7570-45-8Relevant academic research and scientific papers
Red-emitting fluorescent probe for detecting hypochlorite acid in vitro and in vivo
Chen, Hong,Sun, Tao,Qiao, Xiao-Guang,Tang, Qian-Oian,Zhao, Shan-Chao,Zhou, Zhan
, p. 196 - 202 (2018)
Due to the importance of hypochlorous acid (HClO) in biological and industrial, development of fluorescent probes for HClO has been an active research area. Here, a new red-emitting ratiometric fluorescent probe (P) was synthesized and well defined characterization via NMR, HR-MS, and fluorescence spectrum, which serves as a selective and sensitive probe for ClO? group. The probe showed a ratiometric fluorescent response to hypochlorite at the emission intensities ratio (I480/I612) increasing from 0.28 to 27.46. The emission intensities ratio (I480/I612) was linearly enhanced (I480/I612 = 0.064 X + 0.096) with the ClO? concentration range from 1 to 30 μM. The detection limitation for ClO? in aqueous solution is 0.47 μM. Moreover, this biocompatible red-emitting ratiometric fluorescent probe was utilized to the fluorescence imaging of ClO? in living cells and Zebrafish.
Facile Synthesis of Some 3-(Benzimidazol-2-yl)-And 3,6-Di(Benzimidazol-2-yl)-9-ethyl-9H-carbazoles
Kandemir, Hakan,Sengul, Ibrahim F.
, p. 2583 - 2591 (2015)
A simple and efficient synthesis of novel 3-(benzimidazol-2-yl)-And 3,6-di(benzimidazol-2-yl)-9-ethyl-9H-carbazoles is described. The synthetic approach for the preparation of 2-substituted benzimidazoles 4-8 and bis-benzimidazoles 9-12 was achieved by the condensation of carbazole-3-carbaldehyde 2 and carbazole-3,6-dicarbaldehyde 3 with o-phenyldiamines in dimethylformamide or dimethylsulfoxide in moderate to excellent yield. The identities of synthesized compounds were confirmed using 1H NMR, 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS).
Carbazole–azine based fluorescence ‘off–on’ sensor for selective detection of Cu2+ and its live cell imaging
Christopher Leslee, Denzil Britto,Karuppannan, Sekar,Vengaian, Karmegam Muthu,Gandhi, Sivaraman,Subramanian, Singaravadivel
, p. 1354 - 1360 (2017)
A new carbazole–azine based fluorescent sensor was synthesized and characterized. The selectivity of the sensor for Cu2+ over other counter ions in a dimethyl sulfoxide/H2O mixture was shown through enhancement in fluorescence – an off to on transformation. The specificity of the probe towards Cu2+ was evident in ultraviolet/visible, fluorescence, Fourier transform infrared and mass studies. Application of the probe in the cell imaging and cytotoxicity of living cells is illustrated.
Fast detecting hypochlorous acid based on electron-withdrawing group promoted oxidation and its biological applications in cells and root tips of plants
Li, Ming,Chao, Jianbin,Liu, Yaoming,Xu, Miao,Zhang, Yongbin,Huo, Fangjun,Wang, Juanjuan,Yin, Caixia
, (2020)
Hypochlorous acid, a type of reactive oxygen species, has been shown to play an important role in organisms. Nowadays, there are many kinds of fluorescence detecting mechanisms to detect hypochlorous acid in vivo. Due to the high selectivity, the mechanism of using the strong oxidation of hypochlorous acid to break carbon?carbon double bonds has been favored by many scientists. However, the reported probes of breaking carbon?carbon double bonds still had drawback such as slow response. Based on this, we introduced electron-withdrawing group malonitrile to accelerate the oxidation of hypochlorous acid, resulting in reaction time less than 150 s. Meanwhile, the probe exhibited excellent selectivity, optical stability, high sensitivity and the detection limit as low as 0.19 μM. More importantly, we also successfully proved the potential application of the probe for the detection of intracellular ClO? living cells and Arabidopsis root tip by fluorescence imaging.
Microwave assisted one-pot synthesis, photophysical and physicochemical studies of novel biologically active heterocyclic Donor (D)-π-Acceptor (A) chromophore
Khan, Salman A.,Ullah, Qasim,Syed, Salahuddin,Alimuddin,Almalki, Abdulraheem S.A.,Kumar, Sanjay,Obaid, Rami J.,Alsharif, Meshari A.,Alfaifi,Parveen, Humaira
, (2021)
A donor-π-acceptor (D-π-A) chromophore, 2-amino-4-(9-ethyl-9H-carbazol-3-yl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (AEDQ) was synthesized from the condensation of 6-methoxy-3,4-dihydronaphthalen-1(2H)-one, 9-ethyl-9H-carbazole-3-carbaldehyde, malononitrile and NH4OAc in ethanol. Spectroscopic techniques and elemental analysis were employed to establish the structure of AEDQ. Photophysical parameters and fluorescence quantum yield were calculated in the different polarity solvents to evaluate the interactions of the solvent with AEDQ chromophore. Further, the interaction of the AEDQ with cationic and anionic surfactants (CTAB, SDS) were also evaluated by using fluorescence spectroscopy techniques. The intensity of the fluorescence spectrum increased as the concentration of surfactants increased, suggesting that strong interaction occurs between AEDQ with surfactants, and this interaction arises from electrostatic forces. As a result, the AEDQ chromophore could be used to determine the CMC of surfactants. The disc diffusion and minimal inhibitory concentration (MIC) technique were used to test in-vitro antibacterial activity against Gram +ve and Gram ?ve bacteria, and the results are compared with the standard drug, tetracycline. AEDQ also showed good ADMET, pharmacokinetics and drug-likeness properties, which are desirable for a good drug candidate. The molecule also fits well in the DNA gyrase A active pocket site with the binding free energy of ?17.92 kcal/mol, which testifies its good antibacterial activity.
Rational Development of a New Reaction-Based Ratiometric Fluorescent Probe with a Large Stokes Shift for Selective Detection of Bisulfite in Tap Water, Real Food Samples, Onion Tissues, and Zebrafish
Yuan, Gangqiang,Zhou, Liyi,Yang, Qiaomei,Ding, Haiyuan,Tan, Libin,Peng, Longpeng
, p. 4894 - 4902 (2021)
Bisulfite (HSO3-) is usually widely added to tap water and food because it has antibacterial, bleaching, and antioxidant effects. However, its abnormal addition would cause a series of serious diseases related to it. Therefore, development of an effective method for HSO3- detection was of great significance to human health. In this work, a new reaction-based ratiometric fluorescent probe KQ-SO2 was rationally designed, which could be used for the highly selective detection of HSO3- in tap water, real food samples, onion tissues, and zebrafish. Specifically, a positively charged benzo[e]indolium moiety and a carbazole group through a condensation reaction resulted in KQ-SO2, which displayed two well-resolved emission bands separated by 225 nm, fast response (1 min), and high selectivity and sensitivity toward HSO3- upon undergoing the Michael addition reaction, as well as low cytotoxicity in vitro. In addition, KQ-SO2 has been successfully applied for the detection of HSO3- in tap water, real food samples, onion tissues, and zebrafish with satisfactory results. We predict that KQ-SO2 could be used as a powerful tool to reveal the relationship between HSO3- and the human health.
Properties, theoretical study and crystal structure of 3-benzothiazole-9-ethyl carbazole
Gu, Yingchun,Fei, Xuening,Wang, Cuihong,Li, Ling,Zhou, Jianguo,Tang, Yalin,Lin, Dayong
, p. 1229 - 1236 (2016)
The title compound of 3-benzothiazole-9-ethyl carbazole was synthesized by the reaction of 3-aldehyde-9-ethyl carbazole and 2-aminothiophenol. The compound was characterized by 1H nuclear magnetic resonance (NMR) and mass spectrometry (MS). Its crystal structure was obtained and determined by single crystal X-ray diffraction. The results showed that the crystal belongs to the orthorhombic crystal system and the cell parameters of space group P2(1)2(1)2(1) were a?=?5.6626 (12) ?, b?=?12.606 (3) ?, c?=?22.639 (5) ?, α?=?90°, β?=?90°, γ?=?90°, V?=?1616.0 (6) ?3, Z?=?4, Dc?=?1.350?mg/m3. The UV–vis and fluorescence spectra were also studied preliminarily. The fluorescence spectra of the title compound with bovine serum albumin (BSA) showed that BSA could be marked with the compound and the stability constant between them was 0.82?×?107?M?1. Meanwhile, the crystal and molecule were theoretically surveyed by density functional tight-binding (DFTB). The results showed that there was an orbital overlap for lowest unoccupied molecular orbital (LUMO) between the neighbouring molecules for the crystal, which is different from the molecule structure. It was also showed that the crystal structure is a non-conductor. Copyright
Spectra, stability and labeling of a novel carbazole derivative as a fluorescent turn-on DNA probe
Fei, Xuening,Li, Ran,Lin, Dayong,Gu, Yingchun,Yu, Lu
, p. 1251 - 1258 (2015)
A novel fluorescent dye, 1-(6-carboxyhexyl)-4-(2-(9-ethyl-carbazole-3-yl) vinyl) quinolizinium bromide, was synthesized, and its structure was characterized by 1H NMR, 13C-NMR, IR and HRMS. The spectra properties of this dye in different solvents and under different pH value were invest'igated preliminarily, and the results showed that its fluorescent properties was affected by the polarity and the dipole moment of the solvent. The photostability and thermostability test results showed that its photoreduction rate constant was 1.64×10-5 mol/Min and its fluorescent intensity decreased little after heating at 80 °C for 6 h, suggesting the dye was quite stable. In the labeling experiment of BSA and DNA with the dye, the fluorescent all intensity increased with the addition of BSA and DNA. Specially, the dye showed an excellent turn-on effect upon binding with ctDNA.
Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging
Gawale, Yogesh,Adarsh, Nagappanpillai,Kalva, Sandeep Kumar,Joseph, Joshy,Pramanik, Manojit,Ramaiah, Danaboyina,Sekar, Nagaiyan
, p. 6570 - 6578 (2017)
Four new N-ethylcarbazole-linked aza-boron-dipyrromethene (aza-BODIPY) dyes (8 a,b and 9 a,b) were synthesized and characterized. The presence of the N-ethylcarbazole moiety shifts their absorption and fluorescence spectra to the near-infrared region, λ≈650–730 nm, of the electromagnetic spectrum. These dyes possess strong molar absorptivity in the range of 3–4×104 m?1 cm?1 with low fluorescence quantum yields. The triplet excited state and singlet oxygen generation of these dyes were enhanced upon iodination at the core position. The core-iodinated dyes 9 a,b showed excellent triplet quantum yields of about 90 and 75 %, with singlet oxygen generation efficiency of about 70 and 60 % relative to that of the parent dyes. Derivatives 8 a,b showed dual absorption profiles, in contrast to dyes 9 a,b, which had the characteristic absorption band of aza-BODIPY dyes. DFT calculations revealed that the electron density was spread over the iodine and dipyrromethene plane of 9 a,b, whereas in 8 a,b the electron density was distributed on the carbazole group and dipyrromethene plane of aza-BODIPY. The uniqueness of these aza-BODIPY systems is that they exhibit efficient triplet-state quantum yields, high singlet oxygen generation yields, and good photostability. Furthermore, the photoacoustic (PA) characteristics of these aza-BODIPY dyes was explored, and efficient PA signals for 8 a were observed relative to blood serum with in vitro deep-tissue imaging, thereby confirming its use as a promising PA contrast agent.
A large stokes-shifted fluorescent dye synthesized as a new probe for the determination of protein
Lin, Dayong,Fei, Xuening,Li, Ran,Gu, Yingchun,Tang, Yalin,Zhou, Jianguo,Zhang, Baolian
, p. 1511 - 1520 (2016)
A novel fluorescent dye, 1-(2-hydroxyethyl)-4-((E)-2-(3-benzothiazol-2yl-9-ethyl-carbazole-3yl)vinyl) pyridinium bromide, was synthesized for determination of protein and its structure was characterized by 1H NMR. Photophysics of the new probe in different solvents has been delineated in this paper, the new fluorescent molecular dye exhibited a large stokes-shifted and fluorescence quantum yields in organic solvent. The photostability and thermostability of the new dye were also studied and the results suggested the stable was excellent. The interactions of the dye with bovine serum albumin (BSA) , Human serumal bumin (HSA) and calf thymus deoxyribonucleic acid (ctDNA) were studied by fluorescence and absorption spectroscopy. The binding constant for BSA, HSA and DNA were calculated to be 8.91?×?107, 1.86?×?106 and 2.9?×?104, respectively. The experimental results indicated a potential value of the new dye for biomarker.
