29636-96-2Relevant articles and documents
Pyridine-Spiropyran Derivative as a Persistent, Reversible Photoacid in Water
Halbritter, Thomas,Kaiser, Christoph,Wachtveitl, Josef,Heckel, Alexander
, p. 8040 - 8047 (2017)
A highly versatile water-soluble pyridine-spiropyran photoswitch is reported which functions as photoacid in a wide pH range. Under neutral conditions, the open-ring merocyanine (MC-) exists to 48% and closes quantitatively by irradiation with visible light, while the reverse reaction occurs rapidly in the dark or by irradiation at 340 nm. The different pKa of the pyridine nitrogen in the closed spiropyran (4.8) and open merocyanine form (6.8) leads to a reversible proton release in a pH range of 3-7. Only negligible hydrolytic decomposition was observed in the pH range from 1 to 12. The application of potentially harmful UV light can be circumvented due to the fast thermal ring-opening except for pH values below 3. Its photoacidic properties make this compound an effective pH-regulating photoswitch in water and enable controlled proton-transfer processes for diverse applications. Additionally, all of the involved protonated states of the compound exhibit discriminative fluorescence features within certain pH ranges, which even expands its utility to a light-controllable, pH-sensitive fluorophore.
Synthesis and systematic evaluation of symmetric sulfonated centrally C-C bonded cyanine near-infrared dyes for protein labelling
Van Der Wal, Steffen,Kuil, Joeri,Valentijn, A. Rob P.M.,Van Leeuwen, Fijs W.B.
, p. 7 - 19 (2016)
The most commonly used near-infrared cyanine dyes contain an aryl ether that is not fully stable towards nucleophiles. Replacement of the aryl ether by a more stable carbon-carbon bond can improve the stability. In this work we have synthesized a series o
Water soluble squaraine dyes for use as colorimetric stains in gel electrophoresis
Lynch, Daniel E.,Kirkham, Andrew N.,Chowdhury, Mohammed Z.H.,Wane, Elizabeth S.,Heptinstall, John
, p. 393 - 402 (2012)
Here we report that the difficulties encountered in the synthesis of a dual-pendant sulfonate bis(indolenine)squaraine dye can be overcome through the use of equimolar amounts of the common reaction catalyst, thus creating an organic salt between the sulfonate groups and the protonated catalyst. Thus, a range of water-soluble dyes can further be prepared, by simply altering the catalyst. Crystal structures of four subsequent derivatives, prepared in this manner, are reported and show that, although the squaraine moieties remain essentially planar, the packing lattices can vary significantly, and the expectation that both sulfonic acid groups will protonate a stoichiometric amount of the available organic base catalyst is also demonstrated by one structure to not be fully true. Two of the dyes, whose crystal structures are reported, proved to be suitable as colorimetric stains for protein separation in sodium dodecylsulphate polyacrylamide gel electrophoresis (SDS-PAGE), and an optimal method for staining is reported. Results obtained for a fifth dye, crystal structure not obtained, are also reported. In all cases the results were compared against non-colloidal Coomassie Brilliant Blue (CBB) and it was found that the limit of detection for all squaraine derivatives examined were comparable with that of CBB although the resolution between protein bands was better. In addition, it was discovered that gels stained with the fifth dye (presented in this study) could be imaged in UV excitation/fluorescent imaging mode. The image robustness (or colour fastness) of all squaraines was found to be good for only a few hours.
Instantaneous fluorescent probe for the specific detection of H2S
Lin, Xianfeng,Lu, Xiuhong,Zhou, Junliang,Ren, Hang,Dong, Xiaochun,Zhao, Weili,Chen, Zhongjian
, p. 416 - 422 (2019)
Novel cyanine-based fluorescent probes for the detection of H2S were developed. The probes developed are stable under physiological conditions. The water soluble fluorescent probe 2 displayed ultrafast and specific response to H2S di
A dual functional probe: Sensitive fluorescence response to H2S and colorimetric detection for SO32-
Chen, Sheng,Ma, Chao,Yuan, Mao-Sen,Wang, Wenji,Wang, Dong-En,Chen, Shu-Wei,Wang, Jinyi
, p. 85529 - 85537 (2016)
Hydrogen sulfide (H2S) and sulfite (SO32-) are two important sulfur-containing species that play different and important roles in industrial and biological processes. Accordingly, the development of efficient methods for simple, rapid, sensitive and selective monitoring of H2S and SO32- is of the utmost importance in both environmental and biological sciences. In this study, we developed a new dual functional probe NIR-DNP for discriminative detection of H2S and SO32-. This probe can sense H2S and SO32-via two different approaches, a significant near-infrared fluorescence enhancement and color change from purple to cyan induced by H2S as well as a visible color change from purple to colorless caused by SO32-. The detection limits of the probe NIR-DNP for H2S and SO32- in aqueous solutions were 36.53 nM and 33.33 nM, respectively. Competitive experiments demonstrated that the probe NIR-DNP had a high fluorescence selectivity for H2S and excellent colorimetric selectivity for SO32- over other analytes. The sensing mechanism of the probe toward H2S and SO32- was based on the H2S-induced thiolysis of dinitrophenyl ether and SO32--induced nucleophilic addition, respectively. Further investigation showed that the probe NIR-DNP could be used to develop an easy-to-prepare and easy-to-detect paper-based test strip for cheap and effective detection of SO32-. Also, the probe NIR-DNP has the potential to image exogenous and endogenous H2S in living cells.
Fabrication of a water-soluble near-infrared fluorescent probe for selective detection and imaging of dipeptidyl peptidase IV in biological systems
Gao, Hong,Guo, Xiumei,Li, Jian,Liu, Xiaoyan,Mu, Shuai,Zhang, Haixia,Zhang, Yintang
, p. 767 - 775 (2020)
Dipeptidyl peptidase IV (DPP-IV) is a transmembrane glycoprotein known to regulate T cell activation, which is related to various pathological processes and has become a potential target to treat type 2 diabetes mellitus. Therefore, it is significant for the evaluation of endogenous DPP-IV activity in various biological systems. Herein, a water-soluble near-infrared (NIR) fluorescent probe HCA-D based on cyanine dyes as the fluorophore and glycyl-prolyl peptide as the specific recognition sequence was developed for the assay of dipeptidyl peptidase IV (DPP-IV) activity. Upon addition of DPP-IV, HCA-D can emit a significant turn-on NIR fluorescence signal under physiological conditions and exhibit high selectivity toward DPP-IV. This feature was available for quantifying DPP-IV in the range from 0.62 to 10 ng mL-1 with a detection limit of 0.19 ng mL-1. Furthermore, the present probe was successfully employed for monitoring DPP-IV in serum samples from diabetic and healthy people, and imaging of DPP-IV in living cells and tumor mice models. These results demonstrate that the designed probe provides a promising tool to explore the relationship between DPP-IV and diabetes mellitus or other diseases. Perhaps, it may become a prospective image-guided tumor resection indicator based on the abnormal expression of DPP-IV activity in the future.
A hemicyanine-based fluorescent probe for hydrazine detection in aqueous solution and its application in real time bioimaging of hydrazine as a metabolite in mice
Li, Tao,Liu, Jian,Song, Linjiang,Li, Zicheng,Qi, Qingrong,Huang, Wencai
, p. 3197 - 3200 (2019)
A hemicyanine-based fluorescent probe, Hcy-Ac, was developed for the specific detection of hydrazine. With good water solubility and high sensitivity, Hcy-Ac has been successfully applied for the monitoring of in situ hydrazine release during the metabolism of isoniazid in mice.
Solid-state photochromic molecular switches based on axially chiral and helical spiropyrans
Qu, Lang,Song, Jintong,Wang, Lei,Wu, Dehua,Xiang, Haifeng,Xu, Xuemei,Zhou, Weilan,Zhou, Xiangge
, (2020)
Solid-state photochromic switches with reversible luminescence modulation property have wide applications in optical data storage, anticounterfeiting, sensing, and bioimaging, however, it is a significant challenge to design and prepare such materials. In the present work, a novel class of chiral and helical binaphthyl-substituted spiropyrans has been synthesized and characterized. The introduction of binaphthyl can not only promote the solid-state luminescence but also achieve the interesting chiroptical switching properties for the potential applications in chiral recognition and circularly polarized luminescence. The single-crystal structures and density functional theory calculations reveal that the presence of strong electron-withdrawing nitro groups can promote photoswitch efficiency by stabilizing the electron-rich conjugated merocyanine with the lower electron cloud density and LUMO/HOMO levels. For charge transfer in excited states, π → π* transition would enhance emission, but n → π* transition and intramolecular charge transfer show the opposite effect. Therefore, these photochromic switches provide a novel paradigm in the design of multiple-responsive, chiral, and luminescent materials.
Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins
Dong, Kui,Li, Xiang-Sheng,Liu, Qiang,Wu, Li-Zhu,Yang, Biao
supporting information, (2022/03/17)
An environmentally friendly and highly diastereoselective method for synthesizing indanes has been developed via a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water is the only byproduct.
A ratiometric fluorescence mitochondrial-targeted probe for imaging HOCl in vitro and in vivo
He, Qiong,Jiang, Chen,Li, Yingxue,Yan, Lingjuan,Yao, Cheng,Ye, Aiying
, (2021/12/07)
HOCl, as one of reactive oxygen species, could cause tissue damage and induce various disease when it is at abnormal level or improper location. To monitor HOCl, we developed a near infrared ratiometric fluorescence probe C3H, which is capable to detect HOCl in real time. This probe gives two emission signals with no cross-talk in the process of monitoring HOCl, accompanied by a considerable variation (up to 348-fold) in its fluorescence intensity ratio (F480 nm/F750 nm). Additionally, probe C3H exhibited excellent properties such as fast response (? in vivo.
