7570-45-8Relevant articles and documents
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.
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.
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.
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
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.
Microstructure elucidation of poly(9-ethyl-3-hydroxymethylcarbazolyl methacrylate) using two-dimensional NMR spectroscopy
Brar, Ajaib Singh,Gandhi, Sonia,Markanday, Meghna
, p. 35 - 44 (2005)
The configurational assignments of poly(9-ethyl-3-hydroxymethylcarbazolyl methacrylate) prepared by solution polymerization with 2,2′- azobisisobutyronitrile (AIBN) as free radical initiator were studied by combination of one- and two-dimensional NMR spec
Carbazole substituted BODIPY dyes: Synthesis, photophysical properties and antitumor activity
Sengul, Ibrahim F.,Okutan, Elif,Kandemir, Hakan,Astarci, Erhan,?o?ut, Bünyemin
, p. 32 - 38 (2015)
Abstract In this study, two different BODIPYs containing carbazole groups at the meso position were designed and synthesized. All compounds were fully characterized by elemental analysis, FT-IR, matrix-assisted laser desorption/ionization time-of-flight m
Synthesis, one and two-photon optical properties of two asymmetrical and symmetrical carbazole derivatives containing quinoline ring
Li, Liang,Wang, Ping,Zhang, Yichi,Wu, Yiqun,Chen, Zhimin,He, Chunying
, p. 23 - 29 (2013)
The carbazole derivatives are suitable for two-photon absorption optical storage and photoluminescence material. Two carbazole derivatives, asymmetrical and symmetrical type molecules containing quinoline rings as electron acceptors and an N-ethylcarbazole group as electron donor, 9-ethyl-3-(2-quinolin)viny- carbazole (4) and 9-ethyl-3,6-bis(2-(quinolin)vinyl)-carbazole (5), had been synthesized by the Vilsmeier reaction of formylation and Knoevenagel condensation. The one-photon properties including absorption, fluorescence emission spectra, fluorescence quantum yields and fluorescence decay behaviors were investigated in N,N-dimethylformamide. Meanwhile, these compounds were theoretically surveyed by the density functional theory (DFT) and the time-dependent functional theory (TD-DFT). The two-photon excited fluorescence and two-photon absorption cross-sections were measured for the compounds by 120 fs pulse at 800 nm Ti: sapphire laser operating at 1 kHz repetition rate. The results showed that both of the two compounds 4 and 5 had higher fluorescence quantum yield (Φ) of 0.77 and 0.81 comparing with carbazole. Compounds 5 with symmetric π conjugated structure possessed longer fluorescence lifetime (τ) of 21.4 ns and larger two-photon absorption cross-sections (δTPA) of 364 × 10-50 cm4 s/photon than those of compounds 4 with asymmetric π conjugated structure (τ = 10.03 ns and δTPA = 81 × 10-50 cm4 s/photon). It was indicated that the one and two-photon optical properties of carbazole derivatives are influenced strongly by the symmetry and length of π conjugated structure.
Ferrocenes conjugated with thiophene, carbazole, and pyrimidine fragments: Synthesis and properties
Abashev,Antuf'eva,Bushueva,Kudryavtsev,Osorgina,Syutkin,Shklyaeva
, p. 1435 - 1439 (2010)
Ferrocenyl-containing chalcones containing π-excessive heterocyclic fragments capable of electrochemical polymerization (carbazole, thiophene, 2,4-ethylenedioxythiophene) were prepared by the Claisen-Schmidt reaction. 2,4,6-Trisubstituted pyrimidines deri
Carbazole-based π-conjugated 2,2′-Bipyridines, a new class of organic chromophores: Photophysical, ultrafast nonlinear optical and computational studies
Bodapati, Ramakrishna,Das, Samar K.,Dey, Gaurav Ranjan,Jose, K. V. Jovan,Krishnakanth, Katturi Naga,Ramteke, Gunjan R.,Rao, S. Venugopal
, (2020/11/03)
The developmen of donor-acceptor (D-A) architecture based organic chromophores with large two-photon absorption (2 PA) cross-sections are essential for myriad of applications, ranging from nonlinear microscopy to biomedical imaging. Here, we present the results from a comprehensive study of 2 PA cross-sections of a new series of carbazole mono substituted-π-conjugated-2,2′-bipyridine derivatives with D-π-A architecture, possessing carbazole as the donor moiety and bipyridine core as an acceptor. Further, we have extended the π-conjugation by introducing the phenyl and butoxy substituted phenyl linkers. The fluorescence properties of these D-A chromophores are highly sensitive to solvent polarity and alteration of electron donor functionalities. The relevant computation studies support our experimental results, e.g., a shift in emission maxima and band gaps of the molecules. The third-order nonlinear optical (NLO) properties of the title donor-acceptor (D-A) chromophores demonstrated that 2 PA cross-section values are in the range of 6–39 GM, obtained using ~50 fs (fs) laser pulses at a wavelength of 800 nm. Further, the nonlinear refractive indices (n2) of these chromophores were found to be ~10?14 cm2/W, rendering them potential optical switching candidates since the coefficients were obtained with kHz, fs pulses extracting pure electronic nonlinearities. Based on our experimental findings and theoretical calculations presented in this study, we believe that carbazole-based π-conjugated 2,2′-bipyridines, demonstrated in this work, would be potential ligands to obtain a series of transition metal coordination complexes of interesting physical properties (for example, superior NLO behaviour).
Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents
Xue, Yi-Jie,Li, Ming-Yue,Jin, Xue-Jun,Zheng, Chang-Ji,Piao, Hu-Ri
, p. 295 - 306 (2021/01/13)
Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 μg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 μg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect.
