- Microtubule formation using two-component gel system
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We report a two-component gel system in which an amphiphile group and aromatic cores act as organic gelators by the process of self-assembly. The shape and size of the aromatic cores have a pronounced effect on the gel properties and on structures such as fibers and microtubules. Copyright
- Ho, Yong Lee,Seong, Ryong Nam,Hong, Jong-In
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- Binary Supramolecular Chirality “1/0” Switched by Hierarchical Photoisomerization of a Flower-Like Compound with a Binaphthol Core and Alkyl-Functionalized Azobenzene Side Chains
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Chiral supramolecular assemblies are abundant in nature, but controlling the chirality of artificial systems still remains a challenge. In this work, we developed a system where supramolecular chirality can be controlled between chiral and achiral states, namely a chiral “1/0” switch using a flower-like azobenzene compound with a binaphthol core. Upon photoisomerization by ultraviolet irradiation, the terminal alkyl tails envelop the chiral “centre” with a reduction in the dihedral angle of the binaphthol moiety from 76.1° to 61.4°, like “closing petals”. In the doped liquid crystal E7 matrix, this hierarchical conformational transition prevents the transfer of chirality to the host liquid crystal, resulting in a degradation from cholesteric phase (HTP value: 13.84 μm?1) to an achiral nematic phase.
- Hou, Jiaxin,Liao, Jinglun,Feng, Yancong,Feringa, Ben L.,Chen, Jiawen,Li, Hao,Zhou, Guofu
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- Effective luminescence sensing of Fe3+, Cr2O72-, MnO4- and 4-nitrophenol by lanthanide metal-organic frameworks with a new topology type
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Lanthanide MOFs (Ln-MOFs), {[Ln2(L)2(H2O)2]·5H2O·6DMAC}n, [Ln = Eu(1) and Tb(2); H3L = 4,4′-(((5-carboxy-1,3-phenylene)bis(azanediyl))bis(carbonyl)) dibenzoic acid, DMAC = N,N′-d
- Ma, Jing-Jing,Liu, Wei-Sheng
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Read Online
- Asymmetric chiral disazo dopants with high anisotropy for versatile modulation of liquid crystal optics
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As key elements, anisotropic chiral dopants determine the helical twisting power (HTP) of doped cholesteric liquid crystal (CLC) system by the host–guest interaction. To reveal the intrinsic structure–function relationship, we developed 3 novel asymmetric and photo-responsive chiral derivatives bearing axial chiral binaphthol moiety and disazo chromophore. They exhibited reversible photoisomerization, and rapidly induced helical degeneration of the doped CLC mixture under UV irradiation. Furthermore, highly asymmetric (R)-2′-hydroxy-[1,1′-binaphthalen]-2-yl 3,5-bis((E)-(4-butoxyphenyl)diazenyl)benzoate (molar absorption coefficient: 28,090 L?mol?1?cm?1; half-life period: 10.28 h; HTP: ?34 um?1 in E7) was adopted to construct the CLC film with excellent NIR-reflection adjusted by light, heat, and electric field. It is a promising photoswitch agent for application in advanced smart materials and optical devices.
- Liao, Jinglun,Feng, Yancong,Zhang, Jingxing,Li, Hao,Zhou, Guofu
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- Anion Recognition through Multivalent C–H Hydrogen Bonds: Anion-Induced Foldamer Formation and Transport across Phospholipid Membranes
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A series of triazole–cyanostilbene receptors were designed and synthesized. The receptor binds with the anions through various CH···anion hydrogen bonding interactions, where strong binding was observed for SO42– anions followed by C
- Mondal, Debashis,Ahmad, Manzoor,Panwaria, Prakash,Upadhyay, Avisikta,Talukdar, Pinaki
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- New diarylsulfonamide inhibitors of Leishmania infantum amastigotes
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New drugs against visceral leishmaniasis with mechanisms of action differing from existing treatments and with adequate cost, stability, and properties are urgently needed. No antitubulin drug is currently in the clinic against Leishmania infantum, the causative agent of visceral leishmaniasis in the Mediterranean area. We have designed and synthesized a focused library of 350 compounds against the Leishmania tubulin based on the structure-activity relationship (SAR) and sequence differences between host and parasite. The compounds synthesized are accessible, stable, and appropriately soluble in water. We assayed the library against Leishmania promastigotes, axenic, and intracellular amastigotes and found 0, 8, and 16 active compounds, respectively, with a high success rate against intracellular amastigotes of over 10%, not including the cytotoxic compounds. Five compounds have a similar or better potency than the clinically used miltefosine. 14 compounds showed a host-dependent mechanism of action that might be advantageous as it may render them less susceptible to the development of drug resistance. The active compounds cluster in five chemical classes that provide structure-activity relationships for further hit improvement and facilitate series development. Molecular docking is consistent with the proposed mechanism of action, supported by the observed structure-activity relationships, and suggests a potential extension to other Leishmania species due to sequence similarities. A new family of diarylsulfonamides designed against the parasite tubulins is active against Leishmania infantum and represents a new class of potential drugs with favorable cost, stability, and aqueous solubility for the treatment of visceral leishmaniasis (VL). These results could be extended to other clinically relevant species of Leishmania spp.
- González, Myriam,Alcolea, Pedro José,álvarez, Raquel,Medarde, Manuel,Larraga, Vicente,Peláez, Rafael
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- Based on molecular glue of the fluorescence-labeled nucleotide and its use in DNA sequencing
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The invention discloses a fluorescence labelled nucleotide based on a molecular glue and a use thereof in DNA sequencing. The structure formula of the fluorescence labelled nucleotide is shown in a formula (I) in the specification, wherein R1 is shown in the specification, R2 is fluorescein or shown in the specification, and dNTP is ribonucleoside triphosphote which contains four different base groups; the fluorescein is selected from one of the BODIPY, rhodamine, coumarin, xanthene, cyanin, pyrene, phthalocyanine, alexa, a squarene dye, a composition for generating energy transfer dye and the derivatives thereof. The fluorescence labelled nucleotide can be used for DNA sequencing; simultaneously the raw materials for synthesizing the fluorescence labelled nucleotide are simple and easy to obtain and the fluorescence labelled nucleotide can be used for large-scale popularization. The biological assessment result shows that all the requirements of the high-throughput sequencing biochemical reaction can be satisfied by the reversible terminal, and the reversible terminal has good practical prospect.
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Paragraph 0103; 0106
(2018/01/05)
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- Hexafluoro-2-propanol-assisted quick and chemoselective nitro reduction using iron powder as catalyst under mild conditions
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Hexafluoro-2-propanol as the promoter for the quick nitro reduction using a combination of iron powder and 2 N HCl aqueous solution is reported. This methodology has several positive features, as it is of room temperature, remarkably short reaction time. A wide range of substrates including those bearing reducible functional groups such as aldehyde, ketone, acid, ester, amide, nitrile, halogens, even allyl, propargyl and heterocycles are chemoselectively reduced in good to excellent yields, even on gram scale. Notably, the highly selective reduction of 3-nitrophenylboronic acid is achieved quantitatively. The reduction is also tolerant of common protecting groups, and aliphatic nitro compound, 1-nitrooctane can be reduced successfully.
- Chen, Xu-Ling,Ai, Bai-Ru,Dong, Yu,Zhang, Xiao-Mei,Wang, Ji-Yu
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supporting information
p. 3646 - 3649
(2017/08/23)
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- Redox-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-lactic acid) for intracellular drug delivery
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Redox-responsive micelles self-assembled from triblock copolymers of poly(l-lactic acid)-poly(ethylene glycol)-poly(l-lactic acid) (PLA-PEG-PLA) with double-disulfide linkage in the backbone were synthesized and characterized by proton nuclear magnetic resonance (1H NMR) and size exclusion chromatography (SEC), in which both PEG (Mn = 1000, 2000 and 4000 g mol-1) and PLA (Mn = 1600 g mol-1) have different molecular weights respectively. The triblock copolymers PLA3000-PEG2000-PLA3000 and PLA3000-PEG4000-PLA3000 can self-assemble into flower-like micelles in aqueous media with average diameters 110 nm and 43 nm and lower critical micelle concentrations (CMC) 0.017 and 0.014 mg mL-1 respectively compared with that of diblock copolymers. Moreover, in vitro drug release analyses indicated that reductive environment can result in triggered drug release profiles. 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl- 2-H-tetrazolium bromide (MTT) assay in vitro showed no significant cytotoxicity as NIH 3T3 cells incubated in the micelles even when the concentrations up to 1000 μg/mL. Additionally fluorescence microscopy measurements and MTT assay demonstrated that the micelles exhibited a faster drug release and higher cellular proliferation inhibition due to the effect of intracellular reduction responsiveness compared with that of diblock copolymers. The above results suggest that the reduction-responsive, biodegradable and biocompatibility micelles could provide a platform to construct potential drug delivery systems for cancer therapy.
- Yang, Qinglai,He, Changyu,Zhang, Zhen,Tan, Lianjiang,Liu, Bingya,Zhu, Zhenggang,Shao, Zhifeng,Gong, Bing,Shen, Yu-Mei
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p. 351 - 362
(2016/04/05)
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- Alkylated aromatic dyeworks composition for the phase-selective binding
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Disclosed is a process which comprises mixing an alkylated aromatic acid with a mixture comprising a first liquid and a second liquid, thereby causing formation of an organogel comprising the alkylated aromatic acid and the first liquid.
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Paragraph 0190
(2017/04/21)
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- Dynamic covalent diblock copolymers: Instructed coupling, micellation and redox responsiveness
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Instructed by association units that allow reversible and unsymmetrical disulfide bond formation, hydrophilic (PEG) and hydrophobic (PLA) polymer chains are efficiently coupled into amphiphilic diblock copolymers. The desymmetrization of otherwise symmetrical reversible disulfide bond formation is achieved with amide association units that integrate both directional H-bonding and reversible disulfide bond formation, which ensure the connection of different polymer blocks while minimizing self-coupling. The resultant amphiphilic block copolymers self-assemble into long-lasting spherical micelles that are responsive to free thiols.
- Yang, Qinglai,Bai, Ling,Zhang, Yuanqing,Zhu, Fangxia,Xu, Yuhong,Shao, Zhifeng,Shen, Yu-Mei,Gong, Bing
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p. 7431 - 7441
(2015/01/08)
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- Chemoselective reductions of nitroaromatics in water at room temperature
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A robust and green protocol for the reduction of functionalized nitroarenes to the corresponding primary amines has been developed. It relies on inexpensive zinc dust in water containing nanomicelles derived from the commercially available designer surfactant TPGS-750-M. This mild process takes place at room temperature and tolerates a wide range of functionalities. Highly selective reductions can also be achieved in the presence of common protecting groups.
- Kelly, Sean M.,Lipshutz, Bruce H.
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supporting information
p. 98 - 101
(2014/01/23)
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- Organogel Compositions Comprising Alkylated Aromatic Acids
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Disclosed is a composition comprising an organogel which comprises: (a) an alkylated aromatic acid compound of the formula or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, are hydrogen, alkyl, aryl, arylalkyl, or alkyl, provided that at least one of R1, R2, R3, R4, and R5 is —X—Rc, wherein —X— is a linking group between Rc and the aromatic group and Rc is alkyl; and (b) an organic liquid.
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Paragraph 0132
(2013/06/28)
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- Design, synthesis, and biological activity of isophthalic acid derivatives targeted to the C1 domain of protein kinase C
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Protein kinase C (PKC) is a widely studied molecular target for the treatment of cancer and other diseases. We have approached the issue of modifying PKC function by targeting the C1 domain in the regulatory region of the enzyme. Using the X-ray crystal structure of the PKC δ C1b domain, we have discovered conveniently synthesizable derivatives of dialkyl 5-(hydroxymethyl)isophthalate that can act as potential C1 domain ligands. Structure-activity studies confirmed that the important functional groups predicted by modeling were indispensable for binding to the C1 domain and that the modifications of these groups diminished binding. The most promising compounds were able to displace radiolabeled phorbol ester ([3H]PDBu) from PKC α and δ at Ki values in the range of 200-900 nM. Furthermore, the active isophthalate derivatives could modify PKC activation in living cells either by inducing PKC-dependent ERK phosphorylation or by inhibiting phorbol-induced ERK phosphorylation. In conclusion, we report here, for the first time, that derivatives of isophthalic acid represent an attractive novel group of C1 domain ligands that can be used as research tools or further modified for potential drug development.
- Af Genn?s, Gustav Boije,Talman, Virpi,Aitio, Olli,Ekokoski, Elina,Finel, Moshe,Tuominen, Raimo K.,Yli-Kauhaluoma, Jari
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supporting information; experimental part
p. 3969 - 3981
(2010/01/16)
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- Self-assembled organogels based on two-component system
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Organogels were produced by the self-assembly of two organogelators, 3,5-bis(dodecanoylamino)benzoic acid and aromatic amines, in nonaromatic hydrocarbon solvents, through hydrogen bonding, aromatic stacking, and van der Waals interactions. 3,5-Bis(dodecanoylamino)benzoic acid has one carboxylic acid group for hydrogen bonding with amines and two alkylamide groups that can participate in interlayer hydrogen bonding and van der Waals interactions. The shape and size of the aromatic amines have a significant effect on the gel properties as well as their structures. A variety of organogels were realized by forming complexes of 3,5-bis(dodecanoylamino)benzoic acid and various amines with an aromatic group in nonaromatic hydrocarbon solvents.
- Nam, Seong Ryong,Lee, Ho Yong,Hong, Jong-In
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p. 10531 - 10537
(2008/12/23)
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- Functionalized Photoreactive Compounds
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The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.
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- Photochemical reactivity of trifluoromethyl aromatic amines: The example of 3,5-diamino-trifluoromethyl-benzene (3,5-DABTF)
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This work presents the application of an on-line photoreactor to the detection of 3,5-diamino-trifluoromethyl-benzene (3,5-DABTF) in aqueous solutions. When irradiated at 310 nm, this compound is defluorinated to 3,5-diaminobenzoic acid by a nucleophilic substitution of the fluoride by water. Concomitantly, defluorination intermediates polymerize through amide bonds to give dark-colored compounds. We take advantage of the photocatalyzed defluorination and the subsequent decrease in pH to develop an original and specific photoreactor. Continuous recording of pH and temperature in the outlet of the reactor by a dual electrode gives us an opportunity to optimize the system. In the photoreactor, 3,5-DABTF is immediately and totally transformed as attested by the rapid drop of the flowing solution pH from 6.2 to 3.2 and the chromatographic analysis of the outgoing solutions. The detection remains effective from 1 to 1000 parts per million.
- Chaignon, Philippe,Cortial, Sylvie,Guerineau, Vincent,Adeline, Marie-Therese,Giannotti, Charles,Fan, Gerard,Ouazzani, Jamal
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p. 1539 - 1543
(2008/02/01)
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- 2,4-Bis(octadecanoylamino)benzenesulfonic acid sodium salt as a novel scavenger receptor inhibitor with low molecular weight
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In order to investigate the effect of the fixation of the orientations of the two long chains, three types of novel derivatives of scavenger receptor inhibitor 1 were synthesized, and their biological activities were evaluated. Among the novel derivatives
- Yoshiizumi, Kazuya,Nakajima, Fumio,Dobashi, Rika,Nishimura, Noriyasu,Ikeda, Shoji
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p. 2791 - 2795
(2007/10/03)
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- Benzimidazole derivatives
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Disclosed are compounds represented by the following chemical formula (I) and pharmacologically acceptable salts thereof which are novel compounds useful as anticancer agents, antiviral agents or antimicrobial agents. STR1
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- Self-association of branched and dendritic aromatic amides
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Several branched and dendritic aromatic amides have been obtained by reacting tris(4-aminophenyl)-methane 3 either with aryl iodide 1 in a Pd-catalysed carbonylation or with carboxylic acids in the presence of the coupling agent triphenyl phosphite. Nonpolar aromatic substituents and solubilising groups at the periphery ensured that the resulting oligoamides were soluble in chloroform, whereas amide groups in the structural centre of the molecules accounted for strong self-association through hydrogen bonding in solution as evidenced by 1H NMR and vapour-pressure osmometry data. An alternative approach towards branched aramides is also presented which was based on the self-assembly of 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene 12 and various (amido)carboxylic acids.
- Kraft, Arno,Osterod, Frank
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p. 1019 - 1025
(2007/10/03)
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- Synthesis of philanthotoxin analogs with bulky heads including porphyrins. Self-assembly monitored by circular dichroism
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Philanthotoxin (PhTX) analogs with bulky bis-iminodibenzyl and porphyrin head groups have been prepared. Exciton coupled CD studies show that dependent on the hydrophobicity of the head group PhTX analogs may get amphiphilic properties forming micelles in
- Huang, Danwen,Matile, Stefan,Berova, Nina,Nakanishi, Koji
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p. 723 - 736
(2007/10/03)
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- Synthesis of divalent α-D-mannopyranosylated clusters having enhanced binding affinities towards concanavalin A and pea lectins
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Two different α-D-mannopyranosides having aminated heteroaliphatic (2) and p-isothiocyanatophenylated (10) aglycones were prepared and used as key precursors for the conjugation to a 3,5-diaminobenzoic acid core (3) using thiourea and amide coupling chemi
- Page, Daniel,Roy, Rene
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p. 1765 - 1770
(2007/10/03)
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