This study presents the synthesis of new fluorosulfate derivatives of 1,4-naphthoquinone by the SuFEx reaction. Anticancer properties of obtained compounds were studied on PC-3 (prostate adenocarcinoma), SKOV-3 (ovarian cancer), MCF-7 (breast cancer), and Jurkat cell lines. All the studied compounds showed higher cytotoxic effects than Cisplatin. The DFT method was applied to determine the electronic structure characteristics of 1,4-naphthoquinone derivatives associated with cytotoxicity. A method of determination of 2,3-dichloro-1,4-naphthoquinone (), 3-chloro-2-((4-hydroxyphenylamino)-1,4-naphthoquinone (), and 4-((3-chloro-1,4-naphthoquinon-2-yl)amino)phenyl fluorosulfate () in a pharmaceutical substance using an impregnated graphite electrode (IMGE) was developed. The morphology of the IMGE surface was studied using scanning electron microscopy (SEM). The electrochemical behavior of , , and was studied by cyclic voltammetry (CV) in 0.1 M NaClO (96% ethanol solution) at pH 4.0 in a potential range from -1 to +1.2 V. Electrochemical redox mechanisms for the investigated compounds were proposed based on the determining main features of the electrochemical processes. Calibration curves were obtained by linear scan voltammetry in the first derivative mode (LSVFD) with the detection limit (LOD) 7.2 × 10 mol·L for , 8 × 10 mol·L for , and 8.6 × 10 mol·L for , respectively.
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http://dx.doi.org/10.3390/ijms252212245 | DOI Listing |
Int J Mol Sci
November 2024
The School of Advanced Manufacturing Technologies, National Research Tomsk Polytechnic University, Lenin Avenue, 30, Tomsk 634034, Russia.
Anal Chem
May 2024
Jiangsu Provincial Key Laboratory of Drug Metabolism and Pharmacokinetics, State Key Laboratory of Natural Medicines, China Pharmaceutical University, Tongjiaxiang No. 24, Nanjing 210009, Jiangsu, China.
Genetically encoding proximal-reactive unnatural amino acids (PrUaas), such as fluorosulfate-l-tyrosine (FSY), into natural proteins of interest (POI) confer the POI with the ability to covalently bind to its interacting proteins (IPs). The PrUaa-incorporated POIs hold promise for blocking undesirable POI-IP interactions. Selecting appropriate PrUaa anchor sites is crucial, but it remains challenging with the current methodology, which heavily relies on crystallography to identify the proximal residues between the POIs and the IPs for the PrUaa anchorage.
View Article and Find Full Text PDFBioorg Med Chem Lett
January 2024
Calibr, a Division of Scripps Research, La Jolla, CA 92037, USA.
To identify new compounds that can effectively inhibit Mycobacterium tuberculosis (Mtb), the causative agent of tuberculosis (TB), we screened, synthesized, and evaluated a series of novel aryl fluorosulfate derivatives for their in vitro inhibitory activity against Mtb. Compound 21b exhibited an in vitro minimum inhibitory concentration (MIC) of 0.06 µM against Mtb, no cytotoxicity against both HEK293T and HepG2 mammalian cell lines, and had good in vivo mouse plasma exposure and lung concentration with a 20 mg/kg oral dose, which supports advanced development as a new chemical entity for TB treatment.
View Article and Find Full Text PDFTransformation of carbon dioxide (CO) into value-added organic compounds has attracted increasing interest of scientific community in the last few decades, not only because CO is the primary greenhouse gas that drives global climate change and ocean acidification, but also because it has been regarded as a plentiful, nontoxic, nonflammable and renewable one-carbon (C1) feedstock. Among the various CO-conversion processes, carboxylation reactions represent one of the most beautiful and attractive research topics in the field, since it offers the possibility for the construction of synthetically and biologically important carboxylic acids from various easily accessible (pseudo)halides, organosilicon, and organoboron compounds. The purpose of this review is to summarize the available literature on deoxygenative carboxylation of alcohols and their derivatives utilizing CO as a carboxylative reagent.
View Article and Find Full Text PDFRSC Chem Biol
August 2022
Center for Protein Degradation, Dana-Farber Cancer Institute Boston MA USA
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