14134-81-7Relevant academic research and scientific papers
Synthesis of A2-D2-A1-D1 type red-emitting unsymmetrical squaraine dye: Influence of additional pyridine moiety on photophysical, electrochemical, photo and thermal stability
Bhise, Rupali,Jachak, Mahesh,Khopkar, Sushil,Mehta, Viral,Shankarling, Ganapati
, (2022/03/01)
We have synthesized a π-conjugated acceptor–donor–acceptor-donor (A2-D2-A1-D1) type of unsymmetrical squaraine dye, signified by USQ-1 based on 1-ethyl-2,3,3,8-tetramethyl-2,3-dihydro-1H-pyrrolo[3,2-h] quinoline moiety to improve the absorption as well as emission spectra to the red-emitting region. The influence of pyridine as a subsidiary electron acceptor unit on various properties in USQ-1 dye was compared with their close relative dye (USQ-2). The synthesized dyes were examined by FT-IR, HR-MS, 1H, and 13C NMR spectroscopy. This novel unsymmetrical squaraine dye shows a strong absorption with high molar absorptivity (?105 L mol?1 cm?1) in the range of 676–661 nm from non-polar to polar solvents. The intramolecular charge transfer (ICT) process from donor to the acceptor moiety in a non-polar to polar solvent has been investigated with the help of oscillator strengths (f), as well as transition dipole moments (μeg). These dyes showed a negative solvatochromic shift from non-polar to polar solvent. The quantitative analysis of charge transfer from the ground to the excited state of these squaraine dyes was calculated by Reichardt's ET (30) scale plot. The comparative electrochemical, as well as the thermal study of these unsymmetrical squaraines, were studied with the aid of cyclic voltammetry and thermogravimetric analysis (TGA), respectively. Additionally, A2-D2-A1-D1 type dye (USQ-1) showed an improved photo-stability compared to D2-A1-D1 type dye (USQ-2). The computational (theoretical) study of these dyes was supported with the assistance of density functional theory (DFT) together with time-dependent density functional theory (TD-DFT).
Bioorthogonal Ligation-Activated Fluorogenic FRET Dyads
Albitz, Evelin,Kern, Dóra,Kormos, Attila,Bojtár, Márton,T?r?k, Gy?rgy,Biró, Adrienn,Szatmári, ágnes,Németh, Krisztina,Kele, Péter
supporting information, (2021/12/30)
An energy transfer-based signal amplification relay concept enabling transmission of bioorthogonally activatable fluorogenicity of blue-excitable coumarins to yellow/red emitting cyanine frames is presented. Such relay mechanism resulted in improved cyani
The Development of Highly Fluorescent Hemicyanine and Dicyanoisophorone Dyes for Applications in Dye-Sensitized Solar Cells
Shabir, Ghulam,Arooj, Sama,Javed, Ahad Hussain,Saeed, Aamer,Shahzad, Nadia,Iqbal, Naseem,Jabeen, Erum
, p. 799 - 815 (2022/02/05)
Ruthenium-based metal complex dyes have been employed extensively in dye-sensitized solar cells (DSSCs) as photosensitizers, but the cost and toxicity of metal complexes have promoted the development of metal-free organic dyes. The present investigation d
Acridinium-conjugated aromatic heterocycles as highly potent FtsZ inhibitors: Design, synthesis, and biological evaluation
Chen, Weijin,Guo, Ting,Ma, Shutao,Ma, Yangchun,Song, Di,Zhang, Nan,Zhang, Shenyan
, (2022/03/15)
The epidemic of multidrug resistance (MDR) is a serious threat to public health, and new classes of antibiotics with novel mechanisms of action are in critical need. We rationally designed and efficiently synthesized three series of new chemical entities with potential antibacterial activity targeting filamenting temperature-sensitive mutant Z (FtsZ). Evaluation of these compounds against a panel of Gram-positive bacteria including MDR and vancomycin-resistant Enterococcus?strains indicated that most compounds showed enhanced antibacterial efficacy, comparable or even superior to the reference drugs. The newly synthesized compounds proved to be substrates of the Escherichia coli efflux pump AcrB, thus affecting the activity. Their structure–activity relationships?were summarized in detail. The most potent compound 10f quickly eliminated bacteria in a bactericidal mode, with low susceptibility to induce bacterial resistance. Further mechanistic studies with the BsFtsZ protein revealed that 10f functioned as an effective FtsZ inhibitor through altering the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which leads to inhibition of cell division and cell death. Besides, 10f not only displayed no obvious cytotoxicity to mammalian cells but also had a high efficacy in a murine model of bacteremia in vivo. Regarded as a whole, our findings highlight 10f as a promising new FtsZ-targeting bactericidal agent.
The Impact of Chiral Citronellyl-Functionalization on Indolenine and Anilino Squaraine Thin Films
Balzer, Frank,Beverina, Luca,Lützen, Arne,Mattiello, Sara,Meerholz, Klaus,Schiek, Manuela,Schmidtmann, Marc,Schulz, Matthias,Schumacher, Marvin F.,Serdar Sariciftci, N.,Zablocki, Jennifer
, (2021/11/09)
The impact on chiral aggregation in solution processed and thermally annealed thin films of two indolenine and one anilino squaraines with chiral (S)-citronellyl functionalization at the nitrogen of the squaraine backbone is investigated. A pseudo polymor
A Molecular-Splicing Strategy for Constructing a Near-Infrared Fluorescent Probe for UDP-Glucuronosyltransferase 1A1
Cui, Jingnan,Feng, Lei,Gao, Jian,James, Tony D.,Liu, Tao,Ma, Xiaochi,Ma, Yinhua,Tian, Xiangge
supporting information, p. 24566 - 24572 (2021/10/12)
UDP-glucuronosyltransferase 1A1 (UGT1A1) is a vital metabolic enzyme responsible for the clearance of endogenous substances and drugs. Hitherto, the development of fluorescent probes for UGTs was severely restricted due to the poor isoform selectivity and
Pyroptosis drug prodrug, preparation method thereof and pyroptosis drug
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Paragraph 0088; 0091-0092, (2021/06/13)
The invention discloses a pyroptosis drug prodrug, a preparation method thereof and a pyroptosis drug. The pyroptosis drug prodrug provided by the invention can cause mitochondria damage, release cytochrome c and activate Caspase3 to shear GSDME by targeting mitochondria, so that pyroptosis of cells occurs. The prodrug (NCyNH2) has selectivity to tumor cells, damage to normal cells is reduced, and the activation condition of the prodrug (NCyNH2) can be detected through recovery of self-fluorescence. After intratumor administration, the prodrug can effectively regulate the tumor immune microenvironment and activate T cell mediated anti-tumor immune response. The molecule has huge application prospects in the aspects of mitochondrial targeting, cell respiration inhibition, pyroptosis induction, tumor immune microenvironment improvement, T cell mediated anti-tumor immune response activation and the like.
The design of a novel near-infrared fluorescent HDAC inhibitor and image of tumor cells
Bao, Bin,Huang, Ying,Li, Jia,Lu, Wei,Ru, Hong-bo,Yu, Jia-hui,Zang, Yi
supporting information, (2020/07/15)
Histone deacetylases (HDACs) have been found to be biomarkers of cancers and the corresponding inhibitors have attracted much attention these years. Herein we reported a near-infrared fluorescent HDAC inhibitor based on vorinostat (SAHA) and a NIR fluorop
The effect of bis-carboxylic groups of squarylium dyes on the efficiency of dye-sensitized solar cells
Al-horaibi, Sultan A.,Garoon, Eman M.,Bhise, Narendra A.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
, p. 1769 - 1778 (2019/12/27)
Symmetric squarylium dye (SQIND1) with bi-carboxylic groups has been synthesized and photoelectrochemical properties have been studied in comparison with its non-functionalized analog groups (SQIND2). The experimental results showed that the introduction of anchor carboxylic groups in SQIND1 sensitizer provides a more intimate contact with nanoparticles TiO2 which increases the number of charge carriers transferred from the SQIND1 to the semiconductor. The theoretical calculations and absorbance results show that the electron density of LUMO of SQIND1 is delocalized in the whole chromophore, leading to strong electronic coupling between SQIND1 sensitizer and conducting band of TiO2, resulting in improved dye-sensitized solar cell efficiency compared to SQIND2. Hence, the SQIND1 sensitized exhibit better photovoltaic performance. Although, the absence of any linker groups in the SQIND1, then SQIND1 was perfect efficiently sensitized on porous TiO2 with the long UV–Vis and NIR region up to 800?nm of the spectrum and showed higher remarkable performance of values, such as η of 3.3%, a Jsc of 7.6?mA/cm2, a Voc of 0.59, and FF of 0.73.
Photodynamic activity of indolenine-based aminosquaraine cyanine dyes: Synthesis and in vitro photobiological evaluation
Lima, Eurico,Ferreira, Octávio,Silva, Joana F.,Santos, Adriana O.,Boto, Renato E.,Fernandes, José R.,Almeida, Paulo,Silvestre, Samuel M.,Reis, Lucinda V.
, (2019/11/28)
The synthesis and characterization of several indolenine-based symmetrical squaraine dyes is herein reported. These compounds, possessing different amine groups bound to the squaric ring, display strong absorption within the so-called “phototherapeutic window”, have high singlet oxygen generation ability and high stability in the presence of radiation. Moreover, their potential as photosensitizers was evaluated in vitro by a photodynamic activity test in several tumor (Caco-2, MCF-7 and PC-3) and non-tumor (NHDF and N27) cell lines. Light-emitting diode systems emitting radiation at wavelengths close to those of maximum dye absorption were constructed and used in the in vitro assays. Of these, the dye with the unsubstituted four-membered central ring exhibited the most relevant photodynamic properties, with an interesting selectivity for PC-3 cells when compared to the normal human cell line (NHDF) being observed. Aminosquaraine dyes bearing amino and ethanolamino groups, despite showing marked cytotoxicity compared to the zwitterionic dye, produced some phototherapeutic effect. Flow cytometry, using propidium iodide as a viability staining, demonstrated that this zwitterionic dye induces death within the range of 4–24 h after exposure to light. Our study also showed that this dye does not accumulate preferentially in cell's mitochondria. Although in different extents, the squaraine dyes involved in this work presented promising in vitro results as photosensitizers.
