613-28-5Relevant academic research and scientific papers
3-hydroxy flavone compound and application thereof
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Paragraph 0043; 0047; 0048; 0050; 0055-0057, (2019/11/28)
The invention belongs to the technical field of biological fluorescence analysis, and particularly relates to a 3-hydroxy flavone compound and an application thereof. The compound is particularly a 4-n,n-dialkylamino-3-hydroxy flavone compound, and when the compound is used as a fluorescent dye, the lipid droplet targeting property is better, and a cytoskeleton is hardly colored. When conjugated structures such as a benzene ring and the like are added to the left side of a molecule of the compound, the emission wavelength of the molecule can be greatly prolonged, and fluorescence crossing of the molecule from yellow to red is realized. The compound can be applied to the aspects of dynamic lipid droplet imaging in cells, lipid droplet growth process imaging, adipose tissue imaging, even simultaneous imaging of intramuscular fat and intermuscular fat in skeletal muscle tissues, and the like, and has important application values in the fields of fluorescent dyes, biological fluorescent labels and the like.
N -Alkyl substituted 1 H -benzimidazoles as improved n-type dopants for a naphthalene-diimide based copolymer
Saglio,Mura,Massetti,Scuratti,Beretta,Jiao,McNeill,Sommer,Famulari,Lanzani,Caironi,Bertarelli
, p. 15294 - 15302 (2018/08/17)
Doped polymer semiconductors are actively studied for opto- and micro-electronic applications including thermoelectric generators, where a high electrical conductivity is a key factor. In general, n-type doping is more challenging to achieve than p-type doping. Here we study n-type doping of a commonly used electron transporting naphthalene-diimide bithiophene copolymer with a series of air-stable and solution-processable benzimidazole dopants. To understand the role of dopant structure on miscibility and the resulting conductivity, benzimidazoles with different linear and branched alkyl substituents were synthesized, and their doping efficacy compared through combined morphological, electrical and thermoelectric characterization. We observe a clear dependence of the nature of the alkyl substituent on dopant intercalation into the semicrystalline morphology. By increasing the length or the steric hindrance of the alkyl substituents, the miscibility between dopant and copolymer is enhanced leading to optimized electrical conductivity.
Monocarboxylate transporter 1 inhibitors as potential anticancer agents
Gurrapu, Shirisha,Jonnalagadda, Sravan K.,Alam, Mohammad A.,Nelson, Grady L.,Sneve, Mary G.,Drewes, Lester R.,Mereddy, Venkatram R.
supporting information, p. 558 - 561 (2015/05/27)
Potent monocarboxylate transporter 1 inhibitors (MCT1) have been developed based on α-cyano-4-hydroxycinnamic acid template. Structure-activity relationship studies demonstrate that the introduction of p-N, N-dialkyl/diaryl, and o-methoxy groups into cyanocinnamic acid has maximal MCT1 inhibitory activity. Systemic toxicity studies in healthy ICR mice with few potent MCT1 inhibitors indicate normal body weight gains in treated animals. In vivo tumor growth inhibition studies in colorectal adenocarcinoma (WiDr cell line) in nude mice xenograft models establish that compound 27 exhibits single agent activity in inhibiting the tumor growth.
Discovery of indanone derivatives as multi-target-directed ligands against Alzheimer's disease
Huang, Ling,Miao, Hui,Sun, Yang,Meng, Fanchao,Li, Xingshu
, p. 429 - 439 (2015/01/08)
A series of indanone derivatives were designed, synthesized, and tested using a variety of assays to assess their potential as anti-Alzheimer's disease (AD) agents. The investigations assessed the activities of the agents for the inhibition of cholinesterases (AChE and BuChE), the inhibition of amyloid beta (Aβ) self-assembly, and the catalysis of the disassembly of preformed Aβ oligomers and measured their antioxidant activities. Our results demonstrate that most of the synthesized compounds demonstrated good inhibitory activity against AChE with IC50 values in the nanomolar range. In particular, compounds 9 (IC50 Combining double low line 14.8 nM) and 14 (IC50 Combining double low line 18.6 nM) exhibited markedly higher inhibitory activities than tacrine and similar activities to donepezil. In addition, 9 and 14 significantly inhibited Aβ aggregation (inhibition rates of 85.5% and 83.8%, respectively), catalysed the disaggregation of Aβ fibrils generated by self-induced Aβ aggregation, and exhibited antioxidant activity. Furthermore, these two compounds can cross the blood-brain barrier (BBB) in vitro. These properties highlight the potential of these new compounds to be developed as multi-functional drugs for the treatment of Alzheimer's disease.
Relationship between molecular stacking and optical properties of 9,10-bis((4-N,N-dialkylamino)styryl) anthracene crystals: The cooperation of excitonic and dipolar coupling
Li, Feng,Gao, Na,Xu, Hai,Liu, Wei,Shang, Hui,Yang, Wenjun,Zhang, Ming
supporting information, p. 9991 - 9997 (2014/08/18)
Five 9,10-bis((4-N,N-dialkylamino)styryl) anthracene derivatives (DSA-C1-DSA-C7) with different length alkyl chains were synthesized. They showed the same color in dilute solutions but different colors in crystals. The absorption, photoluminescence, and fluorescence decay indicate that there exist both excitonic and dipolar coupling in crystals of DSA-C1-DSA-C7. X-ray crystallographic analysis revealed that all the crystals belong to the triclinic space group P1 with one molecule per unit cell and that the molecules in every crystal have the identical orientation. This offers ideal samples to investigate the impact of the molecular stacking on the optical properties of the crystals. For the first time, the cooperation of excitonic and dipolar coupling has been comprehensively studied, and the contribution to the spectral shift from the excitonic and dipolar couplings quantitatively obtained. The experiments of amplified spontaneous emission (ASE) together with measurements of the quantum efficiency further confirmed this interpretation. The results suggest that the excitonic and dipolar couplings between the adjacent molecules are both important and jointly induce the spectral shifts of the crystals.
Design, synthesis, and evaluation of resveratrol derivatives as Ass1-42 aggregation inhibitors, antioxidants, and neuroprotective agents
Lu, Chuanjun,Guo, Yueyan,Li, Jianheng,Yao, Meicun,Liao, Qiongfeng,Xie, Zhiyong,Li, Xingshu
supporting information, p. 7683 - 7687 (2013/02/21)
A series of novel resveratrol derivatives were designed, synthesised and evaluated as potential therapeutic agents for the treatment of Alzheimer's disease. Among these compounds, compound 7l, (E)-5-(4-(isopropylamino)styryl) benzene-1,3-diol, exhibited potent ss-amyloid aggregation inhibition activity, which was confirmed by a ThT fluorescence assay (71.65% at 20 μM) and transmission electron microscopy (TEM). Compound 7l also exhibited good antioxidant activity (4.12 Trolox equivalents in an oxygen radical absorbance capacity assay and a 37% reduction in reactive oxygen species in cells at 10 μM). The cytotoxicity analysis of compounds 7f, 7i, 7j and 7l indicated that these compounds have lower toxicities than resveratrol at 60 μM.
Multitarget-directed benzylideneindanone derivatives: Anti-β-amyloid (Aβ) aggregation, antioxidant, metal chelation, and monoamine oxidase B (MAO-B) inhibition properties against Alzheimer's disease
Huang, Ling,Lu, Chuanjun,Sun, Yang,Mao, Fei,Luo, Zonghua,Su, Tao,Jiang, Huailei,Shan, Wenjun,Li, Xingshu
, p. 8483 - 8492,10 (2020/09/15)
A novel series of benzylideneindanone derivatives were designed, synthesized, and evaluated as multitarget-directed ligands against Alzheimer's disease. The in vitro studies showed that most of the molecules exhibited a significant ability to inhibit self-induced β-amyloid (Aβ 1-42) aggregation (10.5-80.1%, 20 μM) and MAO-B activity (IC 50 of 7.5-40.5 μM), to act as potential antioxidants (ORAC-FL value of 2.75-9.37), and to function as metal chelators. In particular, compound 41 had the greatest ability to inhibit Aβ1-42 aggregation (80.1%), and MAO-B (IC50 = 7.5 μM) was also an excellent antioxidant and metal chelator. Moreover, it is capable of inhibiting Cu(II)-induced Aβ1-42 aggregation and disassembling the well-structured Aβ fibrils. These results indicated that compound 41 is an excellent multifunctional agent for the treatment of AD.
Alkyl substituent effects on J- or H-aggregate formation of bisazomethine dyes
Kinashi, Kenji,Lee, Kyun-Phyo,Matsumoto, Shinya,Ishida, Kenji,Ueda, Yasukiyo
experimental part, p. 783 - 788 (2012/02/05)
Bisazomethine dyes with terminal alkyl substituents of different chain lengths (BAR: R = 1, 2, 3, 4, 5 and 6) were synthesized and deposited on a glass substrate to investigate the effect of the alkyl chain length on aggregate formation. Methyl- and ethyl-substituted bisazomethine dyes (BA1 and BA2) formed J-aggregates in thin films (ca. 50 nm), whereas, propyl-, butyl-, pentyl- and hexyl-substituted derivatives (BA3, BA4, BA5 and BA6) formed H-aggregates in thin films (ca. 50 nm). The aggregate formation of the BARs changed drastically between ethyl- and propyl-substituents (BA2/BA3). However, no remarkable changes were observed in the surface morphologies of BA2 and BA3 films. It is suggested that the critical determinant of aggregate formation of BAR is the molecular packing in the film, which depends on the chain length of the terminal alkyl substituent.
Emission wavelength prediction of a full-color-tunable fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one
Kim, Eunha,Koh, Minseob,Lim, Byung Joon,Park, Seung Bum
supporting information; experimental part, p. 6642 - 6649 (2011/06/19)
In this paper we report on a novel fluorescent core skeleton, 9-aryl-1,2-dihydropyrrolo[3,4-b]indolizin-3-one, which we named Seoul-Fluor, having tunable and predictable photophysical properties. Using a concise and practical one-pot synthetic procedure, a 68-member library of new fluorescent compounds was synthesized with diverse substituents. In Seoul-Fluor, the electronic characteristics of the substituents, as well as their positional changes, have a close correlation with their photophysical properties. The systematic perturbation of electronic densities on the specific positions of Seoul-Fluor, guided with the Hammett constant, allows emission wavelength tunability covering the full color range. On the basis of these observations and a computational analysis, we extracted a simple first-order correlation of photophysical properties with the theoretical calculation and accurately predicted the emission wavelength of Seoul-Fluors through the rational design. In this study, we clearly demonstrate that Seoul-Fluor can provide a powerful gateway for the generation of desired fluorescent probes without the need for a tiresome synthesis and trial-and-error process.
One- and two-photon excited dual fluorescence properties of zinc(II) and cadmium(II) complexes containing 4-dipropylamino-benzaldehyde thiosemicarbazone
Xue, Zhao-Ming,Tian, Yu-Peng,Wang, Dong,Jiang, Min-Hua
, p. 1373 - 1378 (2007/10/03)
A new ligand, 4-dipropylaminobenzaldehyde thiosemicarbazone (HL) and its complexes (ZnL2, CdL2), which exhibit intense two-photon excited (TPE) dual fluorescence using 800 nm laser pulses in the femtosecond regime, were synthesized and fully characterized. The measured power dependence of the fluorescence signals provides direct evidence for TPE. The two-photon excited dual fluorescence spectra were compared and contrasted with the corresponding results obtained from one-photon excitation. Emission peaks of the ligand and its complexes were assigned with the aid of PM3 calculations.
