99-24-1Relevant academic research and scientific papers
Anti-tyrosinase, antioxidant and antibacterial activities of gallic acid-benzylidenehydrazine hybrids and their application in preservation of fresh-cut apples and shrimps
Chen, Lu,Li, Yufeng,Liu, Haiquan,Peng, Zhiyun,Shi, Qiandai,Tan, Lijun,Wang, Jing Jing,Zeng, Qiao-Hui,Zhao, Yong
, (2022/01/19)
A series of gallic acid-benzylidenehydrazine hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. Thereinto, compounds 5d and 5f potently inhibited tyrosinase with IC50 of 15.3 and 3.3 μM, compared to kojic acid (44.4 μM). The inhibition mechanism suggested that 5d and 5f not only chelated with Cu2+, but also reduced Cu2+ to Cu1+ in the tyrosinase active site. Additionally, 5d and 5f exhibited strong DPPH scavenging and antibacterial activities against Vibrio parahaemolyticu and Staphylococcus aureus, which can be attributed to the function of gallic acid and hydrazone moiety. These compounds also exhibited capacity to preserve fresh-cut apples and shrimps. Finally, 5d and 5f exhibited low cytotoxic activity in a human cell line (HEK293). Therefore, these compounds possess anti-tyrosinase, antioxidant, and antibacterial activities, and can be used in the development of novel food preservatives.
One-Component Multifunctional Sequence-Defined Ionizable Amphiphilic Janus Dendrimer Delivery Systems for mRNA
Atochina-Vasserman, Elena N.,Billingsley, Margaret M.,Huang, Ning,Kim, Kyunghee,Liu, Matthew,Maurya, Devendra S.,Mitchell, Michael J.,Ni, Houping,Ona, Nathan,Percec, Virgil,Pochan, Darrin J.,Shahnawaz, Hamna,Weissman, Drew,Xiao, Qi,Zhang, Dapeng
supporting information, p. 12315 - 12327 (2021/08/20)
Efficient viral or nonviral delivery of nucleic acids is the key step of genetic nanomedicine. Both viral and synthetic vectors have been successfully employed for genetic delivery with recent examples being DNA, adenoviral, and mRNA-based Covid-19 vaccines. Viral vectors can be target specific and very efficient but can also mediate severe immune response, cell toxicity, and mutations. Four-component lipid nanoparticles (LNPs) containing ionizable lipids, phospholipids, cholesterol for mechanical properties, and PEG-conjugated lipid for stability represent the current leading nonviral vectors for mRNA. However, the segregation of the neutral ionizable lipid as droplets in the core of the LNP, the "PEG dilemma", and the stability at only very low temperatures limit their efficiency. Here, we report the development of a one-component multifunctional ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA that exhibits high activity at a low concentration of ionizable amines organized in a sequence-defined arrangement. Six libraries containing 54 sequence-defined IAJDs were synthesized by an accelerated modular-orthogonal methodology and coassembled with mRNA into dendrimersome nanoparticles (DNPs) by a simple injection method rather than by the complex microfluidic technology often used for LNPs. Forty four (81%) showed activity in vitro and 31 (57%) in vivo. Some, exhibiting organ specificity, are stable at 5 °C and demonstrated higher transfection efficiency than positive control experiments in vitro and in vivo. Aside from practical applications, this proof of concept will help elucidate the mechanisms of packaging and release of mRNA from DNPs as a function of ionizable amine concentration, their sequence, and constitutional isomerism of IAJDs.
Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo
Zhao, Xiao-Long,Li, Chun-Qing,Song, Xiao-Mei,Yan, Shuang-Mei,Luo, Du-Qiang
, p. 38 - 43 (2021/02/01)
A series of alkyl gallates was synthesized by reacting gallic acid with the corresponding alcohols. Their structures were determined on the basis of spectroscopic data, including NMR and MS. The antifungal activities of these compounds against plant pathogenic fungi in vitro and in vivo were assessed.
A novel colorimetric and ratiometric fluoride ion sensor derived from gallic acid
Shi, Heng,Li, Xiangguo,Chen, Hongjin,Xing, Jieni,Zhang, Rui,Liu, Jian
, p. 597 - 602 (2021/01/25)
A novel colorimetric and ratiometric probe (SH-GA) for the fluoride ion detection was designed and synthesized from gallic acid. SH-GA exhibited a selective color change from colorless to yellow in the presence of F- among the eight anions (F-, Cl-, Br-, I-, H2PO4-, HSO4-, CH3COO-, and ClO4-), either in THF or DMF solutions. The binding stoichiometry between SH-GA and fluoride ions was determined to be 1?:?1, and the complexation constant was 1.5 × 103 M-1 in THF. The detection limit of the SH-GA probe reached as low as around 1 μM in THF. 1H NMR titration results and DFT calculations suggested a deprotonation process via hydrogen bonding interactions between the fluoride ion and amino group of SH-GA.
Polyhydroxybenzoic acid derivatives as potential new antimalarial agents
Degotte, Gilles,Francotte, Pierre,Pirotte, Bernard,Frédérich, Michel
, (2021/08/07)
With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).
Highly luminescent liquid crystals by connecting 1,3,4-oxadiazole with thiazolo[5,4-d]thiazole units
Bechtold, Ivan H.,Cazati, Thiago,Curcio, Sergio F.,Eccher, Juliana,Falc?o, Eduardo H. L.,Farias, Giliandro,Gallardo, Hugo,Girotto, Edivandro,Malvestiti, Ivani,Manfredi, Alex M.,Salla, Cristian A. M.,Santos, Arthur B. S.,Westphal, Eduard
, (2020/12/17)
The direct bonding between a thiazolo[5,4-d]thiazole and two 1,3,4-oxadiazole units allowed us to create a new and versatile rigid core for luminescent liquid crystal, which showed interesting and variable mesomorphic and photophysical properties. From the 5-bis(5-phenyl-1,3,4-oxadiazol-2-yl)thiazolo[5,4-d]thiazole new core, three molecules with different number of alkoxy chains were synthesized and had their properties correlated with the molecular structure. The molecule with two chains showed a smectic C mesophase, while the mesogens with four and six chains presented hexagonal columnar mesomorphism, which was confirmed by POM and XRD measurements. In addition, the molecule with six chains presented liquid crystalline behavior close to room temperature. In solution, the molecules presented strong photoluminescence ranging from blue to yellow, with quantum yields higher than 0.6. Excited state lifetimes allowed to correlate the fluorescence component associated to the different emitting species to the molecular organization in spin coated films. The molecular energy levels, together with thermal stability and possible charge carrier transport due to molecular packing, suggest that these molecules are promising for optoelectronic applications. Overall, this work contributes to the development of the use of thiazolo[5,4-d]thiazole in liquid crystals, demonstrating its great efficiency and versatility.
α-D-Mannoside ligands with a valency ranging from one to three: Synthesis and hemagglutination inhibitory properties
Al-Mughaid, Hussein,Khazaaleh, Maha
, (2021/07/25)
Six mono-, di-, and trivalent α-D-mannopyranosyl conjugates built on aromatic scaffolds were synthesized in excellent yields by Cu(I) catalyzed azide-alkyne cycloaddition reaction (CuAAC). These conjugates were designed to have unique, flexible tails that combine a mid-tail triazole ring, to interact with the tyrosine gate, with a terminal phenyl group armed with benzylic hydroxyl groups to avoid solubility problems as well as to provide options to connect to other supports. Biological evaluation of the prepared conjugates in hemagglutination inhibition (HAI) assay revealed that potency increases with valency and the trivalent ligand 6d (HAI = 0.005 mM) is approximately sevenfold better than the best meta-oriented monovalent analogues 2d and 4d (HAI ≈ 0.033 mM) and so may serve as a good starting point to find new lead ligands.
Cannabidiol derivative, preparation method and application thereof
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Paragraph 0027; 0035-0037; 0051-0053, (2021/07/28)
The invention discloses a cannabidiol derivative, a preparation method and application thereof, and belongs to the technical field of medicinal chemistry, wherein the cannabidiol derivative is obtained by taking cannabidiol as a main body through a synthesis means, and an anti-tumor activity determination result shows that the cannabidiol derivative prepared by the invention has an inhibition effect on lung cancer cell strains, human breast cancer cell strains, nasopharynx cancer and drug-resistant strains thereof.
CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation
Agrahari, Anand K.,Jaiswal, Manoj K.,Yadav, Mangal S.,Tiwari, Vinod K.
, (2021/07/30)
Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.
Dinuclear Copper(I) Thiodiacetate Complex-Mediated Expeditious Synthesis of the Chlorine-Containing Cyclen-Cored 36-Glucose-Coated Glycodendrimer
Agrahari, Anand K.,Kumar, Sunil,Sharma, Anindra,Tiwari, Vinod K.
, (2021/11/17)
High-sugar-tethered glycodendrimers are a remarkable tool in glycobiology for the investigation of carbohydrate-protein interaction using its multivalency property. An enthralling double-stage convergent synthetic approach was selected to build a novel class of chlorine-containing glucose-coated dendrimers using an efficient click catalyst 'dinuclear copper(I) thiodiacetate complex.' In this context, cyclen core was developed through a divergent approach, while the glucodendron was developed via a convergent approach independently. Both azide-alkyne partners were coupled through a modular copper azide-alkyne cycloaddition (CuAAC) strategy to afford a high yield of the desired 36-glucose-coated glycodendrimer. The synthesized glycodendrimer has been elucidated by NMR, gel permeation chromatography (GPC), and IR spectral analysis.
