4-aminobenzoic acid
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This study describes a one-pot synthesis of superparamagnetic maghemite-based 4-aminobenzoic acid-coated spherical core-shell nanoparticles (PABA@FeNPs) as suitable nanocomposites potentially usable as magnetic carriers for drug delivery. The PABA@FeNPs system was subsequently functionalized by the activated species (1* and 2*) of highly in vitro cytotoxic cis-[PtCl2(3Claza)2] (1; 3Claza stands for 3-chloro-7-azaindole) or cis-[PtCl2(5Braza)2] (2; 5Braza stands for 5-bromo-7-azaindole), which were prepared by a silver(I) ion assisted dechlorination of the parent dichlorido complexes. The products 1*@PABA@FeNPs and 2*@PABA@FeNPs, as well as an intermediate PABA@FeNPs, were characterized by a combination of various techniques, such as Mössbauer, FTIR and EDS spectroscopy, thermal analysis, SEM and TEM. The results showed that the products consist of well-dispersed maghemite-based nanoparticles of 13 nm average size that represent an easily obtainable system for delivery of highly cytotoxic cisplatin-like complexes in oncological practice.
- MeSH
- cisplatina aplikace a dávkování chemie MeSH
- indoly chemická syntéza chemie MeSH
- kyselina 4-aminobenzoová aplikace a dávkování chemická syntéza chemie MeSH
- lékové transportní systémy * MeSH
- lidé MeSH
- nádory farmakoterapie MeSH
- nanočástice chemie MeSH
- nosiče léků chemická syntéza chemie MeSH
- protinádorové látky chemie MeSH
- stříbro chemie MeSH
- železité sloučeniny chemická syntéza chemie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
4-aminobenzoic acid (PABA), an essential nutrient for many human pathogens, but dispensable for humans, and its derivatives have exhibited various biological activities. In this study, we combined two pharmacophores using a molecular hybridization approach: this vitamin-like molecule and various aromatic aldehydes, including salicylaldehydes and 5-nitrofurfural, via imine bond in one-step reaction. Resulting Schiff bases were screened as potential antimicrobial and cytotoxic agents. The simple chemical modification of non-toxic PABA resulted in constitution of antibacterial activity including inhibition of methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 15.62 µM), moderate antimycobacterial activity (MIC ≥ 62.5 µM) and potent broad-spectrum antifungal properties (MIC of ≥ 7.81 µM). Some of the Schiff bases also exhibited notable cytotoxicity for cancer HepG2 cell line (IC50 ≥ 15.0 µM). Regarding aldehyde used for the derivatization of PABA, it is possible to tune up the particular activities and obtain derivatives with promising bioactivities.
- MeSH
- antibakteriální látky chemie farmakologie MeSH
- buňky Hep G2 MeSH
- cytotoxiny chemie farmakologie MeSH
- kyselina 4-aminobenzoová chemie farmakologie MeSH
- kyselina listová chemie farmakologie MeSH
- lidé MeSH
- methicilin rezistentní Staphylococcus aureus účinky léků růst a vývoj MeSH
- mikrobiální testy citlivosti MeSH
- viabilita buněk účinky léků MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The voltammetric behavior of 4-aminobenzoic acid (PABA) and its acetylated metabolite on glassy carbon, carbon fiber or carbon paste electrodes was investigated in an aqueous supporting electrolyte. 4-Aminohippuric acid (4-AHA), 4-acetamidobenzoic acid (4-AMB) and 4-acetamidohippuric acid (4-Ac-AHA) can be separated on a capillary carbon paste electrode in 0.1 M lithium perchlorate. The oxidation potentials of PABA, 4-AHA, 4-AMB and 4-Ac-AHA were 0.70, 0.88, 1.06 and 1.10 V on capillary CPE, respectively. The electrooxidation process is used for simultaneous quantitative determination of acetylated metabolites in urine.
- MeSH
- cholecystokinin diagnostické užití moč MeSH
- chymotrypsin * izolace a purifikace metabolismus MeSH
- experimenty na zvířatech MeSH
- klinické enzymatické testy metody využití MeSH
- kyselina 4-aminobenzoová * diagnostické užití MeSH
- pankreas exokrinní enzymologie metabolismus MeSH
- para-aminobenzoáty diagnostické užití MeSH
- peptidy * diagnostické užití MeSH
- potkani Wistar MeSH
- sekretin diagnostické užití moč MeSH
- statistika jako téma MeSH
- tenké střevo enzymologie metabolismus MeSH
- zvířata MeSH
- Check Tag
- ženské pohlaví MeSH
- zvířata MeSH
