52559-37-2Relevant articles and documents
Targeted tumor detection: guidelines for developing biotinylated diagnostics
Jang, Joo Hee,Kim, Woo Ri,Sharma, Amit,Cho, Suk Hee,James, Tony D.,Kang, Chulhun,Kim, Jong Seung
, p. 2154 - 2157 (2017)
The challenge in achieving precision medicine relies on how to advance and/or enhance new as well as old therapeutic strategies. Here, we highlight the significant role hydrophilicity of biotinylated fluorescent probe's plays on their cellular uptake behaviour.
Solid fluorescence sensors obtained by functionalization of photocrosslinked water-swollen acrylic membranes with 4-piperazine naphthalimide derivatives
Fernández-Alonso,Corrales,Pablos,Catalina
, p. 139 - 150 (2017)
A photocrosslinked membrane (M-Cl) based on vinyl-pyrrolidone/butyl acrylate containing ethylene glycol dimethacrylate as a crosslinking agent and methacryloyl chloride as reactive monomer has been prepared for further functionalization. A series of hydroxy substituted piperazine naphthalimide compounds have been synthetized as pH sensitive Off-On fluorescence probes using two methods: microwave and reflux. Three of the derivatives were selected to be anchored to the M-Cl membrane through the acid chloride groups by the Schotten-Baumann reaction. All the obtained water-swollen membranes were characterized using different techniques. Photo-induced electron transfer (PET) and its pH-dependent optical changes were investigated and various photochemical parameters were determined by using pH-dependent absorption and fluorescence spectroscopies. In the pH range of 9.0–4.0, these solid sensors undergo PET process from the piperazine to the naphthalimide moiety leading to a fluorescence quenching. However, in the pH range of 4.0–1.0, the PET is inhibited to give a fluorescence enhancement. The sensitivity of the functionalized membranes to pH changes depended on the size and position of the naphthalimide substituents.
A ratiometric lysosomal pH chemosensor based on fluorescence resonance energy transfer
Fan, Jiangli,Lin, Chunying,Li, Honglin,Zhan, Peng,Wang, Jingyun,Cui, Shuang,Hu, Mingming,Cheng, Guanghui,Peng, Xiaojun
, p. 620 - 626 (2013)
In this work, we presented a naphthalimide-rhodamine based fluorescence resonance energy transfer system (FRET) NR1 as a ratiometric and intracellular pH probe, in which 1,2,3-triazole was identified as an ideal bridge and biocompatibility. It could selectively monitor pH variations in methanol/HEPES solution at room temperature. When the pH changed from 6.20 to 2.00, both the fluorescence intensities at 580 nm and the intensity ratios, R (I 580 nm/I538 nm) increased, which allowed the detection of pH changes by both normal fluorescence and ratiometric fluorescence methods. The observation is consistent with the increased FRET from the 1,8-naphthalimide (donor) to the ring-opened, colored form of rhodamine (acceptor). Moreover, as NR1 is lysosomal with low cytotoxicity, it will be helpful for investigating the pivotal role of H+ in a biological context, especially in lysosomes through direct intracellular imaging.
A dual pH and temperature responsive polymeric fluorescent sensor and its imaging application in living cells
Yin, Liyan,He, Chunsheng,Huang, Chusen,Zhu, Weiping,Wang, Xin,Xu, Yufang,Qian, Xuhong
, p. 4486 - 4488 (2012)
A polymeric fluorescent sensor PNME, consisting of A4 and N-isopropylacrylamide (NIPAM) units, was synthesized. PNME exhibited dual responses to pH and temperature, and could be used as an intracellular pH sensor for lysosomes imaging. Moreover, it also could sense different temperature change in living cells at 25 and 37°C, respectively.
Ratiometric fluorescent detection of acidic pH in lysosome with carbon nanodots
He, Yangyang,Li, Zhanxian,Jia, Qingyan,Shi, Bingjie,Zhang, Hongyan,Wei, Liuhe,Yu, Mingming
, p. 1969 - 1974 (2017)
It is significant for cell physiology to keep the homeostasis of pH, and it is highly demanded to develop ratiometric fluorescent sensors toward pH. In this work, under mild condition, through the electrostatic interaction between carbon nanodots (CDs) and organic molecules, two novel ratiometric fluorescence hybrid nanosensors were fabricated for sensing acidic pH. These nanohybrid systems possess dual emission peaks at 455 and 527 nm under a single excitation wavelength of 380 nm in acidic pH condition. With the increasing of pH, the fluorescence of the 1,8-naphthalimide derivative completely quenches, while the blue fluorescence of CDs keeps constant. Furthermore, the CDs?organic molecular nanohybrids exhibit excellent anti-disturbance ability, reversible pH sensing ability, and a linear response range in wide pH range respectively. Besides the ability to target lysosome, with one of the nanosensor, stimulated pH change has been successfully tracked in a ratiometric manner via fluorescence imaging.
Different Steric-Twist-Induced Ternary Memory Characteristics in Nonconjugated Copolymers with Pendant Naphthalene and 1,8-Naphthalimide Moieties
Wang, Ming,Li, Zhuang,Li, Hua,He, Jinghui,Li, Najun,Xu, Qingfeng,Lu, Jianmei
, p. 2744 - 2748 (2017)
Herein, novel random copolymers PMNN and PMNB were designed and synthesized, and the memory devices Al/PMNN and PMNB/ITO both exhibited ternary memory performance. The switching voltages of the OFF–ON1 and ON1–ON2 transitions for both memory devices are around ?2.0 and ?3.5 V, respectively, and the ON1/OFF, ON2/ON1 current ratios are both up to 103. The observed tristable electrical conductivity switching could be attributed to field-induced conformational ordering of the naphthalene rings in the side chains, and subsequent charge trapping by 1,8-naphthalimide moieties. More interestingly, by adjusting the connection sites of 1,8-naphthalimide moieties to tune the steric-twist effect, different memory properties were achieved (PMNN showed nonvolatile write once, read many (WORM) memory behavior, whereas PMNB showed volatile static RAM (SRAM) memory behavior). This result will offer a guideline for the design of different high-performance multilevel memory devices by tuning the steric effects of the chemical moieties.
Synthesis of novel C4-benzazole naphthalimide derivatives with potent anti-tumor properties against murine melanoma
Lu, Yen-Ta,Chen, Tien-Ling,Chang, Kuo-Song,Chang, Chia-Ming,Wei, Tsai-Yin,Liu, Jen-Wei,Hsiao, Chih-Ang,Shih, Tzenge-Lien
, p. 789 - 794 (2017)
Novel C4-benzazole naphthalimide derivatives were synthesized and tested in vitro and in vivo as anti-cancer drugs. Among these synthetic molecules, compounds 9 and 10 exhibited cytotoxicity against murine B16F10 melanoma cells. In addition, the above-mentioned compounds significantly suppressed lung tumor metastasis with no visible sign of toxicity.
A New Reactive 1,8-Naphthalimide Derivative for Highly Selective and Sensitive Detection of Hg2+
Lv, Feng,Chen, Yufen,Tang, Tengxuan,Chen, Yuhua,Xu, Dongmei
, p. 1285 - 1292 (2017)
A 1,8-naphthalimide derivative with a reactive aliphatic hydroxyl was designed and synthesized as a fluorescent probe. Its structure was characterized by IR, 1H NMR, 13C NMR, LC-MS and HPLC. The probe showed high selectivity and sensitivity to Hg2+ over other metal ions such as Pb2+, Na+, K+, Cd2+, Cr3+, Zn2+, Cu2+, Ni2+, Ca2+, Fe3+, Fe2+, Co2+, Mn2+ and Mg2+ in MeCN/H2O (15/85, v/v). The increase in fluorescence intensity was linearly proportional to the concentration of Hg2+ in the range of 18–40?μM with a detection limit of 1.38?×?10?7?mol/L. The probe could work in a pH span of 4.3–9.0 and respond to Hg2+ quickly with strong anti-interference ability. Job’s plot suggested a 1:2 complex of the probe and Hg2+.
A novel bacteriochlorin-styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging
Panchenko, Pavel A.,Grin, Mikhail A.,Fedorova, Olga A.,Zakharko, Marina A.,Pritmov, Dmitriy A.,Mironov, Andrey F.,Arkhipova, Antonina N.,Fedorov, Yuri V.,Jonusauskas, Gediminas,Yakubovskaya, Raisa I.,Morozova, Natalia B.,Ignatova, Anastasia A.,Feofanov, Alexey V.
, p. 30195 - 30206 (2017)
Propargyl-152,173-dimethoxy-131-amide of bacteriochlorin e (BChl) and a 4-(4-N,N-dimethylaminostyryl)-N-alkyl-1,8-naphthalimide bearing azide group in the N-alkyl fragment were conjugated by the copper(i)-catalyzed 1,3-dipolar cycloaddition to produce a novel dyad compound BChl-NI for anticancer photodynamic therapy (PDT) combining the modalities of a photosensitizer (PS) and a fluorescence imaging agent. A precise photophysical investigation of the conjugate in solution using steady-state and time-resolved optical spectroscopy revealed that the presence of the naphthalimide (NI) fragment does not decrease the photosensitizing ability of the bacteriochlorin (BChl) core as compared with BChl; however, the fluorescence of naphthalimide is completely quenched due to resonance energy transfer (RET) to BChl. It has been shown that the BChl-NI conjugate penetrates into human lung adenocarcinoma A549 cells, and accumulates in the cytoplasm where it has a mixed granular-diffuse distribution. Both NI and BChl fluorescence in vitro provides registration of bright images showing perfectly intracellular distribution of BChl-NI. The ability of NI to emit light upon excitation in imaging experiments has been found to be due to hampering of RET as a result of photodestruction of the energy acceptor BChl unit. Phototoxicity studies have shown that the BChl-NI conjugate is not toxic for A549 cells at tested concentrations (8 μM) without light-induced activation. At the same time, the concentration-dependent killing of cells is observed upon the excitation of the bacteriochlorin moiety with red light that occurs due to reactive oxygen species formation. The presented data demonstrate that the BChl-NI conjugate is a promissing dual function agent for cancer diagnostics and therapy.
A fluorogenic probe for tracking GSH flux in developing neurons
Zong, Haichao,Peng, Jiayi,Li, Xiao-Rong,Liu, Meng,Hu, Yongzhou,Li, Jia,Zang, Yi,Li, Xin,James, Tony D.
, p. 515 - 518 (2020)
Understanding GSH flux in developing neurons is prerequisite to reveal its role in neuronal development but necessiates an ultrasensitive assay. By systematically exploring key structural factors determing probe sensitivity in live cells, we developed a fluorogenic probe capable of imaging subtle GSH fluctuations in developing neurons.
An ICT-Based Hydrogen Sulfide Sensor with Good Water Solubility for Fluorescence Imaging in Living Cells
Xu, Qiuyan,He, Longwei,Wei, Haipeng,Lin, Weiying
, p. 5 - 11 (2018)
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A high-performance polyurethane sponge for the detection, adsorption and separation of Cu2+ ions
Yu, Yun,Wang, Jianrui,Lian, Jiansheng,Cheng, Xinjian
, p. 18222 - 18228 (2014)
The simultaneous detection and separation of copper ions is important. In this study, a fluorescent chemosensor (a copper sensitive molecule), was prepared using 6-bromo-benzo[de]isochromene-1,3-dione as a precursor. The as-prepared fluorescent molecule contains a hydroxyl group and an aminoquinoline moiety. The hydroxyl group enables the fluorescent molecule to anchor to a porous polyurethane (PU) sponge. The chemosensors still retained their recognition ability after they were introduced to PU. Upon the addition of Cu2+ ions to the PU sponge, both the color and the fluorescence intensity changed, suggesting that the chemosensor-functionalized PU sponges could be used as a Cu2+ ion sensor. The copper ions could also accumulate and be enriched on the sponges. The adsorption capacity of the PU sponge (containing 2 wt% of the chemosensor) reached 97.26 mg g-1, which was higher than that of the solid PU membranes (52.62 mg g-1). These polymeric, highly sensitive chemosensors may potentially be applied in the detection of water pollution generated by sources such as electroplating and drain outflow.
An unanticipated discovery towards novel naphthalimide corbelled aminothiazoximes as potential anti-MRSA agents and allosteric modulators for PBP2a
Zhang, Peng-Li,Gopala, Lavanya,Zhang, Shao-Lin,Cai, Gui-Xin,Zhou, Cheng-He
supporting information, (2021/12/20)
Available therapeutic strategies are urgently needed to conquer multidrug resistance of MRSA. A visible effort was guided towards the advancement of novel antibacterial framework of naphthalimide corbelled aminothiazoximes, and desired to assert some insight on the conjunction of individual pharmacophore with distinct biological activities and unique action mechanism. Preliminary assessment displayed that dimethylenediamine derivative 13d presented a wonderful inhibition on MRSA (MIC = 0.5 μg/mL), and showed excellent membrane selectivity (HC50 > 200 μg/mL) from an electrostatic distinction of the electronegative bacterial membranes and the electroneutral mammalian membranes. Moreover, 13d could effectually relieve the development of MRSA resistance. Investigations into explaining the mechanism of anti-MRSA disclosed that 13d displayed strong lipase affinity, which facilitated its permeation into cell membrane, causing membrane depolarization, leakage of cytoplasmic contents and lactate dehydrogenase (LDH) inhibition. Meanwhile, 13d could exert interaction with DNA to hinder biological function of DNA, and disrupt the antioxidant defense system of MRSA through up-regulation of ROS subjected the strain to oxidative stress. In particular, the unanticipated mechanism for naphthalimide corbelled aminothiazoximes that 13d could suppress the expression of PBP2a by inducing allosteric modulation of PBP2a and triggering the open of the active site, was discovered for the first time. These findings of naphthalimide corbelled aminothiazoximes as a small-molecule class of anti-MRSA agents held promise in strategies for treatment of MRSA infections.
Naphthaleimide compounds with active ends and preparation methods and applications thereof
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Paragraph 0092-0094, (2022/01/04)
The present invention provides an active end of the naphthaleneimide compound and preparation method and application thereof, the compound to 1,8-naphthalene dimethylamide as an electron absorber, to 9,9-dimethylfluorene as the electron body, by changing
