- A novel selective mitochondrial-targeted curcumin analog with remarkable cytotoxicity in glioma cells
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Naturally occurring polyphenol curcumin (4) or demethoxycurcumin (5) and their synthetic derivatives display promising anticancer activities. However, their further development is limited by low bioavailability and poor selectivity. Thus, a mitochondria-targeted compound 14 (DMC-TPP) was prepared in the present study by conjugating a triphenylphosphine moiety to the phenolic hydroxyl group of demethoxycurcumin to enhance its bioavailability and treatment efficacy. The in vitro biological experiments of DMC-TPP showed that it not only displayed higher cytotoxicity as compared with its parent compound 5, but also exhibited superior mitochondria accumulation ability. Glioma cells were more sensitive to DMC-TPP, which inhibited the proliferation of U251 cells with an IC50 of 0.42 μM. The mechanism studies showed that DMC-TPP triggers mitochondria-dependent apoptosis, caused by caspase activation, production of reactive oxygen species (ROS) and decrease of mitochondrial membrane potential (MMP). In addition, DMC-TPP efficiently inhibited cellular thioredoxin reductase, which contributed to its cytotoxicity. Significantly, DMC-TPP delayed tumor progression in a mouse xenograft model of human glioma cancer. Taken together, the potent in vitro and in vivo antitumor activity of DMC-TPP warrant further comprehensive evaluation as a novel anti-glioma agent.
- Shi, Lei,Gao, Li-li,Cai, Shi-zhong,Xiong, Qian-wei,Ma, Zhou-rui
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Read Online
- Mitochondrial-targeting curcumin derivative as well as preparation method and medical application thereof
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The invention relates to the field of natural medicines and medicinal chemistry, in particular to a mitochondria-targeting curcumin derivative. The invention also discloses a preparation method of the curcumin derivative and application of the curcumin de
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Paragraph 0089-0092; 0104-0107; 0100-0103; 0115-0118
(2021/07/21)
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- A highly efficient artificial light-harvesting system with two-step sequential energy transfer based on supramolecular self-assembly
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A highly efficient artificial light-harvesting system (ALHS) in the aqueous phase with a two-step sequential energy transfer process has been successfully constructed based on the host-guest interaction between a water-soluble pillar[5]arene (WP5) and a b
- Han, Tingting,Hu, Xiao-Yu,Jiao, Jianmin,Qian, Weirui,Shi, Yukun,Sun, Guangping,Wang, Leyong
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supporting information
p. 9590 - 9596
(2020/06/05)
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- Preparation of aggregation-induced emission material with light stability
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The invention discloses a hindered amine light stabilizer with an aggregation-induced emission (AIE) performance and a synthesis method thereof. The hindered amine light stabilizer is formed through steps including a step of ensuring that AIE pyrone deriv
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Paragraph 0052; 0053
(2019/02/27)
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- Governing the DNA-binding mode of styryl dyes by the length of their alkyl substituents-from intercalation to major groove binding
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A series of monomeric and homodimeric 4-alkoxystyryl(pyridinium) dyes was synthesized and their DNA-binding properties were investigated. We found that the length of the alkyl substituent has a crucial influence on the binding mode of the dyes, although t
- Berdnikova, Daria V.,Sosnin, Nikolai I.,Fedorova, Olga A.,Ihmels, Heiko
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p. 545 - 554
(2018/02/07)
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- Synthesis and comparative studies of phase transition behaviour of new dimeric liquid crystals consisting of dimethyluracil and biphenyl cores
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A new homologous series of mesogens containing 6-amino-1,3-dimethyluracil moiety have been synthesized. The structures of the compounds were characterised by elemental analysis, FT-IR, 1H and 13C NMR spectroscopic techniques. Their m
- Abdulkarim-Talaq, Mohammad,Srinivasa,Sie-Tiong, Ha,Hariprasad,Guan-Yeow, Yeap
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p. 765 - 772
(2016/04/26)
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- 1,4-naphthoquinone cations as antiplasmodial agents: Hydroxy-, acyloxy-, and alkoxy-substituted analogues
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Cations of hydroxy-substituted 1,4-naphthoquinones were synthesized and evaluated as antiplasmodial agents against Plasmodium falciparum. The atovaquone analogues were found to be inactive as antagonists of parasite growth, which was attributed to ionization of the acidic hydroxyl moiety. Upon modification to an alkoxy substituent, the antiplasmodial activity was restored in the sub-100 nM range. Optimal inhibitors were found to possess IC50 values of 17.4-49.5 nM against heteroresistant P. falciparum W2.
- Lu, Xiao,Altharawi, Ali,Gut, Jiri,Rosenthal, Philip J.,Long, Timothy E.
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supporting information
p. 1029 - 1033
(2013/02/22)
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- Design of guanidinium porphyrins as potential G-quadruplex ligands
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We report herein an easy and smooth synthesis of two novel tetra-meso-substituted porphyrins bearing terminal guanidinium functionalities. These two guanidine derivatives are the porphyrin-based analogs of ZnPC, a closely related phthalocyanine-based molecule with four guanidinium arms already reported as an efficient G-quadruplex ligand.
- Xu, Hai-Jun,Richard, Philippe,Barbe, Jean-Michel,Gros, Claude P.
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p. 1073 - 1081
(2013/01/15)
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- BENT-CORE LC DECORATED GOLD NANOCLUSTERS
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Novel thiol-terminated bent-core liquid crystals (LCs) are used to decorate gold nanoparticles. Thioacetate or xanthate/xanthogenate functional groups are used to effect the attachment of the LCs to the gold nanoparticles. Such bent-core decorated nanoparticles may be dissolved in bent-core liquid crystal host media to provide polarizable systems which respond quickly to applied electric fields and exhibit other interesting and useful optical and electro-optic behaviour.
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- Synthesis of 4-[(diethylamino)methyl]-phenol derivatives as novel cholinesterase inhibitors with selectivity towards butyrylcholinesterase
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A series of novel cholinesterase inhibitors, being composed of 4-[(diethylamino)methyl]-phenoxy and secondary amine which were linked with a different length alkyl chain, were designed and synthesized from the starting material p-hydroxybenzaldehyde. Thes
- Yu, Liang,Cao, Rihui,Yi, Wei,Yan, Qin,Chen, Zhiyong,Ma, Lin,Peng, Wenlie,Song, Huacan
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experimental part
p. 3254 - 3258
(2010/09/04)
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- Bent-core liquid crystal (LC) decorated gold nanoclusters: Synthesis, self-assembly, and effects in mixtures with bent-core LC hosts
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We present the first synthesis of a series of thiol-, thioacetate-, and xanthate-terminated bent-core derivatives, as well as the preparation of gold nanoclusters using the thiol-terminated bent-core compounds. The mesomorphic properties of the bent-core compounds have been investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), small angle X-ray scattering (SAXS), and electro-optic tests. From this series, the mono-xanthate derivatives form rectangular or hexagonal columnar phases, and the mono-thiol derivative with shorter alkyl chains forms a metastable, likely smectic, phase. All other bent-core compounds and intermediates exclusively form disordered or multi-layer lamellar crystalline solid modifications. High-resolution transmission electron microscopy (HR-TEM) images of the bent-core functionalized gold nanoclusters prepared from the thiol-terminated derivatives, taken after slow evaporation of the solvent, provide evidence for the formation of self-assembled nanocluster arrays. Upon dispersion of these gold nanoclusters in two structurally related bent-core LC hosts (one forming a SmCPA, and the second with a terminal double bond displaying a Colr phase), a shift in the surface plasmon resonance was observed indicating a LC host-dependent aggregation of the nanoparticles. Finally, we report initial results on the effects of different concentrations of these nanoclusters on the thermal properties as well as the applied voltage/current response of the parent SmCPA host.
- Marx, Vanessa M.,Girgis, Hidy,Heiney, Paul A.,Hegmann, Torsten
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supporting information; experimental part
p. 2983 - 2994
(2010/02/27)
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- Surface monolayers and aqueous bilayers of single-chain ammonium amphiphiles which contain benzylideneaniline and salicylideneaniline units
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The assembling properties of single-chain ammonium amphiphiles containing benzylideneaniline and salicylideneaniline units as rigid segments in the formation of aqueous bilayers, cast multi-bilayers, and surface monolayers were studied.Electron microscopy indicated that aggregate morphologies observed in water, such as vesicles and fibers, were dependent on the nature of the aromatic unit and the alkyl-chain length of the component amphiphiles.The patterns of molecular assembly in bilayers were examined by absorption spectroscopy of aqueous bilayers and X-ray diffraction of cast multi-bilayer films.The patterns were virtually identical to those of the corresponding azobenzene bilayers, and commonly determined by combinations of alkyl-chain lengths.This alkyl-chain combination was crucial for formation of stable surface monolayers.
- Nishimi, Taisei,Ishikawa, Yuichi,Ando, Reiko,Kunitake, Toyoki
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p. 201 - 208
(2007/10/02)
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- Formation of Stable Bilayer Assemblies in Dilute Aqueous Solution from Ammonium Amphiphiles with the Diphenylazomethine Segment
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Quarternary ammonium amphiphiles of the following structures were synthesized: Cn-BB-N+3C1 and Cn-BB-Cm-N+3C1, where Cn and Cm are hydrocarbon chains of n =
- Kunitake, Toyoki,Okahata, Yoshio
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p. 549 - 553
(2007/10/02)
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