ and Au3+ has been designed and synthesized. Upon addition of Hg2+, Fe3+ and Au3+ to the aqueous solution of compound BODIPY-TRIA, the dosimeter gave a rapid fluorescence response and displayed an obvious fluorescence enhancement with a blue-shift. Meanwhile, a sharp color change from purple to pale yellow occurred, which was readily detected by the naked eye. The hydrolysis of the Schiff base promoted by Hg2+, Fe3+ and Au3+ has been discussed, and the possible mechanism was confirmed by 1H NMR and MS studies. The dosimeter showed high sensitivity (10 nM for Au3+), good stability, and excellent selectivity for Hg2+, Fe3+ and Au3+ with interference by other metal ions.
