23051-44-7Relevant articles and documents
Synthesis of a water soluble red fluorescent dye and its application to living cells imaging
Gao, Zheng,Zhang, Xu,Zheng, Meiling,Chen, Yi
, p. 37 - 43 (2015)
Abstract A water soluble red fluorescent dye (TD-mPEG750) has been prepared by treatment of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile with 4-(diethylamino)-2-mPEG benzaldehyde (mPEG-OH, average MW = 750). TD-mPEG750 exhibits red emission at λem = 664 nm in water, a small fluorescence quantum yield (Pdblf = 0.01) and a large Stoke's shift (Δλ = 145 nm) are obtained. Using HeLa cells as prototype, the application of TD-mPEG750 to living cells imaging has been investigated. It is found that TD-mPEG750 can be clearly expressed in mitochondria with high contrast in HeLa cells imaging.
A novel dicyanoisophorone-based ratiometric fluorescent probe for selective detection of cysteine and its bioimaging application in living cells
Zhang, Hengrui,Qin, Nan,Fang, Zhijie
, (2018)
A selective and ratiometric turn-on fluorescent probe was designed and synthesized by using a novel dicyanoisophorone-based derivative and acrylate moiety. The probe displayed high stability and good selectivity to cysteine (Cys) over homocysteine (Hcy) and glutathione (GSH). It also exhibited rapid response to Cys within 180 s. Most importantly, the fluorescence intensity ratio at 590 and 525 nm (I590/I525) was linearly dependent on the Cys concentration in the range from 0 to 40 μM and the detection limit calculated to be 0.48 μM. This probe was also applied for bioimaging of intracellular Cys in living HeLa cells with low cytotoxicity.
Monitoring of Au(III) species in plants using a selective fluorescent probe
Li, Zhen,Xu, Yuqing,Fu, Jie,Zhu, Hailiang,Qian, Yong
, p. 888 - 891 (2018)
A colorimetric and ratiometric probe with a push-pull chromophore dicyanoisophorone system, AuP, has been developed for the detection of Au(iii) species with highly sensitive and selective response to real-water samples and living tissues of Arabidopsis thaliana.
Aminopeptidase N Activatable Fluorescent Probe for Tracking Metastatic Cancer and Image-Guided Surgery via in Situ Spraying
Chung, Jeewon,Du, Jianjun,Fan, Jiangli,Kim, Dayeh,Li, Haidong,Li, Yueqing,Long, Saran,Lu, Yang,Peng, Xiaojun,Shao, Kun,Sun, Wen,Wang, Jingyun,Yao, Qichao,Yoon, Juyoung
, p. 6381 - 6389 (2020)
The recurrence of malignant tumors is mostly caused by incompleted surgical resection. Especially, it is difficult for surgeons to detect and accurately remove metastatic tumors by predominantly using visual examination and palpation owing to the lack of effective means to specifically distinguish the boundary range between normal and tumor tissues. Thus, the development of activated fluorescent probe with superior tumor-to-normal (T/N) tissue ratios is particularly urgent in clinics. In view of CD13/aminopeptidase N (APN) regarded as a cancer-specific biomarker, mediating with progression, invasion, and migration of malignant tumor, herein, we reported an APN-responsive fluorescent probe YH-APN and demonstrated its application to distinguish cancer cells. Through in situ spraying manner, fluorescent superior tumor-to-normal (T/N) tissue ratios (subcutaneous transplantation tumor, 13.86; hepatic metastasis, 4.42 and 6.25; splenic metastasis, 4.99) were achieved. More importantly, we have demonstrated the ability to image metastasis tumor tissue less than 1 mm in diameter, highlighting the potential for this probe to be used as a tool in surgical resection. This research may spur the use of enzyme-activatable fluorescent probes for the progress of tumor diagnosis and image-guided surgery (IGS).
A NIR fluorescent sensor for biothiols based on a dicyanoisophorone derivative with a large Stokes shift and high quantum yield
Qian, Ming,Zhang, Liuwei,Wang, Jingyun
, p. 9614 - 9622 (2019)
Herein, a NIR fluorescent probe N-Bio was developed for the effective detection of biothiols by exploiting a dicyanoisophorone derivative (N-OH) as the fluorophore and a thiol-responsive 2,4-dinitro-benzenesulfonyl (DNBS) group as the recognition group. T
A far-red to NIR emitting ultra-sensitive probe for the detection of endogenous HOCl in zebrafish and the RAW 264.7 cell line
Natarajan, Vijay,Thirumalaivasan, Natesan,Wu, Shu-Pao,Sivan, Velmathi
, p. 3538 - 3544 (2019)
Fluorescence imaging is a dynamic tool for monitoring the functions of biomolecules in living systems. Probes with emission in the far-red to near-infrared range have been found to demonstrate great application prospects in bioimaging due to their deep ti
A selective and sensitive fluorescent probe for homocysteine and its application in living cells
Qiu, Xiaoying,Jiao, Xiaojie,Liu, Chang,Zheng, Dasheng,Huang, Kun,Wang, Qing,He, Song,Zhao, Liancheng,Zeng, Xianshun
, p. 212 - 221 (2017)
Biological thiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) are important for maintaining the cellular redox equilibrium and play critical roles in physiological and pathological processes. It is necessary to detect Cys, Hcy and GS
A novel fluorescent probe with a large stokes shift for cysteine based on dicyanoisophorone
Hou, Jiaqi,Cai, Pengfei,Wang, Chengyun,Shen, Yongjia
, p. 2581 - 2585 (2018)
In this work, a dicyanoisophorone-based turn-on fluorescent probe, DCIP, for highly selective and sensitive detection of cysteine was designed based on nucleophilic substitution mechanism. Moreover, compared with typical cysteine probes, DCIP showed great selectivity and sensitivity for cysteine over other amino acids including the similar structured homocysteine (Hcy) and glutathione (GSH). Further, the detection limit toward cysteine was calculated to be as low as 0.70 μM. In addition, the utility of DCIP as a bioanalytical molecular tool was demonstrated by fluorescence imaging of biothiols in living cells.
An Endoplasmic Reticulum-Targeted Ratiometric Fluorescent Probe for the Sensing of Hydrogen Sulfide in Living Cells and Zebrafish
Gao, Mengxu,Jing, Jing,Shu, Wei,Wang, Chong,Zang, Shunping,Zhang, Xiaoling
, p. 9982 - 9988 (2020)
Hydrogen sulfide (H2S) is an endogenous gaseous signaling molecule in many physiological processes. Relevant investigations indicated that H2S plays a cytoprotective effect under endoplasmic reticulum stress. Currently, it is still a challenge to design e
A near-infrared fluorescent probe based on boric acid hydrolysis for hydrogen peroxide detection and imaging in HeLa cells
Wang, Tao,Yang, Xiaojun,Men, Jinxia,Zhou, Jinpei,Zhang, Huibin
, p. 208 - 214 (2020)
Using the characteristics of hydrogen peroxide that are able to cleave phenyl-boric acid selectively and efficiently, we here report a dicyanoisophorone-boric acid (DCP-BA)-based near-infrared (NIR) fluorescent probe for detection of hydrogen peroxide. Th
A novel near-infrared fluorescent probe for cysteine in living cells based on a push-pull dicyanoisophorone system
Yu, Yuewen,Xu, Hongping,Zhang, Wang,Han, Qiaorong,Wang, Bingxiang,Jiang, Yuliang
, p. 215 - 220 (2017)
The near-infrared (NIR) fluorescent probe for rapid, highly sensitive and selective detection of cysteine (Cys) has great significance in both biological and environment sciences. In this work, a novel and specific dicyanoisophorone-based NIR probe for Cy
Growth, spectral, laser damage and hirshfeld surface studies on configurationally locked 2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-enylidene) malononitrile (OH1) single crystal- A potential terahertz emitter
Brahadeeswaran, S.,Chaudhary, A. K.,Ganesamoorthy, S.,Ganesh, D.,Karthick, S.,Santha, A.,Thirupugalmani, K.
, (2021)
We report on the growth, spectral, optical, laser damage and Terahertz (THz) wave generation studies and Hirshfeld analysis of the pyrrolidine-based, configurationally locked, polyene single crystals 2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-enylidene
Synthesis, crystal growth, and second-order nonlinear optical properties of new configurationally locked polyene derivatives
Zhang, Xinyuan,Jiang, Xingxing,Li, Yin,Lin, Zheshuai,Zhang, Guochun,Wu, Yicheng
, p. 1050 - 1055 (2015)
Five new crystals based on configurationally locked polyene (CLP) structure are synthesized. This series of crystals all consists of a π-conjugated hexatriene bridge between the dicyanomethylidene electron acceptor and the electron donors with strong hype
Two-isophorone fluorophore-based design of a ratiometric fluorescent probe and its application in the sensing of biothiols
Wang, Chengcheng,Wang, Yang,Wang, Guanyang,Chen, Shangjun,Huang, Chusen
, p. 5633 - 5639 (2019)
2,4-Dinitrobenzenesulfonyl (DNBS) has been widely used for the design of small fluorescent probes for biothiols due to its high reactivity. However, most DNBS-based fluorescent probes exhibit "off-on" fluorescence response towards biothiols due to the str
A simple probe with visible color change for selective detection of cysteine
Yin, Hai-Feng,Gao, Meng-Jiao,Jiang, Wen-Jing,Gan, Yu-Han,Li, Chen,Kang, Yan-Fei,Meng, Ya-Li,Xin, Zhen-Hui
, p. 664 - 670 (2020)
In this work, we synthesized a simple fluorescent probe, which can selectively detect cysteine. With addition of cysteine, the probe solution showed marked color change from pale yellow to orange color by naked eye. There was an excellent linear relations
Dicyanoisophorone-Based Near-Infrared-Emission Fluorescent Probe for Detecting NAD(P)H in Living Cells and in Vivo
Zhao, Yuehui,Wei, Keyan,Kong, Fanpeng,Gao, Xiaonan,Xu, Kehua,Tang, Bo
, p. 1368 - 1374 (2019)
NADH and NADPH are ubiquitous coenzymes in all living cells that play vital roles in numerous redox reactions in cellular energy metabolism. To accurately detect the distribution and dynamic changes of NAD(P)H under physiological conditions is essential f
Development of a near-infrared fluorescent probe with large Stokes shift for carboxylesterases detection and its application in living systems
Chai, Yuna,Li, Ying,Liu, Suna,Peng, Youmei,Qin, Chongzhen,Wang, Ning,Wang, Xinru,Zhang, Jingmin,Zhang, Wenda,Zhang, Xiaojian,Zhou, Yubing
, (2021/12/07)
Accurate detection of carboxylesterases (CEs) plays a crucial role in various disease physiological processes and ester-containing drug metabolism. However, the reported near-infrared (NIR) fluorescent probes with short Stokes shift (a new “turn-on” NIR fluorescent probe for CEs detection (termed as CE-1) was developed based on dicyanoisophorone with large Stokes shift over 100 nm for the first time. The probe CE-1 (λex/em = 535/665 nm) featured low cytotoxicity and high sensitivity (detection limit of 2.76 × 10?3 U/mL). Moreover, the CE-1 was successfully used to detect the level changes of CEs under drug-induced modulation in cell imaging, and real-time monitor the activity of CEs in mice models for biological imaging. Notably, these results indicate that the probe CE-1 can be applied for imaging and monitoring endogenous CEs in living systems. We believe that the probe CE-1 will be applied as a potential indicator of CEs for the clinical diagnosis of CEs-related diseases and rational use of drugs.
Modulating donor of dicyanoisophorone-based fluorophores to detect human serum albumin with NIR fluorescence
Liu, Bin,Zhao, Xiongfei,Zhou, Mei,Song, Chao,Zeng, Conghui,Qin, Tianyi,Zhang, Mingyuan,Xu, Zhongyong
supporting information, (2021/12/14)
It is urgently needed to develop NIR-fluorescent probe for detection of human serum albumin (HSA) since the interference of short-wavelength-fluorescence from endogenous species in real serum and urine. However, most previous reports were located in the short-wavelength region (a series of dicyanoisophorone (DCO)-based fluorophores 1–4 with different donor groups have been designed and investigated. A systematic study of their photophysical properties has been carried out. Among these probes, 4 exhibited NIR emission with the highest fluorescence brightness and the most sensitive signal response to HSA. Further studies demonstrated that 4 could strongly bind into the DS1 pocket of HSA with a 1:1 ratio. Importantly, the method based on 4 has been proven to be capable of sensing HSA in real serum and urine samples.
Rational design of near-infrared fluorophores with a phenolic D-A type structure and construction of a fluorescent probe for cysteine imaging
Chen, Dugang,Dang, Yecheng,Li, Wanqing,Liang, Wenjie,Nie, Gang,Zhong, Cheng
supporting information, p. 18528 - 18537 (2021/10/19)
Fluorescent probes with near-infrared (NIR) emission have attracted great attention in biological applications because of the low background interference and deep penetration depth. Therefore, as an important component of the fluorescent probe, the develo
